The Inside-Out Retirement

I’ve spent a lot of time in these pages talking about the math of longevity. Readers may even remember when I coined the acronym YOAMLAW (Your Old Age May Last A While). The core of that idea was simple: if your "old age" is going to be a thirty-year marathon rather than a five-year sprint, your financial strategy needs to be built for the long haul.

But lately, I’ve been thinking about what happens to the person during those thirty years.

Recently, I was corresponding with a friend who retired from a decades-long career just a few years ago.  Our conversation turned to his “next act,” and he mentioned the book The Second Mountain, by David Brooks.

I confess that I’m just getting started, but I think I’ve picked up on the main theme. Life is a journey across two peaks. The First Mountain is the one we are all told to climb. It’s about building a career, establishing an identity, and racking up those "resume virtues." We spend decades checking boxes, accumulating assets, and trying to win the game of life.

Eventually, many of us reach that first summit, look around, and realize the view isn't quite what we expected, or perhaps, we just get knocked off the peak.

The Second Act

There is a trap I see many people fall into when we begin the financial planning process. We talk about "Time Horizons" as if they are finish lines. The problem is that the office door isn't a finish line; it’s often just a rest station at the halfway point of the marathon. Because YOAMLAW is real, that horizon may be several decades away. That’s actually good news!

We can build portfolios to last the rest of your life, and all investing involves risk, but that’s not the real risk to someone’s long-term well-being.  In this 2020 article, I wrote about the danger of failing to have “A Second Act.”

Defining your second act is a product of getting to know yourself, and it is never too late to do that.  Now is a great time to start.  Many retirees take a little time off to reset and discover who they may be without the shackles of the working world. Some, like my retired friend, discover that the first phase may have been about acquisition (How can I get what I need), but the second mountain is about contribution (What can I give back?).  

Designing from the Inside Out

I can’t tell anyone what their second act should look like, only that they should plan for it.

What I can strongly recommend is that this planning phase be slow and deliberate.  

The intermission between two acts isn’t just downtime.  It is an opportunity to engage in a design project.  In my 2025 book Waypoints, I introduced a method for making decisions from the “inside out.”  This “PRism PRotocol” involves first defining your Principles, Priorities, and Preferences and letting those be your guide.  This approach helps you build a solid foundation for a second act of personal significance and satisfaction.

The best planning isn’t only about making sure your money lasts, but that your purpose does too.