Free Time with Jenny Blake

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. Todd is so committed to helping his authors succeed that he only publishes one book each year. Today he's sharing how to investigate and possibly reposition a book when a launch isn't gaining traction, his three-sentence problem statement to attract ideal readers, and why the Table of Contents and first chapter are essential parts of the marketing process.

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 appreciate the even deeper dive with my longtime friend (and first coach) Adrian Klaphaak in Pivot episode 360:

“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 clients who work for highly bureaucratic companies that insist on their “standard” net-120 terms? In this illuminating conversation, Joey shares his best practices for getting paid on time—every time by setting, stating, and upholding better boundaries (and contracts) with clients. More About Joey: As an award-winning speaker for over twenty years, Joey Coleman works with organizations around the world ranging from small startups to major brands such as Volkswagen Australia, Zappos, and Whirlpool. His First 100 Days® methodology fuels the remarkable experiences his clients deliver and dramatically improves their profits.

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 2023, you'll hear him generously talk me through how I could help Free Time get there—with a much-needed morale boost at the end. More About Todd: Todd Sattersten is the publisher and owner of Bard Press, a book publisher that works with authors to create best-selling books in business, personal development and technology. Before Bard Press, Todd served as general manager of IT Revolution and president of business book retailer 800-CEO-READ. He is the author of Every Book Is a Startup and the co-author of The 100 Best Business Books of All Time (Portfolio, 2009). Todd lives in Portland, Oregon with his wife Amy and their three awesome kids.

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 talking about her forthcoming book, Uptime: A Practical Guide to Personal Productivity and Wellbeing. We discuss what the most senior-level executives do differently when it comes to time management (and what they still struggle with), five strategies for saying no, taming inbox stress with The Laundry Method, cozy corners, pairing activities with certain locations (hot spots and not spots), and what differentiates truly excellent executive assistants. More About Laura: During her nearly fourteen-year tenure at Google, Laura Mae Martin has worked in sales, product operations, event planning, and now executive coaching. She holds a bachelor of science in business administration from the University of North Carolina at Chapel Hill and lives in Charlotte, North Carolina, with her husband and three children under five.

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 to the groups you care most about reaching. I shared this in June 2023 as a follow-up to the fantastic workshop that Pamela Slim did for us on Certification and Licensing. You can access over 100 bonus episodes and that workshop by joining Free Time as a paying subscriber. You'll get instant access to Stephanie Huston's How to Batch Create and Customize Your Annual Content Calendar, with an epic multi-tab template in Google Sheets. Be sure to also check out the resources below, including Wes Kao's detailed LinkedIn post on how to turn your ideas into frameworks.

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, and favorite Heart-Based Business owners who are speaking from experience about how they've handled situations just like this. If you want the full scoop on what founding BFF member Leanne Hughes calls “business reality TV” on how I have been handling losing my biggest favorite client, I encourage you to check out the full series of posts at Rolling in D

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 that now it's what I wish I could see, read, and hear. Today's compilation episode is here to fix that! If you've been reading Rolling in D

“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 relationship-based sales and marketing, borrowing aligned audiences, leading a free monthly Q&A to “catch” their interest afterward, imagining sales as a downhill snowball, and how to scale while still staying Delightfully Tiny. More About Michelle: Michelle Warner designs tiny companies that are built to last. With an MBA from one of the world's top business schools and 15+ years experience growing small businesses, Michelle focuses on layering real world experience on top of classic business fundamentals to design businesses that are sustainable and scalable in the long term and resilient and adaptable in the short term. It's the way she grew her first business to 7+ figures, and it's what she's used to help 300+ CEO's create businesses that work for the important stuff: profit, energy, passion + time. She's also the creator of Networking That Pays, the introvert-friendly, always awkward-free connection system that brings in reliable leads, consistent referrals and meaningful connections for your business - in 5 minutes a day.

“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 I first encountered the Apple billboard a few days after Christmas. I was walking down Fourteenth Street in the Meatpacking district, and there it was—an Apple ad declaring “Newphoria!” in enormous print. We don't need newphoria. We need oldphoria, the joy in what already exists. We need simplephoria, the joy in streamlining. We need enoughphoria, the celebration that what we have and who we are is already enough. Newphoria, at least as it relates to running a small business, is not always all it's cracked up to be. Today's post is a crossover from Rolling in D

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 draining; how to set up automated or evergreen launches (and her take on the pros and cons of these); how to find non-cringey launch strategies; be willing to take on clients or projects that have nothing to do with your business. More About Anne: Anne Samoilov is a launch strategist and VFX Producer. She started her work online as the creator of Fearless Launching, an online training program that teaches impact-driven entrepreneurs how to create simple, streamlined, and standout launches without relying on templates or cookie-cutter strategies. She has also led the VFX teams for TV shows on Paramount Plus and Starz. Check out Anne's podcast, The Fearless Launching Show, where she shares insights and tips on how to have an amazing product or business launch—your way.

