Free Time with Jenny Blake
Free Time with Jenny Blake is a Webby-nominated business podcast that explores how to earn more while working less by streamlining systems and focusing on meaningful work. Host Jenny Blake, author of three award-winning books including 'Free Time' and 'Pivot', shares strategies for reducing busywork and increasing joy and ease in your career. The podcast releases new episodes on Tuesdays and Fridays, and has won three W3 awards for best show and best host. Listeners are encouraged to subscribe, leave reviews, and share episodes to support the show's growth.
Episodes
273: Navigating Time Anxiety, Reducing Inbox Dread, and Creating Ease Loops with Chris Guillebeau
👋 Hello Free Timers! While we’re still not resuming the podcast’s regular publishing schedule, I’m popping into your feed today to share a fun conversation with my friendtor of over fifteen years, Chris Guillebeau. We’re discussing his new book, Time Anxiety: The Illusion of Urgency and a Better Way to Live — it was too aligned with Free Time not to share!
📝 View full show notes with all resource
272: Seth Godin on Publishing Strategy, Missed Opportunities, Sunk Costs, Social Media, and Smart Risks
“How do you decide who has the power to judge you? Who are you seeking to please? Is that validation directly in alignment with how you are rewarded and how you're organized?”
Seth Godin is back with a brand new book, This Is Strategy: Make Better Plans, and if you loved Free Time, I know you will love this one for geeking out on systems thinking!
We discuss how his author strategy has shifted ove
271: Specific Road-Tested Tips for Book Sales and Marketing with Todd Sattersten (Part Two)
Hi Friends! Although the podcast is still paused, I'm dropping into the feed this week and next with two very special conversations :)
Today is a bonus episode from February for paid subscribers with Todd Sattersten, publisher and owner of Bard Press, and next week features Seth Godin and his new book, This Is Strategy.
If you haven't already listened, check out part one here (episode 261) first.
270: 🌈 Taking a Quiet Sabbatical and Pausing the Podcasts — For Now . . .
As I round the corner into this ninth year of podcasting and after over 700 episodes, today I’m announcing a pause for both shows.
Listen in to hear what factors helped me reach this decision across time, money, energy, depressing industry articles, the pace of both shows’ growth, and mix of additional business factors that make this an important moment to pause and regroup. You might also appreci
269: 🏦 “I am not a bank” — Strategies for Getting Corporate Clients to Pay on Time with Joey Coleman
“I don’t get on the airplane—and definitely not the stage—unless all invoices are paid in full.”
When my friend and fellow keynote speaker Joey Coleman said this to me over coffee, I started drilling him for details: Really?! How do you have the nerve to say that to a speaking client?! How do you avoid caving in to make sure their event doesn’t fall apart if they haven’t paid in time? What about c
268: Strategies for Surpassing “The Magic Number” of Book Sales with Todd Sattersten
What mysterious ingredients make a book launch successful? What number of first-week and first-year sales truly make a difference to a book’s longevity? What can you do to turn lagging numbers around?
In a flagship illuminating post for the industry, Todd Sattersten, publisher and owner of Bard Press, shared his findings in The Magic Number. In this behind-the-business conversation from October 20
267: Insights from Google's Productivity Expert—On Saying No, Cozy Corners, The Laundry Method, and More with Laura Mae Martin
Laura Mae Martin has a fascinating role as the Executive Productivity Advisor at Google in the Office of the CEO—one that she helped create six years ago (with big thanks to Jenny Wood for introducing us!). ****She coaches Google’s top executives on the best ways to manage their time and energy and sends out a weekly productivity newsletter that reaches over fifty thousand employees.
Today we’re t
266: The Framework Framework™️ (BFF Bonus Replay)
While the title of this episode, The Framework Framework™ is tongue-in-cheek, I’m pulling this out of the BFF bonus vault because it’s one of the community’s favorites.
