“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 over time, why he’s piloting a new type of publishing contract with this book, how he felt when asked to leave a weekly poker game for not taking big enough risks, and how The Innovator’s Dilemma relates to companies like Google, NPR, and Netflix (he was in the room as NPR purposefully missed the boat on podcasting).

More About Seth: Seth Godin is a renowned author, entrepreneur, and marketing expert who has profoundly influenced modern business thinking through his blog, with over 9,000 daily posts and counting. Known for his innovative ideas on marketing, leadership, and personal growth, Godin has authored 22 bestselling books in over 39 languages. He is also the coordinator of The Carbon Almanac, which he calls “the most important project of my career.”

🌟 5 Key Takeaways from This is Strategy

• Social media: Avoid projects where the system is organized to take all the value you create.
• Building community: Create a strategy where the scale is the magic. Start by serving a small group of people who would miss us if we didn't exist.
• Pricing: Price is a story, a signal, and a symptom of your strategy. “Low price is the last refuge of a marketer who has run out of useful ideas."
• Decision-making: It's impossible to consistently have perfect outcomes. It's easier to imagine that we're able to make good decisions on a regular basis.
• Ignoring sunk costs: All of your assets and experiences are a gift from your former self. You're welcome to leave them behind.

📝 Permission

Stop seeking authority and start taking responsibility. Time is ours; sooner or later, the story we tell ourselves belongs to us. That doesn't mean it's easy. It just means that given the situation you're in, you could make something better and no one can stop you.

✅ Do (or Delegate) This Next

If you feel creatively stagnant, try switching up your environment. For example, Seth took train rides with no destination in mind to get into a writing groove. Bonus: Try asking Claude.ai to expand on a list or framework you’ve created. What might you be missing?

🔗 Resources Mentioned

• Seth on the web
• New Book: This Is Strategy
• Community: Purple.space
• Udemy course: This Is Strategy
• Publisher: Authors Equity
• Seth's articles: Books don’t sell and Firing the New York Times Bestseller List
• Rolling in Doh: Is Kevin Bacon in His Flop Era?
• 🚬 Smoking is Essential for Your Success, They Said 🙄
• If Your Business Could Talk, What Would It Say?
• People: Shawn Coyne of Story Grid
• Tools: Claude.ai

📚 Books Mentioned

• This Is Strategy
• Song of Significance
• The Practice: Shipping Creative Work
• Visit the shop to see all of Seth’s books . . .
• Your First 1,000 Copies
• The Innovator’s Dilemma
• Atomic Habits
• Thinking in Systems
• Free Time: Lose the Busywork, Love Your Business
• Pivot: The Only Move That Matters Is Your Next One
• Life After College

🎧 Related Episodes

• Seth’s podcast: Akimbo
• Free Time: 092: Train the System, Then the Person
• 056: Set Your Compass—Systems vs. Goals
• 268: Strategies for Surpassing “The Magic Number” of Book Sales, and 271: Todd Sattersten Part Two
• Pivot: 254: The Practice—On Generosity, Peculiarity, and Showing Up with Seth Godin

🌟Enjoying the show? The best way to thank us is by leaving a rating or review

✍️ Check out Jenny’s personal business essays on Substack, Rolling in D🤦🏻‍♀️h

💌 Subscribe to the Time Well Spent newsletter for access to the Free Time Toolkit

📝 Check out full show notes and share with friends: https://itsfreetime.com/episodes/272

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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.

🌟 5 Key Takeaways

• Advance copies are a marketing event: Will they do something with the physical book?
• Two B’s for categories of people that can be most helpful: bulk and broadcasters.
• Most book launch activities don’t scale: You are the beacon for people to find the book.
• Title should always be a change function: show the change that they will experience reading the book with the title, subtitle, and book description. 1) State the truth. 2) What's the surprise? 3) Twist to drive the point home.
• The Table of Contents is marketing copy! It should read like sales copy to draw people in. Chapter one is also marketing copy, and be sure to include a quick win, because most people won’t finish (sadly). Write short chapters! Give the reader payoffs.

