“Small hinges move big doors.” That one thought helped Karen Allen pick herself up from the depths of grief after losing her husband in a tragic, senseless act of violence nearly a decade ago. Shortly afterward, she lost her house, her car, and then one year later — her job.

Getting fired followed just a few months after an intuitive hit that corporate wasn’t the best fit for her any longer was a blessing in disguise that precipitated the founding of her now-thriving business, one where she puts her son front-and-center as her North star.

In this conversation, Karen shares how she navigated overwhelming grief while parenting, structuring her business for free time as a single parent, and how her business has evolved as she continues gaining clarity about who she wants to be and how she wants to serve.

Time- and money-based targets don’t always serve the purpose we intend. In fact, sometimes, they actively work against us. Today we’re spelunking into a few related principles like Goodhart’s Law, The Cobra Effect, and why vanity metrics are often no more than a hungry ghost lurking in the shadows of your business. I couldn’t resist sprinkling pop culture clips throughout to illustrate these concepts, so I hope you enjoy the ride :)

In episode 181: Be Irreplaceable, you heard from my creative coach, Jay Acunzo about how to prioritize resonance over reach. I’ve been working with Jay for a few months now, and it has completely transformed the way I think about creating content—primarily my two podcasts. He just launched his own community, Creator Kitchen, and I feel lucky to have been part of his early testers for the soft launch.

One of the videos he shared with us in the kitchen is a walkthrough of his Intellectual Property (IP) Development OS—how he collects ideas, chooses which one/s to pursue, and how he decides which channel of his universe they belong in. Think of this whole process like an idea funnel, one where Jay is “applying pressure by aerating it constantly” through testing and publishing in different formats.

When today’s guest, Kelli Thompson, was overwhelmed by opportunity—a level of success she had been dreaming of and working diligently toward—she knew she needed a roadmap to better manage her time and energy, stat.

In this conversation, we unpack how she created an Energy Capacity Plan (a woman after my own spreadsheet-loving heart!), how to create yours, why it doesn’t need to be a detailed calendar grid sliced into specific 15-minute increments, and how that plan can inform your pricing.

“A shoe is just a shoe until my son steps into it.”

—Deloris Jordan

When negotiating Michael Jordan's famous shoe deal with Nike, his mom Deloris “made an additional demand: Her son must receive not only a $250,000 fee, but also a cut from every sneaker sold,” making her case with that mic drop moment above.

That, my friends, is the power of licensing :)

“A shoe is just a shoe until my son steps into it.”

—Deloris Jordan

When negotiating Michael Jordan's famous shoe deal with Nike, his mom Deloris “made an additional demand: Her son must receive not only a $250,000 fee, but also a cut from every sneaker sold,” making her case with that mic drop moment above.

That, my friends, is the power of licensing :)

I'm excited to bring you an episode from the Pivot podcast vault today. This is a conversation with a longtime friendtor, Mike Michalowicz, that stuck in my mind long after we recorded on February 5, 2020. The episode launched on March 20, 2020, and the last group gathering I attended was Mike's in-person Fix This Next workshop at his office in New Jersey on Friday, March 13. Boy was the world about to get weird!

Mike explains how to identify and serve the Queen Bee Role in your business, the cliffhanger phrase that freed up even more of his time to write and speak, his unique approach to IP licensing, “guinea pigging” new book ideas, how to stop keeping up with the EntrepreJoneses, and the secret to how he has been so prolific in publishing 8+ books in the last 15 years.

It was a hot summer day, and I’m grumbling while dragging a rolling carry-on suitcase full of books to sign and send to the post office, starting to build resentment at how much time it was taking. After two hours of signing, writing notes, punching endless kiosk buttons, I start tsk taking myself, saying I should never do this myself again (I’m the owner of the business, after all! This is admin I should surely be delegating out!).