I’m sharing the first steps to how you can set up a framework to help bolster your IP and your business; either by scaling through programs like certification and licensing, and to make your material more memorable and accessible t
265: 🦧 What to Do When You Lose Your Biggest Client (Part Two)
What do you do when you lose your biggest client? If you haven’t already, listen to part one for some answers—264: What to Do When You Lose Your Biggest Client— and save these links for a rainy day :)
The next time you’re going through something challenging in your business, remember: you are not alone! I hope you find comfort through the voices of some of my dearest friends, former podcast guests
264: 🦧 What to Do When You Lose Your Biggest Client (Part One)
What do you do when you lose your biggest client? That was my Spotify search query for podcast episodes on this topic in the summer of 2023. It came up empty—there was not a single podcast episode on this topic. Of course not. Who wants to admit out loud and in their archives that they've lost their biggest client? In the past, I probably wouldn't have fessed up to this either. Except for the fact
263: Finding Product-Market-Founder Fit and Launching Downhill Sales Snowballs ☃️ through Relationship-Marketing with Michelle Warner
“I am great in the early, messy days and I know that about myself, so I designed my business around serving others in that stage.”
In this conversation with business strategist (genius!) Michelle Warner, we cover the three growth stages most relevant to tiny business owners, how to fix broken business models, validating product-market-founder fit, the difference between traffic-based versus relati
262: 🪜Climbing Down the Entrepreneurial Ladder — Rolling in D🤦🏻♀️h
“Things today are waaayyyyy better than Things have ever been. Cavemen had sticks. In the Middle ages they had typhoid. We have iPhones and Hermann Miller chairs and shoes with air in the soles. Inside the soles! How do they get the air inside the soles??? We are living in the Golden Age of Things, in the Golden Empire of Things.”
—Shalom Auslander's Fetal Position via Beckett Drove a Deux Chevaux
261: Cringe-Free Launches and Evergreen Sales Considerations with Anne Samoilov
If you’re anything like me, you may find conducting online launches for your programs or events exhausting and sometimes even cringe-inducing. Thankfully, today’s guest, Anne Samoilov, is here to help!
Anne is a long-time expert in the space who has helmed product launches for Laura Roeder, Marie Forleo, and Jonathan Fields. Today, we’re talking about why some of us find big, splashy launches so d
260: How to Focus on Long-Term Thinking in a Short-Term World with Dorie Clark
“Whenever you have a choice of what to do, choose the more interesting path."
In honor of our upcoming Free Time x Long Game IRL event in Miami on February 1 and 2 (it’s not too late to join!), today I’m bringing you a favorite episode from the earliest days of the Free Time pod. In this conversation with Dorie Clark—aka “DC”—one of my closest friendtors, we discuss how she "optimizes for interest
259: Crisis Communication Strategies with Aliza Licht
Before you post anything, ask: Why am I posting this? Is this within my brand guardrails? Even still, you may find yourself in hot water someday, and it’s important to think through how you will respond (and the pop-up team you will assemble to help) in advance. Today, we’re breaking down the tricky art of crisis communications and apologies with Aliza Licht, author of On Brand, who brings two dec
258: To Do—A Small Business Owner’s Checklist (Rolling in D🤦🏻♀️h Crossover)
What’s on your business owner to-do list? Here’s a peek at mine, full of items large, small, and existential. This is another crossover from Rolling in D🤦🏻♀️h, a recent essay that was an unexpected runaway hit—the most popular to date in the six months since I started on Substack.
I had no idea (as usual) whether it would resonate or not when I hit “publish,” until my friend Adam texted to say ho
257: How to Become a Friction Fixer with Huggy Rao
“We don’t want our time to be spread thin like peanut butter on a slice of toast. You will have greater impact when you concentrate your efforts on work that is closely tied to winning—however you define it.”
Are you working in a frustration factory? If so, it’s important to recognize that not all friction is created equal. Some is good, to slow down decision-making in crucial moments, and some is
256: Behind-the-Business: 1:1 Voxer Coaching Summer Pop-Up—Structure, Systems, and Pricing (Listener Q&A from Renee)
I'm so excited to bring you a listener submission today from Renee Rubin Ross about my summer Voxer coaching pop-up. I've done these two summers in a row now, and I've learned so much every subsequent time. In this episode, I’ll share the structure, systems, and pricing that help me create a joyful asynchronous program that keeps our calendars free of “tiny boxes” (as my friend Sarah calls them).