📝 Permission

Drop the idea that your launch day is 24 hours. Taking a page from Tim Grahl’s Your First 1000 Copies, just do one thing a week. Use the HBO model of a little bit every week, not the Netflix binge release-watch.

✅ Do (or Delegate) This Next

With the Free Time book approaching its three-year bookiversary on March 22, 2025, help 🎁 give the gift of free time :D

• Don’t miss the handy Chapter Summaries and Leader Kit (PDFs)
• Want to try before you buy? Read the free excerpt here » (Web)
• Check out my author toolkit here »
• Take the Free Time reader survey I sent, whether you’ve read the book or not
• VIP Day with Jenny: via Free Time Operations Dashboard

🔗 Resources Mentioned

• Todd on the web, IG, X, LinkedIn, Bard Press
• Todd's Articles: The Magic Number, and The Few, The Many, and the Reality of Power Laws
• McSweeney’s: MY COMMENTS ARE IN THE GOOGLE DOC LINKED IN THE DROPBOX I SENT IN THE SLACK 
• What is Net Promoter Score (NPS)?
• Book Indexer: Michelle Guiliano — Line by Line Indexing (web) and This is indexing. (Substack)
• X thread by Jason Colavito: Publishing stats for 2022
• EPJ Data Science: Success in books: predicting book sales before publication

📚 Books Mentioned

• The One Thing by Jay Papasan and Gary Keller
• American Kingpin by Nick Bilton
• Your First 1000 Copies by Tim Grahl
• The Snowball System and Give to Grow by Mo Bunnell
• Free Time: Lose the Busywork, Love Your Business 
• Pivot: The Only Move That Matters Is Your Next One 
• Life After College 

🎧 Related Episodes

• Self-Publishing School: The Engineer Approach to Millions of Copies Sold with Todd Sattersten
• Billion Dollar Creator: 018: How to Write a Book That Sells for Decades with Tim Grahl
• Free Time: 268: Strategies for Surpassing “The Magic Number” of Book Sales
• 064: The Vulnerability of Launching
• 084: Sprinkling the First 1,000 Serendipity Seeds of a Launch
• 103: How to Land a Literary Agent and Publisher with David Moldawer (Part One) and (Part Two)
• 203: 🎢 Riding the Emotional Rollercoaster of Launching with Natalie Lue
• Pivot: 207: How to Develop Your Book and Big Idea (Part 1) and (Part 2)
• 49: The (He)art of Book Publishing Excerpt: Land a Traditional Publishing Deal — Q&A with My Editor at Portfolio/Penguin Random House

✍️ Check out my personal business essays at Rolling in D🤦🏻‍♀️h with Jenny Blake

💌 Subscribe to Free Time with Jenny Blake for access to the Free Time Toolkit

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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: 📦 Unpacking a Big Business Decision and Dissolving Related Doubts.

While I will be sad not to bring fresh episodes to your earbuds every week, I truly want to say thank you so much for being here. This only represents a small fraction of listeners, but I was genuinely touched receiving the Spotify Wrapped for Podcasters stats at the end of 2023 after I knew I would be pausing once all the episodes “in the can” went live.

• Among Pivot listeners: for 681 this show is in your top ten on Spotify, for 373 it’s in your top five, and for 65 of you, this is your number one show (again, at least in Spotify’s podcast player)!
• Among Free Time listeners: for 423 of you this show is in your top ten on Spotify, for 247 it’s in the top five, and for 57 it is your number one show in Spotify—the highest honor!! I was shocked to see even one, truly, with so much other incredible audio content out there.

