I have spent years working as a hospice physician. I have sat at the bedsides of hundreds of dying patients, holding their hands and guiding their families through the most difficult transition of their lives. Because of this, I often tell myself that I am inoculated against the fear of aging.
But I have a confession to make: this week on the podcast, I got shaken.
I was interviewing Dana Anspach—a brilliant certified financial planner, retirement management adviser, and the author of Living Off Your Acorns. While preparing for the episode, I read her description of the final phase of retirement. Despite all my medical training, the reality of my own eventual aging hit me like a ton of bricks. We had a profound conversation in the after-show segment about this, reflecting on how our respective careers—hers as a financial planner, mine as a doctor—have granted us a privileged window into hundreds of lives. We get to see in real-time who ages gracefully, and who struggles.
Dana’s core philosophy is that retirement is not a single, static event where you simply flip a switch and stop working. It is an evolution. She breaks this down into an incredible framework called the Four Seasons of Retirement.
Here is what that journey actually looks like:
1. The Pre-Go Years
This is the decade leading up to retirement, and ironically, it is often the most financially stressful. The transition is finally a visible horizon. This is the phase where we obsessively run our numbers through every possible Monte Carlo simulation to combat a very specific, deep-seated anxiety: the terror of losing our regular paycheck.
2. The Go-Go Years
These are the early, active years of retirement—usually lasting through your early 70s—where energy is high and the world is open. You will likely spend more money here, funding travel, home renovations, and new hobbies. But it also introduces massive new complexities. Suddenly you are navigating private health insurance, COBRA, Medicare, quarterlies for the IRS, and setting aside cash for lump-sum home repairs.
3. The Slow-Go Years
Eventually, the travel bugs fade. You naturally begin to slow down and find a deep, quiet contentment in a comfortable home routine. As your personal spending declines, your focus often shifts outward toward legacy: gifting to children, funding grandchildren’s education, or supporting charitable causes. Crucially, this is the time to start using your wealth to hire help for household chores to protect your physical safety.
4. The No-Go Years
This is the phase that got to me. This is the final season, where physical and cognitive health concerns take center stage. Because cognitive decline can subtly strip away the self-awareness you need to recognize your own limitations, Dana stresses one absolute necessity: you must establish a trusted relationship with an advisor or bring family members into your finances before this phase begins. When the time comes, they act as the critical guardrails against financial mismanagement, missed insurance premiums, or elder scams.
The Leap of Faith
What I love about Dana’s approach is that it forces us to admit a hard truth: retirement is far more than a math problem.
In the financial independence community, we have a terrible habit of stacking overly conservative assumptions on top of each other. We project historically low market returns, pair them with sky-high inflation, and model for worst-case scenarios until we are completely paralyzed by fear.
We act like rigidity is a superpower. It isn’t. Rigidity is a planning weakness.
Life is wildly unpredictable. As Dana realized during a two-week vacation in Colorado that changed her own trajectory, you eventually have to stop “powering through” burnout and start intentionally following your energy. You have to embrace a looser, more optimistic framework.
At the end of the day, leaving the safety of the workforce is a leap of faith. You cannot spreadsheet your way to courage. You simply have to build a flexible plan, take the jump, and trust your ability to pivot as the seasons change.
I want you to hear this conversation. It is a masterclass in bridging the gap between the math of wealth and the emotion of aging.
Let me know which of the four seasons you might struggle with, and how you are preparing for the future.
The No-Go point. I did not wait for old age to get there. Neuropathy and a walker ended my in-person ministry years ago, well before most of Dana’s other seasons technically applied to me. What surprised me: leadership does not stop when the body changes, it just relocates. Mine moved from a pulpit or corner office to a screen. The four seasons framework assumes a rough age-based order. Worth adding: sometimes the No-Go season arrives out of sequence, and the flexibility Dana is describing has to kick in early, not just at the end.
this is great, thank you