Pivot with Jenny Blake
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Pivot with Jenny Blake episodes

  • 343: 🥳 Five Questions and Attempted Answers for My 40th Birthday

    I love celebrating big milestones here on the pod, so in honor of my 40th birthday tomorrow, I decided to do something a little different for today's solo episode.

    In lieu of a “40 things I’ve learned in 40 years listicle,” since I am only sure of less as time passes, I asked my husband Michael if he could think of four questions for me to answer. He threw in a bonus in the middle that nearly made me spit out my coffee :)


    🌟 Michael’s Five Questions
    1. In this new world full of daily disasters, how do you find the courage to be vulnerable?
    2. Systems play a big role in freeing up your time. What is THE system you implemented that had the most significant positive impact on your life?
    3. Do you still love Tim Ferriss more than me? Why or why not? (See also: Michael’s googley-eyed book signing interaction at SXSW)
    4. What are you most looking forward to in this new decade of your life?
    5. Who are the 3 people, dead or alive you’d love to have on your podcasts?

    6. 🔗 Resources Mentioned
      Articles: Oprah.com—What is Your Happiness Formula? (Jenny’s guest post after Pivot launched!) and The Oprah Winfrey Show Finale. Quote mentioned:

      "I've talked to nearly 30,000 people on this show, and all 30,000 had one thing in common: They all wanted validation. If I could reach through this television and sit on your sofa or sit on a stool in your kitchen right now, I would tell you that every single person you will ever meet shares that common desire. They want to know: 'Do you see me? Do you hear me? Does what I say mean anything to you?’”

      • Newsletter: Tim Ferriss’ Five-Bullet Friday
      • Coffee: Tim’s and I also love my monthly surprise bag via Trade
      • Rolling in D🤦🏻‍♀️h: Fearing the Other Shoe—Part One, Part Two; Getaway Car
      • The Mount in Lenox, MA (Edith Wharton’s Estate)
      • Loom Video: Walkthrough of Jenny’s Idea Collection bucket (Notion)
      • Tools: Readwise, Notion, Done-for-you Free Time Operations Dashboard, Substack

        📚 Books Mentioned
        • Building a Second Brain by Tiago Forte
        • The 4-Hour Workweek by Tim Ferriss
        • Letters to a Young Poet by Rainer Maria Rilke
        • Three Novels of New York: The House of Mirth, The Custom of the Country, The Age of Innocence by Edith Wharton
        • Free Time: Lose the Busywork, Love Your Business
        • Pivot: The Only Move That Matters Is Your Next One
        • Life After College

        • 🎧 Related Episodes
          • BFF Bonuses: 098: Moving Through Vulnerability Hangovers
          • The Writing Practice That Changed My Life
          • Free Time: 031: Eleventh-Hour Creative Gremlins
          • 111: Building a Second Brain with Tiago Forte
          • Pivot: 220: Protect Your Flame with Michael Karsouny + Adventure Meditation!
          • 127: Live from the Vulnerability Hangover! Launching @LifeOfALebaneseArtist with Michael Karsouny
          • 342: “Whatever Comes Through Me Comes for Me First,” with Nicole Antoinette
          • 158: Trip Report—Oprah's 2020 Vision Tour

          • ✍️ Connect with me on Substack: http://substack.com/@jennyblake

            ❤️ Enjoying the show? I'd be grateful for a rating and/or review! Even better? Share this episode with a friend :)

            💌 Get my curated twice monthly PivotList newsletter

            💻 Check out Pivot courses on LinkedIn Learning: Figuring Out Your Next Move, Holding 1:1 Career Conversations, Managing Introverts, Coaching New Hires, and Coaching New Managers

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

            ☎️ Submit a question or comment for future episodes

            🎧 Make sure you’re subscribed wherever you listen to ‘casts

            📝 Check out full show notes at http://pivotmethod.com/343

            Learn more about your ad choices. Visit megaphone.fm/adchoices

            28 min
          • 342: “Whatever Comes Through Me Comes for Me First,” with Nicole Antoinette

            “So many things in my past were painful because I stayed on too long.” How do you know when it’s time to say goodbye to something, no matter how good it may seem or how hard it is to leave? For today’s guest, Nicole Antoinette, staying too long created a pattern of “scorched earth change,” where dramatic moves became the only way out.

            In this conversation, we discuss where she thinks the creator economy is heading, why she shut down her successful Patreon, and how she makes tough decisions about what to leave behind: whether it’s a romantic relationship, a job, a friendship, alcohol, or one of her biggest income streams.

            More About Nicole: 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 newsletter on Substack called Wild Letters.