There’s one thing I know for sure: I will miss you during this break 🥹

🌟 ;TLDR/L (Too Long Didn’t Listen) Top Takeaways:

• In addition to pausing my private community, I am pausing both podcasts for a bit (duration TBD) so I can clear financial and energetic space to listen to what my broader business wants to become.
• 🎧 Stay subscribed to both shows: Pivot with Jenny Blake and Free Time with Jenny Blake so that you still get episodes when I release them, even if a bit more sporadically (for now); I may switch to seasons if/when I resume
• 📧 Subscribe to any/all of my three Substacks if you’re not already: I hope to experiment with live tapings with interesting friends and guests, ones that are for paying subscribers where we can go into even more nitty gritty detail behind-the-scenes.

📝 Permission

Pause and regroup on any of your creative projects so you can create space to hear what’s next.

🔗 Resources Mentioned

• Rolling in D🤦🏻‍♀️h: 🏆 Time to Put the Trophies Away
• Do What You Love and the Money Will Follow . . . IF
• Rebuilding from Rubble
• 👟 A Strange and Wonderful Morning: Walking Photo Essay
• Dear 2024: A Letter and From 2024: A Reply
• What Works: Making the Content Math Work
• Edison Research: Podcasting’s Big Hits and Long Tail
• Adam Davidson: The Rise and Fall of Podcasting
• The Daily Beast: Malcolm Gladwell’s Media Empire is Being Torn Apart
• Podcast Production: One Stone Creative
• ListenNotes: Pivot, Free Time

📚 Books Mentioned

• Free Time: Lose the Busywork, Love Your Business
• Pivot: The Only Move That Matters Is Your Next One
• Life After College

🎧 Related Episodes

• SPARKED: Jenny in Conversation with Jonathan Fields (Spotify Playlist)
• BFF Bonus: Upcoming Quiet Sabbatical + Important Membership Updates
• Pivot: 329: Five Types of People-Pleasers from The Joy of Saying No with Natalie Lue
• 342: “Whatever Comes Through Me Comes For Me First,” With Nicole Antoinette
• 360: 📦 Unpacking a Big Business Decision and Dissolving Related Doubts with Adrian Klaphaak
• Free Time: 042: How I Run My Business Without Social Media (Pivot Replay)
• 203: 🎢 Riding the Emotional Rollercoaster of Launching with Natalie Lue
• 250: Do what you love and the money will follow . . . IF you meet at least 3 of these 20 criteria
• 🦧 What to Do When You Lose Your Biggest Client, Part One and Part Two

📝 Check out full show notes and share with friends: https://itsfreetime.com/episodes/270

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“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.

🌟 4 Key Takeaways

• “You should care a lot about what a few people think.” For Joey, it’s his wife, his children, his closest business advisors, longstanding clients. “I don’t want my creativity hampered by one person’s feedback.”
• “You need to know how to ask for the money.” Gem from Joey’s dad growing up on the most important thing to know when running your own business, about having confidence when you state the price and terms of your services without wavering.
• Don’t raise your prices just for the sake of raising them; however, as your expertise and capabilities and the cost of living and costs of running your business increase, there is a necessary understanding that prices will go up. Right before he hit send on a proposal, he would stop, go back to the original contract and raise the fee by ten percent.
• Price is something you pay at the grocery store; investment is something you are going to do to grow your operation and make it better. You will invest with me to grow your returns, and it will continue to pay dividends. As a speaker, you need to be clear on the return on investment that you’re promising.

📝 Permission

It is unbelievably challenging to start and run your own business. Because you are so bold to do that, give yourself permission to courageously set your boundaries. The more clear and comfortable you are stating how to work with you and holding firm when pushed, the happier you will be as a business owner, and the longer you will be in business.

✅ Do (or Delegate) This Next

Try Joey’s approach to sharing the investment for working together. List a range on your website, and the first time your desired client learns how much it costs to work with you should be hearing it from you, not reading a document.

