;TLDR upcoming events in case you’re skimming: is hosting JETPACK: Build your AI Sales System on Monday, and Alex Sherwood and I are hosting a free Intro to Agentic AI for Solopreneurs workshop on Thursday. Register here »

Last weekend I “YOLO’d”1 into letting Claude Code take over my computer for a thorn-in-my-side task that had been bothering me since I migrated to Substack in September 2024: fixing over 350 long, ugly URL strings for the imported Pivot podcast episodes. As a bonus, I also wanted to enable transcripts on each one, which involves editing the post → opening the audio settings → generating a new transcript → waiting for it to load → toggling it on → and hitting save.

I gasped with glee watching Code test this process, debugging itself after the first run, successfully completing the task after twelve minutes of trial and error. By the time I let it loose on all 350, it had the process down to sub-three minutes each.2

Because Mac Minis are back-ordered by over a month here in NYC (OG internet denizen ’s recent Xweet didn’t help), I had to find something else to do while Claude cooked on fixing all those Substack posts.3

I figured I’d go out onto the terrace with Ryder on one of the first truly warm days of Spring, where I thought I smelled the neighbors barbecuing, until I looked down and saw they were burning down piles of dry leaves on their grill.

Meanwhile, with Ryder happily at my feet, I continued replying via voice mode on another Cowork thread using Dispatch in the mobile app, for this insane 100-item taste questionnaire prompt by .

Suddenly, a bright orange flash caught my eye.

A gust of wind scattered the embers from their burning leaves. From two fences over, the flames climbed, suddenly jumping fifteen feet high into the yard next door.

Five other small fires licked around the perimeter of the originating neighbors’ backyard. As the flames spread, it became clear that these (pardon me, IDIOTIC) neighbors didn’t even own a garden hose. They ran into the kitchen to fill a single BUCKET. 🤦🏻‍♀️

My heart hammered as I sprang up and ran into the stairwell to call my husband: “MICHAEL! Get up here, it’s an emergency, there’s a fire!!”

Then I called 911, voice shaking so much I could barely articulate our street address.

While watching the now-billowing flames crawl across our neighbors’ fence toward ours, Michael called out at the top of his lungs as if he were Leonidas in 300 commanding an army: “NEIGHBORS, GET YOUR HOSES!!!”

“NEIGHBORS!!! GET OUTSIDE RIGHT NOW!!! WE NEED YOUR HOSES!!!”

I could have cried with relief and pride that he didn’t waste a second, even as the neighbors who started the fire were flailing and frozen in fear. One sad-but-silver-lining side effect of Michael growing up in war in Beirut is that he learned how to thrive in chaos and crisis; it stills his mind and sharpens his instincts.

He boomed the call across the backyards of our buildings several more times until one by one, neighbors on all sides emerged, each of us stretching our spray as far as we could. We continued barking orders from our third-floor top-down view, acting as side-by-side crisis conductors in this impromptu symphony.

“You! Red shirt across the way! Stand on your table! Point left! Farther!”

“You! Skeleton sweatshirt! Get your upstairs neighbor RIGHT NOW! He needs to point his hose through the fence behind the shed!

“You!” (to the fire starters) “One of you get out front to bring the firefighters in, NOW!”

As the sirens’ wails grew blessedly closer, together we held the flames at bay. By the time the fire crew arrived, the tallest were reduced back to glowing embers. With so many dry leaves and branches from winter, multiple brownstones could have easily caught fire, including ours. Thankfully, FDNY quickly extinguished what remained.

After I confirmed with my own two eyes that the fire was fully out, adrenaline still surging through my body, I ran down to the windowsill at the front of our house. I hoisted the window up, leaned my torso out, and yelled down to thank the two fire truck crews as they reeled in their hoses and closed off the hydrant.

Bless you, thank you! We are so grateful for you!

Yes, it’s a bit hyperbolic, but if Claude hadn’t taken over my computer—allowing me to continue working from Dispatch while relaxing from the terrace—I wouldn’t have seen the neighbor’s yard catch fire just five minutes later.

Ultimately, though, let’s give credit where it’s really due: it is only by God’s grace that I was guided to sit outside at exactly the right time. Who knows what would have happened otherwise.

❤️

📆 Join Us for Three Upcoming Events in April 🎉

• Free: 🤖 Intro to AI Automation—Claude Desktop + Notion Agents for Solopreneurs on April 23 from 10 a.m. ET to 11:30 a.m. ET. ​Notion Pro Alex Sherwood and I will walk you through how we are using agentic AI tools, with easy first next steps to get you set up—so that you can stop peeking over the fence and start putting these systems into practice in your own business. ❌ NOTE: This session will not be recorded, so please join us live!

  🤖 Learn more and enroll »

• Paid: 🐿️ Create Your Idea Collection System ($97)—on April 30 and May 1. ​If you have big creative ideas bubbling, but your notes are scattered across various apps, browser tabs, voice memos, notebooks, and forgotten fragments you thought you’d remember but don’t—this is the workshop for you! You’ll get templates for a Notion idea capture and content calendar system. From there, Custom Agents can help summarize what you’re saving, and even with bulk capture (ie “Save these 20 quotes and fill in as much metadata as you can”).

  🐿️ Learn more and enroll »

• Paid: 🚀 If you’re more advanced, and/or ready to completely geek out with automating your sales systems, don’t miss ’s upcoming JETPACK workshop: Your AI Sales System in Two Hours Ready to Go on Monday, April 20 from 11am ET to 1pm ET. As the registration page says, “​You’re not here to learn about AI sales systems. You’re here to build one. ​Jetpack is a 2-hour live workshop where you walk in with a laptop and walk out with a complete AI sales system — running, not planned.”

  🚀 Learn more and enroll »

🏁 First Steps to Get Started with Agentic AI

If you don’t want to wait for these workshops, scroll down to the “First Steps” section of last week’s newsletter for more on where I’d suggest starting, including some of my favorite context prompts.

And of course, get your copy of Free Time if you don’t already have it! It will teach you (and your agents) how to operate at the intersection of revenue, ease, and joy :)

💬 Have you YOLO’d into Claude Computer Use yet?

Let us know in the comments! I love learning and sharing ideas with each other :)

Leave a comment

🎉 Thank you for reading, and here’s to setting even more time free!

1

😜 “YOLO’ing” in this context is what the kids (and Claude) are calling it when you button-mash accepting all permissions that Claude Desktop asks for without even reading or understanding them (also known as --dangerously-skip-permissions). Will AI take over my computer, email my contacts embarrassing photos, and delete all my files? MAYBE! #YOLOoOooOoo! The bliss—and pure dopamine—of watching it take over draining, drudgerous tasks feels worth the risks . . . for some of us. 😬🤷🏻‍♀️

Saw a guy walking wearing this Serendipity Signage sweatshirt right after the fire debacle:

FWIW, I haven’t been this excited about new technology since I got my first Apple IIc computer, and later, signed onto AOL for the first time with that glorious discordant scratchy-modem sound.

One ;TLDR in case you’re skimming today: My colleague Alex Sherwood and I are hosting a free Intro to Agentic AI for Solopreneurs workshop on April 23 if you’re curious about how agents can set your time free, but are intimidated about where to start. Register here »

For the first time in fifteen years of self-employment, I have landed at something I never thought possible: three weeks in a row of reaching (and staying at) the mythical, formerly-Sisyphean-seeming inbox zero—almost every day, across three main inboxes—even while my EA has been out of the office for two weeks. In the past, I considered it miraculous to hit inbox zero for two seconds once every five years or so.

How is this happening?!

I am not outsourcing writing emails, newsletters, or essays to AI, but I have been automating many other operations-related workflows with absolute glee. I can barely sleep, I’m so excited about what to tackle next, and I can’t wait to crack my laptop open first thing in the morning before the sun even rises—rather than avoiding it. I feel freer, more inspired, more generative, and more creative than I have in years.

Although I also do still share privacy, ethical, and environmental concerns and questions, it feels like AI—for as overhyped as the space can get—has finally caught up with the vision I shared in Free Time (published six months before ChatGPT hit the scene): setting our time free through smarter systems.

Resource-constrained small business owners can now do even more with Delightfully Tiny Teams powered by agentic AI. We can also lift routine maintenance, monitoring, and reporting off contractors’ plates, also freeing them to focus on higher-level, higher-touch work.

🤓 How agents are creating new Free Time breakthroughs

For the first few years of ChatGPT, I was simultaneously impressed (write a poem in ten seconds!) and underwhelmed—generative chat tools did not add anything essential to my business operations, the output always felt Bro-y, and I utterly disdain AI-slop writing output.

But now, in the earliest days of agentic AI, I cannot pry myself away. Every day, I streamline additional layers of my business, following the meta-principle I share in Free Time: Each time you repeat a task, take one step toward automating it.

This goes so far beyond that, though.

Earlier automation tools like Zapier could follow very specific if-this-then-that instructions, but agents are so much more capable, dynamically pulling information from all your systems and software, alongside context about you and your business.

Agents are not transactional like one-off chat threads or tasks—at least not when applied well. With agentic AI, you create context files about you and your business first (more on that below), then you set up recurring or scheduled agents. You can guide them as you would any team member, with patience and feedback, until the output matches exactly what you’re looking for, and then often far beyond.

Now you can also ask for things in your natural language, without any technical or coding skills. Many early adopters aren’t even delegating by typing any longer; they’re just casually voice dictating instructions and replies with tools like WisprFlow.

📜 We are only at the very beginning. The recent timeline:

• Oct. 2024 — Anthropic’s Claude Desktop launched (mostly for developers using Code), the introduction of “vibecoding” as a term in February 2025, followed by OpenAI’s Codex launch in May 2025 (also for software engineers).

• Sept. 2025 — Notion launched a personal AI Agent (embedded as a chat window) that could take multi-step actions across your workspace.

• Nov. 2025: Initial release of an open-source tool called Clawdbot (renamed OpenClaw in January) that went instantly viral as people started setting up second machines so OpenClaw could operate across their entire software stack.

