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Catching Up to FI

Reached FIRE At 50👉🏻 And Here's Why He Still Keeps Climbing | Darrow Kirkpatrick | 167

07 Sep 2025

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Darrow Kirkpatrick retired from a 29-year career in civil and software engineering in April 2011 at the age of 50 and started the blog 'Can I Retire Yet' that same year. The Blog was one of the first in the FIRE (Financial Independence, Retire Early) space and focuses on the personal finance needs of anyone who is thinking about retirement or early retirement. He joins us for a deeply human masterclass on retiring, drawing down without drama, and pursuing hard goals the slow, sane way. In this episode, Darrow shares with us: The origins of his blog 'Can I Retire Yet?' How a nervous breakdown derailed his career His six-year, section-by-section completion of the Colorado Trail on forearm crutches The inspiration behind his new book 'Two Sticks One Path'   📩 Sign up for our newsletter (NEW!) 🌐 Visit Catching Up to FI website  🔗Connect with us ☕ Like what you hear on Catching Up to FI? Support the show at "Buy Me a Coffee"  🎙️We love hearing from you! Record a Voice Message with your feedback or question Record a Voice Message with your feedback or question   RESOURCES MENTIONED ON THE SHOW: (As an Amazon Associate, I earn from qualifying purchases.) Charities: National Alliance on Mental Illness The Colorado Trail   🌐 Can I Retire Yet? 🌐Trail Memoir 📗 Two Sticks, One Path 📘 Can I Retire Yet? 📕 Retiring Sooner Critique circle (Online Writing Workshop) Lessons Learned from Writing a Book Pralana- Personal Financial Modeling   ⏰ 'Catching Up to FI' Episodes The Powers of Starting Late, Retirement Calculators, and More | Chris Mamula | 086 Sustainable FIlosophy with Mr. Money Mustache | Pete Adeney | 073   ===DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS=== 📈 Boldin (formerly NewRetirement): Retirement planning software that's like having a financial advisor at your fingertips. You can get started with the free version or choose the premium option (PlannerPlus) and get a 14-day free trial.   👉🏼 Be sure to use this link to get started:  Go.boldin.com/catchingup   Personal Finance Club: Use code CUTOFI to get $30 OFF any course or PFC investing course only   Nectarine: Advice-Only and Flat-Fee Hourly Fiduciary Financial Advisors (Catching Up to FI will be compensated by Nectarine if you use our affiliate link, which creates an incentive and conflict of interest. We are not current clients or employees of Nectarine.)   For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: catchinguptofi.com/our-partners     If you enjoyed this episode, please follow the show on your podcast player and leave us a rating or review. If you want to watch, be sure to subscribe to our YouTube Channel. This helps others find the show and keeps us creating great content for you!   ⚠️Disclaimer: Our content is for general education and information purposes only. We are not providing financial, legal, or tax advice. Always do your own research or consult a professional before making important decisions.

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