🔗 Resources and Books Mentioned 📚

• Joey on the web, X (Twitter), LinkedIn
• Never Lose an Employee Again: The Simple Path to Remarkable Retention
• Never Lose a Customer Again: Turn Any Sale into Lifelong Loyalty in 100 Days
• Free Time: Lose the Busywork, Love Your Business
• Pivot: The Only Move That Matters Is Your Next One

🎧 Related Episodes

• Joey’s podcast: Experience This!
• Free Time: 083: Breaking through Buyer’s Remorse—Never Lose a Customer Again
• 201: Never Lose a Team Member Again with Joey Coleman
• Pivot: 155: Becoming a Successful Speaker with Grant Baldwin

📝 Check out full show notes and share with friends: https://itsfreetime.com/episodes/269

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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.

🌟 3 Key Takeaways

• A book launch is a set of activities to engage people and create momentum, and there is no common blueprint for success. “Each book is different—in its approach to a problem and delivery of solution. Each author is different—in what they bring to the launch. And the world itself is different every time you bring a book into the world.”
• The Magic Number: The data says is that if you can get into the 10,000 to 25,000 copy range for first year sales, you have a 42% chance of selling more than 25,000 copies in lifetime sales. If you get past that 10K mark, there is a 4 in 10 chance of getting beyond 25K copies sold.
• Endorsements should triangulate the reader to think this book is for them. Who is the highest comp author? A practitioner (someone doing the work or even a related recognizable company), a reader who demonstrates utility.

📝 Permission

Put your ego down. Remember, you want your readers to be better, to improve their lives. Our job is to find more people to help, and there are still so many opportunities for that. You don’t actually have to stop promoting the book after it’s launched—there is nobody stopping you!

✅ Do (or Delegate) This Next

Send a survey out to your readers and community, ideally 90 to 120 days after the book comes out. Check out the one Jenny sent here—and please take it if you can at the same time!

🔗 Resources Mentioned

• Todd on the web, IG, X, LinkedIn
• Publisher: Bard Press
• Take the Free Time reader survey Jenny sent here, whether you’ve read the book or not!
• Bard Press Articles: The Magic Number and The Few, The Many, and the Reality of Power Laws
• Net Promoter Score (NPS): https://en.m.wikipedia.org/wiki/Net_promoter_score
• Technology Adoption Life Cycle: Innovators → early adopters → early majority → late majority → laggards
• BookBub and The Fussy Librarian for ebook promotions
• Jenny’s Author Toolkit and Free Time Leader Kit

📚 Books Mentioned

• The One Thing by Jay Papasan and Gary Keller
• Atomic Habits by James Clear
• Your First 1000 Copies by Tim Grahl
• Free Time: Lose the Busywork, Love Your Business
• Pivot: The Only Move That Matters Is Your Next One
• Life After College

🎧 Related Episodes

• Self-Publishing School: The Engineer Approach to Millions of Copies Sold with Todd Sattersten
• Billion Dollar Creator: 018: How to Write a Book That Sells for Decades with Tim Grahl
• Free Time: 249: Systems for Selling Over One Million Books and 012: Generating Personal MBA Momentum with Josh Kaufman
• 117: Tiny Marketing Actions with Pamela Slim
• Pivot: 207: How to Develop Your Book and Big Idea (Part 1) and 208: Your Book and Big Idea (Part 2)
• 49: The (He)art of Book Publishing Excerpt: Land a Traditional Publishing Deal — Q&A with My Editor at Portfolio/Penguin Random House

📝 Check out full show notes and share: https://itsfreetime.com/episodes/268

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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.

🌟 3 Key Takeaways

• Laura’s 5 C’s of Productivity: Calm, Create, Capture, Consolidate, Close. Create a system that you truly trust: where new tasks get captured and where you know you will see them again. No matter when or where a loop comes from (i.e. on a walk), ensure you have systems in place for the entire loop lifecycle from capturing to closing.
• Five Ways to Say No to Incoming Requests: ask more questions to better understand the time commitment and see if it aligns with your top three priorities; say you’ll think about it or don’t respond right away to buy yourself time and prevent a knee-jerk response; imagine two scenarios playing out for yes and for no (to help you decide); say no, but _______ (send helpful resources); say no, because _______ (give a little context).
• The Laundry Method: Think about your inbox the way you think about your dryer. You would never process clothes one item at a time—whether drying, folding or putting away—and yet that’s how many people tackle email. Process in batches instead. Treat sorting, reading, and answering as separate activities. If you have only twenty minutes, pick one of those activities.

