"For the first time in a decade, I feel free again." That’s how one of my earliest blogging friends, longtime community leader David Spinks, was feeling when I caught up with him in-person in the middle of his yearlong sabbatical, after selling his community-based business. David and I discuss best practices for creating and nurturing communities, for engineering serendipity, what it’s like to build and run a conference (and later sell it), and the freedom that comes with taking a deliberate sab...
Nov 21, 2023•57 min•Ep. 243
“The world doesn’t need another expert.” So says today’s guest, Andrew Davis. Experts rely on hacks, tips, tricks, teaching, preaching, and over-promising. Visionary leaders a) tend not to call themselves that and b) focus on the quest for knowledge itself, with enough humility to admit what they don’t know, or the problems they are exploring even while still in process. In today’s conversation, you’ll learn how to move past commoditized content toward launching a quest that builds trust and bri...
Nov 17, 2023•49 min•Ep. 242
“You do not need to cannibalize your healing for content.” Today, I’m in conversation with longtime blog-turned-IRL friend Nic Antoinette, diving deeper into her decision to shut down her Patreon community (taking a $30,000/year haircut to do so), then pivoting to a private paid Substack while she navigated her way through decisions about what might follow. We discuss the generosity of being honest, the trap of wanting to be special, knowing where to draw the line on how much or how little you s...
Nov 14, 2023•1 hr 3 min•Ep. 241
If you have been in business for any amount of time, then you know the feeling when a launch just isn’t working. The sales are crawling, you start doubting yourself, wondering if you created the right thing in the first place, if you built a big enough audience to sell anything at all. All kinds of additional questions and insecurities follow when sales aren’t flowing: is that the offer that’s off? Your sales page invitation letter? The pricing? Is it you? It’s so hard not to get a big morale di...
Nov 10, 2023•30 min•Ep. 240
“I only write books for problems I can’t otherwise solve,” Nir Eyal says. “I don’t write my books for my readers; I write my books for myself.” Driven by curiosity to fix his own problems, Nir’s books have sold over one million copies. Listen to today’s conversation on how he weathered the criticism storm around his first book, Hooked; the one essential skill to being an entrepreneur; how to turn your values into time, and turn time into traction; and if you’re an aspiring author, why the fear o...
Nov 07, 2023•40 min•Ep. 239
Abundance was my word of 2019. I’d love to tell you I meant abundance in the broadest possible sense, appreciating the bounty already in my life, financial and otherwise. But mostly, my theme was about money. Specifically: to surpass one million dollars in revenue by the end of the year. I was going to build the sexiest small business rocket ship to achieve time-and-money escape velocity with my Delightfully Tiny Team. *Today's post is a crossover from Rolling in D🤦🏻♀️h. Check out my profile ...
Nov 03, 2023•20 min•Ep. 238
What is your relationship to rest? How about your caretakers’ relationship to rest while you were young? What examples did they set? What attitudes, beliefs, and behaviors did they hold, and how does that still influence you today? Today I’m talking with Ximena Vengoechea about the five rest profiles, productivity dysmorphia, “tiny transition time,” why paid work (no matter how much you love it) doesn’t count as pure play, and how she designed the book to deliver a restful experience beyond just...
Oct 31, 2023•48 min•Ep. 237
“Startup CEOs should not play the odds. When you are building a company, you must believe there is an answer and you cannot pay attention to your odds of finding it. You just have to find it. It matters not whether your chances are nine in ten or one in a thousand; your task is the same.” —Ben Horowitz, The Hard Thing About Hard Things We are not meant to compare ourselves to eight billion people. I know I’m not the first to remind you that social platforms are status games on globalized steroid...
Oct 27, 2023•18 min•Ep. 236
You can calm chaos at work, but it starts with a reality check from Charlie Gilkey, delivered with his signature wit and generosity: You might not have a team problem, you have a you problem. It’s time to 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. Today we’re talking about his new book Team Habits: How Small Actions Lead to Extraordinary Results. We a...
Oct 24, 2023•57 min•Ep. 235
“As long as we settle for thinking inside the brain, we’ll remain bound by the limits of that organ. But when we reach outside it with intention and skill, our thinking can be transformed. It can become as dynamic as our bodies, as airy as our spaces, as rich as our relationships—as capacious as the whole wide world.” —Annie Murphy Paul, The Extended Mind In this second half of a two-part solo series, I’m sharing 6 more strategies that have helped me build (and trust) my intuition at increasingl...