            🌟 3 Key Takeaways
            • Think of your creative light on a dimmer switch: Is your work helping you feel alive and vibrant? Notice when the dimmer starts going down. As Nicole says, “I start have a sense that the heat or light is leaving something, I am not as energetically pulled any longer.”
            • Dig deeper to break the burnout cycle: While in a period of creative recovery, consider not just what a more sustainable business model looks like, but a more regenerative one.
            • Just because you can handle something, doesn’t mean it’s what is best for you. “Over and over again, I have been shown that wanting to change is reason enough, wanting to walk away from something is reason enough,” Nicole says. “98 plus percent of the time, it's not that I don't know what I want, it's just that it's easier to say I don't know than it is to say, ‘I know exactly what I want, but I'm afraid that I can't have it, or I don't know how to get it.’”


              ✅ Try This Next: Break out of the all-or-nothing mindset. Give yourself permission to end things early, with grace—and no other “good” reason than you want to—before you reach “scorched earth” burn-it-all-down mode from staying too long.


              🔗 Resources Mentioned
              • Nicole on the web, IG: @nic.antoinette
              • Substack: Wild Letters
              • Adventure writing: Backpacking Books
              • Patreon: Honest Conversation Club
              • Coworking: Get Sh*t Done Club
              • Jenny’s BFF Community

                📚 Books Mentioned
                • How To Be Alone: an 800-mile hike on the Arizona Trail
                • Free Time: Lose the Busywork, Love Your Business
                • Pivot: The Only Move That Matters Is Your Next One
                • Life After College

                • 🎧 Related Episodes
                  • Nicole’s podcasts: Real Talk Radio and The Pop-Up Pod
                  • Good Life Project: Ann Patchett | On Solitude, Writing & Indie Bookstores
                  • Pivot: 327: 🐺The Wolf You Feed — On Addiction, Recovery & Codependency — and What We Get Wrong About All Three with Eric Zimmer
                  • 302: Moving Beyond Burnout with Dr. Susan Biali Haas
                  • 338: Is Midlife Messing With Your Enoughness? With Mandy Lehto
                  • 305: Is What You Are Wanting Actually What’s Best For You? With Luke Burgis
                  • Free Time: 141: Process, Permission Slips, and Business Pivots with Tara McMullin
                  • 042: How I Run My Business Without Social Media
                  • 183: Letting Go of Productivity Guilt with Madeleine Dore
                  • 205: Why Paul Millerd Turned Down a $200K Two-Book Traditional Publishing Deal

                  • ❤️ Enjoying the show? I'd be grateful for a rating and/or review! Even better? Share this episode with a friend :)

                    📝 Check out full show notes at http://pivotmethod.com/342

                    Learn more about your ad choices. Visit megaphone.fm/adchoices

                    1 hr
                  • 341: Pivoting from Prestigious Consulting Jobs to the Pathless Path with Paul Millerd

                    “I was in the wrong environment, playing the wrong game . . . so I started self-sabotaging.”

                    That’s how today’s guest, Paul Millerd, knew it was time to opt out of conventional thinking about his career, and turn slowly but deliberately in a new direction. In this conversation we talk about how important it is to define enough, develop an immunity to what other people are doing, and his mantra, “coming alive over getting ahead.”

                    Be sure to listen to our Free Time conversation 205: Why Paul Millerd Turned Down a $200K Two-Book Traditional Publishing Deal, and our conversation for Paul’s podcast, Pathless Path on 156: Saying "no" to something good.


                    More About Paul: Paul Millerd is an independent writer, freelancer, coach, and digital creator. He is the author of The Pathless Path: Imagining a New Story for Work and Life, in which he explores the invisible scripts that constrain our lives. He is also the host of The Pathless Path podcast where he talks with the most interesting people on unconventional paths**.**


                    🌟 3 Key Takeaways
                    • Be wary of the achievement narrative: If you don’t define “enough” for yourself, it’s easy to default to more, which makes it impossible to understand when to say no.
                    • The trap of prestigious career paths: Instead of thinking about what you want to do with your life, you default to the options, norms, and desires most admired by your peers.
                    • Embracing the pathless path requires grappling with the feeling of being a bad egg

                      ✅ Try This Next

                      Paul’s process for new ideas: ship, quit, and learn. What small experiments can you set up that you can quit quickly? How can you take action in the next week, and design it for quitting?