📝 Permission

Give yourself plenty of down time in order to have highly productive uptime; drop the guilt! Rest leads to better overall productivity.

✅ Do (or Delegate) This Next

Stop wasting energy points! Eliminate any emails from your inbox that you don’t need to see: the unread, notifications, newsletters (Jenny uses SaneBox for this), and make sure you help the things you need to see stick out.

🔗 Resources Mentioned

• Laura on the web, IG, LinkedIn
• Articles: Business Insider—6 tips a productivity advisor gives Google executives to better manage their email, meetings, and workload
• Google Blog—5 things I learned from Google’s productivity expert
• CNN—She helps Google workers be productive. Here are her pro tips.
• Video: Top 3 Google Workspace tips
• Apps: SaneBox, TextExpander, HelpScout

📚 Books Mentioned

• Uptime: A Practical Guide to Personal Productivity and Wellbeing
• Free Time: Lose the Busywork, Love Your Business
• Pivot: The Only Move That Matters Is Your Next One
• Life After College

🎧 Related Episodes

• Free Time: 019: Most Valuable Activities with Dave Crenshaw
• 154: The Hard No
• 027: Time Management for Mortals with Oliver Burkeman
• Pivot: 289: Stealing Wi-Fi as Career Strategy with Jenny Wood
• 307: Pivoting from Google to Launching People Playbook with Tony McGaharan
• 318: The Beauty of Late Bloomers with Jenna Valovic
• 309: Wayfinding and Developing Identity Agency with Ciela Hartanov

📝 Check out full show notes and share with friends: https://itsfreetime.com/episodes/267

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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.

🌟 3 Key Takeaways of the Framework Framework™

• Solves a problem (people know they have), answers a question (BookRx)
• Action-oriented → Transformation Journey or Comprehensive (Whole body/self/org). Name your process
• Memorable, concise name and stages (ideally 3 to 4 stages)
• Bonus: Tie-in a metaphor, hook, and/or story

📘 From Built to Sell:

• TED’S TIP # 3 Owning a process makes it easier to pitch and puts you in control. Be clear about what you’re selling, and potential customers will be more likely to buy your product.
• TED’S TIP # 6 Don’t be afraid to say no to projects. Prove that you’re serious about specialization by turning down work that falls outside your area of expertise. The more people you say no to, the more referrals you’ll get to people who need your product or service.

🔗 Resources Mentioned

• Here's a photo of my journal where I first started trying to piece the Free Time Framework together, brainstorming themes before eventually shifting from Mind/Time/Team to Align -> Design -> Assign :)
• Articles: Martha Beck’s Growing Wings: The Power of Change
• TED—The 7 types of rest that every person needs
• Wes Kao’s detailed LinkedIn post on how to turn your ideas into frameworks

📚 Books Mentioned

• Built to Sell
• The Referral Engine
• Finding Your Own North Star
• E-Myth Revisited
• The Power of Full Engagement
• The Lean Start-up
• Free Time: Lose the Busywork, Love Your Business
• Pivot: The Only Move That Matters Is Your Next One
• Life After College

🎧 Related Episodes

• BFF Bonus Workshops: Pamela Slim’s Certification and Licensing
• Stephanie Huston’s How to Batch Create and Customize Your Annual Content Calendar
• Free Time: 189: Jay Acunzo's walkthrough of his Intellectual Property (IP) Development OS — check out the diagram here
• 256: Behind-the-Business: 1:1 Voxer Coaching Summer Pop-Up—Structure, Systems & Pricing
• 135: How to Rapidly Prototype a Course (Pivot Replay from Dec. 2019)
• 187: Licensing 201 — Q&A on Pricing + Packaging, Train-the-Trainer, Delivery, and Legal
• 186: Licensing 201 — Q&A on Product Development, Attracting Clients, and Sales Process
• 185: How Licensing Helps Serve the Queen Bee Role + Stop Keeping up with the EntrepreJoneses with Mike Michalowicz
• 140: How to License Your IP (Intellectual Property)
• Pivot: 281: Feeling Impostery? Become a Qualified Curator Instead of an End-All-Be-All Expert