“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 interesting," says no to good opportunities, builds relationships by following her "no asks for a year" rule, and when to call on trusted advisors to ensure you don't quit something too soon. We're discussing her bestselling fourth book, The Long Game: How to Be a Long-Term Thinker in a Short-Term World—be sure to grab your copy for even more insights on how to apply strategic thinking to your biggest vision. This episode originally aired on September 28, 2021. More About Dorie: Dorie Clark helps individuals and companies get their best ideas heard in a crowded, noisy world. She has been named one of the Top 50 business thinkers in the world by Thinkers50, and was honored as the #1 Communication Coach in the world by the Marshall Goldsmith Leading Global Coaches Awards. She is a keynote speaker and teaches executive education for Duke University's Fuqua School of Business and Columbia Business School. Dorie is the author of The Long Game: How to Be a Long-Term Thinker in a Short-Term World, Reinventing You, Stand Out, Entrepreneurial You.

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 decades of PR experience to the conversation. More About Aliza: Aliza Licht is an award-winning marketer, bestselling author, podcaster, personal branding expert, and the founder of LEAVE YOUR MARK, a multimedia brand and consultancy. She advises businesses and mentors individuals on brand building and career development. Licht leverages over two decades of expertise in marketing, communications, and digital strategy in the fashion industry. She was named one of "America's Next Top Mentors" by The New York Times. Her new book, On Brand: Shape Your Narrative. Share Your Vision. Shift Their Perception is a comprehensive roadmap to building your personal brand. As a social media pioneer and one of the first fashion influencers, Licht created and was the voice of the anonymous social media phenomenon DKNY PR GIRL.

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

“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 bad, getting in the way of progress. You'll need to tap into your inner “grease” and “gunk” sides to address both. In the introduction to their book, The Friction Project, coauthors Huggy Rao and Bob Sutton share a quote from Ed Catmull, former president of Pixar. He believes that if Pixar followed overreaching executives' advice to wring maximum efficiency and scale out of the organization, it would “kill the goose that lays the golden eggs.” "The goal isn't efficiency, it is to make something good or even great,” Catmull says. “We iterate seven to nine times, with friction in the process.” More About Huggy: Huggy Rao is the Atholl McBean professor of Organizational Behavior at the Stanford Graduate School of Business and a fellow of the Center for Advanced Study in Behavioral Science, the Sociological Research Association, and the Academy of Management. He has written for Harvard Business Review, Business Week, and the Wall Street Journal. He is the author of Market Rebels and coauthor of the bestselling book Scaling Up Excellence. Today we're talking about his new book, also coauthored with Bob Sutton, The Friction Project: How Smart Leaders Make the Right Things Easier and the Wrong Things Harder.

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). More about Renee: Dr. Renee Rubin Ross is a recognized leader on board and organizational development and strategy and the founder of The Ross Collective, a consulting firm that designs and leads inclusive, participatory processes for social sector boards and staff.

“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 Hotel closed and thereby ending the lease on their first location, then parlaying those funds into two new stores (and the growing pains that followed); and the moment he had to tell his entire team they were furloughed indefinitely when New York City delivered the shut-down order; losing four stores but bouncing back to 14 (when so many other coffee shops closed down). More About Paul: Paul Schlader co-founded Birch Coffee, a New York City-based coffee company, in 2009. Since then, the company has grown to fourteen locations and is doing 10x the revenue by the end of year three. Paul and his business partner Jeremy have been focused on bettering the industry through their work in coffee and service over the past fifteen years. Paul's work directly focuses on quality of product. As a licensed Q grader, he manages all of Birch's green coffee purchases, and oversees their roasting, wholesale program, and espresso training. Though the coffee side is important, leadership is where Paul spends most of his time, building teams and working to teach their leaders to follow the mission, "Serve our customers every need, every time, knowing every moment counts.”

