Free Time with Jenny Blake

Free Time with Jenny Blake

💌 Time Well Spent

💌 Time Well Spent: Minimizing the Social Overhead of Managing Teams

❤️ Jenny Blake's avatar
❤️ Jenny Blake
Oct 27, 2023
∙ Paid

Hi Friends,

You can calm chaos at work, but it starts with a reality check fromCharlie Gilkey, delivered with his signature wit and generosity: you might not have a team problem, you might have a you problem.

Stop catering to air sandwiches, Crisco watermelons, broken printers, ghost plans, and other corrosive practices, and start implementing Charlie’s finely-tuned, road-tested systems instead.

This week on the pod, we’re talking about his new book, Team Habits: How Small Actions Lead to Extraordinary Results. We also discuss scaling from maker to manager (and sometimes back again). Listen and view show notes here »

235: Minimizing the Social Overhead of Managing Teams with Charlie Gilkey

235: Minimizing the Social Overhead of Managing Teams with Charlie Gilkey

❤️ Jenny Blake and Charlie Gilkey
¡
October 24, 2023
Read full story
This week’s Time Well Spent round-up is brought to you by InboxDone: a company that replies to your email and manages your calendar so you can get back to what matters most.

Now onto this week’s round-up + Plus extra goodies over the paywall rainbow at the end . . .

⚙️ Tips & Tools

Check out Charlie’s newsletters, Better Team Habits and Productive Flourishing.

Here are some of my favorite takeaways from our most recent conversation:

  • VUCA: Volatile, Uncertain, Complex and Ambiguous. Operating in VUCA environments can be frustrating for free timers with a “thing for control.” At the same time, the status quo broken printers get thrown out too—it forces us to reimagine how we work.

  • Shrink the scope of your world enough so that you don’t have to fix everything, everywhere, all at once. What small team habit can you examine and improve this month? i.e. Leaving five minutes at the end of meetings to capture action items and next steps.

  • The $300,000 speed bump: If you’re stuck getting over this revenue hump, you may need to decide whether you want to scale or not. Bigger teams have social overhead and hidden costs at work that aren’t dollarized.

  • DRIP: Decision, recommendation, intention, and/or plan. Take off the Chief Question Answerer hat by asking team members to come back to you with a DRIP before punting a “thoughts?” question onto your plate.

📣 Today’s TWS is brought to you by Inbox Done

How many hours have you spent on email this week?
What would happen if it was someone else's job to reply for you?

Thankfully, Inbox Done is here to help! When you become a client, they assign two email assistants (not software or AI) who custom build a system to filter, reply to, and follow up on your messages to reach inbox zero every day (cue angels singing!). Your assistants can also manage your calendar, write social media replies, follow up with leads, create SOPs, help plan events, and more.

More good news! Inbox Done is offering Free Timers a complimentary strategy session to see if delegating email could work for you.

Book your free discovery call today Âť

📆 Upcoming Events

🎙 Podcasters: Don’t miss this year’s Podcasting for Business Conference by One Stone Creative, the production wizards behind Free Time and Pivot.

I’ll be delivering a session on Private Podcast Feeds: 3 Creative Ways to Enhance Your Business and Serve Your Community on Nov. 15 at 10:30am ET.

  • Free Timers (that’s you!) can get 15% off registration with promo code JBE15. Or upgrade to an annual subscription here and you’ll get a promo code to enroll for free ($197 value) in the footer of today’s email.

  • Paid subscribers and BFFs: You are invited to attend at no cost as my VIP guests! Scroll down below my signature for instructions on getting your comped pass.

💬 Quote

“What did I do on my week off? Very, very little indeed. I put up my Out Of Office and let my week unfold from there, following my desires from day to day, hour to hour.

My friend Neil Baker once told me that creative people need to make space and not time: to drop the obsession with ‘putting in hours’ or ‘squeezing in some time to make work’, and enter into a more ambiguous, less directive place where anything can happen.”

—Katherine May, Returning to My Trees

💭 Questions

If you’re getting overwhelmed by uncertainty, pause and ask: What are the gifts of not knowing? What constraints are you willing to accept? What permission slip allows you to build a business that meets your needs in a sustainable way?

As always, I would love to hear from you: How do you practice following your intuition? Leave a voice note for a future listener-submission episode at http://itsfreetime.com/ask.

📝 Permission

Center your needs and wants into how you build your business and your teams. Build so that you want to show up and do the work.

🎙 Recent Episodes

Free Time:

  • 235: Minimizing the Social Overhead of Managing People with Charlie Gilkey

  • 233: On Sensitive CEOs and Building a Soulful Business with Rose Cox

  • 232: 11 Practices That Help Me Strengthen My Business Intuition Part One and Part Two

  • Subscribe wherever you listen here Âť

Pivot:

  • 345: How are we holding ourselves back? with Adrian Klaphaak

  • 344: Navigating Workquakes in a Post-Career World with Bruce Feiler

  • 343: 🥳 Five Questions and Attempted Answers for My 40th Birthday

  • 342: “Whatever Comes Through Me Comes for Me First,” with Nicole Antoinette

  • Subscribe wherever you listen here Âť

Thank you for being here reading and listening!

❤️ With Gratitude,

Refer a friend

💌 Did you get this from a friend? If so, sign-up to get my Time Well Spent round-up for small business owners and add 🎧 Free Time with Jenny Blake wherever you listen :)


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

🔐 Thank you to our generous paying subscribers who help sustain Time Well Spent! Upgrade to unlock this week’s make-you-smile memes as a token of my gratitude ☺️

User's avatar

Continue reading this post for free, courtesy of ❤️ Jenny Blake.

Or purchase a paid subscription.
© 2025 Jenny Blake Enterprises, LLC · Privacy ∙ Terms ∙ Collection notice
Start your SubstackGet the app
Substack is the home for great culture