🌟Enjoying the show? The best way to thank us is by leaving a rating or review

✍️ Check out Jenny’s personal business essays on Substack, Rolling in D🤦🏻‍♀️h

💌 Subscribe to the Time Well Spent newsletter for access to the Free Time Toolkit

💬 I’d love to hear what’s on your mind! Take the Free Time listener survey

🎧 Make sure you’re subscribed wherever you listen to podcasts

📝 Check out full show notes and share with friends: https://itsfreetime.com/episodes/266

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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🤦🏻‍♀️h. Thank you for listening, and huge thanks to our contributors to this series!

📝 Contributors & Permission Slips:

• Stephanie Polen, founder of The Polen Group: “Give yourself permission to be emotional and recognize that that's your humanity - that is the thing that makes you special and the work that you do. And it's probably why that big client hired you in the first place.”
• Khe Hy, founder of RadReads: “View these challenges not as a death of identity, but an opportunity to recalibrate your emotional resilience.”
• Marisol Dahl, cofounder of Together Agency: “When you part ways with a big client, give yourself permission to take a beat so that you can reflect and digest on your own experience with this client.”
• Chris Wilson, founder of Simplify Your Why: “Try more experiments with your business; give yourself the chance to iterate and fail (it helps if you live below your means!). It's rare that your first business model will work.”
• Maya Middlemiss, founder of Remote Work Europe: “Give yourself permission to do something for yourself in terms of your interests and professional development. Don't let anybody own so much of your time.”
• Check out the other half here, from Kelli Thompson, Kristoffer Carter, Pamela Slim, and Charlie Gilkey: 264: What to Do When You Lose Your Biggest Client (Part One)

🔗 Articles Mentioned

• Rolling in D🤦🏻‍♀️h
• This is a Wonderful Day
• An Honest Accounting: Part One, Part Two, Part Three
• Am I Running a Zombie Business? Part One and Part Two
• Ghost Self: Part One, Part Two, Part Three

📚 Books Mentioned

• The Big Leap by Gay Hendricks (mentioned by Chris Wilson)
• Free Time: Lose the Busywork, Love Your Business
• Pivot: The Only Move That Matters Is Your Next One
• Life After College

🎧 Related Episodes

• Free Time: 264: What to Do When You Lose Your Biggest Client (Part One)
• 173: Cut Your Losses—Even While Pivoting in Public—with Khe Hy
• Check out our full Rad Reads x Pivot Spotify Playlist
• Pivot: 355: Building a Brand Strategy from Scratch with Adam Chaloeicheep of Together Agency and 356: Four Brand Personas with Adam Chaloeicheep
• Future is Freelance with Maya Middlemiss: From Freelancing to Delightfully Tiny Teams: Embracing Automation, Empowerment, and Emojis with Jenny Blake

🌟Enjoying the show? The best way to thank us is by leaving a rating or review

✍️ Check out Jenny’s personal business essays on Substack, Rolling in D🤦🏻‍♀️h

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📝 Check out full show notes and share with friends: https://itsfreetime.com/episodes/265

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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🤦🏻‍♀️h, you know that the origin story for my new-ish paid Substack was losing my biggest, most beloved corporate client in the summer of 2023. Getting The News shook me up so much because not only was it one of my longest-running favorite licensing clients, but it also represented at least six figures of income for the next six months being instantly wiped off the table.

Now, at least, we will all have something to turn to (and return to). My goal is not to provide advice but rather to offer some comfort through the voices of some of my dearest friends and favorite Heart-Based Business owners who are speaking from experience about how they've handled situations just like this.