• Jan 12, 2026 — Claude Cowork launched as a research preview, making all the functionality and possibilities of Claude Code more accessible to non-developers.

• Feb 24, 2026 — Notion’s Custom Agents launched (free to try until May 4)

• Feb 25, 2026 — Perplexity Computer launched the following day, and now connects to Plaid so you can create personal finance and business dashboards.

• Mar 23, 2026 — Claude Desktop’s Computer Use Agent launched in research preview mode, where it can take over your computer to complete tasks in Chrome (you’ll need the Claude Extension).

Q1 2026 has been a paradigm shift because we went from developer-only coding geekery to anyone-can-do-this powerful, custom building with natural language and a willingness to try—what I describe in Free Time as techtuition.

Other than the small handful of tech companies furiously competing for market share, bigger businesses are like lumbering dinosaurs when it comes to experimenting with these tools, while creative small business owners like us can roll up our sleeves and dive in with so much more agility and freedom to play!

I’m not suggesting all this so you can simply cram more work into the day (one common critique), I’m talking about what I have been for years: completely eliminating the busy work so that you (and your team) can do more of your best work.

I’m talking about freeing the next five to ten hours of your time each week so you can step away from the computer, get outside, exercise, be even more present with family, and free your mind to think at increasingly higher, more creative levels.

For example…

and . . .

✅ Every morning, a team of Notion Custom Agents sends me the following:

• A high-level morning brief of the day ahead

• A summary of what’s happening with my speaking and coaching clients by scanning my calendar, inboxes, and client trackers, noting what’s coming up next and any action items that are at risk of falling through the cracks.

• A summary of 50+ publications in my SaneBox filter, taking special care to call out the ones it knows are most relevant to my interests (and ignoring all retailers)

• . . . and I know I’m only just getting started

Sometimes I assign a one-off task or project that I know will take time, leave my computer running, and take Ryder out for a two-hour walk while listening to podcasts and generating new ideas. By the time I’m back, it’s done. I second :

On that note, it would be my highest honor to help you set even more time and creativity free!

📆 Two Upcoming Events

• Free: 🤖 Intro to AI Automation—Claude Desktop + Notion Agents for Solopreneurs on April 23 from 10 a.m. ET to 11:30 a.m. ET. ​Notion Pro Alex Sherwood and I will walk you through how we are using agentic AI tools, with easy first next steps to get you set up—so that you can stop peeking over the fence and start putting these systems into practice in your own business. ❌ NOTE: This session will not be recorded, so please join us live!

  🤖 Learn more and enroll »

• Paid: 🐿️ Create Your Idea Collection System ($97)—on April 30 and May 1. ​If you have big creative ideas bubbling, but your notes are scattered across various apps, browser tabs, voice memos, notebooks, and forgotten fragments you thought you’d remember but don’t—this is the workshop for you! You’ll get templates for a Notion idea capture and content calendar system. From there, Custom Agents can help summarize what you’re saving, and even with bulk capture (ie “Save these 20 quotes and fill in as much metadata as you can”).

  🐿️ Learn more and enroll »

🏁 First Steps to Get Started

If you don’t even want to wait for the workshop, here’s where I’d suggest starting:

1. Download the following desktop apps for your computer: Claude Desktop, Notion, and Obsidian. Obsidian helps you more easily read the markdown files Claude will create; markdown is the cleanest way AI reads and creates files, without the extra formatting of Google or Word Docs.
   

2. Claude Desktop has three tabs: Chat, Cowork, and Code—you’ll mainly use Cowork if you’re not building software. Here’s ’s Every Claude Concept explained for Normal People and ’s How to Use Projects.
   

3. For setting up Claude Desktop: Follow Sandy Carter’s Getting Started Guide, combined with Rebecca from ’s copy-paste prompts to set up your context files before working on any project. If you get stuck during set up, just ask Claude (in Cowork or Code) to help you troubleshoot.
   

4. Part of the setup will involve opening Terminal; use Spotlight or the search function on your computer to find and open it. Claude will give you a line of code to copy-paste; do that in Terminal where you see the little rectangle and hit enter.
   

5. If you already use Notion on the Business Plan ($20/month per team member), here’s how to build your first Custom Agent, and many more starting ideas in Notion’s AI Agent marketplace. Run a template, give it feedback, and tell it how to improve the output to fit your business. I suggest creating one central database called “Reports” or “Hub” that all agents feed into (in addition to Tasks, Meetings, Client Trackers, etc.). Here’s the February Time Well Spent with 5 Simple Notion Agents to Try This Week »
   

6. Once your context files are built, have Claude create this epic council skill, Rebecca’s productivity system, and/or try one of these ten “RIP McKinsey” prompts 😂 For those make sure to say, “Read all my context files first.” (now copy-paste their prompt), and at the end of their prompts add: “AskUserQuestion first until you are 95% confident with how to proceed. Do not guess.”
   

7. In general, start with friction areas in your business where you’ll be motivated to persist through any early stumbling blocks. What do you dread doing? What drains you? of the How I AI podcast suggests asking: What do I already do on a regular basis? What do team members already do? If we had more time, what would we do next? And then? And then? Or tell the agent to read your context files, then describe your problem and ask for recommendations about what it can do for you. Ask: What am I missing? What else?

💬 Have you set up agents to help remove any friction areas in your business?

Let us know in the comments! I’d love to learn and share ideas with each other :)

Leave a comment

🎉 Thank you for reading, and here’s to setting even more time free!

If you have big creative ideas bubbling, but your notes are scattered across various apps, browser tabs, voice memos, notebooks, and forgotten fragments you thought you’d remember but don’t—I see you! And I’ve been there.

As AI writing slop continues sliming across the Internet, the best way to stand out now depends on your ability to curate, synthesize interesting sources, and express yourself—your true self—with heart, soul, and your own quirky voice. Don’t let scattered systems get in the way of that!

That said, I will show you how Notion’s new AI features can enhance your workflow behind the scenes, giving your creativity an even bigger boost and freeing your mind from busywork and bottlenecks so you can do even more of your best work.

If your idea-capturing systems are disorganized (or nonexistent), it would be my greatest joy to help organize your mind and get more of your best ideas into the world. After a successful pilot at the end of 2025, I’m bringing back the two-day Idea Collection Systems workshop this Spring, and I would love for you to join us!

When I ran this in December, I was worried that not even five people would sign up; to my delightful surprise, we ended up with seventy students! Here’s what one said:

📆 Learn more and enroll »

🙋🏻‍♀️ More About My Background

I set up my first proper digital collection bucket in September 2021 (also referred to as a commonplace book), after reading How to Take Smart Notes by Sönke Ahrens.

Setting up this system sparked new creative magic for me, as I started connecting disparate stories and snippets in unique ways. I’m only going to toot my own horn here for a brief moment, to show you what is possible when you have a home for the random, serendipitous idea-scraps that fly across your day (that’s just one metaphor, several more to follow since I can’t help myself 😂).

With the help of this idea-collection bucket system . . .

• I wrote and published my third book, Free Time, in one year; my two previous books took three years each.

• For over two years, I published twice-weekly personal essays at Rolling in Doh about the stickier sides of self-employment; that’s nearly 350,000 words, the equivalent of five non-fiction book-sized drafts. My collection bucket system helped me re-embrace my writer identity and dormant creative expression.

• Before pausing my two podcasts, for two years I produced fourteen episodes a month, aided by this system (alongside an incredible production team), including: weekly Pivot episodes, twice weekly Free Time (one solo, one guest), and two private episodes for the BFF community.

What creative superpowers are lying dormant for you, waiting to be unlocked?

My best writing doesn’t start when I sit down to draft: I save these idea ingredients multiple times a day, throughout every day, so that when it’s time to write, I’m synthesizing more than thinking from scratch (that’s a recipe for writer’s block).

🌰 What do squirrels, acorns, and compost piles have in common with your creative process?

💡🪣✨ Back by popular demand, Create Your Idea Collection System is a two-day workshop that will give you the tools and practices to build a rich, intuitive system for generating ideas and accelerating creativity; one that saves time, enhances your thinking, feeds your curiosity, and provides abundant material to work with when you’re ready to create.

Novelist Ann Patchett writes:

“I am a compost heap, and everything I interact with, every experience I’ve had, gets shoveled onto the heap where it eventually mulches down, is digested and excreted by worms, and rots. It’s from that rich, dark humus, the combination of what you encountered, what you know, and what you’ve forgotten, that ideas start to grow.”

Together, we will build the container for all your rich idea compost. You will learn to move through the world like a squirrel, pocketing away quotes, questions, stories, facts, photos, writing samples, snippets of overheard dialogue, and other miscellaneous acorns that pique your curiosity throughout the day.

You’ll learn how to tuck these treasures into your digital collection bucket, connecting new acorns to similar, related older ones—with everything readily available when it’s time to synthesize your experiences and thinking into new work.

Once a rough draft takes shape, intuition and serendipity also work their magic, dropping just-right acorns into your awareness (often at the last minute) to round out the final version.

🌱🐿️ This class will provide ready-made templates and teach you practical daily creative habits to use them, so that you, too, can become an expert idea composter and acorn-collector :)

🪞 Who this course is best for:

If you’re working on something big this year, and you have scattered notes everywhere but no system for making sense of them, this class is for you.

• Who it’s best for: Anyone working on a project that requires your original thinking and/or writing (such as newsletters, essays, books, courses, etc.)

• Prerequisite: You are already using Notion, or curious about how to use it, and willing to experiment with it during our time together.

✅ Over two 90-minute sessions together, we will cover:

• Setting up your own idea collection system in Notion

• Building a collection habit—expanding the range of what you collect as you move throughout your day

• Labeling systems to help create connections between ideas

• Curating from your collection when it’s time to write or create (i.e. for a book, essay, newsletter, course, etc.)

• Leaning into your intuition and serendipity

If you’re working on something big this year, and you have scattered notes everywhere but no system for making sense of them, this class is for you.