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—

“'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 who helps her find her voice and pursue her publishing dream. In today's conversation, Jamie and I go behind the book to talk about how fiction differs from nonfiction, working with a writing coach, the importance of giving yourself permission for a “zero” draft, moving past the mental machinations of envy and the desire for logical explanations for others' success, and so much more. Be sure to check out our previous conversation for the Pivot podcast 278: Radically Content with Jamie Varon. More About Jamie: Jamie Varon's writing has been seen across the internet for over a decade, from her early days of personal blogging all the way to features in publications such as Teen Vogue, HuffPost, GOOD, Complex, and many more. Over the years, both her long-form essays and short-form prose have garnered millions of reads and views, using her signature style of combining personal story with universal themes.

”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 fears that followed; how publishing her process out loud has helped with courage and accountability; and trusting herself to make important decisions when it's time, while also not rushing that process. More About Mel: Mel Dizon is a writer and editor; a runner, CrossFitter, pickleballer, and efficiency fanatic; a former therapist, consultant, and coach; a dog, pool, and scalding-hot-dirty-chai lover. She started writing words for dollars back in 1993. She's written thousands of articles, ghostwritten many books and essays, facilitated hundreds of video interviews, and written copy for everyone from NYT best-selling authors to companies like Google. Melani dreamed about taking a sabbatical for years, and the universe finally conspired to light the way. Turns out she's a big fan. She currently writes life & dying on Substack for those in the middle of the reinvention mess, seeking to “live a life worth writing about.”

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 why business owners often muck up their sales pages (what I call invitation letters), how to reduce friction when attracting clients and customers, and the toll that writing too much takes on the receiver. More About Ben: Ben is former co-founder and managing partner at Digital Natives Group, an award-winning agency that worked with the NFL, I Love NY, Comcast NBCUniversal, Hachette Book Group, The Nature Conservancy, and other major clients. He's an experienced marketing executive and educator on a mission to get leaders to more effectively connect by simplifying their message. Currently, Ben teaches digital marketing at Baruch College in New York City and consults with a range of thought leaders, venture-backed startups, and other brands.

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 of us? Today's essay is a crossover from my paid Substack, Rolling in D

“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 bestselling book, The Personal MBA: Master the Art of Business, that has since surpassed the one million books sold milestone. Today we're diving into the systems behind that success. Check out 012: Generating Personal MBA Momentum with Josh Kaufman if you haven't already! More About Josh: Josh Kaufman's research and books focus on business, entrepreneurship, skill acquisition, productivity, creativity, applied psychology, and practical wisdom. Josh's unique, multidisciplinary approach to business mastery and rapid skill acquisition has helped millions of readers around the world learn essential concepts and skills on their own terms. Josh's TEDx talk on The First 20 Hours is one of the top 25 most-viewed TED talks published to date, with over 37 million views on YouTube.

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 left off in episode 259: Has your Business Brand Become a Liability, diving into Together Agency's four personas of clients who are ready to do brand work, the three types of clients that are deal-breakers for Adam, and the perils of navigating the brand strategy process with a CEO who is in the midst of a spiritual awakening. Be sure to check out our previous conversations, 045: Behind the Free Time Brand with Adam Chaloeicheep and 247: Has your Business Brand Become a Liability? How to Know When It's Time for a Tune-up. More About Adam: Adam Chaloeicheep is co-founder of Together agency with his wife, Marisol Dahl, who I had the great pleasure of working with for five years in the early days of JBE. Adam is a creative business leader with over a decade of experience in a variety of startup areas including product and service concepting, building teams, operations, and brand-focused design and digital solutions. He is one of my closest friends (12 years and counting!), and a creative business leader with over a decade of experience in product and service concepting, building teams, and brand strategy. Together Agency is behind every big brand I have launched into the world including Pivot and Free Time.

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, recently featured on Behance. Adam Chaloeicheep says, “It's about building the relationship with your customer. First impressions are really important.” If you haven't already, I suggest listening to our previous conversation first, 045: Behind the Free Time Brand with Adam Chaloeicheep, for a foundational overview of how Adam and team think about brand strategy more broadly. Today, we're diving into how to know when you're due for a rebrand. More About Adam: Adam Chaloeicheep is co-founder of Together agency with his wife, Marisol Dahl, who I had the great pleasure of working with for five years in the early days of JBE. Adam is a creative business leader with over a decade of experience in a variety of startup areas including product and service concepting, building teams, operations, and brand-focused design and digital solutions. He is one of my closest friends (12 years and counting!), and a creative business leader with over a decade of experience in product and service concepting, building teams, and brand strategy. Together Agency is behind every big brand I have launched into the world including Pivot and Free Time.

