As the saying goes, “Worrying is praying for what you don’t want.” A close cousin is future-tripping: projecting and living in the future instead of being present with what is actually happening, keeping an open mind about whatever might happen next. 

This crossover episode originally aired on the Pivot podcast on March 5, 2023.

Attending conferences can be overwhelming — even for the most excited extroverts among us, let alone the introverts who challenge their comfort zone in the registration process alone.

Today, my friend Alisa and I do an in-person debrief of our recent week-long adventure at the TED global conference in Vancouver (my second time attending, her fifth).

This crossover episode originally aired on the Pivot podcast on June 4, 2023.

“My little pirate.” That’s the nickname Michael has given me this summer, as it feels like many of my corporate (client) income boats have burned these last few years. At the same time, he says he has never seen me so happy and free. “You’re not in a raft anymore,” he said. “You’re in a sailboat. You don’t want to be in the big cruiseliner anyway.”

Not to be confused with Sailing the Sea of Shiny Shoulds (I clearly love ocean metaphors!), today’s episode is all about embracing the agility and freedom that small business owners have to Sail the Free Time Seas. Heck, even one of the richest men in the world, Jeff Bezos, chose to buy a sailing yacht (albeit the world’s largest) rather than the more mechanized superyacht.

“When you’re in debt to the truth, the interest rate sucks.” That’s just one of many so-true-it-hurts gems in Rand Fishkin’s 2018 book Lost and Founder, an accounting of his leadership journey through the often-Faustian bargain of building a company through venture funding, for all but a select few types of start-ups who do benefit from that route.

In this conversation, he shares why he dislikes the term lifestyle business, how he views some of his biggest business regrets in hindsight, his definition of chill work, and how he’s building his new business through open-sourced angel funding (and profit sharing) with a Delightfully Tiny Team of three.

What do Manuka honey, brown M&Ms, chocolate milk, vanilla gelato, rose petals, fair trade bananas, and Twizzlers have in common? No, they’re not ingredients for a bizarre ice cream sundae. Listen to today’s episode to find out . . .

The best systems aren’t cumbersome sources of frustration collecting dust in the cloud—they save you so much time, that creating even more streamlined solutions becomes a personal passion. That’s the case for me and today’s returning guest, Karen Allen. We’re going behind-the-business, swapping ideas for client-facing pages, client tracking databases, course resources pages, personal journaling, and more. Although we are talking specifically about Notion (this isn’t #sponcon, I swear!), any software that has similar functionality can work :)

In 2021, I paid nearly a thousand dollars to hire a plumber to fix something that wasn't absolutely necessary and that no one would ever see. Why did I do that? And what on earth does it have to do with running your business? More on that in today’s episode, along with twelve examples of tiny things to celebrate in your business operations, even if they forever remain a secret to the outside world. Outside of big launches, awards, and accomplishments.

Paul Millerd is an independent writer, freelancer, coach, and digital creator. He is the author of The Pathless Path: Imagining a New Story for Work and Life, in which he explores the invisible scripts that constrain our lives. He is also the host of The Pathless Path podcast, where he talks with the most interesting people on unconventional paths.

Today, I’m sharing eight reasons I really appreciate having a team inbox using HelpScout. They’re not paying for this episode; I just can’t help but share software solutions that help me move from friction to flow in my business, especially when I have already spent a lot of time and money on ones that don’t work.

Today we’re going behind the scenes of book launching, sharing the good, the bad, and the ugly (cries) resulting from the emotional rollercoaster that often surrounds the process of setting big projects loose into the world, including exhaustion, comparison, dashed hopes, and grief.

🎧 If you haven’t already, be sure to listen to Natalie on the Pivot podcast in episode 329: Five Types of People-Pleasers from The Joy of Saying No.

Welcome to our Episode 200 celebration...part 2! 🎉 These next 20 permission slips all about mindset, staying in the game, and the spiritual aspects of running a Heart-Based Business. Make sure to catch [last week’s episode](https://itsfreetime.com/episodes/200) which had 20 of my favorites about doing less, charging more, and working in your zone of genius.

You’ve heard of buyers remorse—but what about new hire’s remorse? That is the feeling of worry, regret or uncertainty that a new team member might have when taking a new role with your team. Today, returning guest Joey Coleman shares insights his new book, [Never Lose an Employee Again: The Simple Path to Remarkable Retention](https://amzn.to/42sgSCC).

