The Secret Art of Finding Work You Love and Funding the Life You Want | Chris Hutchins

Listen to this episode from Your Money Guide on the Side on Spotify. Guest: Chris Hutchins, host of All the HacksEpisode theme: Building wealth with meaning—how to design a career (and life) you actually want, while optimizing the money side.What we cover:Meaning > money-first: Chris didn’t start out chasing wealth; he chased options. Early jobs in consulting/banking felt misaligned (little meritocracy, lots of “performance”). That tension pushed him toward work that creates—startups, product, and eventually a podcast.From layoff to leverage: A 2008 layoff forced reinvention. He broke into tech by doing unglamorous, high-initiative work, learning in public, and obsessively networking. Key tactic: create value before you’re hired (he built a full market brief to win a BD role).Career as a cash-flow asset: Once he found work he loved, savings were easier because the job itself provided energy, purpose, and upside. That shift—liking the work—reduced the need to “buy happiness” elsewhere.Optimization without overwhelm: All the Hacks exists to find the 80/20 in money, travel, health, and life. You don’t need to become a points guru or biohacker; borrow Chris’s research and apply the simple levers.Counterintuitive insurance take: When he priced plans, the “best” (premium) plan cost ≈$24k/yr more than the “worst,” while the “worst” plan’s out-of-pocket max was less than that difference. With a real emergency fund and a strong stomach, a high-deductible plan can be rational. (Psychology is the hard part.)Prepay for joy: Pre-buying (subscriptions, passes, prepaid trips) can remove friction and guilt, increasing actual use and happiness.Know your enough: People who don’t know what money is for default to “more.” Define the life you want, price it, then fund that—not a moving target.Audience resonance: “Mini-retirements,” negotiation tactics, and insurance optimization were huge hits; even niche episodes can be life-changing for the right listener.Actionable takeawaysDesign a role you’ll keep doing. Treat your job like part of your portfolio’s fixed-income sleeve: dependable cash flow, lower stress, and compounding skills.Front-load value. Pitch with a one-pager or mini-audit tailored to the company—proof you’ll do the work.Run the insurance math (with your EF). Price premiums vs. out-of-pocket max; let your emergency fund shoulder higher deductibles if the numbers favor it.Prepay strategically. Use prepayment to align behavior with values (fitness classes, transit, annual memberships).Write money rules. E.g., “Invest 20% before lifestyle,” “Use points for intl. biz class only,” “If it saves 10+ hours/yr, buy it.”Lightning-round funBest <$100: Ultrasonic cleaner (for retainers/aligners)—tiny daily upgrade.Most overrated advice: Social-media tax “hacks” that cross legal lines.Apps he likes: A clean net-worth tracker + Copilot for spending (iOS).Guilty pleasure spend: Big annual fees on premium cards—only if the benefits net out.Find Chris: All the Hacks (weekly deep dives). A great starting point: his “Top 50 Lessons” episode.