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 was time to release her first business; how she came up with her unique process, The Dig®️ (then later trained a dozen facilitators to help conduct sessions); volunteering as one of the best ways to try on new business ideas; and setting intentions with a word of the week and for the year, in addition to your core word at the center of who you are. ⛔️ For listeners who wish to avoid sensitive content: This episode contains a story about violent crime. More About Erin: Erin Weed is an intuitive communications expert with a passion for truth and storytelling, dedicated to helping leaders discover their purpose and express it succinctly. With a background in PR and documentary production, she has a wealth of experience. Erin's journey took a transformative turn when the tragic murder of her sorority sister inspired her to launch Girls Fight Back!, a global women's safety education company. Erin is also renowned 22-year professional speaker who coaches TEDx and TED speakers using her unique approach, The Dig®, to distill their messages down to simple words.

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 vital to get your offer right before you focus on branding, how he makes time for 12 hours of creating each week (even with four kids), and the sacrifices he made after his business started taking off. More About Terry: Terry Rice is a performance coach and business development consultant. He is a staff writer at Entrepreneur magazine and host of Launch Your Business, a podcast that helps entrepreneurs make money, save time and avoid burnout. Terry is also the author of Start Your Own Consulting Business: Your Step-By-Step Guide to Success. A recognized marketing expert, Terry's previous experience includes internal consulting roles at Adobe and Facebook. Terry is an instructor at New York University, and has been featured as a subject matter expert by Good Morning America, Fast Company and the Wall Street Journal. Terry is based in Brooklyn; he is a husband and father of four children.

“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 delegating replies, and the importance of asking better questions—of yourself and in your business. More About Claire: After an extensive career in academia, Claire Giovino began optimizing inboxes for industry leaders, launching InboxDone in 2017. She and her cofounder Yaro quickly scaled the business 10X in three years with no startup capital. Her proprietary recruitment, training and onboarding process ensures that each client is matched with a carefully-selected Inbox Manager and represented with a superior level of communication. These clients now check their inbox just once per month — or not at all. Claire has always been a seeker, maneuvering her way through life with constant questioning. She now has the lifestyle freedom to seek out her dream podcast guests and to start conversations at her Better Question Dinners. She cherishes books, quotes and good listeners.

"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 build and run a conference (and later sell it), and the freedom that comes with taking a deliberate sabbatical. More About David: David Spinks is the author of The Business of Belonging and a popular weekly newsletter for community creators. Previously he co-founded CMX, the leading network for community professionals that was later acquired by Bevy.

“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, you'll learn how to move past commoditized content toward launching a quest that builds trust and brings your audience along for the ride—while embracing digital doppelgängers to help you get there. More About Andrew: Andrew Davis is a bestselling author and internationally acclaimed keynote speaker. Recognized as one of the industry's "Jaw-Dropping Marketing Speakers," Andrew is a mainstay on global marketing influencer lists. Wherever he goes, Andrew Davis puts his infectious enthusiasm and magnetic speaking style to good use teaching business leaders how to grow their businesses, transform their cities, and leave their legacy. He is the author of Brandscaping, Town Inc., and The Referable Speaker.

“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 honest, the trap of wanting to be special, knowing where to draw the line on how much or how little you share, and much more. Be sure to also check out our earlier Pivot conversation in episode 342: “Whatever Comes Through Me Comes for Me First,” with Nicole Antoinette. More About Nic: Nicole Antoinette is a writer, long-distance hiker, and former indoor kid who never imagined she'd wind up spending months of each year pooping in the woods. In 2017, stuck in a loop of codependency and people-pleasing, Nicole set off to find her self-belief and inner resilience by doing something she did not for one second believe she could actually do. The results are two adventure memoirs, How To Be Alone: An 800-mile hike on the Arizona Trail, and What We Owe to Ourselves, and a weekly Substack newsletter called Wild Letters.

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? Your sales page invitation letter? The pricing? Is it you? It's so hard not to get a big morale dip in the middle of the sales dip during a launch. So this month's bonus is on a few strategies that I've picked up over the years. This is a replay of our bonus episode

“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 your values into time, and turn time into traction; and if you're an aspiring author, why the fear of not being qualified should not be one of your fears. If you haven't already, check out Pivot episode 131: Indistractable with Nir Eyal. More About Nir Nir Eyal writes, consults, and teaches about the intersection of psychology, technology, and business. He is the author of two bestselling books, Hooked: How to Build Habit-Forming Products and Indistractable: How to Control Your Attention and Choose Your Life. In addition to blogging at NirAndFar.com, Nir's writing has been featured in The New York Times, The Harvard Business Review, Time Magazine, and Psychology Today.