                      🔗 Resources Mentioned
                      • Paul on the web, IG: @pathlesspaul, Twitter, LinkedIn, Facebook, YouTube
                      • Articles: Paul’s Substack, essays, Ben Hunt’s Epsilon Theory—The Industrially Necessary Egg, Rad Reads—The $645,099 Business Pivot
                      • Reflections on Saying No to a Book Deal & Betting on Myself #219, Original Twitter thread, and From Blog to Book: How to Self-Publish on Your Own Terms
                      • Swag: StickerMule (Bubble Envelopes)
                      • Tools and Templates: Jenny’s Author Toolkit

                        📚 Books Mentioned
                        • The Pathless Path: Imagining a New Story for Work and Life
                        • Free Time: Lose the Busywork, Love Your Business
                        • Pivot: The Only Move That Matters Is Your Next One
                        • Life After College

                        • 🎧 Related Episodes
                          • **The Pathless Path with Paul Millerd:** Ben Hunt on Industrially Necessary Paths & How To Live In The Now
                          • Free Time’s full Behind-the-Book Playlist (Spotify), 205: Why Paul Millerd Turned Down a $200K Two-Book Traditional Publishing Deal, 173: Cut Your Losses—Even While Pivoting in Public—with Khe Hy
                          • Pivot: Rad Reads x Pivot (Spotify playlist)


                            ❤️ Enjoying the show? I'd be grateful for a rating and/or review! Even better? Share with a friend :)

                            💌 Get my curated weekly(ish) PivotList newsletter

                            ✍️ Connect with me on Substack: http://substack.com/@jennyblake

                            💻 Check out Jenny’s Pivot courses on LinkedIn Learning: Figuring Out Your Next Move, Holding 1:1 Career Conversations With Your Team, Managing Introverts, Coaching New Hires, and Coaching New Managers

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

                            ☎️ Submit a question or comment for future episodes

                            🎧 Make sure you’re subscribed wherever you listen to ‘casts

                            📝 Check out full show notes at http://pivotmethod.com/341

                            Learn more about your ad choices. Visit megaphone.fm/adchoices

                            42 min
                          • 340: 8 Lessons Learned from 8 Years of Hosting the Pivot Podcast

                            We are celebrating a very special milestone today—the Pivot podcast’s eighth birthday! It's a veritable third-grader by now.

                            This podcast first launched in September 2015 as a teeny tiny scrappy side project to supplement the Pivot book while I was writing it. I had so much fun interviewing people and hitting record that by the time the book launched in the fall of 2016 one year later, the podcast had almost eclipsed it as the favorite thing that I do on a day-to-day basis.

                            Now, thanks to you, we have over 2 million downloads and 340 episodes (not including another 230 on the Free Time podcast). There have been many ups and downs along the way, where I wondered if I should stop doing this podcast. Today, I'm sharing eight things that help me stay in the game.


                            🌟 8 Key Takeaways
                            1. Ride out the inevitable dips and plateaus: Ask, how can I fall in love with this again? Keep the bar high—strive for jump-out-of-the-chair-with-glee-to-record level of guests and topics.
                            2. (Re)connect with the even more meaningful metrics: Don’t obsess over download numbers or charts. They can be instructive, but they don’t have to be the one-and-only indicator of whether or not to continue.
                            3. 51/49: My antidote to inexplicable nerves and overthinking: 49% fear and anxiety, 51% take one small step forward. Just tip the scale toward action by two percent.
                            4. Eyes on your own paper: Don’t get lost in what other people are doing or how fast they are going. Remind yourself what’s in it for you, regardless of what “the competition” is up to. There may even be downstream benefits of having others in the same space.
                            5. Keep up with new software, don’t worry too much about sunk costs: While you want to avoid chasing shiny software objects, don’t be afraid to jump from one lily pad to the next when it improves your systems and process.
                            6. Hire help! To truly achieve consistency escape velocity, hire a team so that someone else owns the outcome and you can show up and do what only you can do.
                            7. Go your own way: Be aware of diminishing returns on shiny shoulds that, if you were to chase them, would stop you from doing the creative thing you enjoy altogether.
                            8. Keep experimenting—one might say pivoting! There is no there there. The project will evolve alongside you, even when you lose steam for a little bit. You will always find a new way forward. And if you’re so stuck you truly can’t see straight, it’s okay to call it quits too.