👉 What’s Included:

• You will get: Two 90-minute sessions (plus recordings), five done-for-you templates so you’re not setting up your Idea Collection system from scratch, and detailed follow-up notes.

• Format: Within each session, we’ll have a mix of instruction and a handful of quick 5-10 minute creative practices to accelerate what you collect every day.

• Timing: We will meet live from 12 p.m. ET to 1:30 p.m. ET, two days in a row. (After you enroll, you will get a link to add the second session to your calendar.)

• Recording: Sessions will be recorded if you can’t make it live, or if you need to step out at any point.

🐿️ Save Your Seat! »

Hit reply if you have any questions before enrolling — I would love to see you there! Happy Friday and Weekend :)

This week marks my fifteen year biziversary — I honestly never thought I’d make it to five months when leaving my corporate job all those years ago.

I’m still working through this awkward teenage stage, but one thing I am proud of is taking a stand for free time in the midst of all the upheaval these last six years. Not for the sake of more time spent sitting on the couch—but for helping all of us reduce those Burdensome B’s of boredom, bureaucracy, burnout, and bottlenecks.

The world needs more of our best work (not our busy work), and it desperately needs those of us who are Heart-Based Business owners now more than ever.

As I say in the introduction to Free Time, I wrote Pivot for people who are high net growth; you’re here reading if you’re also high net freedom, where money is important but it is certainly not everything—especially not ego-based expansion that sacrifices our integrity, our relationships, or our health.

The other day I heard a fellow business owner share that they created a “Prosperity Pyramid,” to remind them of what matters most in the face of a society obsessed with materialism and hyper-productivity.

Their Prosperity Pyramid, in order of importance, includes:

1. Connection to their higher power

2. The strength of their relationships

3. Thriving health, and only then—in fourth place,

4. Material wealth

Even material wealth is “not about the numbers, but about gratitude for the abundance I already have—in all areas of my life.”

💬 I’d love to hear from you in comments . . .

How would you order your prosperity pyramid? What else would you include?

Leave a comment

📆 Upcoming Events

Are any of you attending SXSW this weekend? Even though it’s one of my all-time favorites, sadly I won’t be able to make it to my favorite serendipity scene this time around 😢 — but Free Time will be!

and the team are doing another famous seven-minute book giveaway this Sunday, on March 15 at 12:30 p.m. Please help spread the word if you know anyone who is going! 🎉

📚 Official Book Giveaway Session Info » (but you don’t need a badge to go)

📆 All Non-Obvious events at SXSW 2026 »

💻 Join our Free Time Hang Next Week

Register to join our next Free Time Community Call coming up next week on March 19 at 12:30 ET! We’ll meet for 45 minutes with a new format: a short reading from Free Time, followed by optional 2-3 minute shares and optional hot-seats for getting group input on a question or challenge in your business.

🗓️ Register to Join »

🎙 Check out these related episodes from the archives:

📝 Permission Slip

Redefine what prosperity means to you. If your balance sheet temporarily looks like this right now . . . so what? What abundance is already present in your life based on the values-based choices you are making while running your business?

Leave a comment

🎉 Thank you for reading, and here’s to embracing a more expansive prosperity pyramid for all of us!

When I published Free Time in March 2022 to help creative business owners set their time free through smarter systems, I had no idea that, a year and a half later, AI would explode onto the scene.

While the systems-thinking principles in the 27 chapters are evergreen (check out the Chapter Summaries PDF), every single one could be rewritten with agentic AI in mind to automate even more, taking ever more pressure off of you—the business owner—to remove any bottlenecks getting in the way of your highest and best work.

I’m inspired by systems superstar , who built a whole AI Chief of Staff last week!

🤖 What is an AI Agent? How is it different from AI chat?

During yesterday’s Free Time Operations Dashboard quarterly office hours call, Notion superstar and our resident tech expert walked us through Notion’s brand new AI Agents feature release earlier this week; it’s free to experiment with until May 4, when Notion will start charging on a credit-based system for usage.

While chats with AI can help you handle one-off tasks, Custom Agents run automatically on schedules or triggers, automating recurring work.

You design a workflow—what data to pull, how to format it, and where to post it—then set a trigger or schedule, and the agent handles it from there, whether you’re online or not.

All Notion users get Notion Agent. Business and Enterprise customers get Custom Agents, priced under the Notion credit system. JB Note: I’m on the Business plan at $20 per person per month, and it is well worth it since Notion powers my entire business!

👉 Here’s how to build your first Custom Agent, and . . .

✅ Here are 5 starting Notion AI Agent ideas to try:

• Style Guide: Create a style guide for my writing voice based on the content of this page: {@-reply the page with writing samples; I included the entire Free Time manuscript}

• Weekly Status Update: create a weekly update for my business every Friday at 5 a.m. by searching across Slack {add connection so Notion can access} and these databases: {i.e. Tasks, Meeting Notes, and Speaking Clients CRM.}

• Chosen Slack emoji reaction creates new tasks: {Connect the agent to Slack} Automatically turn something into a task based on a specific emoji reaction.

• Morning Brief: Create a summary of my agenda for the day with calendar events, the tasks database, and unread emails in my inbox.

• Idea Collection: Automatically summarize saves into my collection bucket each week (or month); note key themes and possible related pages elsewhere in Notion.

• And many more ideas in Notion’s AI Agent marketplace . . .

💬 Have you experimented with AI agents at all? Let us know in the comments!👇

Leave a comment

📆 Hosting: Join our Next Free Time Hang

Register to join our next Free Time Community Call on March 19 at 12:30 ET! We’ll meet for 45 minutes with a new format: a short reading from Free Time, followed by optional 2-3 minute shares and optional hot-seats for getting group input on a question or challenge in your business.

🎙 Check out this related episode from the archives:

🎧 Listening

With thanks to and her fabulous taste in music, I’ve got this Spotify playlist queued for the recent Lunar New Year transition from the snake to the fire horse: 🐎

🎉 Thank you for reading, and here’s to setting even more time free through automated systems!

Is anyone else feeling the February frenzy? Or is that as silly a question as commenting on the weather? The “new year, new you” calendar bill comes due for me right around now—peaking in Spring as people ramp up before summer holidays, with S-Corp taxes already around the corner, due March 15 😭.

In Free Time, I shared many of my time-blocking strategies, including blocking off the entire fourth week of every month for deep work and/or deep rest. Sometimes we teach or write what we needed to hear—past tense—and sometimes it serves as a reminder for our future forgetful self (more on that from kening zhu below).

When my calendar starts filling up (Gratefully! #BookedAndBountiful!), it’s so easy to override what I know is essential for me: saying no to certain requests and delaying other ones, so I maintain spaciousness throughout my days and weeks. If I were scheduling on my own, I would fail at this; just as I would if someone put a pile of Sour Rings in front of my face—at least before quitting refined sugar two years ago.

So I rely on scheduling via sending Calendly links only, as much as I can, making rare exceptions by sending one-off suggestions for client meetings with Notion Calendar.

🗓️ Three examples (among many):

• Someone wants to catch up or schedule a get-to-know-you call? When things get tight, my impulse is to squeeze them in somewhere . . . wrong! 🙅🏻‍♀️ Send the damn link! The link protects me from myself: it means I only do networking or catch-up calls on Tuesdays at 3 or 3:30 p.m., via phone call (no video), while taking Ryder out. If that person finds a time a month-and-a-half out, so be it! Most things aren’t urgent.

• Calls with prospective speaking or coaching clients happen on Tuesdays or Thursdays, so I can get in the zone and stay there.

• VIP Day scheduling options are Mondays and Fridays so I know those days are always protected; no other scheduling links include those days for availability.

• (I use TextExpander to create shortcuts for 10+ types of scheduling links with things like ;cal30 or ;vipcal so I don’t have to remember each one).

🎙 Check out these related episodes from the archives

💬 How about you? What systems do you put in place to protect your calendar from an overly optimistic mind prone to over-stuffing it?

Leave a comment

📆 Hosting: Join our Next Free Time Hang

Register to join our next Free Time Community Call on March 19 at 12:30 ET! We’ll meet for 45 minutes with a new format: a short reading from Free Time, followed by optional 2-3 minute shares and optional hot-seats for getting group input on a question or challenge in your business.

🎧 Listening

I love ’s botanical studies of internet magic podcast — her voice and message always soothes my creative soul. This recent episode, “the work is the medicine you need” is a favorite, along with “money as creative practice”:

💬 Quote

💭 Questions

We know growth is cyclical, not linear. I’m curious: When have you created something for your past self, a resource you felt was missing after struggling through a tough situation? Have you ever created something that supported your future self in a surprising way, perhaps as you spiraled up / over / around to new understanding?

Leave a comment

📝 Permission

You hereby have permission to create the medicine you need, even if it doesn’t make sense for “the market” (yet).

Leave a comment

🎉 Thank you for reading, and here’s to even more abundant free time, energy, creativity, and serendipity!

I’ve been sending a newsletter on-and-off for fifteen years now . . . big thanks to those of you who have been reading different versions of these weekly(ish) missives for months, years, or even over a decade! Today I’m revisiting a tried-and-true format, bringing you some of my favorite things and people from around the web :)

I would also be grateful to hear from you: What are some of your favorite email newsletters? What is it about them that gets you to, you know, actually read and open them, rather than sending them sight-unseen straight into junk or promotions?

💬 Please share in the comments so all of us Free Timers can learn from each other!

Leave a comment

📆 Hosting: Join our Next Free Time Hang

Register to join our next Free Time Community Call on March 19 at 12:30 ET! We’ll meet for 45 minutes with a new format: a short reading from Free Time, followed by optional 2-3 minute shares and optional hot-seats for getting group input on a question or challenge in your business.

📚 Reading

In addition to ’s Blank Slate, I’m also super excited to dive into a few other new books for indie business owners:

• ’s Leaving the Casino: Stop Betting on Tactics and Start Building a Business that Works

• ’s Your Attention is Sacred (Except on Social Media)

• ’s The Radical Business Owner’s Guide to Profit

• ’s Frictionless Growth (and related Substack, )

• And just for fun, this Instagram account I recently stumbled upon (the handle says it all): @sobaditsgoodreads (So Bad It’s GoodReads!)