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 Delightfully Tiny Team. *Today's post is a crossover from Rolling in D

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) doesn't count as pure play, and how she designed the book to deliver a restful experience beyond just the words themselves. Listen to our previous conversation on the Pivot podcast, 263: Conduct a Relationship Audit with Ximena Vengoechea. More About Ximena: Ximena Vengoechea is a researcher, writer, and illustrator. She previously worked at Pinterest, LinkedIn, and Twitter, and currently advises select startups and executives on user research, executive communication, and resting well. She is the author of Listen Like You Mean it: Reclaiming the Lost Art of True Connection, and today we're talking about her new book, Rest Easy: Discover Calm and Abundance through the Radical Power of Rest.

“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. I know I'm not the first to remind you that social platforms are status games on globalized steroids. With so much exposure to people who are (actually) smarter, funnier, prettier, and/or fill-in-the-blanker, the logical conclusion would be not to jump in. Right? In Zero Sum Logic, this is correct. If you can't be the best author, the best podcaster, the best thinker about your topic, the prettiest/skinniest/curviest/strongest in physical appearance, why try? Today's post is a crossover from my newest project, Rolling in D

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 we're talking about his new book Team Habits: How Small Actions Lead to Extraordinary Results. We also talk about scaling from maker to manager (and sometimes back again), accounting for those who don't want the added social overhead of that (often due to some combination of hoarding control, people-pleasing, introversion, and empathy). More About Charlie: Charlie Gilkey has advised hundreds of teams, from Fortune 100 companies to tiny nonprofits, through Productive Flourishing, the coaching and training company he founded. Charlie is a former Army logistics officer and near-PhD in philosophy living in Portland, Oregon. He is the author of Start Finishing: How to Go from Idea to Done, and today we're talking about his new book, Team Habits: How Small Actions Lead to Extraordinary Results.

“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 series, I'm sharing 6 more strategies that have helped me build (and trust) my intuition at increasingly subtle levels. If you haven't already, be sure to listen to Part One here first. As always, I would love to hear from you! How do you practice the skill of following your intuition? Leave a voice note for a future listener-submission episode at http://itsfreetime.com/ask.

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 business world, with plenty of permission slips to stop doing what drains you. We discuss how to build a sustainable, soulful business that aligns with your energy, while embracing the strengths and challenges of being a sensitive CEO. Finally, we touch on Rose's decision to pause her podcast (at least for now) after a year of releasing weekly episodes. More About Rose: Rose Cox is an ICF-credentialed and Certified Human Potential Coach, 3 Brains Coach, Business Coach + Strategist, Advanced Rapid Transformational Therapist, Clinical Hypnotherapist and Energy Practitioner. Rose's unique blend of soul, science, systems and strategy combines her 20+ years' experience in the fields of online business, hypnotherapy, coaching, and psychology to help her clients build a successful and sustainable business that is aligned with their energy and their soul. She works with highly sensitive people, empaths and introverts who have amazing gifts to share with the world but struggle with both the business strategies and mindset to fully step into their own.

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

“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 Tao's take on the media landscape and how to build a profitable content-based business; raising a seed round of funding from friends and family after getting rejected from every venture pitch; the biggest mistake he made while experimenting with monetization strategies; and how he navigated a successful acquisition with a shared vision at the new parent company, Pillar4. More About David: David Thomas Tao is an entrepreneur and writer based in NYC. He's the co-founder and former CEO of BarBend.com, the world's premiere strength sports and strength training media platform. A proud Kentucky native, David is also a Forbes 30 Under 30 Listmaker, Kentucky Colonel, and a noted whiskey/spirits writer and judge, appearing yearly on national tasting panels. BarBend was recently acquired in a thrilling deal that included hiring all employees and the executive team has chosen to stay on as well.

“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 (that I tackle every five years or so), I seem to do better with ongoing creative work by sticking to a stretch-worthy production schedule. These days I'm running a Delightfully Tiny media company that produces the following on a monthly basis: 14 podcast episodes across Pivot, Free Time, and BFF Bonuses ~14 essays or newsletters: 8 ‘Doh posts, 4 Time Well Spent newsletters, 2 PivotList round-ups, and 1-2 BFF mailers This does not include guest appearances on other people's shows By stretching myself to show up in these ways, I have discovered that there's not always an inverse relationship between consistency and quality—at least for me.