But alas, I ended up with one extra copy, curious at who I missed or how I miscalculated. And then . . . right as I was walking out, someone walked through the door that made my heart leap out of my chest—and making the entire errand worth far more than the time-price of admission.

“You have to live spherically—in many directions. Never lose your childish enthusiasm—and things will come your way.” —Federico Fellini

This week’s delightful guest, Madeleine Dore, reminded me of this wonderful quote while reading her book, one that I know you will love as much as I did: I Didn’t Do The Thing Today: Letting Go of Productivity Guilt.

We talk about widening the measure and meaning of a day beyond our to-do lists, discovering the call of a new topic, shaping a big idea “blob of clay,” how she collects all the great quotes and stories for her book, why she sees herself as more of a guinea pig than an expert (and freelancer valuing independence even more than business owner), and how she decides when to sunset a project, rather than “maintaining something at all costs.”

Most of all, Madeleine reminds us to trust in new beginnings, saying we’re never truly starting from scratch. “Trust in yourself and the process; you bring yourself and your skills with you.”

There’s a wall in my house that I know would look gorgeous if it were painted a deep, velvety, rich navy blue. It’s behind the TV, so every day I stare in its general direction while watching shows, and on some days I even remember (*fantasize about!*) my vision of painting it blue.

But the wall remains stubbornly bare, stuck on factory settings. Why is it so hard to change one seemingly simple thing, even when a future vision is strong?

“Don’t be the best, be their favorite.” That’s just one of countless gems of creative wisdom that I’ve picked up from Jay Acunzo over the years. Jay is one of my favorite friendtors and coaches, and I know you will love every minute of this conversation as much as I did!

One thing I love about Jay is that his body of work is a love letter to craft and quality. In this conversation, we talk about mindset shifts and practices to help you focus more on resonance than reach; how to do work that matters to you so that your work can matter more; how he worked through his own existential creative crisis upon hitting the 200th episode milestone of his podcast; thinking like an explorer, not an expert; and “making the leap from what best practices say you should do to what your intuition is urging you to try.”

What business best practices drive you nuts? What are the best practices you *wish* people would follow, but they don't? These are clues to things you can be doing differently or stop doing altogether in your business.

Today’s episode starts with a few of my pet rants—err, peeves—followed by six specific examples of activities with diminishing returns in my business, ending with one big question antidote for when you, too, find yourself Sailing the Sea of Shiny Shoulds.

“Start with the truth, then edit.” That’s a gem that today’s guest picked up while working in corporate communications that maps directly to how she encourages business owners to write: quickly, and from the heart. Go for speed, not sense. Edit later.

In this conversation with copywriter Jacqueline Fisch, we talk about why she “quit video” in her business and how it has helped her focus; how you can make writing for your business faster *and* easier by leaning into your intuition; tackling bigger writing projects like a book by working with moon cycles; and how sending a “See You Soon” kit when wrapping up with a client helps her run a primarily referral-based business.

What if time wasn’t something we had to hoard, protect, or chase? What if we could change our relationship to time—to life itself—expanding beyond the linear, grid-like units running out as we race against the clock, and toward a true sense of aliveness instead?

Today’s I’m trying an experimental format: diving deep into a book that relates to so much of what we talk about here, Jenny Odell’s Saving Time: Discovering a Life Beyond the Clock. I haven’t landed an interview with her (yet!), but I also really appreciated her previous book, How to do Nothing: Resisting the Attention Economy, so am happy to spotlight both.

I’m delighted to welcome Daniel Doyon to the pod this week, co-founder of one of my favorite software services, Readwise. Every morning while I have my coffee, I look forward to checking out the daily email roll-up of five serendipitous snippets pulled from my entire library of Kindle highlights.

Readwise has also been a game-changer in preparing for podcast interviews with authors, and for book and newsletter writing, especially once they added the export to Notion feature. Now my entire Kindle library of highlights also lives within Notion, with pages for each book that are interlinkable and searchable from my externalized business mind.

**“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.