Make sure to also check out our previous conversation 083: Breaking through Buyer’s Remorse—Never Lose a Customer Again with Joey Coleman.

Hey, hey, Free Timers, we have arrived at episode 200! 🎉 To celebrate, I’m giving you the ultimate permission slip compilation (two in fact). At the end of every episode, I ask our guests to give fellow business owners a permission slip to do something differently or drop something altogether.

This week, you’ll hear 20 of my favorites about doing less, charging more, and working in your zone of genius. Next Friday will be all about mindset, staying in the game, and the spiritual aspects of running a Heart-Based Business.

What’s the daily free time sweet spot? Between two to five hours, according to today’s guest, professor and researcher Cassie Holmes. In this conversation, you’ll hear about the wedding that wasn’t — sparking Cassie’s quest to determine the areas of highest agency for improving our own happiness, why time well spent is such a big factor to that end, the powerful question her now husband opened with on their first date, and how to buy better time.

When you catch a wishie, what do you yearn for? Today’s book club episode might shift your “wish” hereafter to just *one* powerful offering.

Tosha Silver’s grassroots-to-bestselling book Outrageous Openness: Letting the Divine Take the Lead is a cornerstone of my collection, one that changed my life when I first read it nearly a decade ago.

The stories from this book were adapted from two years of Tosha’s columns for the San Francisco Examiner*after she spent 25 years giving nearly 30,000 readings to people from all over the world. After OO became a self-published sensation, she got a traditional book deal and republished with Atria a few years later.

Tosha’s words from OO (as loyal readers affectionately call it) resonate daily in my mind and heart, reminding me to transmute *all* specific wishes and unmet needs or longings into just one—listen to today’s episode to find out what it is.

“Liking is the great fog of the mind.”—Todd Herman

You’ve heard the adage that people need to know, like, and trust you to want to do business with you. But is that really true?

Today’s guest, longtime entrepreneur and peak performance coach Todd Herman, believes liking is not nearly as important as respect, and can even prevent us from making strong decisions. We also cover how to organize your work according to your strengths, creating growth loops for growing the business, and making key adjustments as your business grows.

What’s it like to be at a conference with “fancy” people, when you’re the one feeling like you snuck in a side door as a seat filler? Okay, okay — that’s just my imposter monster talking. In today’s experimental episode, I’m taking you behind-the-scenes of the recent 5-day main TED conference in Vancouver, building on Pivot episode 325: 10+ Conference Networking Strategies with Alisa Cohn.

In full-on morning voice with a travel mic, I do a daily check-in about what I was nervous about, spontaneous serendipitous invites, fan-girling my favorite authors and podcasters, falling off the energy cliff, what gave me FOMO and JOMO, and my daily quest for coffee. Always. Find. The. Coffee.

Does the world really need this? This is one of the inevitable existential dilemmas of creative work. You have to decide that your work is worth your time and energy, because no one is asking you for it. Today’s guest, Jessica Abel, is someone whose work I have long admired for its richness and depth.

In this conversation, we talk about navigating the “Dark Forests” of creativity; go behind the business when one of her most successful books, Out on the Wire, was taking off; the causes behind cyclical burnout; three revenue-generating paths that she’s seen work best; and calculating your enough number as a small business owner.

Today I'm sharing ten more of my favorite recent GPT4 prompts and experiments for creative business owners.

This episode originally aired as a bonus episode for the private BFF community, as a follow-up to a case study on how ChatGPT has helped me draft a few solo podcast episodes.

The average American worker gets 11 days of paid vacation per year. Among those with unlimited paid time off (PTO), the average person takes 19 days off per year, yet 48% of Americans say they still check their work email while away.

What about business owners? Although it seems like we have more free time, the reality is that life as a business owner can be a 24/7 unceasing, all-consuming task. Even if you’re not at the computer, your passing thoughts probably drift toward what you need to do, projects to tackle, revenue gaps to make up for.

Today’s guest, DJ DiDonna, is an advocate for taking more abundant time off—ideally measured in months, not days or weeks. By DJ’s definition, sabbaticals should go beyond recovering from burnout; instead offering extended time to learn more about yourself in unstructured, even “unproductive” ways.