Free Time with Jenny Blake

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...

“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...

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 fel...

“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 a...

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 Even...

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 am...

“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...

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 y...

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 bo...

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...

Today’s solo riff is on a three-word phrase that has helped quell countless waves of anxiety in the decade since I first heard it, wisdom passed from my friend Monica McCarthy's (aka MonBon’s) mom then to the pages of Pivot. Pardon the occasional panting (lol) and background noise—err New York City soundscape—as I recorded this one on a big hill at the park, running up and down while throwing a gi...

Who is sitting in the boardroom of your brain? Who is sitting around the table, challenging your decisions, making noise, and offering critiques? Today Adrian and I are walking through one of our favorite coaching exercises by offering up (and coaching each other through) identifying and describing three of our current loudest board members and who we want to hire moving forward. This work connect...

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.  If you are inclined to catastrophize, you’re not alone! But getting caught in a fictional movie can mean missing out on important opportunities, ide...

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). We cover conversation openers, the power of a gen...

“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...

“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 t...

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 . . . 🌟 3 Key Takeaways Botching the basics: **A term my friend and I use for companies who fail to deliver the baseline minimum expected customer experience. See also: unf...

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, a...

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...

From a certain outside perspective, turning down a $200,000 two-book deal from a traditional publishing house makes no sense. But for today's guest, Paul Millerd, it fits perfectly into his operating paradigm of what David Whyte calls the pathless path. After climbing the ranks in corporate consulting but feeling increasingly empty, Paul shifted away from chasing status and approval, and started h...

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. 📝 Permission: Stop managing a zillion inboxes and narrow them down to one centraliz...

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-Pl...

Welcome to our #200 celebration...part two! 🎉 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 which had 20 of my favorites about doing less, charging more, and working in your zone of genius. 📝 #202 Permission Slips 🎧 027: Time Management for Mortals with Oliver Burkeman —...

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. Make sure to also check out our previous conversation **083: Breaking th...

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.  📝 Permission Slips 🎧 123: “Pricing is Branding” — Anti-Time Management with Richie Norton — 📝 Rethin...