Would earning $1 million dollars in revenue this year solve all of your problems? It might, but it could also cause a whole set of new ones, inspiring you to scale back. That’s the story behind the business of today’s guest, Kaneisha Grayson. She shares how she built a seven-figure business, and why she later restructured to one that better honors her energy and goals.

Consistently creating high-quality content can be challenging. To practice what I call ongoing original public thinking, I am often brainstorming how to make the processes involved as smooth, simple, and searchable as possible. This episode originally aired as a Loom video for the private BFF community, where I walked through my Notion podcast production dashboard and content calendar. Here’s what I have learned (and optimized!) in these last seven years of podcasting. You can also watch the video walkthrough of this episode here.

Think of your day-to-day work as fitting into one of four quadrants, as defined by today’s guest Khe Hy in a recent issue of his fantastic RadReads newsletter:

• $10 Work is low-leverage, low-skilled work that you can do when you’re hungover.

• $100 Work is when you leverage the wrong thing – and get overwhelmed by meta-work.

• $10K Work consists of high-leverage skills that exponentially grow your business and bring you closer to your dream life.

As Khe writes, “The quadrant people high-performers really get stuck in is the $1,000/hour quadrant . . . the domain of unique skills that have no leverage.” That’s what we’re discussing in today’s episode so you can learn strategies to stop struggling and do more of your best work.

Nothing makes me more frustrated than poorly run companies that essentially steal time and money from the customers through bureaucracy and botching the basics. If you’re a longtime listener of this show, you might remember episode 83: Breaking Through Buyers Remorse, Never Lose a Customer Again with Joey Coleman. Today, I am sharing a tale of two contrasting customer service stories: one that devolved into disappointed buyer’s remorse, and the other that surprised and delighted my family and I, while creating memories of a lifetime.

Today’s guest is an expert in cultivating creativity — and in remaining consistent over the long arc of content creation. Todd Henry is the author of six books, and today we’re talking about how to stay motivated in the publishing industry, where the market reflects winner-take-all dynamics, and the long tail is verrrry long.

According to The New York Times, Penguin Random House (the largest U.S. publisher) said just 35 percent of books the company publishes are profitable. Among those that make money, just 4 percent account for 60 percent of those profits. Todd shares why many of those numbers are arbitrary, and emphasizes focusing on impact and practices to lead a more satisfying business and creative career.

“If you’re on time you're late.” That’s one of my favortie mantras that I picked up from my dad, second to, “These are the grrrreat times!” (no matter what is going on in his life or the world).

My dad was always early for our meet-ups, something I experienced as a sign of respect and ease. This relationship to punctuality has stayed with me as an adult, and I’m not the only one. I once bumped into a first date who was killing time at the same west village park as me around the corner from the restaurant where we were set to meet fifteen minutes later, since we were both sticklers for showing up early!

If there’s one software question that invokes a near-universal groan among small business owners, it’s “What do you use for a CRM?” Much of the existing software is clunky, expensive, or at worst—both. Today I’m chatting with Notion pro Alex Sherwood, a former Salesforce CRM manager, on how he built his own Customer Relationship Manager tool in Notion, and inspired me to do the same (although because even the acronym CRM gives me shudders, I renamed mine “K.I.T.”, Keep In Touch, in a nod to high school yearbook sign-offs).

How often do you feel blocked when it comes to creating new content? If you want to be more consistent and confident, today I’m sharing the 5 C’s System that I use to create 12 podcast episodes a month, two newsletters, and bonus content for my private BFF community. Ongoing Public Original Thinking is a central part of my business, and this is my ever-evolving system that facilitates it.

“Time collapses when something you think takes 100 steps takes only one.” That’s just one of many gems from this week’s guest, Richie Norton. Richie is teaching us how to optimize for time flow and cash flow; to act from our future, not toward it. As he says, “It’s time to rescue your meta-goal from the ledge of your long-distance timeline and bring it home by placing it directly at the center of your life.”