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 twenty five years ago, building tolerance for silence and small experiments, and why she puts her phone number in her newsletter, on her website, and in the “from” line of her emails. If you haven't already, check out our previous conversation in episode 165: Are your clients bringing out the best in you? Engineering the Evolution of Your Business with Ilise Benun and episode 467 of Marketing Mentor on How to Free Your Time. More About Ilise: Ilise Benun is the founder of Marketing-Mentor.com, the go-to online resource for creative professionals who want better projects with bigger budgets, through which she offers business coaching. She is also a national speaker and author of 7 books, including "The Creative Professional's Guide to Money," three online courses via CreativeLive and Domestika.org, and The Simplest Marketing Plan – all tailored to the needs of creative professionals. She has also been hosting the Marketing Mentor Podcast since 2008, with over 465 episodes at the time of this recording.

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 do you keep it inside, bottled up for a future sell-by date? Scott asks: I'd love to hear you talk about seeking recognition / validation from others. Yep, kinda personal, so a bit vulnerable sharing here in direct email, but I do wonder if it's something that lies beneath the surface for me. Possibly combined with an uncertainty about taking a step out of the corporate path about 5 years ago to go into full-time sports coaching and having a lot of pondering about that decision esp based on financial implications that came with it. "Somebody tell me I'm doing the right thing / doing well / pat on the back" kinda chat would be amazing. Thanks again.

“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 neither person's fault per se (though we can all take responsibility, of course). As I say in Free Time, business stress is a systems problem. Today I'm sharing the signal flares to look out for indicating that something needs to change, with ways to communicate (and delegate) to stop the stressful pile-up languishing on your desk.

“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 up brilliant systems to make sure it all actually happens (such as setting a robust annual gifting budget aside off of top-line revenue). John is long overdue for a free time appearance, and I hope you enjoy this conversation as much as I did! More About John: John Ruhlin is the world's leading authority in maximizing customer loyalty through radical generosity. He is the founder and author of Giftology: The Art and Science of Using Gifts to Cut Through the Noise, Increase Referrals, and Strengthen Retention and has been featured in Fox News, Forbes, Fast Company, Inc and New York Times. He and his firm now help automate this process for individuals and organizations like UBS, Raymond James, DR Horton, Keller Williams, the Chicago Cubs, and Caesar's Palace.

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, Rolling in D

“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 the conclusion, her favorite tried-and-true question to solicit “unexpected, delicious responses from interviewees,” and how to calibrate expectations for timing around the writing, editing, and creative process. More About AJ: AJ Harper is an editor and publishing strategist who helps authors write transformational books that enable them to build readership, grow their brand, and make a significant impact on the world. As ghostwriter and as developmental editor, she has worked with hundreds of authors, from newbies to New York Times bestselling authors with millions of books sold. She is writing partner to business author Mike Michalowicz, and together they've written ten books, including Profit First. AJ is the author of Write a Must-Read: Craft a Book That Changes Lives—Including Your Own.

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 excited to bring you this listener submission episode from previous guest and BFF, Jacqueline Fisch.

“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 and, when they learn to harness these experiences, revelation and even reinvention.” That's how my longtime friendtor Jonathan Fields describes this episode, a crossover from his fantastic SPARKED podcast, where I'm honored to be on a panel of rotating advisor co-hosts (here's our Spotify playlist). In this crossover episode, we discuss seasons of confidence, struggle, renewal, and my 51/49 mantra on courage. I hadn't yet spoken about the new secret Substack publicly, so I thought Free Timers might benefit from a spontaneous (and nerve-wracking!) reveal that I didn't see coming. As Jonathan writes, “In an unexpected, yet deeply powerful moment, Jenny shares a ‘Sparked Exclusive' revealing that she began, almost covertly, creating something ‘from the mess' in hopes of helping others feel less alone in their struggles. She wonders: Can sharing our human flaws and uncertainties actually complement our expertise and advice, providing value in its own way?” More About Jonathan Fields: Jonathan Fields—the Good Life Guy—delivers insights that spark purpose, possibility, and potential. On a decades-long quest to discover what makes people come fully alive, Jonathan is an award-winning author, Webby-nominated producer, business innovator, and host of one of the world's top podcasts, Good Life Project. He is the author of Sparked: Discover Your Unique Imprint for Work that Makes You Come Alive.

Now that I'm one month into Rolling in D