255: Operationalizing Kindness and Absolute Excellence while Building Birch Coffee with Paul Schlader
“It wasn’t about being better than others, it was being ourselves, and true to our ideals in our work.” That’s just one of many gems from today’s guest, Birch Coffee co-founder Paul Schlader, who says, “I don’t accept anything less than absolute excellence.”
In this conversation we talk about how he stands out in the New York City noise by hiring for kindness; getting bought out when the Gershwin
254: 8 Lessons Learned from 8+ Years of Podcasting (Pivot Crossover)
Today is a crossover episode from the Pivot podcast celebrating eight lessons learned from over eight years of podcasting.
The Free Time podcast is now approaching its third birthday—I launched it on March 21, 2021—a year prior to the book coming out. I encourage you to grab your copy if you haven’t already, or even better—🎁 give the gift of free time to a loved one in your life for 2024!
As we st
253: Channeling Main Character Energy into Writing a Debut Novel with Jamie Varon
“’Something I always say: at the very least, do it for the plot. Do it for the story. Be bold in life, mostly because not being bold is boring as hell.’ Margot tipped her head back in glittery laughter and I felt my chest expand in hope.”
That’s just one of many glittering conversations that the main character of Jamie Varon’s debut novel, Main Character Energy, has with her Aunt, a guiding light
252: Taking an Accidental Sabbatical with Mel Dizon
”In a society that glorifies titles, visibility, reach, and the grind, taking a beat to opt out of all that isn’t easy,” today’s guest Mel Dizon writes in the origin story to her pop-up Substack.
Mel shares how she defines an accidental sabbatical; the energetic urgency and pent up ambition that let her know it was time to leave her job; the permission she needed to give herself; navigating the fe
251: Simply Put—Reducing Friction on Sales Pages and in Business Communication with Ben Guttmann
Just because you use pretty words that sound nice doesn’t mean they are effective. Although we know what we do because we do it all the time; it’s hard to separate that from what your audience wants and experiences. Thankfully, today’s guest is here to help.
Ben Guttmann is a marketing and communications expert and author of Simply Put: Why Clear Messages Win — and How to Design Them.
We discuss w
250: Do what you love and the money will follow . . . IF you meet at least 3 of these 20 criteria (Rolling in D🤦🏻♀️h)
The phrase is emblazoned at WeWorks across the globe: in large neon lights across lobby walls, bedecking laptops via swag stickers, and printed in playful cursive on the mugs that facilitate bottomless free coffee—with the addition of always in small print at the top.
But what becomes of the adage to do what you love when the company blasting it everywhere declares bankruptcy? What about the rest
249: Systems for Selling Over One Million Books with Josh Kaufman
“The biggest breakthroughs came from the random side projects that I had no expectation would turn into anything.” Josh Kaufman is a longtime friendtor (13 years and counting!) who I admire for his streamlined approach to running his business in a way that supports family life and creative solitude.
In our last conversation we spoke about releasing the ten-year anniversary edition of his bestselli
248: Four Brand Personas, Biggest Mistakes, and Best/Worst Clients with Adam Chaloeicheep
Are you running a Franken-Brand? A quick, inexpensive logo here. And then someone a few months later tries to write the brand strategy. And then another junior hire adds in graphics and you don’t even know where they came from. Suddenly, you have this brand that is cobbled together, and no one on the team is feeling compelled.
Today, returning guest Adam Chaloeicheep and I are picking up where we
247: Has your Business Brand Become a Liability? How to Know When It’s Time for a Tune-up with Adam Chaloeicheep
Has your business brand become stale, perhaps to the point of being a liability? After a few years, especially with major pivots, you may run the risk of losing clients and credibility. Sometimes it’s time for a tune-up and fresh tires, and sometimes, it’s time for a whole new brand engine.
As today’s returning guest, my good friend and part of the team behind the award-winning Free Time brand, re
246: The Unsustainability of Inauthenticity with Erin Weed
What do you do when a business area becomes energetically draining, or the income isn’t flowing? Today’s guest has many intuitive superpowers, and one of them is “following the data points of truth.”
