“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

How do we use technology to facilitate real relationships? That’s the big question driving Gina Bianchini’s epic entrepreneurial quest. Today we’re talking about the magic phrase that will transform what you’re building, the difference between social networks versus social media, why a course is not a community, how to avoid working too hard as the host, and why you might benefit from building a small, tight-knit group before trying to grow a bigger audience.

As Gina writes in her new book, Purpose, “Community takes things from incremental to exponential: If a community of just five people each helped the other members get just one percent better every day, that one percent compounded by four over a year ends up making everyone two million times better.”

How many times have you gone skidding into vacation, arriving exhausted from trying to “earn” it before you leave? Then feeling guilty for any loose ends you were unable to tie up in time, maybe even brooding the first few days because you’re so burned out that you aren’t even enjoying your precious time off nearly as much as you thought you would?

Research shows that we can experience diminishing returns when we have too much free time, which might explain the onset of vacation blues. In this episode, I’m sharing my rollercoaster that arises at the beginning of longer stretches of free time and a few strategies for settling in to find true peace and relaxation.

Here are a few food-for-thought reflection questions, inspired by today’s guest: Are you working with amateur clients or ones who bring out the best in you? Are you pricing the “aggravation factor” into your proposals when necessary? What about “throwing proposals over the fence,” creating self-inflicted stress when prospective clients ghost you as a result? Finally, are you stuck in the feast-or-famine cycle of your business?

If any of the questions above resonate, you will love this conversation with Ilise Benun, who has been running her business helping creative professionals for over 35 years. Ilise shares The Proposal Oreo Strategy; how she stays consistent with content creation while walking the line between discipline and rigidity; why she sees word-of-mouth marketing as a result, not real marketing; and creating abundant interstitial time by embracing eigenzeit—the German term meaning “the time inherent to a process itself.”

You’ve probably heard the phrase, “A book is a business card.” That’s because what you don’t hear is that a book is a wonderful revenue generator! It isn’t — at least not directly. The extreme Time-to-Revenue Ratio of writing and marketing a book is not for the faint of heart, unless the book connects directly to a larger part of your business model, serving as lead generation for more profitable products and services.

Some interesting stats for you: Even the big behemoth, Penguin Random House, reports that just 35 percent of books they publish are profitable. Among those that make money, just 4 percent account for 60 percent of those profits. In 2021, fewer than one percent of the 3.2 million titles that BookScan tracked sold more than 5,000 copies.

Continuing on last week’s conversation about the three different publishing options and how to choose which one is right for you, today I’m diving deep into the mysterious royalty waters. How do each of the three methods — self, hybrid, traditional — stack up? Listen in to find out.

Prolific punchy pontificator Khe Hy—creator of the $10K work accelerator and Supercharge Your Productivity—returns to the pod to share his strategy for collecting inspiring content, repackaging interesting tidbits, and regularly hitting “publish” on his newsletter, RadReads.

Today we’re talking about idea kernels: micro-ideas that can be elaborated upon and turned into different kinds of content that help you connect with your audience, and your fellow creators. If you haven’t already, be sure to check out Khe’s earlier episode on 129: The $10K Work Framework.

Should you self-publish? This is a big debate among aspiring authors, and there is no one right answer. Today I’m sharing my take on the three main publishing options you have to get a book into the world:

1. Self-publishing (including direct-to-ebook or audiobook) where you hire your own team of specialists along the way.

2. Hybrid where you partner with an established publisher, while fronting the costs as an author (for the team they assemble and either print-on-demand or funding a larger print run), and

3. Traditional publishing with one of the “Big Five” publishing houses, where they give you an advance, and you get the cache of making it through the “gatekeeper” gauntlet.

Processing email and social media inboxes is overwhelming enough for one person — can you imagine creating an entire company to help entrepreneurs do this at scale?! Communication curmudgeon that I am, I most certainly cannot.

That’s why I invited today’s guest, Yaro Starek, to share the systems and approaches behind Inbox Done, his company that helps clients tame the never-ending email beast.

Do you ever feel like you’re just not good with systems? If so, then this is the episode for you. The more efficient we can be on the backend in our operations, the more time we can set free. Today, I’m going to share 5 questions you should ask to increase your awareness, heighten your senses, and be able to find those golden nuggets of opportunity that might be right under your nose but you're just not seeing. Identifying candidates for automation is a skill, and this episode will help you get better at it.

