Les Sherry Built Time Freedom Inside a Corporate Career

Building Time Freedom in Public: The Season 2 Finale

Top 5 Takeaways:  1. Time freedom doesn't have to come at the end. Listener stories: Audrey dancing ballet in Mexico, Matthew working 15 hours a week from Canada, show people designing the life now rather than waiting for some finish line.  2. Your voice is part of the message. When a book weaves personal stories in with the frameworks, narrating the audiobook yourself builds trust and rapport faster than a hired reader or an AI voice ever could. New skills take reps before they take off.  3. Brian's first keynote went blank mid-speech, and he walked away more committed, not less. Mastery lives on the other side of looking bad in public.  4. Get specific about your path. Season 3 trades general advice for six listener avatars—from the DIY money person to the near-retiree—each getting a three-episode series that maps out exactly how they'd reach time freedom.  5. You don't have to do it alone. Big life changes are where support matters most. The Time Freedom Community (launching October) turns the book into group coaching, shared accountability, and relationships with others on the same path. Chapters: * 00:00 Season Two Reflections and Lessons Learned * 02:49 Growing the Time Freedom Community * 05:13 Behind the Scenes of the Book and Audiobook Launch * 10:05 Listener Feedback and the Impact of Shared Stories * 17:01 Looking Ahead to Season Three * 20:03 Understanding the Different Paths to Time Freedom * 26:28 Building Connection, Community, and Support * 32:36 Brian's Speaking Journey and Future Vision * 37:07 Special Offers, Giving Back, and What's Next Summer Offer: Get More, Give More For 60 days only (June 15–August 15) * get six months in the Time Freedom Community * 25 copies of the book (one signed, the rest to share or to have Brian and Kirby place with ideal readers) * A one-hour webinar Brian will deliver for your clients  Most of the cost goes to the books, and Brian's proceeds (about $100) are donated in your name to Donate Life America, supporting registerme.org and donor families. Claim it at timefreedom.life/summeroffer [https://timefreedom.life/summeroffer].     🎧 Pre-order Time Freedom and get the audiobook FREE today. Normally it takes three copies to unlock the audiobook, but for podcast listeners, just one. 👉timefreedombook.com [https://timefreedombook.com] | code: PODCAST Enter code PODCAST and you'll get instant access (your paper copy arrives in September). Pre-orders help the book land on more shelves on launch day, so thank you!

Tim Jenkins and Darran Littlefield Built Time Freedom Before It Had a Name

Top 5 Takeaways: 1. Time freedom doesn't have to come at the end. Tim and Darran built it into Point B from the very beginning, designing work around their lives rather than the other way around. 2. Company culture is like a bank. If everyone makes deposits, it scales infinitely. If people only make withdrawals, it quietly collapses. The CEO isn't the keeper of culture, because everyone is. 3. Partnerships survive when you commit to them like a marriage. Tim, Darran, and their third co-founder Jim Hodge made a five-year no-exit pact and stayed unified through it all. 4. You have time capital and financial capital, and the ratio shifts throughout your life. Managing both intentionally is the real game. 5. Retirement is a myth. Work isn't the opposite of freedom. When you get the work right, it's what sustains you. The goal isn't to stop, but to find work worth doing until you can't anymore. Chapters:  * 00:00 Introduction and Everyday Leadership * 07:35 The Origins and Vision Behind Point B * 12:15 Building an Intentional Company Culture * 16:23 Rethinking Consulting and Flexible Work * 22:31 Time Freedom vs. Financial Freedom * 30:07 The Power of Partnerships and Collaboration * 38:13 Culture, Leadership, and Employee Well-Being * 40:38 Redefining Retirement and Work-Life Balance * 45:17 Career Transitions, Contribution, and Community * 54:22 Introduction to Time Freedom Book Promotion TIM JENKINS is the co-founder and former co-CEO of Point B, Inc., a national management consulting firm he built from three partners in 1995 to a 100% employee-owned firm with over a thousand professionals. In 2010 he was named Ernst and Young's Entrepreneur of the Year in Services for the Pacific Northwest. Today he is President of Colchuck, a purposeful private investment company based in Leavenworth, Washington, where he focuses on backing founders who are doing well and doing good at the same time. You can connect with Tim [https://linkedin.com/in/timothybjenkins] on LinkedIn. DARRAN LITTLEFIELD is the co-founder and former co-CEO of Point B, Inc., where he helped build one of the most admired people-first cultures in the consulting industry. He served alongside Tim for nearly two decades before the founders transitioned full ownership to their employees through an ESOP. Darran now lives in Dallas, Texas, where he relocated to be closer to family, and continues to collaborate with Tim on new work. You can connect with Darran [https://linkedin.com/in/darran-littlefield-64b7071] on LinkedIn.   🎧 Pre-order Time Freedom and get the audiobook FREE today. Normally it takes three copies to unlock the audiobook, but for podcast listeners, just one. 👉timefreedombook.com [https://timefreedombook.com] | code: PODCAST Enter code PODCAST and you'll get instant access (your paper copy arrives in September). Pre-orders help the book land on more shelves on launch day, so thank you!

