Mini Retirements: How to Take a Break Sooner That Could Also Boost Your Career and Income with Jillian Johnsrud

Mini Retirements: How to Take a Break Sooner That Could Also Boost Your Career and Income with Jillian Johnsrud

Author: Chris Hutchins July 30, 2025 Duration: 1:00:36
#239: Why wait until you're 65? It's feasible for almost anyone to take a mini retirement and when done right, it can also fast-track your career and income. Learn how to plan one, negotiate time off, manage costs, avoid pitfalls, and make it work if you’re self-employed. Plus, we share tips for handling health insurance and other logistics during your mini-retirement. Jillian Johnsrud is the author and host of Retire Often. She’s taken more than a dozen mini-retirements and coaches people to pursue meaningful goals, take mini-retirements, and align their money with what matters most. Link to Full Show Notes: https://chrishutchins.com/mini-retirements-jillian-johnsrud Partner Deals Stable: 50% off your first year of my favorite digital mailbox DeleteMe: 20% off removing your personal info from the web Bilt Rewards: Earn the most valuable points when you pay rent Long Angle: Join a free private community for high net worth investors Shopify: $1/month trial for the easiest e-commerce platform For all the deals, discounts and promo codes from our partners, go to: chrishutchins.com/deals Resources Mentioned Jillian: Website | Podcast | Instagram Jillian's Book: Retire Often Free Worksheets: Planning | Negotiating Full Show Notes (00:00) Introduction (02:12) Why Traditional Retirements Are Flawed (04:32) What Is a Mini Retirement? (06:50) How to Make More Money by Working Less (09:46) Managing Your Time During a Mini Retirement (11:57) Common Types of Mini Retirements (15:43) Ways to Design an Impactful Mini Retirement (18:19) Financial Implications of a Mini Retirement (20:40) Chris and Amy's Mini Retirement (22:57) How to Negotiate a Mini Retirement With Your Employer (30:41) Paid Leave vs. Unpaid Leave (37:18) Finding Work After a Mini Retirement (42:10) Tips for People Who Are Self-Employed (46:52) How to Plan, Save, and Spend for Your Mini Retirement (49:33) Estimating the Cost of a Mini Retirement (53:45) All the Different Ways a Mini Retirement Can Go Wrong (56:55) Should You Take a Mini Retirement With or Without Your Partner? (59:07) Health and Travel Insurance Options (1:01:09) Jillian's Parting Advice (1:02:23) Where to Find Jillian and Her Work Connect with Chris Newsletter | Membership | X | Instagram | LinkedIn Editor’s Note: The content on this page is accurate as of the posting date; however, some of our partner offers may have expired. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. Learn more about your ad choices. Visit megaphone.fm/adchoices

Ever feel like there's a smarter, more efficient way to navigate your finances, your travels, and your daily routines? That's the core question driving All the Hacks: Money, Points & Life. Hosted by Chris Hutchins, this podcast is built on a simple, powerful idea: maximizing value doesn't mean sacrificing enjoyment. Instead, it's about the strategic choices that free up resources-both money and time-for what truly matters. Chris approaches life as a series of systems to be optimized, drawing from his own experience saving millions through meticulous analysis. The conversations here are practical and wide-ranging, moving seamlessly from credit card points strategies and investment philosophies to the less tangible hacks for personal fulfillment. You'll hear from a diverse roster of experts and icons, including Tim Ferriss, Tony Hawk, Codie Sanchez, and Gary Vaynerchuk, who all bring their unique perspectives on building wealth and designing a compelling life. Each episode feels like a focused workshop, offering actionable advice you can use immediately, whether it's planning a luxury vacation for a fraction of the cost or rethinking your approach to career and leisure. This isn't just about frugality; it's about unlocking freedom and excitement through smarter decisions. Tune in for a consistently insightful blend of tactical moves and deeper conversations that challenge the conventional trade-offs between spending, saving, and living well.
Author: Language: English Episodes: 100

All the Hacks: Money, Points & Life
Podcast Episodes
The Custom Everything Era with Kevin Rose [not-audio_url] [/not-audio_url]

Duration: 1:07:14
#275: Chris and Kevin dig into how they're actually using AI tools in their daily lives right now. They explore real-world AI use cases, the tradeoffs of sharing personal data, the collapse of trust online, and what all…
The Surprising History of Points and Miles [not-audio_url] [/not-audio_url]

Duration: 42:25
#274: Chris walks through the complete history of points and miles and breaks down the $140 billion machine behind them, so you can get more out of every point you earn. He covers the legal accidents that made credit car…
Stop Overthinking and Start Deciding with Derek Sivers [not-audio_url] [/not-audio_url]

Duration: 1:52:11
#273: Learn to stop overthinking and make better decisions. Chris and Derek discuss how optimizing can go wrong, a coin flip trick for making decisions, journaling as a superpower, how your actions might reveal what you…
My Process for Booking Travel with Points & Miles [not-audio_url] [/not-audio_url]

Duration: 54:29
#272: Learn how to turn your points into significantly better travel experiences by following a simple, repeatable system. We cover how to plan, find award availability, choose the right tools, and decide between portals…
How to Actually Live the Life You're Optimizing For with Sahil Bloom [not-audio_url] [/not-audio_url]

Duration: 56:41
#271: Learn why over-optimizing your life can quietly destroy the things you actually care about. Chris and Sahil explore the doorman fallacy, why big life decisions should happen fast, how to use AI as a thinking partne…
Ski Trip Mishaps, AI Interior Design, Reflecting on Life and More [not-audio_url] [/not-audio_url]

Duration: 1:08:15
#270: Chris and Amy discuss lessons from three ski trips with kids, using AI to redesign rooms on a budget, their favorite new gadgets, navigating high-deductible health plans, and more. Link to Full Show Notes: https://…
Credit Cards: What's in My Wallet for 2026 [not-audio_url] [/not-audio_url]

Duration: 1:14:45
#267: Chris reviews his credit card lineup for 2026, sharing which cards he's keeping and canceling and why. He also covers how to evaluate annual fees, the best cards across major spending categories, and the apps he us…
Why Change Is Hard and How to Make It Your Advantage with Maya Shankar [not-audio_url] [/not-audio_url]

Duration: 45:22
#266: Chris and Maya break down the science-backed tools that make change easier and more intentional. They explore why most people misunderstand change, how to anchor your identity to your deeper “why,” and practical to…