✍️ Journal-Planning

, a Business Bestie Brunch alum, created a series of quarterly journal-planners — from a tiny spark of idea-pollen to the full-blown gorgeous expression!

🎧 Listening

Like a delicious PB&J, here are two author-friends featured above, and jammin’ about their Fall book launches on Aggressively Human:

🎉 Featured

Big thanks to for spotting Free Time in the YouTube wild! And to Deya for the wonderful nod alongside some of my favorite authors in “If I had to start a business from scratch, I'd read these 12 books,” and in these two IG carousels 🙏

⚙️ Tip

📲 Just in case it’s not on your radar: I’m a big fan of setting iPhone reminders when leaving a location (i.e. stop at the grocery store after the gym) or when arriving home (put the laundry in the dryer).

💬 Quote

💭 Question

What truth is quietly asking for your attention this week?

📝 Permission

You hereby have permission to listen to that inner whisper, even if it’s telling you something you’re not sure you are ready to hear or act on (yet).

Leave a comment

🎉 Thank you for reading, and here’s to even more abundant free time, energy, and serendipity!

I tried a fun prompt with ChatGPT the other day, attaching P&Ls from 2018 to 2025:

Please provide an analysis of my business from 2018 through 2025 by looking at these P&L statements. Tell me the story of my business over the last seven years, including (obviously) the pandemic disruption, and how my numbers do or don’t correlate with broader economic trends and small-business data in the years since. Do not hallucinate; please cite all sources.

The eight-year arc it narrated was fascinating!! It offered a new perspective, helping me see my business from a more neutral point of view than some of the stories I had been telling myself.

I don’t know about you, but I remember feeling so optimistic in ye old 2021 that, economy-wise, “things would surely turn around any day now.” Okay, okay, for sure in 2022. Hah! Then I said it again in 2023 (I had thusfar learned nothing), which proved to be an even bigger doozy, as described so generously on her podcast, and many business owners I spoke with said that last year, 2025, their client pipeline and cash flow were even trickier than in 2020.

So, it turns out, “ThE eCOnoMy” is not coming to save us.*

*Unless you run an AI startup 😭 And: I know, I know—you could have told me this years ago.

And yet, there is hope! We are learning so much through these wacky years, and if you have made it this far, then I know you are far stronger and more resilient for it—even if you’re also savoring a big ol’ slice of humble pie as I have been. 😋

Thankfully, one of my favorite people and small-business thinkers, , just launched (yesterday!) a new guide to help re-think our approach. More on that in a moment . . . but first, please join me for one or both of these free upcoming events!

📆 Upcoming Free Time Events

• I’m excited to be part of Mike Michalowicz’s Money, Mindset & Mastery Summit on January 27 — my session is early, at 8:40 a.m. ET, so grab your coffee or tea and join us at the start! The day-long extravaganza kicks off his book launch for The Money Habit.

• Register to join our Free Time Community Call the following day, January 28, at 12:30 p.m. ET. We’ll meet for 45 minutes with a new format: a short reading from Free Time, followed by optional 2-3 minute shares about anything you’re working on, what you’re excited about this year, and/or any challenges you’re facing.

🗒️ Rethink Your Small Business Status Quo

Here’s more on Tara’s Blank Slate, a guide to help you “Start Fresh, Challenge Your Assumptions, and Redesign Your Business for Long-Term Sustainability.”

In Tara’s words:

“Whether you and your business are in a rut, bogged down by old decisions, or perched on a plateau (and not in a good way), breaking free from the past can be a challenge.

You add new ideas without taking away the old ones. You start to assume that the way things are is the way things have to be. You work with what you’ve got rather than imagining what you could create.

If you’re looking for a way to declutter, start fresh, and build a business for long-term sustainability, you need a blank slate.

Blank Slate is a process for reimagining your business to meet your needs now and into the future. Step-by-step, you’ll design a business that prioritizes what’s most important to you, facilitates the work you love, and creates remarkable experiences for your customers or clients.”

Check out this What Works podcast episode with a sample exercise to help you outline base case and best case scenarios for the following categories: income, type of work, schedule, customers, career goals, community, predictability, health, and team.

🗒️ Get the Blank Slate Guide »

What resources are helping you start 2026 on a powerful, hopeful note? Please share in the comments! This can include books or articles you’re reading, courses you’re taking, podcast episodes you’re loving — anything to help fellow Free Timers work with greater joy and ease :)

Leave a comment

🎉 Thank you for reading, and here’s to even more abundant free time, energy, and serendipity!

If you have big creative ideas bubbling for 2026, but your notes are scattered across various apps, browser tabs, voice memos, notebooks, and forgotten fragments you thought you’d remember but don’t—I see you! And I’ve been there.

If your idea-capturing systems are disorganized (or nonexistent), it would be my greatest joy to help organize your mind and get more of your best ideas into the world. I’m teaching a two-day workshop during the first week of December.

Skip straight to securing your seat:

🪣 Learn more and enroll »

Or keep reading . . .

I set up my first proper digital collection bucket in September 2021 (also referred to as a commonplace book), after reading How to Take Smart Notes by Sönke Ahrens.

Setting up this system sparked new creative magic for me, as I started connecting disparate stories and snippets in unique ways. I’m only going to toot my own horn here for a brief moment, to show you what is possible when you have a home for the random, serendipitous idea-scraps that fly across your day (that’s just one metaphor, several more to follow since I can’t help myself 😂).

With the help of this idea-collection bucket . . .

• I wrote and published my third book, Free Time, in one year; my two previous books took three years each.

• After launching Rolling in Doh in July 2023 as a “super secret summer pop-up,” I’ve published 232 posts (two every week); that’s nearly 350,000 words, the equivalent of five non-fiction book-sized drafts.

• Doh is one of the projects I am proudest of in my career; my collection bucket system and practices have helped me re-embrace my writer identity, recovering creative expression that had gone dormant when I was busy serving corporate clients’ needs pre-pandemic.

• Before pausing my two podcasts in February 2024, for two years I produced fourteen episodes a month, aided by this system (alongside an incredible production team), including: weekly Pivot episodes, twice weekly Free Time (one solo, one guest), and two private episodes for the BFF community.

I think of my best writing output as a chopped salad (new metaphor alert!): a little bit of everything, including quotes, questions, research, personal stories, photos, memes, books, and podcast references. I enjoy mixing all these elements together when exploring a topic, and I couldn’t do it without my collection bucket ready and easily searchable (and cross-reference-able) at my fingertips.

But the work doesn’t start when I sit down to draft: I save these idea ingredients multiple times a day, throughout every day, so that when it’s time to write, I’m synthesizing as much as I am thinking from scratch (that’s a recipe for writer’s block).

What do squirrels, acorns, and compost piles have in common with your creative process?

💡🪣✨ Create Your Idea Collection Bucket is a two-day workshop that will give you the tools and practices to build a rich, intuitive system for generating ideas and accelerating creativity; one that saves time, enhances your thinking, feeds your curiosity, and provides abundant material to work with when you’re ready to create.

As novelist Ann Patchett says:

“I am a compost heap, and everything I interact with, every experience I’ve had, gets shoveled onto the heap where it eventually mulches down, is digested and excreted by worms, and rots. It’s from that rich, dark humus, the combination of what you encountered, what you know, and what you’ve forgotten, that ideas start to grow.”

Together, we will build the container for all your rich idea compost. You will learn to move through the world like a squirrel, pocketing away quotes, questions, stories, facts, photos, writing samples, snippets of overheard dialogue, and other miscellaneous acorns that pique your curiosity throughout the day.

You’ll learn how to tuck these treasures into your digital collection bucket, connecting new acorns to similar, related older ones—with everything readily available when it’s time to synthesize your experiences and thinking into new work.

Once a rough draft takes shape, intuition and serendipity also work their magic, dropping just-right acorns into your awareness (often at the last minute) to round out the final version.

🌱🐿️ This class will provide ready-made templates and teach you practical daily creative habits to use them, so that you, too, can become an expert idea composter and acorn-collector :)

Over two 90-minute sessions together, we will cover:

• Setting up your own idea collection system in Notion

• Building a collection habit—expanding the range of what you collect as you move throughout your day

• Labeling systems to help create connections between ideas

• Curating from your collection when it’s time to write or create (i.e. for a book, essay, newsletter, course, etc.)

• Leaning into your intuition and serendipity

If you’re working on something big in 2026, and you have scattered notes everywhere but no system for making sense of them, this class is for you.

Additional details:

• What it costs: $49

• Who it’s best for: Anyone working on a project that requires your original thinking and/or writing (such as newsletters, essays, books, courses, etc.)

• Prerequisite: You are already using Notion, or curious about how to use it and willing to experiment with it during our time together.

• You will get: Two 90-minute sessions (plus recordings), five done-for-you templates so you’re not setting up your Idea Collection system from scratch, and detailed follow-up notes.

• Format: Within each session, we’ll have a mix of instruction and a handful of quick 5-10 minute creative practices to accelerate what you collect every day.

• Timing: We will meet live on Thursday, December 4, and Friday, December 5, from 12 p.m. ET to 1:30 p.m. ET. (After you book here, you will get another link in the confirmation email to add the second session to your calendar.)

• Recording: Sessions will be recorded if you can’t make it live, or if you need to step out at any point.

🪣 Save Your Seat »

I look forward to seeing you soon—here’s to making 2026 your most prolific and creative year yet!

The primary diagnostic for Free Time is understanding where you are in friction and how you can move toward flow, an immersive state where work feels engaging and joyful. McKinsey research shows we are five times more productive when operating in flow states.

When you’re in survival mode, creating space for flow requires you to also build the muscle of saying no to more than you otherwise would. You must give responsibilities back that aren’t yours, ones weighing you down to the point where your mind writes checks your body can’t cash. Many of you have already experienced these somatic signals, warning you that the way you are working is no longer working.