Maybe you don't need this episode right now, but if something does happen in the future (even if we hope not), you'll remember that you can come back and listen on a proverbial rainy day.

Please share with any fellow business owner friends who might be going through a tough time, and enormous thanks to the wonderful group of friends and former podcast guests who shared their stories for this two-part episode!

📝 Contributors & Permission Slips:

• Kelli Thompson, author of Closing the Confidence Gap: “Diversify your business income and give yourself permission that you can do a lot of things that align with your mission, but offer it in many different ways that feel good for you.”
• Kristoffer ‘KC’ Carter, author of Permission to Glow: “Drop the self-judgment, give yourself more self-compassion, and just get back to work with creating the next even better client.”
• Pamela Slim, author of The Widest Net: “Give up the idea that you are in control of the success of your business. When you release that idea, then you can be more curious about how to step in and fix things that aren't working.”
• Charlie Gilkey, author of Team Habits: “Do not take the client loss personally. Stand tall, take care of yourself, and go get your next client.”

🔗 Articles Mentioned

• Rolling in D🤦🏻‍♀️h
• This is a Wonderful Day
• An Honest Accounting: Part One, Part Two, Part Three
• Am I Running a Zombie Business? Part One and Part Two
• Ghost Self: Part One, Part Two, Part Three

📚 Books Mentioned

• Closing the Confidence Gap by Kelli Thompson
• Permission to Glow by Kristoffer ‘KC’ Carter
• Escape from Cubicle Nation, Body of Work, and The Widest Net by Pamela Slim
• Start Finishing and Team Habits by Charlie Gilkey
• Free Time: Lose the Busywork, Love Your Business
• Pivot: The Only Move That Matters Is Your Next One
• Life After College

🎧 Related Episodes — Part One

• Free Time: 188: Energy Capacity Planning, Pricing, and Finding Resonant Masterminds with Kelli Thompson
• 039: Permission to Glow with Kristoffer (KC) Carter
• 117: Tiny Marketing Actions with Pamela Slim
• 143: Exploring Time, Money, and Energy Capacity with Tara McMullin and Charlie Gilkey
• 091: Quarterly Planning with Charlie Gilkey
• Pivot: 315: Intuition-Building, Spotting Pedestal Syndrome, and Closing the Confidence Gap with Kelli Thompson
• 136: Start Finishing—Pricing, Projects, and Momentum Planning with Charlie Gilkey

📝 Check out full show notes and share with friends: https://itsfreetime.com/episodes/264

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“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.

🌟 3 Key Takeaways

• Three small business stages most relevant to tiny business owners (adapted from HBR): Validate—product-market-founder fit; Sell—repeatable and predictable marketing and sales; Foundation—process, team, culture)
• Relationship- versus traffic-based sales and metrics: Relationship-based business are going for smaller reach, with ideally at least a fifty-percent conversion rate on sales calls. Traffic-based marketing aims at bringing in much bigger audiences, with smaller conversion rates for things like selling digital products (pushing a boulder up hill).
• Three marketing stages: Awareness (imagine a snowball running downhill—people need to have a really big moment with you; you’ve made 80% of the sale by blowing their mind during the awareness stage) engagement, and sales.

📝 Permission

Focus on sequence over strategy: you can execute strategies perfectly, but if you’re doing them in the wrong order, it’s not going to do a thing for you.

✅ Do (or Delegate) This Next

Take five minutes a day to reach out to one person across any of these four themes: thank you’s (be specific!), connections, asks, and catch-ups.

🔗 Resources Mentioned

• Michelle on the web, IG, Twitter, LinkedIn
• Articles: HBR—The Five Stages of Small-Business Growth
• Rolling in D🤦🏻‍♀️h—Climbing Down the Entrepreneurial Ladder, An Honest Accounting (Part One)
• People: Margo Aaron, Pamela Slim, Jay Acunzo
• Tiny + Strong Table Talk: Michelle’s free monthly Q&A if you need a good idea, fresh perspective or to get inspired by what others are thinking and doing. Register here.

