623 | 20 Things to Do Before You Retire | Fritz Gilbert

Most people treat retirement as a numbers game. Hit your target, claim victory, and coast into the sunset. But 85% of retirees crash into a wall of disorientation two years in—not because they ran out of money, but because they never planned for what comes after the paycheck stops: identity, purpose, structure, relationships. The spreadsheet can't solve those problems. Key Topics Make Your Numbers Real (3 Years Out) 00:05:30 Track every dollar for a full year to capture one-off expenses spreadsheets miss. Project retirement costs with granularity—model RV trips, healthcare scenarios, travel frequency. Build cash flow projections to age 95, not just to retirement day. The goal: eliminate guesswork and replace fear with data. Start to Experiment (3 Years Out) 00:18:45 Test potential retirement activities now. Don't wait until you retire to discover what you actually enjoy versus what sounds good in theory. Experimentation builds identity beyond work before the structure disappears. Most retirees skip this step and pay the price in phase two disorientation. Prepare for Withdrawals (2 Years Out) 00:28:20 The psychological shift from accumulation to spending is brutal after decades of saving. Build liquidity buckets to handle sequence of return risk. Develop a drawdown strategy that accounts for market volatility. Practice spending before you retire—buy the RV or boat while you still have paycheck confidence. Schedule a Mini-Retirement and Build Your Dream (2 Years Out) 00:38:10 Take a week-long break with your partner to envision retirement together. Discuss "he time, she time, we time"—how much individual versus shared activity each person wants. Align expectations before conflicts arise. This conversation prevents the retirement disappointment that ends marriages. Pursue Your Four C's (1 Year Out) 00:48:00 Dan Hallett's framework: Contribution (being needed), Creation (making things instead of consuming), Curiosity (exploring and learning), Connection (relationships). These four pillars replace what work provided beyond money. Retirees who nail the Four C's thrive; those who don't struggle. Build a Life Outside of Work (1 Year Out) 00:55:30 Work gives you 60+ hours of weekly structure. When that disappears, what fills the void? Design your post-work life intentionally—hobbies, volunteering, learning, relationships. The transition only works if you've built something to transition to. Fill Your Activity Jar (1 Year Out) 01:02:15 A practical exercise: each week, both partners write one retirement activity idea on an index card. After a year, you have 100 things to do in retirement. Planning is half the joy. The jar becomes a tangible reminder that retirement is abundance, not void. Enjoy Crossing the Starting Line 01:08:40 Retirement isn't the finish line—it's the starting line. Savor your final month of work. Express gratitude to colleagues. View retirement as the beginning of your best years, not the end of your productive ones. Notable Quotes Fritz Gilbert: "Only five of the twenty steps are financially related. The other fifteen are about everything the spreadsheets cannot solve." Fritz Gilbert: "Retirement isn't the finish line—it's the starting line." Fritz Gilbert: "My two favorite words in retirement are curiosity and experiment." Fritz Gilbert: "Both physical fitness and FI get you more years of freedom." Fritz Gilbert: "Eighty-five percent of retirees go through phase two—loss and disorientation—because they haven't thought about replacing what work gave them beyond a paycheck." Brad Barrett: "Much of FI success is psychological, not mathematical. Conservative estimate stacking often stems from fear rather than necessity." Key Takeaways Track a full year of spending three years before retirement to understand actual costs and project expenses accurately Start experimenting with potential retirement activities now—don't wait until you retire to discover what you enjoy Schedule a mini-retirement with your partner to envision your future life and discuss expectations around individual versus shared time Develop a retirement withdrawal strategy two years out, including liquidity buckets and plans for sequence of return risk Create an activity jar with your partner: each week, write one thing you want to do in retirement (100 total ideas over a year) Write your personal "Ten Commandments of Retirement"—your North Star principles for how you want to live Update your estate plan and move all personal items (contacts, files, subscriptions) off work systems before you retire Purchase retirement toys (RV, boat, etc.) before retiring while you still have paycheck confidence and cushion for overspending Resources and Links The Retirement Manifesto Keys to a Successful Retirement (Book) The Forever Paycheck (Book by Gina Chaneski) ChooseFI Episode 475: How to Access Retirement Accounts Before 59.5 with Sean Mullaney Our Retirement Investment Drawdown Strategy (Fritz's Article) Health Decoder AI The Four C's of a Fulfilling Retirement (Dan Hallett's Article) Join the Community Connect with thousands on the path to financial independence. 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