I love the Polish saying, “Not my circus, not my monkeys.” It’s a perfect tie-in to one of my favorite tiny old-school business books, The One-Minute Manager Meets the Monkey, based on one of the most popular HBR articles of all time, both building on the following bit of Hollywood lore that I shared in Free Time (still just $0.99 on Kindle through Labor Day!).

One day film executive Peter Guber, running a Hollywood studio at twenty-nine years old, vented to Jack Warner, president of Warner Bros. Studios, that he was overwhelmed and left with a million problems at the end of every day. Warner replied:

“Don’t be confused. You’re only renting that office. You don’t own it. You’re the zookeeper in a zoo. Every person arrives with a monkey. Think of that monkey as their problem. They’re trying to leave it with you. Sometimes you have to discover where the monkey is. It’s hidden or dressed up. But remember you’re the zookeeper. You’ve got to keep the place clean. So when you walk them to the door, be sure they’ve got their monkey by the hand. Don’t let them leave without it. And if they come back, make sure it’s trained, i.e. they have solutions to their problems. Otherwise at the end of the day, you’ll have a screaming, jumping troop of monkeys, and monkeys shit all over the place.”

💬 Questions to Consider

🎧 Related Episodes

🎧 Listen to the Free Time podcast »

🧭 Watch the Full Replay

Check out my recent Free Time workshop for Georgetown’s Pivot with Purpose series; you can sign up for additional summer seminar series here.

🎉 I hope you can enjoy some extra free time this summer — time to give even more monkeys back!

Research from Cassie Holmes, author of Happier Hour, shows that having too little free time (less than approximately two hours a day) is associated with less happiness because of stress.

Yet, having too much discretionary time (more than approximately five hours a day) is also associated with less happiness, because it fosters a sense of lacking purpose.

Sometimes, due to a layoff or losing a “big gorilla” client, you end up with free time you didn’t ask for.1 Now what do you do with it?

In a few short hours, at 12 p.m. ET, I’ll be delivering the second of two open-enrollment workshops for Georgetown University’s summer Pivot with Purpose series. They created this robust program in record speed for the many international development professionals affected by mass layoffs earlier this year, estimated at nearly 20,000 in the U.S. and over 200,000 globally.

💻 I would love for you to join us!

• Register for “From Vision to Action: Staying Focused and Energized During Your Pivot” (June 26 at 12pm ET) — based on Free Time, currently $0.99 on Kindle!

🎧 And check out these related Free Time podcast conversations:

On the other side of the equation, sometimes we experience a feeling of time poverty—the feeling of too much to do, and not enough time to do it.

🥵 Business stress is a systems problem, and it can be solved more easily and quickly than you think.

When your mind is cluttered, it’s impossible to keep up with the endless pings and inboxes, and even worse, important information about your business and clients starts falling through the cracks.

If you are drowning in the riptide of reactive work, barely treading water even on your best days, you and your team may be trapped by what I call The Burdensome B’s: getting bored, bottlenecked, burned out, and/or buried by bureaucracy.

Even if the phrase operational efficiency makes you cringe, once you have the right business back-end, so much will click into place, and everyone you interact with will start thanking you.

This isn’t about creating more work; the mark of a good system is that it’s harder not to use it.

​If any of the above describes you, I have good news! As I mentioned last time, my friend and I have already done 90% of the systems set-up for you :D We are bringing you the best deal yet on our two business operations dashboards, expiring in four short days!

👉 If you purchase CreatorHQ by the end June (Monday) with promo code FREE TIME, you’ll get 20% off, bringing the total to $238.

I’m also including access to the Free Time Operations Dashboard at no additional cost (normally it starts at $997), plus a live office hours Zoom with me in August to talk through any questions or sticking points.

CreatorHQ has everything you need (and much, much more!) to get your business operations out of your brain—freeing up hours of time every week, and tens of thousands of dollars in team costs every year. Just a few of the many benefits:

⚙️ Ready to get your business systems squared away once and for all this summer?

You’re getting two done-for-you Notion dashboards for just $238 (a $1,500 value), so that you can mix and match the templates that serve your business best.

Don’t forget to enter promo code FREETIME at checkout:

🧰 Get CreatorHQ »

🧾 After you purchase, forward your receipt to hi@itsfreetime.com and we’ll get you squared away with the Free Time Operations Dashboard and a calendar invite for the August Office Hours :)

🎧 Related Episodes

🎧 Check out Jay’s show, Creator Science, wherever you subscribe to podcasts:

🎧 Listen to Creator Science »

🎉 I can’t wait to hear how you free even more time this summer, and what you do with it!

1

📝 I wrote a little pep talk for this group yesterday on , in case you know someone who might need to hear it:

Rolling in D🤦🏻‍♀️h with Jenny Blake

🧭 Pivot with Purpose: A Pep Talk

I had a virtual keynote at noon yesterday, one with heightened importance and the nerves to match. I would be delivering the kick-off session for Georgetown’s Pivot with Purpose series, an offering backed by the Rockefeller Foundation to serve the tens of thousands of development professiona…

Read more

10 months ago · 7 likes · 2 comments · ❤️ Jenny Blake

🦧 And on losing your biggest client, here’s some wise words from fellow Free Timers on how they’ve handled situations like these:

In honor of working less and having more fun this summer, Ideapress and I have teamed up to bring you the Kindle edition of Free Time for just $0.99 through Labor Day! That’s over 95% off the hardcover collector’s edition (also 33% off at $21 :)

Take it from Oliver Burkeman, author of the global bestseller Four Thousand Weeks:

“Free Time is a revelation—a detailed road map for building a business that fulfills you and serves the world, leaving anxiety and burnout behind. Jenny Blake’s advice is grounded and inspiring, and always connected to life as it is actually lived, at the human scale.”

🔥 Get it while it’s hot!

🧰 Two Done-for-You Dashboards for 85% Off

While we’re getting into the Free Time Summer spirit, I also asked my fellow structure-loving super-creator if I could bundle his brilliant CreatorHQ with the Free Time Operations Dashboard in an epic systems summer sale. Both are based in Notion, the tool we both use to run our businesses.

CreatorHQ has everything you need (and much, much more!) already done for you to get your business operations out of your brain once and for all—freeing up hours of time every week, and tens of thousands of dollars in team costs every year. Jay writes:

The problem is, most productivity systems were built for managers, not makers.

They assume your work is linear, when the creative process is fluid and multidimensional. So you end up fighting your tools instead of using them to bring your best work to life.

CreatorHQ is a “thinking system” that brings all your work into one clear view — so you spend less time context switching and more time in creative flow.

It’s the same system we use to support Creator Science — by leveraging CreatorHQ, we’re publishing more than ever and are nearing $1 million in annual revenue because of it.

We spent more than three years building this. And now, you can have it out of the box.

Jay is generously offering Free Timers a 20% discount through the end of June if you use promo code FREETIME, bringing CreatorHQ to just $238.

👉 If you purchase in June, I’ll also include the Free Time dashboard for free so you can mix and match templates from both that best fit your business (it usually starts at $997).

📆 You’ll also be invited to our next live Office Hours session on August 21 with our Notion pro , where we geek out as a group over new feature releases, share wins, and work through any sticking points.

All-in, that’s a combined value of over $1,500 for two done-for-you dashboards at $238 🙌 Don’t forget to enter promo code FREETIME at checkout:

🧰 Get CreatorHQ »

🧾 After you purchase, forward your receipt to hi@itsfreetime.com and we’ll get you squared away with the Free Time Operations Dashboard and a calendar invite for the August Office Hours :)

🎧 If you enjoyed the Free Time podcast, be sure to also subscribe to Jay’s show, Creator Science.

🎧 Listen to Creator Science »

🎉 I can’t wait to hear how you free even more time this summer, and what you do with it!

P.S. 📸 Send me a photo of you and/or the book in a fun summer location, and I’ll share it in a future edition of Time Well Spent :)

We’re all about setting time free through smarter systems, so I don’t have to tell you about how helpful AI can be for certain parts of the writing process, whether you’re drafting a newsletter, tackling a personal essay, or going all-in on a book. But it’s not necessarily helpful for every stage.

The one thing AI can’t do is be you—an authentic, imperfect messenger, telling your stories and lessons learned with your unique spin. As Free Timer Kyle Wood puts it, “How can I really cultivate my voice, not the best or most correct voice?”

To see where AI can plug in, let’s break “writing” down into its many stages:

• Harvesting ideas, gathering inspiration from reading others’ work, and collecting your own personal stories

• Thinking, doing the harder work of synthesizing your take on those inputs

• Outlining (if needed; AI is superb at this)

• Writing, where you season the work with your unique voice while deepening your thinking. (AI can help you expand here, but it’s terrible at replacing this stage)

• Editing and revising (overall structure, tone, clarity, punctuation, punching up description, etc. — don’t miss ’s prompt for this!)

• Polishing and finally, publishing!

There was enough cliché spammy click-bait cOntEnT on the internet before AI was everywhere, now we have terms for the inbound tsunami like slop and gruel.

It’s important to know where you stand when it comes to AI’s involvement with your writing and thinking—and what intellectual muscles you’re willing to let atrophy in favor of its alluring speed and (seeming) ease.

I do not use AI to draft newsletters or essays—I find the output banal, and I miss out on the best part: writing to explore and unearth what I think, especially the deeper layers and connections that I don’t make until I’m writing.

I’m sharing a list of my favorite resources below, but first, as promised from last time:

🔘 Our poll results from the previous 💌 TWS:

Are you surprised by these results, or do they sound close to your conversations among friends?

I’m sending love to the 41% of you (within those who answered) who are in full-blown meltdown or hanging on by a thread—you are not alone, and you’ve got this!!

🎧 I created this podcast playlist on Spotify just for you »

✍️ My Favorite Tools for Supporting Your Writing

In her oft-quoted 1976 Regents Lecture at UC Berkeley, “Why I Write,” a title borrowed from George Orwell, Joan Didion famously said, “I write entirely to find out what I’m thinking, what I’m looking at, what I see and what it means. What I want and what I fear.”