In this episode, Erin Weed and I discuss why you shouldn’t just stick with something that is no longer aligned; the tragic event that launched her journey into entrepreneurship; the moment she knew it
245: Business Development Misfires and Best Practices with Terry Rice
How can you get paid for who you are, not just what you do? Today’s guest, Terry Rice, is teaching us his Golden Link Strategy for creating a steady stream of potential clients, without giving them (or you) “the ick” through cold outreach misfires.
He also shares speaking and marketing tips he pulled from one of his mentors, Daymond John, how he reframes business development activities, why it’s v
244: Asking Better Questions and Designing Your Ideal Day with Claire Giovino
“What am I pretending not to know?” There is tremendous power in asking better questions, whether it comes to ideal day design, creating systems in your business, or teaching someone how to help tame your inboxes.
Today’s conversation with Claire Giovino covers all that ground and more. We talk about what qualities make email so vexing for many business owners, how to reduce fear and friction when
243: Engineering Serendipity and Best Practices for Community-Building with David Spinks
"For the first time in a decade, I feel free again." That’s how one of my earliest blogging friends, longtime community leader David Spinks, was feeling when I caught up with him in-person in the middle of his yearlong sabbatical, after selling his community-based business.
David and I discuss best practices for creating and nurturing communities, for engineering serendipity, what it’s like to bui
242: From Commoditized Content to Visionary Quests + Digital Doppelgängers with Andrew Davis
“The world doesn’t need another expert.” So says today’s guest, Andrew Davis. Experts rely on hacks, tips, tricks, teaching, preaching, and over-promising. Visionary leaders a) tend not to call themselves that and b) focus on the quest for knowledge itself, with enough humility to admit what they don’t know, or the problems they are exploring even while still in process.
In today’s conversation, y
241: Finding Freedom and Financial Reciprocity through a Paid Newsletter with Nic Antoinette
“You do not need to cannibalize your healing for content.” Today, I’m in conversation with longtime blog-turned-IRL friend Nic Antoinette, diving deeper into her decision to shut down her Patreon community (taking a $30,000/year haircut to do so), then pivoting to a private paid Substack while she navigated her way through decisions about what might follow.
We discuss the generosity of being hones
240: 3 Ingredients to Fill a Program Faster When Launching (BFF Bonus Replay)
If you have been in business for any amount of time, then you know the feeling when a launch just isn’t working. The sales are crawling, you start doubting yourself, wondering if you created the right thing in the first place, if you built a big enough audience to sell anything at all.
All kinds of additional questions and insecurities follow when sales aren’t flowing: is that the offer that’s off
239: “Don’t Wait Until You’re an Expert” — Scratch Your Own Curiosity Itch with Nir Eyal
“I only write books for problems I can’t otherwise solve,” Nir Eyal says. “I don’t write my books for my readers; I write my books for myself.”
Driven by curiosity to fix his own problems, Nir’s books have sold over one million copies. Listen to today’s conversation on how he weathered the criticism storm around his first book, Hooked; the one essential skill to being an entrepreneur; how to turn
238: Why Revenue Goals Don’t Work (For Me)
Abundance was my word of 2019.
I’d love to tell you I meant abundance in the broadest possible sense, appreciating the bounty already in my life, financial and otherwise.
But mostly, my theme was about money.
Specifically: to surpass one million dollars in revenue by the end of the year. I was going to build the sexiest small business rocket ship to achieve time-and-money escape velocity with my D
237: Rest Easy with Ximena Vengoechea
What is your relationship to rest? How about your caretakers’ relationship to rest while you were young? What examples did they set? What attitudes, beliefs, and behaviors did they hold, and how does that still influence you today?
Today I’m talking with Ximena Vengoechea about the five rest profiles, productivity dysmorphia, “tiny transition time,” why paid work (no matter how much you love it) d
236: Ignore the Odds — Rolling in D🤦🏻♀️h Crossover
“Startup CEOs should not play the odds. When you are building a company, you must believe there is an answer and you cannot pay attention to your odds of finding it. You just have to find it. It matters not whether your chances are nine in ten or one in a thousand; your task is the same.” —Ben Horowitz, The Hard Thing About Hard Things
We are not meant to compare ourselves to eight billion people.