                              🔗 Resources Mentioned
                              • Articles: Rolling in D🤦🏻‍♀️h—The Business Yips & 51/49
                              • Tools: Substack app, Kajabi, Notion, Riverside.fm, Descript
                              • Loom Walkthrough: Day in the Life of a Podcast Episode

                                📚 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
                                  • Pivot: 281: Feeling Impostery? Become a Qualified Curator Instead of an End-All-Be-All Expert, 346: Title with Marc Lesser (coming soon!), Pivot x Career Pathfinder podcast episodes with Adrian (Spotify playlist)
                                  • Free Time: 181: Be Irreplaceable with My Creative Coach Jay Acunzo, 223: The Confidence Trap: Why You Don’t Need It to Do Big Things (SPARKED Crossover), 180: 📉 Diminishing Returns and the True Costs of Shiny Shoulds, 138: ⛵️Stop Sailing the Sea of Shiny Shoulds, 196: 🍩 What Do Donuts, Coffee, Conversation, and Energy Cliffs Have in Common?, 130: Day in the Life of a Podcast Episode + How I Prepare for Guests


                                    ❤️ Enjoying the show? I'd be grateful for a rating and/or review! Even better? Share this episode with a friend :)

                                    💌 Get my curated twice monthly PivotList newsletter

                                    ✍️ Connect with me on Substack: http://substack.com/@jennyblake

                                    📝 Check out full show notes at http://pivotmethod.com/340

                                    Learn more about your ad choices. Visit megaphone.fm/adchoices

                                    36 min
                                  • 339: Moneyzen—Leaving the Cult of More with Manisha Thakor

                                    “To live a rich, joyful, and connected life . . . achieve less.” That’s the counterintuitive path to MoneyZen that this week’s guest Manisha Thakor shares.

                                    For the first half of her life, money represented a scorecard of self-worth and a sense of safety. She says, “For a long time, the equation I operated on was net worth = self worth (which has no end in sight).”

                                    Even with abundant salaries from her financial services roles, Manisha fell into The Cult of Never Enough, often displayed in “the peacock feathers of possessions.” Listen to learn more about the powerful shifts she made toward joy-based spending instead.

                                    More About Manisha: Manisha Thakor is the author of MoneyZen: The Secret to Finding Your "Enough” and has worked in financial services for over thirty years, helping individuals of all ages to balance financial health and emotional wealth.


                                    🌟 3 Key Takeaways
                                    • Societal forces are constantly telling us we should earn more, so we can buy more, in order to be more, “the peacock feathers of possessions”
                                    • Buy few, but buy the best you can afford at that time
                                    • MoneyZen (calm, confidence, clarity) = Financial Health + Emotional Wealth


                                    • ✅ Try This Next

                                      Try joy-based spending. Take a piece of paper, and every time you spend money, write down the item and the amount. At the end of the week or month, highlight anything you spent money on that didn’t bring you joy, what Manisha calls money leaks. Bonus: Every day, eliminate one thing you no longer need from your life (either clutter around the house or even obligations or meetings you no longer want to keep).


                                      🔗 Resources Mentioned
                                      • Manisha on the web, IG: @manishathakor, Twitter, LinkedIn, YouTube, Facebook
                                      • Quiz: Are You Trapped in The Cult of Never Enough?
                                      • Articles: What If You Already Have Enough Money? (The Cut), How Your Money Mindset Can Lead to Burnout at Work (Forbes), Stop Lying To Yourself About Why You Work So Much (Fast Company)

                                        📚 Books Mentioned
                                        • MoneyZen: The Secret to Finding Your "Enough” by Manisha Thackor
                                        • Your Money or Your Life by Vicki Robin and Joe Dominguez
                                        • Free Time: Lose the Busywork, Love Your Business
                                        • Pivot: The Only Move That Matters Is Your Next One
                                        • Life After College

                                        • 🎧 Related Episodes
                                          • Pivot: 338: Is Midlife Messing with Your Enoughness? with Mandy Lehto
                                          • Free Time: 028: When the Financial Tides Recede


                                            ❤️ Enjoying the show? I'd be grateful for a rating and/or review! Even better? Share this episode with a friend :)

                                            💌 Get my curated weekly(ish) PivotList newsletter

                                            💻 Check out Jenny’s Pivot courses on LinkedIn Learning: Figuring Out Your Next Move, Holding 1:1 Career Conversations With Your Team, Managing Introverts, Coaching New Hires, and Coaching New Managers

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

                                            ☎️ Submit a question or comment for future episodes

                                            🎧 Make sure you’re subscribed wherever you listen to ‘casts

                                            📝 Check out full show notes at http://pivotmethod.com/339

                                            Learn more about your ad choices. Visit megaphone.fm/adchoices

                                            43 min
                                          • 338: Is Midlife Messing with Your Enoughness? + Busting Not Enough Scams with Mandy Lehto

                                            “Legacy isn’t something you leave, it’s something you live.”

                                            These are just some of the wise words from this week’s guest, Mandy Lehto, who shares strategies for letting go of being a hard-o-holic, nexting, navigating mid-career pivots, and busting all manner of other “not enough” scams.