July 5 marks two years of writing nearly 200 twice weekly personal essays for my paid Substack about the stickier sides of running a small business, and Didion’s words ring true: I often start with the seeds of an idea—a prompt or small story from my life—but I don’t know how I truly feel about the topic or what I have learned until I start writing, especially as the draft simmers for a few days (ideally weeks) before going live.

🧰 With that, here are a few favorite tools to support and enhance your writing—and more importantly, your thinking!—not replace it:

• 🗣️ Claude allows you to upload work samples and create various “voice” profiles called Writing Styles (here’s their how-to guide, and the video announcement). So, for example, if you upload twenty past newsletters (or podcast show notes), it could better help you draft parts of the twenty-first in your voice and style.

• 🛠️ ’s newsletter is fantastic; read his Claude 4 overview and, as noted above, his incredibly thorough prompt, “Help me edit.”

• 📘 Check out my Author Toolkit for Loom walkthroughs of how I organize ideas, content, and writing projects with Notion.

• 🎧 Listen to the Behind-the-Book podcast playlist on Spotify

• 👀 Follow along as one of my friends tackles his next novel (based on the Story Grid framework) by subscribing to , watch his video on How to write better with ChatGPT and Kindle, and have fun down the rabbit hole of listening to nearly a decade of Story Grid podcast episodes!

• ✍️ New Rules Studio: A monthly membership community (that I’m in) with twelve optional Zooms a month. You write for fifteen minutes around a prompt, then hear a few people read aloud (always optional), then give and receive supportive feedback based on the Gateless Method.

• 💻 OmmWriter is a desktop app that helps me get in a writing mood: you can choose from seven calming music or white noise tracks, and seven (!) different keyboard clacking sounds that harken back to typewriter days.

• Delphi allows you to create an AI “agent” that others can interact with by uploading a tranche of your own materials (and syncing RSS feeds) to aid business-related tasks like drafting newsletters and searching your own work for snippets and recurring themes. Give the JB bot a whirl, trained on over seven million words from Pivot, Free Time, and Rolling in Doh.

• 🔎 I use Grammarly for copy-editing and catching spelling errors or missing words when I’m ready to schedule a newsletter or essay; just beware that sometimes it overcorrects. says, “Be warned that Grammarly will flatten your writing and homogenize your voice. (You know you’ve found your authentic voice if Grammarly hates you.)”

• 🧰 Check out the full Free Time Toolkit in Notion if you haven’t already!

💬 How have you been leveraging AI to help with different writing stages?

Any specific prompts fellow Free Timers might find helpful? Comments are open, so please let us know! 👇

Leave a comment

🎙 Related Episodes

That’s all for now—thank you, as always, for being here!

❤️ With Gratitude,

Refer a friend

Did any of you find yourself oddly optimistic about your business forecast in 2020 despite any short-term losses, only to find that for each subsequent year that you thought ThE eCOnOmy was sure to turn around and things would return to “normal” (lol), they only became rockier?

Is it just me? We’re almost halfway through 2025, and I’d like to grab my 2020 self by the shoulders and say: BATTEN DOWN THE HATCHES!

I’m in a small business mastermind, and in 2021, we all poured more money than we’d ever previously dared into our respective companies. That’s how hopeful we were, relying on a lifetime of sunny optimism and a decade of boom-time number-go-up business returns. We figured that by doubling down while the market was down, we would be rewarded; you know, the creative risk-taking that inspired us to launch our own businesses in the first place!

By the time Free Time book launched in early 2022, and as lockdown restrictions continued easing up, I was sure things would turn around any day now. What things? Who knows! THINGS! For me, that’s mostly in the form of speaking engagements; I went from averaging two a month pre-pandemic to a small handful each year since.

Okay fine, I spoke too soon. Surely by 2023. Nope, not for tech companies, my biggest clients, who declared it their year of efficiency and austerity while announcing waves of mass layoffs. (’s Substack is a favorite recent find.)

Hey, at least Pivot is more relevant than ever, and Free Time teaches operational efficiency through smarter systems. I was onto something. No matter, because in summer 2023, my largest licensing client cancelled our contract, representing over $200,000 per year in lost revenue. It was such a shock (even though I braced every Christmas for seven years for that very possibility) that I started writing twice weekly essays about what I was feeling—and suppressing—and I haven’t stopped since.

I knew that 2024, an election year, wouldn’t prove to be any easier. Survive ‘til 25! became the small fish mantra many of us shared.

Okay, but now 2025 is here, and when I tried to order my husband a $200 baby-blue bass guitar from Germany last week as congratulations for hitting a major milestone, UPS slapped a $350 tariff onto the package, due upon receipt—on top of the $100 for international shipping that we already paid the vendor.

Sorry, but we’re not paying $650 for a $200 guitar. Sadly, we turned “Daphne” away at our front door step, sending her back to whence she came, alongside any remaining hopes that the economic turbulence would let up any day now (lololol).

For years, so many people I have spoken with have seemed anxious, and not just the small business owners. Out of care and concern for my financial anxieties as a breadwinner, many of my loved ones ask why I don’t just get a job (ye ol’ refrain), but I’m not sure that’s any easier.

One friend, a product manager in Silicon Valley, was laid off in 2023 and is still looking for full-time work, while stringing together consulting gigs in the interim; the market is so saturated with PMs who are also out of work that he has a hard time gaining traction during the interview process. Another Director-level friend was laid off from a lucrative job at one of the FAANGs, and the entrepreneurs I know are getting more leads this year, but not necessarily more clients.

Former guest of the pod and Pathless Path author shared a fantastic article from along these lines, “Everyone I know is worried about work,” whether “finding a job, keeping the one they have, or what will happen when the work they do no longer exists.”

The New York Times published a depressing piece about Gen Xers’ career meltdowns, “It’s the end of work as we knew it.” I’m a geriatric Millennial and latch-key kid, so right there on the cusp.

On the other hand, one friend’s Delightfully Tiny company received three six-figure requests for proposals the day after the election, and renewed interest has been bubbling up for them ever since. I have been fortunate to receive a few big leads and clients this year, but trying to plan even a month out still feels like staring into a business abyss.

Or is that just my Millennial midlife crisis talking? You tell me . . .

💬 I’d love to hear from you:

💬 Comments are open, so if you are willing to share more details about your response, we can commiserate—and/or celebrate—together!

Leave a comment

🎙 Related Episodes

🍩 Recent at Rolling in D🤦🏻‍♀️h with Jenny Blake

💬 Chat with Dohnut »

Rolling in D🤦🏻‍♀️h with Jenny Blake

👾 "I'm an alien," part one

“It brings to mind the ways in which really painful experiences in life can make people much more human. It can. I have often thought that. I have often thought that, if you’re lucky, you go through something that just cuts you off at the knees, and you’re humbled. As a result of that, you’re going to be a bigger person—that’s the best-case scenario. As opposed to becoming bitter. So yeah, to be humbled, I think, can be a very good thing ultimately…

Read more

a year ago · 7 likes · 9 comments · ❤️ Jenny Blake

Rolling in D🤦🏻‍♀️h with Jenny Blake

🏐 Cast Away Confidence

I accidentally yelled at a friend last week…

Read more

a year ago · 5 likes · 4 comments · ❤️ Jenny Blake

That’s all for now—thank you for being here, and if you’re in a similar boat, hang in there!

❤️ With Gratitude,

Refer a friend

Happy Friday! This week, I’d love to compare notes on fun AI experiments you’ve tried recently and/or any delightful discoveries, large or small :)

Here are a few of mine . . .

🌬️ My friend just told me about WisprFlow, his favorite new transcription tool (I was mostly using Otter.ai and Descript). They have a desktop app with keyboard shortcut (mobile app coming soon) promising “effortless voice dictation in every application: 3x faster than typing, AI commands and auto-edits.”

⚙️ Check out their sample workflows on how to breeze through your customer emails and set up a comms assistant working with you all day.

🤖 I’m still working on my Delphi AI emissary: give the JB bot a try here, trained on over 7 million words of my podcasts, books, and blog posts from the last two decades.

🥗 Food tracking apps can be such a pain; today I uploaded a photo of my airport lounge breakfast and asked ChatGPT to guesstimate macros — pretty good! And so much better than adding each item one by one. Here are the results:

💪 On another health-related note, my friend and I had a question about how the benefits of a weighted vest differed from being overweight. Check out Peter Attia’s podcast The Drive and his bestselling book, Outlive, for more “Centenarian Decathlon” tips, and shout-out to my friend , who vetted and recommended this 10-pound weighted vest to me! Here’s ChatGPT’s breakdown on the difference:

💬 I’d love to hear from you . . .

What favorite AI experiments, apps, or prompts have you been playing with lately? Let us know in the comments so we can learn from each other!

Leave a comment

🎙 Recent & Related Episodes

🍩 Recent at Rolling in D🤦🏻‍♀️h with Jenny Blake

💬 Chat with Dohnut »

Rolling in D🤦🏻‍♀️h with Jenny Blake

☕️ Daily Rituals: Flip or Flop?

“The best artists are always childish…

Read more

a year ago · 2 likes · 2 comments · ❤️ Jenny Blake

Rolling in D🤦🏻‍♀️h with Jenny Blake

☕️ Daily Rituals: Protect Your Flame 🔥

Read part one here first…

Read more

a year ago · 2 likes · ❤️ Jenny Blake

That’s all for now—thank you for being here!

❤️ With Gratitude,

Refer a friend

Stress, frustration, and overwhelm: these are systems flags from your business, asking for renewed attention on a bottleneck—a friction area slowing things down and draining energy.

One of my biggest pet peeves is repeating myself; thus, a bonus mantra that’s missing from the Free Time book since it popped into my head a few months after the launch: train the system, then the person.

Right after the book launched, as I was onboarding two new virtual assistants (I have since downsized back to the tiniest possible team, thank goodness), I found myself repeating the answer to a small email-related process question to different team members for the fourth time in as many months. This is no one person’s fault—other than mine!