As I ask in the introduction to Free Time: What revenue streams are in that oh-so-sweet spot of profit, ease, and joy in your business? Recurring revenue is one of the holy grails within a sustainable, scalable business. It’s an area that I have focused intently on since 2015, so in a follow-up to episode 112: My 3 Biggest Business Regrets, today I’m sharing more about the recurring income streams in my business.

Take it from a self-described “recovering micromanager,” Annie Hyman Pratt: people are the most underleveraged, underutilized asset you have in your business. And once you see it, she says, you won’t be able to unsee it.

Is your to-do list piled to the sky with uninspiring tasks? Wait until you hear this listener submission from Leanne, sharing one of many favorite gems from participating in mastermind groups and 1:1 coaching with the legendary “Million Dollar Consultant” Alan Weiss.

“Why would someone fly you across the world to do business with them?” That powerful question from a mentor in March 2020 gave today’s guest, Marquis Murray, the courage to go all-in on his passion of helping business owners create order from chaos through greater operational efficiency.

Living in New York City for over a decade, I’ve woken up to many a strange sight over the years: sirens, helicopters overhead, a pre-dawn police chase through the backyard, and a drone buzzing where the birds should be. But never have I woken up to someone doing their job with such delight (who also happened to be smokin’ hot and shirtless) that he drew out fellow neighbors to stand at attention in their windowsills, with coffee mugs in hand, also chatting him up and taking in the view. Today’s episode takes a page out of this memorable man’s customer delight handbook. Daymaker: wherever you are, thank you.

Do you shy away from marketing and metrics, or have trouble figuring out more of your ideal clients? If so, this conversation will give you just the boost you need!

Join me and longtime friendtor Pamela Slim (the one who gave me the courage and encouragement to leave my comfy corporate life back in 2011) as we discuss shifting out of empire culture toward ecosystem culture, identifying watering holes for your ideal community members, working with “PB&J partners,” being the weirdo in the room, and prioritizing outreach even if you’re introverted.

“If you think you’re too small to have an impact, try going to bed with a mosquito in the room.” That’s a gem I found in MBS’s book, How to Begin, from Body Shop founder Anita Roddick. It came to mind last night while I was being plagued by a particularly elusive mosquito my husband dubbed “Maverick.” (Yes, after the Tom Cruise movie.) In my sleep-deprived madness (and MAD-ness) I decided to search for the meaning—and the business metaphor—behind this tiny but pernicious little beast.

We talk about The Fiji Test often here at Free Time HQ on documentation and making ourselves replaceable every day. The central question: Could a stranger to the business take over without much disruption?

That’s exactly what Shannon Minifie and longtime friendtor MBS put to the test several years ago. As he stepped aside as CEO of the company he’d been building for nearly 20 years, Box of Crayons, Shannon took the reins through a two-year transition process. If you haven’t listened yet, be sure to pair this with episode 051: How to Replace Yourself as CEO with MBS.

We’ve got a Grab Bag this week with three favorite time-saving techniques, starting with an image I can’t get out of my mind by @jackbutcher of Visualize Value, followed by two listener submissions for the My Favorite Time-Saving System series.

Sometimes it seems like being a jerk pays off. Society often seems to reward the leaders who don’t mind stepping on others en route to the top. But if you don’t want to live that way, you’re among friends here and with today’s guest Julien Smith. We’re talking about avoiding leadership traps and creating positive boundaries in your business.

As tough as it is to stomach sometimes, regret can be a helpful catalyst. As Daniel Pink shares in his latest book, The Power of Regret: How Looking Backward Moves Us Forward, regret is better understood less as a thing and more as a process; one that doesn’t just make us human, it makes us better.

“By making us feel worse today, regret helps us do better tomorrow,” he says. “Understanding its effects hones our decisions, boosts our performance, and bestows a deeper sense of meaning.” Today I’m sharing three big regrets, or strategic errors, in 11+ years of running my business.