Dr. Sam Chenkin: There's No Finish Line for Health or Money

Top 5 Takeaways: 1. The basics never die. In fitness, it's squat, hinge, push, pull, carry, and power. In finance, it's consistent saving and investing over time. Mastering the fundamentals, and doing them well, beats chasing trends in both. 2. Choose your hard. You can do the hard work of investing in your health now, proactively, or you can face the harder consequences of neglect later. There's no avoiding hard–only choosing which kind. 3. Health and wealth both require progression. Just as fitness requires increasing difficulty over time to keep producing results, your financial plan needs to evolve. Doing the same thing forever eventually stops working. 4. Identity drives sustainability. Doing something to get ready for a deadline is not a habit. Real, lasting change requires becoming the kind of person who does the thing and not just someone who's temporarily trying. 5. There is no finish line. Health, fitness, and financial wellbeing aren't problems you solve and move on from. They require ongoing commitment which only feels sustainable if they become part of who you are. Chapters:  * 00:00 Introduction to Health, Freedom, and Reinvention * 03:58 Sam’s Journey from Exercise Physiology to Entrepreneurship * 09:18 Why Coaching and Accountability Matter * 14:55 Navigating Pain, Injury, and Recovery * 17:32 Building a Flexible Health and Wellness Business * 22:46 Life Pivots, Setbacks, and Growth * 25:53 The Parallels Between Fitness and Finance * 27:49 Consistency Over Complexity * 33:28 Creating Personalized Health Freedom * 36:39 Time Freedom Book Promotion DR. SAM CHENKIN Dr. Sam Chenkin is a chiropractor, exercise physiologist, and personal trainer based in Alameda, California. She holds a Bachelor's in Exercise Physiology from the University of Miami, a Master's in Exercise Physiology and Nutrition from LIU Brooklyn, and a Doctorate of Chiropractic from Palmer College of Chiropractic Florida. Dr. Chenkin recently launched her own training and rehab business, Pivot 2 Health, offering virtual and in-person services built around personalized, long-term health. Her motto: Move, Heal, Thrive. You can connect with Sam at pivot2health.net [https://pivot2health.net/].   🎧 Pre-order Time Freedom and get the audiobook FREE today. Normally it takes three copies to unlock the audiobook, but for podcast listeners, just one. 👉timefreedombook.com [https://timefreedombook.com] | code: PODCAST Enter code PODCAST and you'll get instant access (your paper copy arrives in September). Pre-orders help the book land on more shelves on launch day, so thank you!

