“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.