                                            More About Mandy: Mandy Lehto is a speaker, writer and coach with a Doctorate from Cambridge University and in her former career she was a director at a global investment bank. Mandy is the host of Enough, the podcast, a show for recovering perfectionists and overachievers. When Mandy isn't coaching leaders, she's parenting her two musical teenagers with her husband, or walking Herbie, her toy poodle, on Wimbledon Common.


                                            🌟 3 Key Takeaways
                                            • “Legacy isn’t something you leave, it’s something you live.” What if you embraced more of who you are, quirks and all, rather than trying to please or achieve?
                                            • Not-enough scams are false beliefs, that once we play through them enough times, becomes automated. Our mind wants to automate as much as it can.
                                            • Nexting is our compulsion to continue being dazzled by the mirage shimmering on the horizon that the next thing for sure will fill the void inside us.

                                              ✅ Try This Next

                                              Pick your inner critic that hogs the mic and name it, even something provocative (Mandy’s is Judgy Janet). And also name your inner champion, the wise voice that’s always rooting for you. Give them fun names so you don’t take this all too seriously :)


                                              📚 Books Mentioned
                                              • From Strength to Strength by Arthur Brooks
                                              • Free Time: Lose the Busywork, Love Your Business
                                              • Pivot: The Only Move That Matters Is Your Next One
                                              • Life After College

                                              • 🔗 Resources Mentioned
                                                • Mandy on the web, Instagram: @mandylehto, Twitter, LinkedIn, Pinterest
                                                • People: Arthur Brooks
                                                • Articles: Jennifer Lopez article in Vogue
                                                • Video: Mark Hyman’s podcast with Robert Waldinger

                                                  🎧 Related Episodes
                                                  • Enough, the podcast: 50: Is Middle-Age Messing with your Enoughness?, 36: Busting your not-enough scams, I’m burnt out but I keep pushing
                                                  • Pivot: 319: Who’s Sitting in the Board Room of Your Brain? with Adrian Klaphaak, 329: Five Types of People-Pleasers from The Joy of Saying No with Natalie Lue, 282: The Honor Roll Hangover with Melody Wilding, 056: Perfection Detox with Petra Kolber
                                                  • Free Time: 180: 📉 Diminishing Returns and the True Costs of Shiny Shoulds, 166: Crashing into Quiet Time


                                                    ❤️ Enjoying the show? I'd be grateful for a rating and/or review! Even better? Share this episode with a friend :)

                                                    💌 Get my curated weekly(ish) PivotList newsletter

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

                                                    ☎️ Submit a question or comment for future episodes

                                                    🎧 Make sure you’re subscribed wherever you listen to ‘casts

                                                    📝 Check out full show notes at http://pivotmethod.com/338

                                                    Learn more about your ad choices. Visit megaphone.fm/adchoices

                                                    50 min
                                                  • 337: Cut Your Losses—Even While Pivoting in Public—with Khe Hy (Free Time Crossover)

                                                    “How did you go bankrupt?" Two ways. Gradually, then suddenly.” —Ernest Hemingway

                                                    That’s the kick-off quote from returning guest Khe Hy’s recent pivot-in-progress big reveal, taking us behind the scenes of his business in a recent post titled, “The $645,099 business pivot.” Khe is the founder of RadReads and former Wall Street managing director.

                                                    Khe returns to the pod today (as our first three-peat Free Time guest) to share his experience from the belly of the Pivot beast. If you haven’t already, be sure to check out Khe’s earlier Free Time appearances, linked in the Resources section below and in this Spotify playlist: RadReads x Pivot x Free Time.

                                                    This crossover episode originally aired on the Free Time podcast on March 21, 2023.

                                                    More About Khe: Khe Hy is the founder and CEO of RadReads, an online education company that helps professionals lead productive, examined, and joyful lives. Khe is creator of the $10K Work productivity method and teaches the popular cohort-based course Supercharge Your Productivity. RadReads provides guides, trainings, and coaching for over 36,000 professionals to help them gain back free time, scale their impact and make their little dent in the universe.


                                                    🌟3 Key Takeaways:

                                                    • You’re not alone: Don’t feel bad if you caught a momentum wave during the pandemic that has vanished since. It can feel like you’ve captured success in a bottle, and it will continue just the way you’re experiencing it now, but the same circumstances rarely last.
                                                    • Borrowing other people’s goals can lead to chasing arbitrary success metrics and other people’s work-life balance. Instead, follow the fun! Ultimately, it will be much more sustainable.
                                                    • There’s freedom and surrender in openly sharing your process. Many entrepreneurs are not straightforward about how difficult it can be to maintain and grow a business, and being outwardly transparent helps you be inwardly honest about what you really want to accomplish.