235: Minimizing the Social Overhead of Managing Teams with Charlie Gilkey
You can calm chaos at work, but it starts with a reality check from Charlie Gilkey, delivered with his signature wit and generosity: You might not have a team problem, you have a you problem.
It’s time to stop catering to air sandwiches, Crisco watermelons, broken printers, ghost plans, and other corrosive practices, and start implementing Charlie’s finely-tuned, road-tested systems instead.
Today
234: 11 Practices to Strengthen Business Intuition (Part Two)
“As long as we settle for thinking inside the brain, we’ll remain bound by the limits of that organ. But when we reach outside it with intention and skill, our thinking can be transformed. It can become as dynamic as our bodies, as airy as our spaces, as rich as our relationships—as capacious as the whole wide world.” —Annie Murphy Paul, The Extended Mind
In this second half of a two-part solo ser
233: On Sensitive CEOs and Building a Soulful Business with Rose Cox
I’m excited to bring you this crossover episode with Rose Cox, founder of The HSP Business School and host of The Sensitive CEO Show ****podcast. She is one of the people I have been most excited to connect with across the globe the last few years, even though we have yet to meet IRL!
In this conversation, we dive into the world of highly sensitive people (HSPs), empaths, and introverts in the bus
232: 11 Practices to Strengthen Business Intuition (Part One)
Intuition is always speaking to you in subtle ways. Are you listening?
Intuition isn’t a gift that is only bestowed on a special few; everyone can strengthen this muscle—how loudly you hear these signals, and the trust in yourself to take action on the information you’re receiving.
In the comments of a recent ‘D🤦🏻♀️h post, Claudia asked:
I read your words “all-in on myself” and how you consciousl
231: Building and Selling a Profitable Content-Based Business with David Thomas Tao
“Let’s build ESPN.com for strength, and convince everyone they can lift weights.” With this mission in mind, the first six months of building the BarBend platform were a blur for today’s guest. By the end of the first year in 2016, they had had 1.4 million readers. By 2022, they had over 31 million registered users, allowing them to sell the business in 2023.
In this conversation, we cover David T
230: What’s Your Ratio of Quantity to Quality for Ongoing Creative Work?
“You can’t use up creativity. The more you use, the more you have.” —Maya Angelou
Earlier this summer, I arrived late one day to the podcast studio, laying on the floor in lieu of actually recording anything. Should I take that as a sign to reduce my creative output?
Not necessarily.
Aside from big one-off projects like writing a book, where I pour incredible time and attention to detail into (tha
229: How (and When) to Trust Yourself and Others with Ilise Benun
When we say trusting ourselves, which self are we talking about? Which parts of ourselves can’t be trusted?
That’s what we’re exploring today with returning guest, Ilise Benun. We discuss how confidence is a byproduct of action, what made her so angry that she decided to start her own business 35 years ago, building tolerance for silence and small experiments, and why she puts her phone number in
😬 On Moving Through Vulnerability Hangovers — Preview of October Bonus for Paying Subscribers
This is a free preview of this month's bonus episode for paying Free Time subscribers. Listen to the full episode (plus 100+ in the archives) and join us for live Q&A calls here »
***
They say write from the scar, not the wound—but what do you do when you feel called to write or speak from the wound? Do you forge ahead, knowing you will wake up the next day with a raging vulnerability hangover? Or
228: The Burdensome B’s—Four Red Flags Signaling it’s Time to Make The Big (Delegation) Leap
“I’m at my wit's end.” That was the conclusion of a text message that broke my heart a little bit. when a friend and fellow business owner showed it to me the other day.
Their team member sent it to them, expressing exasperation at the state of unfinished tasks in the business where they were waiting on an answer or action from the owner.
Seeing it bummed me out for both of them because it was nei
227: 🎁 The Best Gifting Strategies and Biggest Mistakes with John Ruhlin
“Nobody’s soul is moved by swag.” So says longtime friendtor of the pod, John Ruhlin, founder of strategic gifting company Giftology.