My aha moment: I needed a strategy for training the system to get smarter first, then I would teach the team how to better leverage that system, which also reduces confusion, making their work faster, easier, and more frictionless. It also means that if there’s any team turnover the system still holds strong and I don’t have to start from scratch teaching-wise.

For example, I use HelpScout for our team email inboxes. It’s great for creating workflows (automation), assigning messages to different team members, writing notes to each other that the client doesn’t see, saving drafts for someone else to take over, and viewing customer communication history.

Instead of just documenting email SOPs in Notion, I now automatically append a note to certain types of frequent incoming messages telling any team member exactly which SOP to reference and what the high-level next steps are.

🎧 Listen to Episode 92 of the Free Time podcast for more details »

🌟 Key Takeaway

Create a Manager Manual and separate Email Guide. With AI, soon you’ll be able to share that database with tools like Delphi, creating a private chatbot for your business, allowing team members to query the AI directly with process questions. Here’s my email guide:

📝 Permission

Stop repeating yourself! That’s a sure sign that the business area is ripe for systems reinvention.

✅ Do (or Delegate) This Next

Start an Email Guide with your most common decisions and process questions. Create filters in Gmail (or workflows in HelpScout) to automatically label incoming email messages with the short link to the Email Guide process entry and/or key next steps.

🔗 Resources Mentioned in the Episode

• Book: Free Time: Lose The Busywork, Love Your Business

• Team Inbox: HelpScout

• Voice Messaging: SpeakPipe, Vocaroo

• Transcription (and Podcast/Video Editing): Descript

• Shortcuts: TextExpander

• Project Management Software: Notion

🎙 Related Episodes

🍩 Recent and Related at Rolling in D🤦🏻‍♀️h with Jenny Blake

Rolling in D🤦🏻‍♀️h with Jenny Blake

🌱 The Lucky Seedling, Part One

This is the fourth installment of the daily ritual series, re-titled since, ironically, I haven’t been swimming since I started it 😭 Catch up on part one, part two, and part three first…

Read more

a year ago · 4 likes · ❤️ Jenny Blake

Rolling in D🤦🏻‍♀️h with Jenny Blake

🪜 Climbing Down the Entrepreneurial Ladder

“Things today are waaayyyyy better than Things have ever been. Cavemen had sticks. In the Middle ages they had typhoid. We have iPhones and Hermann Miller chairs and shoes with air in the soles. Inside the soles! How do they get the air inside the soles??? We are living in the Golden Age of Things, in the Golden Empire of Things…

Read more

2 years ago · 38 likes · 29 comments · ❤️ Jenny Blake

That’s all for now—thank you for reading and listening!

❤️ With Gratitude,

Refer a friend

Ever wonder why some businesses seem to effortlessly attract ideal clients while others struggle to stand out? Organic word-of-mouth referrals have always been my favorite focus as a marketing method, but a close second is building fun, punchy brands for the different facets of my business that get people talking—and sharing.

This was a huge part of launching Free Time. I’m baffled to say that today marks four years since the podcast launched, and the three-year bookiversary. 🎉

And to think the visual elements started with a blue coffee cup left behind on an outdoor cafe table on the Upper West Side, the flying money emoji, and the heart in my signature—with Together Agency to thank for transforming these random visuals in my mind into the award-winning brand and book design they brought to life.

After working with many small businesses across multiple industries, my business besties and his cofounder (and beautiful wife!) have identified four distinct brand personas that can reveal where you are in your branding journey—and what you might consider next if you’re looking for a refresh this year.

🔎 What stage best describes your business?

• Blank Canvas—You have a business idea and nothing else. A branding exercise is helpful at this stage because you’re capturing your core business idea and how it is showing up in the world. It’s a good opportunity to align from the very beginning in a brand-forward way, from the name to the strategy to the identity.

• Frankenstein—Piecemeal elements from different contractors, but no one cohesive strategy. You have a brand that is cobbled together, and no one on the team is feeling inspired by it. It’s confusing, with no clear guide for how to apply the different elements.

• Jeckyll/Hyde—Your business’ brand has taken you this far, but you sense that it’s getting stale, and that some aspects may be holding you back. You’ve got some traction, but you are losing out on bigger opportunities, and are looking for a rebrand to reach the next stage.

• Tune-up—The foundational strategy is strong; now there is an opportunity to see what is out of date and what smaller elements can be refreshed or tightened up.

🔎 Curious where you fall on this spectrum? Dive deeper in our three-part podcast series below, and if 2025 is your year for a brand strategy spruce-up, Together Agency now offers more accessible monthly retainer packages through their Duo option—perfect for systematically working on your brand elements over time.

Learn more about Together & Duo »

🎙 Related Episodes

• 045: Behind the Free Time Brand with Adam Chaloeicheep

• 247: Has your Business Brand Become a Liability? How to Know When It’s Time for a Tune-up

• 248: Four Brand Personas, Biggest Mistakes, and Best/Worst Clients

• 174: What Book Marketing has to do with Glass Blowing: Reflecting on Free Time’s 1-Year Bookiversary 🥂

🍩 Recent at Rolling in D🤦🏻‍♀️h with Jenny Blake

Rolling in D🤦🏻‍♀️h with Jenny Blake

🪵 Stockpiling Marshmallows (Or Not), Part One

Every ten years or so, or when Malcolm Gladwell launches a new book, a formerly obscure social science study surges into the mainstream, fated to live as a citation in every business book across the land until it becomes intolerable…

Read more

a year ago · 8 likes · 2 comments · ❤️ Jenny Blake

Thank you for reading and listening!

❤️ With Gratitude,

Refer a friend

I’ve been geeking out building Delphi.ai clones this week, with thanks to my friend for the nudge to dive in. Cue an eye roll at the landing page tech jargon, but here’s the gist:

“Delphi allows you to build the digital version of you to scale your expertise and availability, infinitely.”

You can train it on your voice, sync RSS feeds for importing, upload affiliate links for products and services to promote, and even monetize the bots if you choose.

Although you can create project folders on other AI platforms like NotebookLM, ChatGPT, and Claude by uploading a tranche of your own materials to aid business-related tasks like drafting newsletters, posts, or even internal process documents, Delphi creates a sophisticated chatbot that others can interact with.

🤖 Here are a few ways that I’m setting mine up:

• One for my entire body of work: Actually, so I don’t completely humiliate myself with 20-year-old cringe content from my early twenties, it mainly draws on the last ten years of publishing; that’s over six million words from two of my books (Pivot & Free Time), 750+ podcast episodes across the Pivot & Free Time podcasts, who-knows-how-many newsletters, online courses, and more.

• One for corporate licensing clients: Drawing only upon official Pivot materials like the Train-the-Trainer facilitator guide, book manuscript, and LinkedIn Learning courses, this bot will help newly minted Certified Pivot Trainers and Pivot coaches answer questions as they prepare to lead sessions for the first time.

• Your new business bestie: Trained only on , my personal essays about the stickier sides of running a small business, this one is explicitly told not to be an expert or give advice, just to relate and refer to related resources for fellow solo+preneurs going through a tough time.

I’m a little nervous to share these with you as I’m still working out awkward kinks (like calling one early tester “honey” 😬), but if you want to give them a spin and help provide feedback, here are the links!

🤖 Chat with my JB clone »

🍩 Chat with Dohnut »

💻 Check out Delphi to build your own »

✍️ For Aspiring Writers: New Rules Studio

“What if writing just felt . . . easier? And—what if you had a place to do it that was critic-free, judgment-free, competition-free?”

My friend Terri Trespicio, who graciously emceed the Free Time book launch party, has been practicing the Gateless Method of writing for over a decade. She has now created a brilliant writing community around it—and I just joined!

There are twelve open sessions each month where you can drop in (no reservation required) and write in real time for anywhere from 15-25 minutes, guided by an optional prompt (and optional feedback).

Learn more and join for the free open house on the first Monday of every month:

New Rules Studio: Writing Open House »

🍩 New at Rolling in D🤦🏻‍♀️h

A three-part series on NYT–bestselling author ’ generous sharing about how she navigated her toughest year in business, “The Crumbling.”

Rolling in D🤦🏻‍♀️h with Jenny Blake

🐦‍🔥 Luvvie's "The Crumbling," Part One

“My CFO said, if we do not bring in one additional dollar—if we do not book one more piece of business—the company would be bankrupt by the end of June. This is March. Awe Luv Media would have zero in less than three months. Y’all, it was red alert time. I was officially the closest to panicking. I remember sitting at my desk with my face in my hands, j…

Read more

a year ago · 5 likes · 2 comments · ❤️ Jenny Blake

And a cross-post from on “Stay in your lane. Wise words, soul-crushing advice, or both?”

🎙 Revisit a Podcast Episode from the Archives

Although the podcast is paused, you can still browse the archives and subscribe here »

Here’s to setting even more time free! 🥂

❤️ With Gratitude,

Refer a friend

If you read Rolling in Doh, you know I’ve been on an Elin Hilderbrand rabbit hole recently. A few aspects of her career as a bestselling author of Nantucket beach reads—producing over 30 books in as many years—have impressed me Free Time-wise.

For starters, I am transfixed by her morning routine, with three hours of exercise every day before starting work:

• She wakes up at 5 a.m.

• She takes a 45-minute Peloton cycling class, followed by

• An hour-long “yog,” a slow run-jog along the water, ending up at

• An hour-long barre class in town

• Only then is she ready to write for the rest of the day

Who has the time to work out three hours a day, you ask? Elin, who is also incredibly prolific. “For me, [writing is] a job,” she says, “so I treat it like a job. I write every single day.”

Here’s what happens after her morning stack:

“In the summer, I try to be at it by eleven, and I stay until six. I can write longhand and in notebooks, so I do it out by my pool.

When I say I write for seven hours, what I mean is that I’m trying to get three hours of composing done. So I give myself seven hours to compose for three.