                                                      📝Permission: To feel. To cry. To fully experience and talk about what you’re going through. Your humanity in the situation is not at odds with who and how you want to be as a founder and CEO—they are perfectly intertwined.


                                                      ✅Do (or Delegate) This Next: Get quiet: What is it that you truly want? What part of my business is driven by ego and “borrowing other people’s goals,” and what part is driven by the pure magic of it? For any friction area where you feel stuck or drained, take a page out of Khe’s business playbook and “follow the fun.” What would following the fun tell you to do next?

                                                       

                                                      📘Books Mentioned:

                                                      • Free Time: Lose The Busywork, Love Your Business
                                                      • Pivot: The Only Move That Matters Is Your Next One
                                                      • We Should All Be Millionaires: A Woman’s Guide to Earning More, Building Wealth, and Gaining Economic Power by Rachel Rodgers


                                                        🔗Resources Mentioned:

                                                        • Khe on the web, Instagram: @radreadsco, TikTok: @radreadsco, Twitter, LinkedIn
                                                        • Courses: Supercharge Your Productivity, $10K Work Accelerator, Life Operating System, Jenny’s Free Time Business Operations Dashboard
                                                        • Rad Reads: The Magic of Doing $10,000 Per Hour Work


                                                          🎧Related Podcast Episodes:

                                                          • Spotify playlist: RadReads x Pivot x Free Time
                                                          • 145: Tips for Training Part-Time Team Members with Kaneisha Grayson
                                                          • Learn more about your ad choices. Visit megaphone.fm/adchoices

                                                            52 min
                                                          • 336: Letting Go of Productivity Guilt with Madeleine Dore (Free Time Crossover)

                                                            “You have to live spherically—in many directions. Never lose your childish enthusiasm—and things will come your way.” —Federico Fellini

                                                            This week’s delightful guest, Madeleine Dore, reminded me of this wonderful quote while reading her book, one that I know you will love as much as I did: I Didn’t Do The Thing Today: Letting Go of Productivity Guilt.

                                                            We talk about widening the measure and meaning of a day beyond our to-do lists, discovering the call of a new topic, shaping a big idea “blob of clay,” how she collects all the great quotes and stories for her book, why she sees herself as more of a guinea pig than an expert (and freelancer valuing independence even more than business owner), and how she decides when to sunset a project, rather than “maintaining something at all costs.”

                                                            This crossover episode originally aired on the Free Time podcast on April 25, 2023.

                                                            More About Madeleine: Madeleine Dore is a writer and interviewer exploring how we can broaden the definition of a day well spent. As a labor of love, Madeleine spent over five years asking creative thinkers how they navigate their days on her popular blog Extraordinary Routines and podcast Routines & Ruts. The lessons culminated in her first book, I Didn’t Do The Thing Today: Letting Go of Productivity Guilt. Madeleine continues to write, speak and ask questions—but mostly tries to hold things lightly.


                                                            🌟 3 Key Takeaways
                                                            • We all go through creative phases of being a sponge vs. squeezing it: the former is a time to absorb the world and take in inspiration, even if it might look from the outside like we’re not doing anything.
                                                            • When caught in a deflating comparison spiral: Get up close, use it as a guide, return to what you want to do, and do it!
                                                            • Identify what is most important to you, and change the questions you ask as a result. For example, Madeleine’s decision to favor more time over more money means when considering a new project or direction, asking not “How much will this earn?” but “How much [free] time will this enable?”


                                                              📝 Permission: Stop measuring the day by how productive you were. Be curious and expansive when reviewing your day, including your internal accomplishments, moments of connection, or even moments of idleness. Instead of trying to optimize your day only through the lens of productivity, occupy and embrace your day for what it wants to be.


                                                              ✅ Do (or Delegate) This Next: Identify one area of your business or creative projects that may be languishing. What would happen if you gave yourself permission to close it out completely to create space for what’s next?


                                                              🔗 Resources Mentioned
                                                              • Madeleine on the web, Instagram: @madeline_dore, Facebook
                                                              • Substack: On Things
                                                              • Madeleine’s podcast: Routines & Ruts

                                                              • 📚 Books Mentioned
                                                                • Madeleine’s book: I Didn’t Do The Thing Today: Letting Go of Productivity Guilt
                                                                • Free Time: Lose the Busywork, Love Your Business
                                                                • Pivot: The Only Move That Matters Is Your Next One

