#41 - 3 Action Items for Your First Years of Retirement
Greetings!
On This Monday’s Episode of Your Money Guide on the Side:
I build on a powerful idea from last week’s guest, Victoria Ferguson: a 3-step universal framework for solving financial problems—and frankly, any life problem. Most of us struggle not because we lack answers, but because we don’t approach our problems with a clear framework.
In this episode, I will explore the following:
Name the real problem (not just the vague stress around it)
Prioritize that single issue instead of juggling competing ones
Vet the right resources to solve it—without falling for the “trust me bro” financial advice culture
So whether you're overwhelmed by debt, unclear about retirement, or just stuck in a loop of anxiety, this episode offers a practical framework to break through.
**And…if the show has been helpful to you in any way, please consider leaving a review here, as the more we grow together, the more we learn together! And if you leave one, please, please, please let me know via email, so I can thank you personally!
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And Now for Your Weekly Newsletter Action Items! :)
3 Action Items for Your First Years in Retirement
1. Map Out Your “Go-Go, Slow-Go, No-Go” Years
Retirement spending isn’t one-size-fits-all, and we’ve been over this before. There is never a formula that will work as well for your neighbor as it will for you. The early years? You might be in your best physical shape. You’re hiking national parks, joining pickleball leagues, and maybe even impulse-booking a flight to Tuscany. (If you do, let me know, and I’ll see you there!)
But around your late 70s, that travel might slow and you find yourself leaning more heavily on great companionship, some culinary experiences, and maybe even some writing! (Slow-Go.)
And eventually, life may center more around home and health. (No-Go.—and note: I don’t love the phrasing of "No-Go”, as I plan on going somewhere, physically or mentally, until I’m at rest. :) )
Why it matters: Even though you’re told to be super conservative in your early years of retirement, front-loading some of your “fun money” early on also makes sense — and helps you avoid feeling guilty for enjoying it. This is huge, as many of my former clients truly couldn’t find a way to feel guilt-free in spending their accumulated money early in retirement.
Action item: Sketch out your retirement decade by decade. It doesn’t have to be perfect — just give your future self a little roadmap, and set some clear, time-bound goals for what you’d hope to accomplish.
2. Create a Retirement Paycheck (I will definitely be doing this one)
No more bi-weekly pay stubs from work? No problem. Let’s build your own.
Think: Social Security + investment withdrawals + pensions (if you're lucky) = your custom income stream.
Why it matters: Without a clear plan, retirees tend to underspend out of fear, as we’ve noted in past letters. And that “just in case” money? It rarely gets used how you wanted. Remember, retirees statistically die with more money than when they first retired!
Action item: Work with a planner (or partner) ((or computer program)) to determine a sustainable withdrawal rate (hint: 4% rule is a fine starting point, not a law), and set monthly transfers to your checking account, just like a paycheck.
3. Get Ahead of the Tax Burden (And yes, it, unfortunately, can get worse with age)
Between Social Security, RMDs, and investment income, taxes in retirement can sneak up on you faster than your neighbor asking if you’ve “started golfing yet.”
Why it matters: Strategic Roth conversions, asset location, and even timing your charitable gifts can save you thousands, but the window is early in retirement before RMDs kick in, and it shuts quickly!
Action item: Talk to a tax-smart financial pro about a 5–10 year forward tax plan. It's not sexy, but it is how you avoid writing a surprise $20k check at tax time.
Quick Note: The early years of retirement are like a new relationship: exciting, nerve-wracking, and full of opportunity.
Be intentional, be flexible, and most importantly (to me), give yourself permission to enjoy the life you worked so hard to build.
As always, hope this gives you something to think about throughout the week.
Tyler
Your Money Guide on the Side