I read—I’m always reading—and if I’m at my pool or the beach, I swim. I take a nap. I have my lunch. All of that’s happening.

But if you compose three hours a day, 350 days a year, you can write two books a year.”

But her productivity alone isn’t what I find most compelling. It’s the long view she has taken toward the arc of her writing career; her persistence, consistency, and patience.

Due to limited publisher investment, her first seven books experienced middling sales. Finally, Hilderbrand and her agent shopped for a new home, landing at Little, Brown. With their help, book by book, she climbed the charts.

But could she hit number one?

She did—at last—on her twenty-third try.

So what if other first-time novelists hit the New York Times list with their debut? She didn’t let compare-and-despair—or vanity metrics—slow her down.

Then again, she didn’t speed up, either. She kept delivering what she promised her publisher and community: one book every summer, still a superhuman feat.

Hilderbrand herself would be the first to say that it would have been fine if she never “hit the list.” She would have kept writing and working because that’s the part she loves. “It was in my blood,” she said, continuing:

“It was my job. It was what I did. I did not have delusions of grandeur. I was happy that I was publishing books. I was happy even with my first five even when they weren’t doing well. I was frustrated because I felt like I wanted more readers . . . but I never considered quitting.”

Cliché as it may be, immersing myself in the Hilderverse reminds me to keep going. To ignore the odds. 51/49.

And that writing poolside, longhand on a legal pad, still counts as work.

Read the full posts in The Formation of an Unlikely Hilderbabe: Part One and Part Two

✍️ For Aspiring Writers: New Rules Studio Open House on October 10

“What if writing just felt…easier? And—what if you had a place to do it that was critic-free, judgment-free, competition-free?”

My friend Terri Trespicio, who graciously emceed the Free Time book launch party, has been practicing the Gateless Method of writing for over a decade. In the last year, she created a brilliant writing community around it, where you can drop into multiple sessions each week to support you in whatever projects you’re working on. Learn more and join for the free open house coming up on October 10 — I’ll see you there!

New Rules Studio: Writing Open House »

🍁 Fall Voxer Coaching: I would love to work with you 1:1!

I’m opening up a few special spots for a two-month 1:1 Voxer coaching program this Fall, thus steering clear of the holidays :) This might be perfect timing if you are looking for a boost as you reflect on 2024 and set your strategy for 2025.

Whether you want to delegate more, streamline your business systems, license your IP, brainstorm a big idea for a book or speech, or talk through other friction areas, I’m an open book with all my clients. That means in addition to a weekly asynchronous “Ask Me Anything” question, you’ll get every template and resource that I’ve spent thousands of dollars creating and learning about the hard way.

If that sounds like just what you need, I would love for you to join me in this special round of 1:1 Voxer coaching!

🎟️ Enrollment is now open through October 13 or when the five spots fill (whichever comes first), and we begin on Monday, October 14.

Learn more and join us »

📆 Upcoming Events for Paid Subscribers

🔗 The links to register are below the paywall in the footer of this email.

✍️ Write the Thing! Our first session this week was a blast, and surprisingly productive! Join us for the second co-working session on November 6; the link to register is in the footer of this email. This is guided co-working time (and moral support) to write what matters most: an essay, a newsletter, morning pages, an autoresponder, an invitation, an important email, a page of your book—whatever surfaces that would leave you feeling lighter ❤️

Might you also be interested in a NaNoWriMo accountability group for the month of November? If so, comment or reply and let me know :)

💻 Quarterly Office Hours — November 20: Ask anything about a question or challenge in your business, and get input from fellow Heart-Based Business owners.

Upgrade to Paid »

🎙 Revisit a Podcast Episode from the Archives

Although the podcast is paused, you can still browse the archives and subscribe here »

Here’s to setting even more time free! 🥂

❤️ With Gratitude,

Refer a friend

P.S. Extra Goodies Over the Paywall Rainbow 🌈💰

🔐 Thank you to our generous paying subscribers who help sustain Time Well Spent! Upgrade to unlock the bonuses and event registration links below ☺️

Read more

Back by popular demand after two rounds of summer Voxer coaching, I’m opening up a few special spots for a condensed two-month version this Fall, thus steering clear of the holidays :) 

This might be perfect timing if you are looking for a boost as you reflect on 2024 and set your strategy for 2025.

Whether you want to delegate more, streamline your business systems, license your IP, brainstorm a big idea for a book or speech, or talk through other friction areas, I’m an open book with all my clients: that means in addition to a weekly asynchronous “Ask Me Anything” question, you’ll get every template and resource that I’ve spent thousands of dollars creating and learning about the hard way.

If that sounds like just what you need, I would love for you to join me in this special round of 1:1 Voxer coaching!

🎟️ Enrollment is now open through October 13 (or when the five spots fill, whichever comes first), and we begin on Monday, October 14.

Learn more and join us »

🐤 Early Birds: Anyone who enrolls by end of day Monday, Sept. 30, will also get:

• The Free Time Operations Dashboard with 30+ Notion templates to externalize your business mind ($1,500 value)

• Two 1:1 onboarding sessions with our Notion Pro Alex for help setting up more complex databases and automations ($600 value), and

• A Strengthscope Assessment to identify your “significant seven” energy-strengths (and your biggest drainers), plus access to the upcoming Upgrade Your Energy workshop in December to debrief your results ($197 value)

It’s time to build the next phase of your business in a spacious, easeful way. With Voxer coaching there is no scheduling or screen fatigue, as the format is asynchronous. For these eight weeks, you’ll get coaching on the go, at any time and place that is most convenient for you.

✅ Together, we can also tackle things like:

• Streamlining your business operations so you can pass The Fiji Test

• Exploring Substack—starting a new publication or moving your existing newsletter—one year in, Rolling in Doh, is a featured Substack and bestseller

• Training others in your method so you can free more time to work on the business

• Delegating more efficiently and scaling with subcontractors

• Ideating and organizing any stage of a book project

• Building or refining revenue streams that are recurring and scalable

• Going meta, if you have questions about how to implement this coaching format in your business (+ check out this related podcast episode)

Voxer has been one of my favorite formats for working with small business clients, and you will be amazed at how much we accomplish! I would be thrilled to be your thought partner for this next round :)

💬 Here’s what a few previous clients shared:

✨ Jenny has a template for everything!

✨ She’s the best. In my 15+ years of working with coaches, nobody has held a candle to Jenny. Present, thoughtful, creative, heart-centered, inspiring, and supportive, Jenny is that loving best friend everyone needs in their life. She’s real, a brilliant facilitator for messy minds, and the co-pilot I always want in my corner. Jenny has been my off-and-on coach for over a decade, and no matter the issue I bring to the table, I get the clarity and direction I need to move forward.

✨ Jenny is someone you can tell is smiling when she talks. She brings joy and genuine excitement to every interaction. She’s not afraid to read between the lines and share or ask something from her intuition, even if that might challenge you.

✨ I designed a VIP Day, landed my first client for this service, and delivered my first VIP day during Voxer coaching. In addition, I refined my system for onboarding new clients. I got out of the weeds of bespoke work and designed three options for a pilot program.

✨ Jenny is knowledgeable about the challenges of small heart-centered businesses, and ways to make them run efficiently with Delightfully Tiny Teams. She knows that most of us are trying to do meaningful work that supports our families, not seeking growth at all costs.

✨ You hire Jenny, which is enough, but you also get access to decades of her own learning and exploration to dive into when you need it.

✨ I figured out a new branding focus and domain name. I clarified my income streams, and how I will need to structure my time to achieve those. I also hired a contractor to help with a project I had been putting off for months.

✨ Jenny is great at getting to the heart of the issue, and is generous and vulnerable about sharing her own experiences and challenges. At times when I felt I could not articulate a particular question, she seemed to know intuitively what I needed.

✨ Her personal reflections were like a customized podcast just for me.

✨ Jenny is incredibly generous, the ideas and supporting resources each week exceeded my expectations. I love her thoughtful ideas and contagious energy!

✨ Jenny is the ultimate thought partner. Social, knowledgeable, with resources at her fingertips and a sharing spirit. It was always clear that she had thoroughly understood what I’d asked and sent info/resources that were wonderfully responsive.

✨ I was experiencing a block with writing, and I felt like I was missing out on an important part of who I am. I was also prioritizing bespoke client work over thinking about ways to scale my business. I feel like I have finally reclaimed my identity as a writer, which has been such a transformation both personally and professionally! I have clarified my book idea and created systems to streamline the writing, editing, and marketing process and ensure that it is aligned with my business. I am experiencing more creativity, flow, and joy in my life and business.

✨ Voxer coaching is a highlight of my year!

✨ We now have a subscription model for our services and a 3-year strategic plan—if you are on the fence, do it!

📲 How it works:

• There are five spots available, and enrollment closes on Sunday, October 13—or whichever comes first.

• We kick off our 8 weeks of asynchronous Voxer coaching on Monday, October 14.

• You will submit one voice memo between Monday and Wednesday of each week with your biggest question—that part of the process alone helps create tremendous clarity!

• I respond by the end of the day on Friday of that week with detailed ideas, guidance, specific templates, and resources that will help you save time and money while rapidly accelerating progress in any area.

Learn More & Enroll »

🐤 Early Bird Reminder—Anyone who enrolls by the end of the day on Monday, September 30 will also get:

• The Free Time Operations Dashboard with 30+ Notion templates to externalize your business mind ($1,500 value)

• Two 1:1 onboarding sessions with our Notion Pro Alex for help setting up more complex databases and automations ($600 value), and

• A Strengthscope Assessment to identify your “significant seven” energy-strengths (and your biggest drainers) plus access to the upcoming Upgrade Your Energy workshop in December to debrief your results ($197 value)

💌 I’ll be back with a Time Well Spent round-up next week!

In the meantime, I’m eager to experiment with different formats here and would love to hear from you in the comments:

• What do you find most helpful in this newsletter?

• How can I serve you best moving forward?

Comments are open to all for this post, so please let me know! 🙏

Leave a comment

🎉 Here’s to setting even more time free :)

Refer a friend