💌 Time Well Spent: Climbing Down the Entrepreneurial Ladder 🪜

Hi Friends,

As I approach my thirteen-year biziversary in March, I can look back and say that my most miserable months coincided precisely with when I ran the biggest team—one that was still tiny by most outside standards.

I thought it was what I was supposed to do—have a growing coterie of consultants on retainer: an attorney, a sales agent (who sold nothing), a program manager for corporate licensing and speaking clients, two entry-level admins, a community manager for my membership program, and a podcast production team.

As my friendCharlie Gilkeycalls it, the “social overhead” of managing that many people made me increasingly miserable. I couldn’t hear myself think, no matter how many systems I devised or how much I delegated.

Keep reading why I decided to climb down the entrepreneurial ladder at D🤦🏻‍♀️h »

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

⚙️ Tips & Tools

I recently exported my entire Google calendar (dating back to 2006) to a CSV file, then uploaded that to ChatGPT.

Now I can prompt it with things like, “Bring up three random calendar entries” to use as a writing/memory prompt, “What was I doing on X date?” and “How many times did I visit Gotham Production Studios in the last two years?”

📆 Upcoming Events

“I don’t get on the airplane—and definitely not the stage—unless all invoices are paid in full.”

When my friend and fellow keynote speaker Joey Coleman said this to me over coffee, I started drilling him for details:

Really?! How do you have the nerve to say that to a speaking client?! How do you avoid caving in to make sure their event doesn’t fall apart if they haven’t paid in time? What about clients who work for highly bureaucratic companies that insist on their “standard” net-120 terms?

🧡 Paying Subscribers: You’re invited to join a live podcast taping on Tuesday, February 13 at 10:30 a.m ET with Joey on his mantra for getting paid on time by corporate and speaking clients, “I am not a bank.” Together, we’ll explore this topic—and his billing best practices—in delightful detail.

🔗 The link to register and attend is below the paywall in the footer of this email. 👇

• Want to join us? Upgrade your membership here.

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

How many hours have you spent on email this week?
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💬 Quote

This cracked me up, from Brendan O’Shannassy, author of Superyacht Captain—a book I discovered through The New Yorker’s fantastic The Floating World: The Haves and the Have-Yachts:

“The interviews always get to a point where, through an overly white smile, the CEO will say: ‘I just hire great people and then I stand back and let it all happen.’

Yep, this is all bullshit…all the billionaire yacht owners of my experience are chronic micromanagers. They ‘sweat the small shit’ constantly: details matter to them, in their businesses and in their private lives. It is not uncommon to sit with a billionaire for more than an hour, with several staff, obsessing over the place settings at the table. Who sits where, size of cards, font—and this is not for a wedding, but for Wednesday night. It matters.

Sometimes it is financial, the billionaire making the point that they are not to be taken advantage of. More often, it is just in their nature and a key component of their incredible and hard-to-place success.”
—Brendan O’Shannassy in Superyacht Captain

💭 Questions

What small stuff are you sweating? Which of those details truly matter, and which ones can you let go of this year?

📝 Permission

Not to delegate everything—this includes small stuff that is vitally important to you (i.e. customer experience-related practices) and stuff that you could delegate, but that happens to bring you immense joy (for me, it’s tinkering in Notion).

See also: khe hy’s why you shouldn’t outsource 100% of your life.

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

A two-part guest post from Brooke Siem of Happiness Is A Skill by Brooke Siem who helped give me the courage to start on Substack this summer:

🧗🏻‍♀️ The Struggle is Sacred, Part One

🎙 Recent Episodes

Free Time:

• 261: Cringe-Free Launches and Evergreen Sales Considerations with Anne Samoilov

• 259: Crisis Communication Strategies with Aliza Licht

• 257: How to Become a Friction Fixer with Huggy Rao

• 256: Behind-the-Business: 1:1 Voxer Coaching Summer Pop-Up—Structure, Systems, and Pricing (Listener Question from Renee)

• 255: Operationalizing Kindness and Absolute Excellence while Building Birch Coffee with Paul Schlader

• Subscribe wherever you listen here »

Pivot:

• 358: Crossing the Cringe Chasm when Taking Career and Creative Risks with Henna Pryor

• 357: Addressing the Mental Health Challenges of Doing Humanitarian Work with Dimple Dhabalia

• 354: How Do You “Un-rut” Yourself? Live Show with Adrian Klaphaak

• Subscribe wherever you listen here »

Thank you for being here reading and listening!

❤️ With Gratitude,

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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 ☺️