Oct 20, 2023•27 min•Ep. 234
I’m excited to bring you this crossover episode with Rose Cox, founder of The HSP Business School and host of The Sensitive CEO Show ****podcast. She is one of the people I have been most excited to connect with across the globe the last few years, even though we have yet to meet IRL! In this conversation, we dive into the world of highly sensitive people (HSPs), empaths, and introverts in the business world, with plenty of permission slips to stop doing what drains you. We discuss how to build ...
Oct 17, 2023•38 min•Ep. 233
Intuition is always speaking to you in subtle ways. Are you listening? Intuition isn’t a gift that is only bestowed on a special few; everyone can strengthen this muscle—how loudly you hear these signals, and the trust in yourself to take action on the information you’re receiving. In the comments of a recent ‘D🤦🏻♀️h post, Claudia asked: I read your words “all-in on myself” and how you consciously cho(o)se to believe that the Universe was/is redirecting you, and can’t but think “Jenny’s so in...
Oct 13, 2023•31 min•Ep. 232
“Let’s build ESPN.com for strength, and convince everyone they can lift weights.” With this mission in mind, the first six months of building the BarBend platform were a blur for today’s guest. By the end of the first year in 2016, they had had 1.4 million readers. By 2022, they had over 31 million registered users, allowing them to sell the business in 2023. In this conversation, we cover David Tao’s take on the media landscape and how to build a profitable content-based business; raising a see...
Oct 10, 2023•46 min•Ep. 231
“You can’t use up creativity. The more you use, the more you have.” —Maya Angelou Earlier this summer, I arrived late one day to the podcast studio, laying on the floor in lieu of actually recording anything. Should I take that as a sign to reduce my creative output? Not necessarily. Aside from big one-off projects like writing a book, where I pour incredible time and attention to detail into (that I tackle every five years or so), I seem to do better with ongoing creative work by sticking to a ...
Oct 06, 2023•30 min•Ep. 230
When we say trusting ourselves, which self are we talking about? Which parts of ourselves can’t be trusted? That’s what we’re exploring today with returning guest, Ilise Benun. We discuss how confidence is a byproduct of action, what made her so angry that she decided to start her own business 35 years ago, building tolerance for silence and small experiments, and why she puts her phone number in her newsletter, on her website, and in the “from” line of her emails. If you haven’t already, check ...
Oct 03, 2023•55 min•Ep. 229
This is a free preview of this month's bonus episode for paying Free Time subscribers. Listen to the full episode (plus 100+ in the archives) and join us for live Q&A calls here » *** They say write from the scar, not the wound—but what do you do when you feel called to write or speak from the wound? Do you forge ahead, knowing you will wake up the next day with a raging vulnerability hangover? Or do you keep it inside, bottled up for a future sell-by date? Scott asks: I'd love to hear you t...
Oct 02, 2023•13 min
“I’m at my wit's end.” That was the conclusion of a text message that broke my heart a little bit. when a friend and fellow business owner showed it to me the other day. Their team member sent it to them, expressing exasperation at the state of unfinished tasks in the business where they were waiting on an answer or action from the owner. Seeing it bummed me out for both of them because it was neither person’s fault per se (though we can all take responsibility, of course). As I say in Free Time...
Sep 29, 2023•29 min•Ep. 228
“Nobody’s soul is moved by swag.” So says longtime friendtor of the pod, John Ruhlin, founder of strategic gifting company Giftology. Since the day I met John and encountered his work in 2016, I have been inspired by his commitment to elevating the relationship game with generosity, “heart bombs,” and expressing genuine appreciation in the business world and beyond. He does this all while setting up brilliant systems to make sure it all actually happens (such as setting a robust annual gifting b...
Sep 26, 2023•30 min•Ep. 227
I used to refer to myself as a hot mess often in the early blogging days circa 2008, until someone scolded me saying it wasn’t a nice way to describe myself, that maybe it wasn’t the best self-image to curate. So I stopped. But I lost something in dropping the “hot” and the “mess” as I now approach middle age (and grandma-status in my soul). Today's post is a crossover from my newest project, Rolling in D🤦🏻♀️h: Divine disaster diaries from a bread-winning business owner living in New York cit...
Sep 22, 2023•14 min•Ep. 226
“A book is not about something. A book is for someone.” That’s the mantra that drives AJ Harper’s work, that includes ghostwriting over one hundred books (and working on many more one-off chapters and projects). In this conversation, she shares the “life of a book” process in her writing partnership with Mike Michalowicz (ten books together and counting!), what most authors get wrong when writing the conclusion, her favorite tried-and-true question to solicit “unexpected, delicious responses fro...
