**“Business, like life, is all about how you make people feel.** It's that simple, and it's that hard.” —Danny Meyer, Setting the Table

Danny Meyer is a famous restauranteur responsible for founding some of my favorite spots, including Gramercy Tavern, Eleven Madison Park, and the popular Shake Shack chain. He pioneered the philosophy of “enlightened hospitality.”

That’s the thing about engineering surprise and delight moments in your business. Like the example I share in this episode, while they may seem small or spontaneous, the best ones have intention and strong systems behind them.

“You are making a choice every time you undercharge.” How’s that for a splash of cold water to the face?! Bad pricing strategy puts your business—and your body—at risk. As today’s guest, Erin Haag says, when your prices are too low, “You are *choosing* to work an additional 10, 20, or 30 hours per week to generate the income you need to survive.”

In this conversation, Erin shares what led to two hospitalizations from back-to-back stress-related illnesses, followed by her aha moment: doing the math to determine ********exactly******** what she needed to do to go from the brink of business collapse to becoming debt-free and selling her pilates studio for a 40x multiple.

🎉 This week marks the one-year bookiversary of Free Time making its way into the world, and the two-year podiversary of launching this show. 🥂 As I reach these milestones, a question looms: Has the book writing, launching, and marketing been a success, as I would define it?

In today’s solo, let’s ride the mindset rollercoaster of launching something new into the world, and I share specific one-year sales stats for those who are curious—similar to episode 096: Book Sales Stats—One Month Post-Launch 🎉 that I know many of you appreciated :) But first: there's an important detour that we need to take. Listen in to find out and join me for the journey.

“How did you go bankrupt?" Two ways. Gradually, then suddenly.” —Ernest Hemingway

That’s the kick-off quote from returning guest Khe Hy’s recent pivot-in-progress big reveal, taking us behind-the-scenes of his business in a recent post titled, “The $645,099 business pivot.” Khe is the founder of RadReads and former Wall Street managing director. As he writes:

Life can come atcha pretty quickly. (At least according to Ernest Hemingway.)

And while RadReads is far from bankrupt. And I ain’t broke – in January of 2023 our business got hit by a quadruple-whammy.

Yes, a mere 55 days after my proudest moment as an entrepreneur – offering our employees healthcare – I did the unthinkable.

Free Time. The phrase connotes leisure, fun, time off, vacation—as if we're skipping through meadows with butterflies! 🦋and unicorns!🦄

But if you’re a long-time listener, you know that I think of free time as a verb. It is a skill, a muscle we can build. Freeing Time is something we can get better at. By creating smarter systems and taking small steps today, we can set our time free far into the future.

Today’s episode is a reminder about why it’s important to leave abundant margin on your calendar, especially for the days when you need it most (what previous guest Laura Vanderkam calls a “time emergency fund”), without punting problems to your future self.

“What’s the highest level I can serve?” That’s one of the driving questions that today’s guest, Melissa Hughes, helps business owners answer while building companies and making an impact on the world with grace and ease. She believes that the more of us who can shine our lights unapologetically, the better off we all are.

In this conversation, Melissa shares how she knew it was time to leave corporate, launching and later shutting down her brick-and-mortar spa business and the “blessing wrapped in sandpaper” of declaring personal bankruptcy. She shares how she started rebuilding by leaning into intuition, her philosophy on giving from the overflow and backing it all up with practical systems that serve your values.

Feeling slow, stuck, uncertain, or in the midst of a morale dip? If so, today’s minisode is for you—or for a business bestie who might need a little pick-me-up. I share a surprising shift from an encounter with Serendipity Signage; a portal to gratitude on a random New York City train station wall under a set of shattered windows.

When you feel down, remind yourself (as I do) what Julian of Norwich, a 14th-century mystic, said: “All shall be well, and all shall be well, and all manner of things shall be well.”

Stephen Shapiro is a quintessential Free Timer. Throughout his 20+ year self-employment tenure, he has run a variety of experiments to optimize for freedom and joy. To name just a few: working one hour a day (for years!), clearing space for 15 weeks of travel and/or vacation each year, and week-long hotel stays for focused work sprints.

We also talk about the “existential meltdown” that led to a business model redesign, and why he doesn’t need or want to build a team right now, beyond an extended network of specialists, and why he’d rather sell 10 copies of his next book to the right readers (potential clients) than 10,000 copies to the masses.

One of the biggest lessons I learned from author Nassim Taleb is that whenever he finds himself bored with what he’s writing, he stops. His logic? Surely if you are bored as the author, your readers will be too. Taleb takes it as a sign to drop that direction or concept altogether unless he figures out a way to get excited about it again.

In Free Time, I share a similar sentiment: how we bake is as important as what we make. That means that working on your big ideas—whether a project as complex as a book or a single article or podcast episode—should be fun! It doesn’t have to be an overwhelming slog where you’re stuck staring at a blinking cursor on a blank page, though even the stress of that is being lessened every day by generative AI tools like ChatGPT