                                                                • 🎧 Related Episodes
                                                                  • 2 Pages with MBS: How to Be Alive: Madeleine Dore [reads] Encyclopedia of an Ordinary Life
                                                                  • Free Time: 170: 🌈 “Imagine a World of Abundance” ✨, 169: Running a Goal-Free Business with Stephen Shapiro, 057: You+ vs. You 2.0 with MBS, 036: Shaping Big Ideas — Notion Walkthrough #2
                                                                  • Pivot: 287: Solving Pivot Puzzles with A.J. Jacobs, 305: Is What You Are Wanting Actually What’s Best For You? With Luke Burgis

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                                                                    44 min
                                                                  • 335: Be Irreplaceable with My Creative Coach Jay Acunzo (Free Time Crossover)

                                                                    One thing I love about Jay Acunzo is that his body of work is a love letter to craft and quality. We talk about mindset shifts and practices to help you focus more on resonance than reach; how to do work that matters to you so that your work can matter more; how he worked through his own existential creative crisis upon hitting the 200th episode milestone of his podcast; thinking like an explorer, not an expert; and “making the leap from what best practices say you should do to what your intuition is urging you to try.”

                                                                    This crossover episode originally aired on the Free Time podcast on April 18 2023.

                                                                    More About Jay: Jay Acunzo is one of the world’s most sought-after business storytellers and brand consultants. He’s worked in marketing for Google, HubSpot, and ESPN before launching his award-winning podcast, Unthinkable, and authoring multiple books on creativity. Today he helps creators learn to increase the power of their creative work, not just the volume, through his membership platform, the Creator Kitchen.


                                                                    🌟 3 Key Takeaways
                                                                    • Reach vs. Resonance: Reach is how many people see something. Resonance is how much they care. No amount of reach will ensure that people care. As David Bowie’s says, “Don’t play to the gallery.”
                                                                    • “Don’t be the best, be their favorite”: Create resonance with the audience relevance pyramid, starting with the base—how relevant you are in topic and theme. Moving up, your content should be enjoyable and entertaining, then impactful, where you are helping people reflect or take action. At the top of the pyramid is personal, where you (and your content) truly becomes irreplaceable.
                                                                    • Jay’s Mastery 3 P’s: Posture, Practice and Process. Posture is how you see yourself in the world. Practice is the cadence you are creating and shipping on (aim for consistent and purposeful), then process emerges.


                                                                      📝 Permission: Focus on resonance before—or even at the expense of—reach. Let go of the idea of adding more people until you have a small group reacting in a big way.


                                                                      ✅ Do (or Delegate) This Next: Define your Even More Meaningful Metrics. For example, Jay’s Unsolicited Response Rate (URR): When he publishes something and someone feels urged to respond in some way without being prompted, or Cackles Per Piece (CPP): points during the process of creating that cause so much joy he cackles out loud.


                                                                      🔗 Resources Mentioned
                                                                      • Jay on the web, Instagram: @jacunzo, Twitter, LinkedIn, Medium
                                                                      • People: Andrew Davis, Hrishikesh Hirway
                                                                      • TV Series: Song Exploder on Netflix
                                                                      • Video: David Bowie on why you should never play to the gallery, and AJ Jacobs: The Importance of Self-Delusion in the Creative Process
                                                                      • Article: The Surprising Thing About Expectations by Seth Godin

                                                                      • 📚 Books Mentioned
                                                                        • Jay’s Books: Break the Wheel: Question Best Practices, Hone Your Intuition, and Do Your Best Work
                                                                        • Free Time: Lose the Busywork, Love Your Business
                                                                        • Pivot: The Only Move That Matters Is Your Next One
                                                                        • Kitchen Confidential: Adventures in the Culinary Underbelly by Anthony Bourdain

                                                                          🎧 Related Episodes
                                                                          • Unthinkable: Fine, I’ll Talk About AI; Song Exploder Exploded, Welcome to the Jumble
                                                                          • Podcasts: Mike Birbiglia’s Working it Out, Song Exploder, Radiolab
                                                                          • 2 Pages with MBS: Making What Matters Most: Jay Acunzo [reads] ‘Kitchen Confidential’
                                                                          • The Tim Ferriss Show: Managing Procrastination, Predicting the Future, and Finding Happiness with Tim Urban
                                                                          • Free Time: 127: Protect Your Idea Factory, Build a Creative Flywheel, and Go Behind-the-Scenes of Book Publishing with Todd Henry, 014: Why It Matters to Celebrate Wins
                                                                          • Pivot: 287: Solving Pivot Puzzles with A.J. Jacobs, 254: The Practice—On Generosity, Peculiarity, and Showing Up with Seth Godin

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                                                                            52 min
                                                                          • 334: 🍩 What Do Donuts, Coffee, Conversation, and Energy Cliffs Have in Common? (Free Time Crossover — Daily Audio Diary from TED 2023)

                                                                            What’s it like to be at a conference with “fancy” people, when you’re the one feeling like you snuck in a side door as a seat filler? Okay, okay — that’s just my imposter monster talking. In today’s experimental episode, I’m taking you behind-the-scenes of the recent 5-day main TED conference in Vancouver, building on Pivot episode 325: 10+ Conference Networking Strategies with Alisa Cohn.