📚 Books Mentioned

• Free Time: Lose the Busywork, Love Your Business
• Pivot: The Only Move That Matters Is Your Next One
• Life After College

🎧 Related Episodes

• Off the Grid: Leaving Social Media Without Losing All Your Clients — Relationship Marketing with Michelle Warner
• Free Time: 042: How I Run My Business Without Social Media
• 181: Be Irreplaceable with My Creative Coach Jay Acunzo
• 117: Tiny Marketing Actions with Pamela Slim
• 261: Cringe-Free Launches and Evergreen Sales Considerations with Anne Samoilov
• 165: Are your clients bringing out the best in you? Engineering the Evolution of Your Business and 229: How (and When) to Trust Yourself and Others with Ilise Benun
• 138: ⛵️Stop Sailing the Sea of Shiny Shoulds
• 136: Why I Stopped Exploring Selling the Pivot Brand and Business

📝 Check out full show notes and share with friends: https://itsfreetime.com/episodes/263

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“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🤦🏻‍♀️h—you can read the post and reply in the comments here: Climbing Down the Entrepreneurial Ladder.

📝 Permission

Celebrate your own -phoria, the joy in running your business in the way that works best for you!

🔗 Resources Mentioned

• D🤦🏻‍♀️h Articles: Love That! For You 🙄, COnTenT cReaToRs exist and subsist in the verrrrrrry looooooooooooong tail’s trough, 🤬 Rant From the Wound: Why This Platitude Meme Engraged Me, Serendipity signage
• Katherine Raz on closing the second location of her Fernseed business in Tacoma
• Emily McDowell’s experience of running a small business that blew up—in a good way—but also led to burnout: The truth about going mega-viral, part one and part two.
• Nathan Barry’s The Ladders of Wealth Creation
• Jonathan Field’s The Unfortunate Middle
• JB for CNBC: Treat your career like a smart phone, not a ladder
• NYT: Climbing Down the Corporate Ladder. Big thanks to Rob Walker for including me in this Workologist column! It’s still a career highlight. He’s now here on Substack at The Art of Noticing
• Video: If you want to geek out further on idea gathering process: here’s a Loom walkthrough of my Collection Bucket in Notion.
• Recent Free Time workshop by Stephanie Huston with a template for creating and batching content for the year ahead.
• Apps: Substack

📚 Books Mentioned

• I’m not immune from status-chasing—none of us are. In his book, The Status Game, Will Storr categorizes these games into three types: dominance, success, and virtue. My two all-time favorite books on this topic are Alain de Botton’s Status Anxiety and Wanting by Luke Burgis who is on Substack at Ride or Drive and Anti-Mimetic.
• Free Time: Lose the Busywork, Love Your Business
• Pivot: The Only Move That Matters Is Your Next One
• Life After College

🎧 Related Episodes

• Listen to the audio version of Jonathan Fields reading “The Unfortunate Middle” here, and check out our series of 12 SPARKED episodes (Spotify Playlist).
• Pivot: 305: Is What You’re Wanting Actually What’s Best For You? With Luke Burgis
• Pivot x RadReads conversations on status with Khe Hy (Spotify Playlist)
• Free Time: Here are some of my favorite Free Time conversations with small business owners who downsized their operations:
• 016: IP Licensing and “No Full-Time Employees” with Lee LeFever
• 131: Scaling Joy While Streamlining Business Overhead with Kaneisha Grayson
• 157: Downshifting to a Delightfully Part-Team Team with Laura Roeder
• 173: Cut Your Losses—Even While Pivoting in Public with Khe Hy
• 205: Turning Down a $200K Two-Book Traditional Publishing Deal with Paul Millerd
• 241: Finding Freedom and Financial Reciprocity through a Paid Newsletter

📝 Check out full show notes and share with friends: https://itsfreetime.com/episodes/262

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