Lee LeFever on Building a Business Around Your Life (Not the Other Way Around)

Top 5 Takeaways: 1. Find the one idea you can make synonymous with yourself. Lee built his entire career around explanation, and that single thread connected Common Craft, two books, a Google partnership, and a new Substack. 2. You get to define what shareholder value means. If you're the only stakeholder, you can choose to maximize time instead of money. 3. Just because you design your business around your lifestyle doesn't mean you can't still have ambition. Stepping back gives you the brain space to make creative connections. 4. A monetorium is a temporary, purposeful season of reduced spending that builds anticipation and reveals what you actually need. Happiness lives in anticipation. 5. Design your life around quality, not quantity. You don't need a mansion to show off. The better option is having a home worth spending time in, right down to the perfect plants in your office. Chapters: * 0:00 – Introduction to Lee LeFever & Common Craft * 1:40 – Personal Background & Designing an Intentional Life * 7:05 – Moving to Orcas Island & Lifestyle Design * 12:39 – The Birth of Common Craft & Explainer Videos * 17:55 – The Science of Explanation * 23:09 – The Internet, Niche Markets & Opportunity * 25:49 – Authenticity in Communication * 27:08 – The “Monitorium” & Values-Based Spending * 31:29 – Craftsmanship, Creativity & Personal Projects * 36:17 – AI, Human Connection & the Future of Communication LEE LEFEVER Lee LeFever is the co-founder of Common Craft, the company behind some of the internet's earliest and most recognizable explainer videos. His "in Plain English" video series helped millions of people understand emerging technologies like RSS, Twitter, and wikis, and landed Common Craft a partnership with Google. Lee is the author of The Art of Explanation and Big Enough, a book about designing a business around your life. You can connect with Lee at leelefever.com, commoncraft.com, and scienceofexplanation.com.   🎧 Pre-order Time Freedom and get the audiobook FREE today. Normally it takes three copies to unlock the audiobook, but for podcast listeners, just one. 👉timefreedombook.com [https://timefreedombook.com] | code: PODCAST Enter code PODCAST and you'll get instant access (your paper copy arrives in September). Pre-orders help the book land on more shelves on launch day, so thank you!

Katrina McGhee Is a Digital Nomad but Maybe Not for Long

Top 5 Takeaways: 1. Variation creates appreciation. Doing different things in life, like working then resting or traveling then staying put, makes you appreciate what you did before and what might come next. The contrast is the point. 2. Consider a career break in the first part of Year 2. If you're following the No-Hustle Transition to entrepreneur, don't just flip from employee to business owner. Take a real break first. Even just three months to decompress. You'll be more productive in the nine months that follow than if you white-knuckled through all twelve. 3. A career break "cracks people open" to living differently. Many of Katrina's clients are corporate 9-to-5ers who return from their breaks realizing they can design life on their own terms, not just go back to the way things were. 4. Plans are cute. It's good to have goals, but always take advantage of the random opportunities that come your way.  5. Digital nomad life has pros and cons, just like traditional living. After eight years of location independence, Katrina is considering settling down for easier dating, fitness routines, and mental space to grow her business. Every lifestyle has its trade-offs. Chapters: * 0:00 – Introduction to Katrina McGhee * 1:21 – The Digital Nomad Lifestyle Explained * 4:09 – The Power of Career Breaks * 6:51 – Transitioning into Remote Work & Coaching * 9:39 – From Nomadic Living to a Home Base * 12:27 – Building a Flexible Coaching Business * 15:10 – The “No Hustle” Transition Approach * 17:44 – Planning for the Future with Flexibility * 32:24 – Navigating Career Transitions & Uncertainty * 36:37 – Building a Brand Around Career Breaks KATRINA MCGHEE Katrina McGhee is a career break and sabbatical coach, digital nomad, and author of Taking a Career Break for Dummies. During her first career break, she traveled the world for 20 months. In her next, she left her corporate job a second time to build her coaching business. Katrina is the co-founder of BreakSpace, the membership community for career breakers and sabbatical takers. You can connect with Katrina at kmcgheecoaching.com [https://kmcgheecoaching.com] or listen to her podcast, Taking a Career Break with Katrina McGhee.   🎧 Pre-order Time Freedom and get the audiobook FREE today. Normally it takes three copies to unlock the audiobook, but for podcast listeners, just one. 👉timefreedombook.com [https://timefreedombook.com] | code: PODCAST Enter code PODCAST and you'll get instant access (your paper copy arrives in September). Pre-orders help the book land on more shelves on launch day, so thank you!