Since the day I met John and encountered his work in 2016, I have been inspired by his commitment to elevating the relationship game with generosity, “heart bombs,” and expressing genuine appreciation in the business world and beyond.
He does this all while setting
226: Is your business a hot mess? If yes, let's celebrate — Rolling in D🤦🏻♀️h
I used to refer to myself as a hot mess often in the early blogging days circa 2008, until someone scolded me saying it wasn’t a nice way to describe myself, that maybe it wasn’t the best self-image to curate. So I stopped. But I lost something in dropping the “hot” and the “mess” as I now approach middle age (and grandma-status in my soul).
Today's post is a crossover from my newest project, Roll
225: How to Write a Must-Read Nonfiction Book with AJ Harper
“A book is not about something. A book is for someone.” That’s the mantra that drives AJ Harper’s work, that includes ghostwriting over one hundred books (and working on many more one-off chapters and projects).
In this conversation, she shares the “life of a book” process in her writing partnership with Mike Michalowicz (ten books together and counting!), what most authors get wrong when writing
224: Create a See You Soon Kit for Clients — Jacq’s Favorite Time-Saving System
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
223: The Confidence Trap: Why You Don’t Need It to Do Big Things (SPARKED Crossover)
“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
222: Why I Migrated My Three Email Lists to Substack (BFF Bonus Replay)
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 felt
221: Publishing and Personal Writing Pointers with Jennie Nash
“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
220: The One Thing You Should Do Now for Next Summer
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
218: 🎉 3 Creative Lessons Learned from 7+ Years of Podcasting (Pivot Crossover)
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
217: ChatGPT as Universal Intern and Permission Not to Be a Billionaire with Kevin Kelly (Pivot Crossover)
“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
216: Feeling Impostery? Become a Qualified Curator Instead of an End-All-Be-All Expert (Pivot Crossover)
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
215: Five Types of People-Pleasers from The Joy of Saying No with Natalie Lue (Pivot Crossover)
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
🥂 You're Invited! IRL Business Bestie Brunch VIP Day+ (Early Bird Pricing Ends 9/1/23)
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
214: “Don’t Suffer Twice” (Pivot Crossover)
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
213: Who’s Sitting in the Board Room of Your Brain? with Adrian Klaphaak (Pivot Crossover)
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
212: Are You Future-Tripping? (Pivot Crossover)
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
211: 10+ Conference Networking Strategies with Alisa Cohn (Pivot Crossover)
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
210: ⛵️Knot a Care—Sailing the Free Time Seas with Joy and Ease
“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
209: From Lost and Founder to Chill Work with Rand Fishkin
“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
208: 😇 Delight Is in the Details
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:
207: Geeking Out on Client-Facing Pages + Favorite Notion Templates with Karen Allen
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
206: 🦊 Celebrate the Small Fixes, aka Your Business Rose 🌹
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
205: Why Paul Millerd Turned Down a $200K Two-Book Traditional Publishing Deal
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
204: 8 Benefits and Strategies for Managing a Shared Team Inbox Through HelpScout
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
203:🎢 Riding the Emotional Rollercoaster of Launching with Natalie Lue
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-Ple
202: 🎉 20+ Free Time Permission Slips for Small Business Owners (Part 2)
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 —
201: Never Lose a Team Member Again with Joey Coleman
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
200: 🎉 20+ Free Time Permission Slips for Small Business Owners (Part 1)
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 — 📝 Rethink
199: Creating Happier Hours and the Diminishing Returns of Too Much Free Time With Cassie Holmes
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 wit
198: Book Club ✨ OUTRAGEOUS OPENNESS: Letting the Divine Take the Lead by Tosha Silver
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 T
197: Growth Loops + Why it’s Better to be Respected than Liked with Todd Herman
“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 w
196: 🍩 What Do Donuts, Coffee, Conversation, and Energy Cliffs Have in Common? (My Mini Daily Audio Diary from Attending TED 2023)
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
195: Traversing the Dark Forests of Creativity and Business with Jessica Abel
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-bu
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