Juggling a schedule for one person is tricky enough; for a two-entrepreneur household with kids, it’s another thing altogether! Learn how Jess and Dave make time for each other, for themselves, and for their deep work in today’s conversation about creating free time together as a family.

One of the most common questions from those accessing the Author Toolkit (an assembly of my best-open-sourced templates and processes from 14+ years and three books) is a variation on: How can I decide on a topic? How do I narrow down my idea? How do I know if/when I have landed on the right idea?

Today I’m sharing ten filters to help you narrow down your book idea — or, if you’re not an aspiring author, perhaps your next “big IP” area that will best serve your body of work, your business, and your future audience.

What type of business would you build if you no longer needed the money? After a life-changing exit from her previous company, Meet Edgar, Laura Roeder’s answer: a fun one.

She is now more focused than ever on building a business that is bootstrapped, agile, asynchronous, joyful for all involved, and powered by part-time team members who love what they do. In this conversation, we discuss why Laura downshifted from a structure with 30 full-time employees to one that’s leaner, saying no to the Business Ops Police, the perks of part-time team members (for you and them), and why “winner take all” markets are a myth.

I had high hopes for the first couple of weeks of the year, but I rang in 2023 in bed, completely uninspired by goals or ideas—anything beyond a desire to get healthy and feel human again, let alone any loftier business aims. Taking a (very loud) hint from the universe, I settled on the theme THRIVE as my focus to start the year.

One of the most common replies to my “wave a magic wand and fix one thing in your business” question when people access the Free Time Toolkit is for help with idea generation. In a meta move—seeing as I was in need of those very strategies myself to create this episode—today I am sharing 8 of them here with you!

What’s the right thing to do, and how do we do it quickly? In this conversation with Strategy Sprints founder Simon Severino, we cover: Why you shouldn’t start with your ideal avatar; setting daily, weekly, and monthly strategy planning (and measuring) habits; how he scales his business through certified Strategy Sprints® Coaches; creating self-healing loops, and greater resilience by tying roles to revenue.

As I shared in last week’s solo episode, Free Time isn’t about time management or productivity, or even simply doing work more efficiently. It is about setting time free.

If our time is trapped like a bird in a cage, unless we break free of shoulds and obligations, there it will remain. We achieve this through smarter systems, and that includes getting better at saying no.

My own tendency to say yes — in an effort to be liked, to please others, to be accommodating, or even to continue trying to “do right” by my work in promoting it — leads to burnout and resentment when to many “yeses” create time confetti and tiredness. In this episode, I’m sharing strategies that I’ve picked up along the way for doing the very hard thing of disappointing others by saying no.

Imagine my surprise when, on the Saturday before I was set to be interviewed on a podcast last summer, my phone dings. It’s Door Dash.

Huh?! I didn’t order anything . . .

Turns out it was a surprise delivery from the producer of that show, Matthew Thompson. Next thing I know, my husband Michael and I are enjoying iced coffee and yummy treats with our Sunday morning reading—I have never felt so taken care of prior to guesting on a podcast!

That’s Matt, and he’s all class (not to mention a fellow systems aficionado). When he suggested we flip the mic to talk more about my podcasting process, I leaped to say yes :) We talk about increasing the surface area of serendipity, saving time, improving interview quality with pre-surveys, and what we both learned from conducting three-month daily podcasting sprints.

As I share in Free Time, nowhere is entropy more visually evident than in older homes or ones in nature. I remember staying at a cabin in the Catskills, where I could see right before my eyes all forms of plants and animals encroaching on the once-pristine house.

Without upkeep, a dead tree teetered precariously toward the roof, weeds started overtaking the grass, spiders made themselves comfortable in bathroom corners, giant carpenter ants traversed the kitchen counters, and we spotted a garden snake crawling into the crevices of the outdoor hot tub.

Entropy, defined as a gradual decline into disorder, is intrinsic to all organic systems, and it’s happening in your business, too. In this episode, I’m talking about entropic bloat and why we need to actively decide to do less, giving our business regular “haircuts” along the way.