                                                                            In full-on morning voice with a travel mic, I do a daily check-in about what I was nervous about, spontaneous serendipitous invites, fan-girling my favorite authors and podcasters, falling off the energy cliff, what gave me FOMO and JOMO, and my daily quest for coffee. Always. Find. The. Coffee.

                                                                            This crossover episode originally aired on the Free Time podcast on June 9, 2023.

                                                                            🌟 3 Key Takeaways
                                                                            • Identify when you’re at your conversation-sparking best: time of day and format (1:1, small group, big group; format vs. informal gatherings)
                                                                            • Trust that less can be more: Fewer, deeper conversations can be just as powerful, if not even longer lasting than more, shorter ones. Resist the pressure to maximize every single element of being at the event.
                                                                            • Put yourself in the path of people: Even when you’re not invited to the fancy formal events, place yourself in a central place — like the hotel lobby or a coffee station — to attract random conversation from other people who are also looking to meet someone new, but may be similarly unsure about how to break the ice of conversation.


                                                                              📝 Permission: Embrace JOMO, knowing you’ll be at your best if you say no to situations that tend to bring out your worst.


                                                                              ✅ Do (or Delegate) This Next: Send a follow-up note to reconnect with someone you met in the last year. Bonus: schedule a small group reunion event over brunch or dinner (or Zoom).


                                                                              🔗 Resources Mentioned
                                                                              • Apply to attend the TED Conference in Vancouver
                                                                              • Travel: Athletic Greens, TripIt Pro, Peloton, Tonal, my favorite Tumi carry-on bag
                                                                              • People: Alexandra Franzen, Alisa Cohn, Jon Levy, Cameron Herold, Gina Bianchini, Amy Cuddy, Dan Harris, Scott Belsky, Krista Tippett, Jacob Weisburg
                                                                              • Articles: Jon Levy Influencer Dinners

                                                                                📚 Books Mentioned
                                                                                • From Start-up to Grown Up: Grow Your Leadership to Grow Your Business by Alisa Cohn
                                                                                • You're Invited: The Art and Science of Connection, Trust, and Belonging by Jon Levy
                                                                                • Presence: Bringing Your Boldest Self to Your Biggest Challenges by Amy Cuddy
                                                                                • The Messy Middle: Finding Your Way Through the Hardest and Most Crucial Part of Any Bold Venture by Scott Belsky
                                                                                • 10% Happier Revised Edition: How I Tamed the Voice in My Head, Reduced Stress Without Losing My Edge, and Found Self-Help That Actually Works--A True Story by Dan Harris
                                                                                • Free Time: Lose the Busywork, Love Your Business
                                                                                • Pivot: The Only Move That Matters Is Your Next One
                                                                                • Life After College

                                                                                • 🎧 Related Episodes
                                                                                  • The Sensitive CEO Show with Rose Cox: An HSP’s Guide to Podcasting with Jenny Blake
                                                                                  • Free Time:
                                                                                  • 043: From Start-Up to Grown-Up (and Coach to Author) with Alisa Cohn
                                                                                  • 166: Crashing into Quiet Time 🏝️
                                                                                  • 126: Creating Time Buffer—7 Strategies for Spacious Scheduling
                                                                                  • 084: Sprinkling the First 1,000 Serendipity Seeds of a Launch
                                                                                  • 167: Transform Your Approach to Community-Building with Gina Bianchini
                                                                                  • Pivot:
                                                                                  • 325: 10+ Conference Networking Strategies with Alisa Cohn
                                                                                  • 298: Networking in a New Niche and Becoming Broadway Investors with Dorie Clark and Alisa Cohn
                                                                                  • 251: Listener Q&A on (Furry) Imposter Monsters
                                                                                  • 324: Six Golden Shadows of the Imposter Complex with Tanya Geisler
                                                                                  • 77: 21+ Travel Tips, Tools and Apps — with Jenny Blake
                                                                                  • 302: Moving Beyond Burnout with Dr. Susan Biali Haas
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                                                                                    48 min

                                                                                  About Pivot with Jenny Blake

                                                                                  From the publisher's feed

                                                                                  What’s next for your career and creative projects? Pivot with Jenny Blake launched in 2015 to help us better embrace fear, insecurity, imperfection, and intuition as the superpowers they are while…