Sep 19, 2023•46 min•Ep. 225
Do you already have an elegant way of wrapping up with clients? If you work with people one-on-one, it's important to systematize business values that you say are important to you, like surprise and delight, or giving clients a red carpet experience from start to finish. Many of us have thought more about that on the front end than when we're actually closing out with a client—that's why I'm super excited to bring you this listener submission episode from previous guest and BFF, Jacqueline Fisch...
Sep 15, 2023•13 min•Ep. 224
“Have you ever looked at someone else, someone you admire, who has accomplished a lot, and just assumed they must be wildly confident and always winning at everything? You’re not alone. But, the truth, it turns out, is much more complex. So many of those luminaries are not, in fact wildly, or even remotely confident. And if they are, they go through cycles of profound change, self-doubt, struggle and, when they learn to harness these experiences, revelation and even reinvention.” That’s how my l...
Sep 12, 2023•44 min•Ep. 223
Now that I’m one month into Rolling in D🤦🏻♀️h, I’m sharing my reflections on Substack as a software platform for personal writing (and potentially moving my newsletters soon too). I recorded this bonus episode for the BFF Community at the end of July; since then, I decided to officially migrate my Pivot and Free Time mailing lists and go all-in. ;TLDR: I’m utterly delighted! The last time I felt this thrilled about software was when I first started tinkering in Notion four years ago, which be...
Sep 08, 2023•42 min•Ep. 222
“I see in books,” says today’s guest. “Every book is, at its heart, an argument for something—for a belief, a way of life, a vision of the future, a way to solve a problem, a way to make a friend, a way to lose your soul. The point is what the entire story drives to. It’s the thing your reader will come away from your book feeling.” That’s just one gem from today’s guest, Jennie Nash, book coach and author of a blueprint series on how to approach your writing. Jennie and I discuss the tumult hap...
Sep 05, 2023•52 min•Ep. 221
I broke one of my own big rules this summer. For the last few weeks, I've been kicking myself, saying, how could I do this? I know better. I wrote a book called Free Time, after all! Well, as I say in the introduction, business stress is a systems problem. Listen in for more on the mistake I made, and the systems and reminders I set up to ensure I have ample free time next summer. 📆 Upcoming Event: Substack Q&A on September 7 I'm falling deeper in love with Substack every day—there are so m...
Sep 01, 2023•19 min•Ep. 220
Since launching this show in September 2015, the podcasting landscape has grown and changed tremendously. What was once a niche sandbox of independent producers pursuing passion projects has blossomed into an abundant field where it seems as though every major media property, celebrity, side hustler, and business owner decided to throw their hat (mic?) into the audio arena. Since I’m not nearly ambitious or prolific enough to share three hundred lessons learned in honor of today’s major mileston...
Aug 25, 2023•46 min•Ep. 218
“Cultivate 12 people who love you, because they are worth more than 12 million people who like you.” That’s just one of many gems from Kevin Kelly’s new book Excellent Advice for Living: Wisdom I Wish I’d Known Earlier, bits of wisdom that he thinks of like handrails to grab when he needs a quick reminder about what is most important. In this conversation, we revisit our 2016 discussion about the power of human-AI partnerships, give you permission not to become a billionaire, help you lean into ...
Aug 22, 2023•43 min•Ep. 217
Self-doubt isn’t all bad. It means you’re stretching outside of your comfort zone, that you’re willing to learn, and that you aim to surround yourself with people who challenge you. So if you often grapple with imposter syndrome (or as I like to call it, an Imposter Monster sitting beside you), you are not alone. If you sometimes fall into the trap of feeling like you’re not good enough or ready yet to tackle your biggest creative aspirations, here’s a new perspective to consider. This crossover...
Aug 18, 2023•15 min•Ep. 216
As “recovering people pleaser” Natalie Lue opens her book, The Joy of Saying No, “Suppressing and repressing my needs, desires, expectations, feelings, and opinions to try to influence and control other people’s feelings and behavior was as natural to me as breathing. I thought it was normal to tell people what they want to hear (read: lie) to make them feel better. I believed I was ticking the boxes of being a Good Person by being kind, generous, hardworking, conscientious, loving, eager to hel...
Aug 15, 2023•47 min•Ep. 215
I'm super excited to pilot a "what would we invent if anything were possible" experience this quarter—and you're invited! Join me and business bestie Sarah Young, founder of Zing Collaborative and author of Expansive Impact, on Sunday, October 22 for a three-hour VIP brunch and brainstorming extravaganza, followed by a decadent buffet at DUMBO house, with inspiring views of the Brooklyn Bridge and lower Manhattan. This is much more than a brunch. As fans of what restauranteur Will Guidara calls ...
Aug 11, 2023•3 min
