Confessions of an Early Retiree

Last March marked the 5th anniversary of my retirement. I earned my last dollar from work at 52, just shy of my 53rd birthday. Now 58, I ask myself what, if any, regrets I have about retiring early.

If I had to confine it to a one-word answer, I might pick one of none, zero, zilch, nada. The slightly longer answer is that I’ve experienced more excitement and adventure the last five years than in all my working years combined.

Was it worth all the money I left on the table; the marginally greater risk of outliving my savings? Hell yes!

The window of my youth was closing. Those years are irreplaceable. The abundance of health and energy I was able to bring to them simply cannot be reduced to a dollars-and-cents calculation.

The Value of Good Health

I am a proponent of retiring as early as possible. The older we get, the more susceptible we become to disease, injury, infirmity and, of course, the inevitable. If we are sick or injured, it’s hard to enjoy life whether we are retired or not.

My immediate goals for retirement—rock climbing and long-distance hiking—were predicated on good physical fitness. I have since aged five years, and the abuse to which I have subjected my body during that time has surely accelerated its breakdown.

Are my climbing and hiking days over? No. But I am coming to grips with the fact that the next five years will permit less of it, and the five years after that less still.

Related: How to Live Long and Live Well In Retirement

The Importance of Having a Plan

I went into retirement with very specific goals. This gave me a roadmap with which to navigate a world with a lot more time on my hands. Without such a plan, my five-year postmortem might be considerably less upbeat.

Some enter retirement with no more detailed a plan than to spend more time with the grandkids, travel the world, live a life of leisure or some such other nebulous objective. The unstated assumption is that anything is better than work. When it’s gone, everything else will take care of itself.

To be sure, those first few weeks and months of retirement will be pure bliss. But like most shiny new things, eventually the luster wears off.

Fuzzy answers to the question, What will I do when I retire?, may be adequate for some. But for most they should probably be treated as a red flag. It is a question that merits thoughtful consideration, ideally before you quit working.

What, specifically, will you do with all that free time?

Related: Finding Your Purpose in a Long Retirement

Related: Living a Purposeful Life After Retirement

Financial and Psychological Preparedness

We spend hours poring over spreadsheets and retirement calculators, or more than a few dollars on professional advice. We consume all manner of financial and early-retirement press; all in service of the question, Do I have enough to retire?

If we are lucky, the day comes when we convince ourselves we have saved enough. Then we jump headlong into the unknown.

The American retirement ethos revolves around the question of financial viability in retirement. Meanwhile, it scarcely acknowledges the psychological challenges of sustaining 20 or 30 (or more) years of self-fulfillment.

Whether we can afford a comfortable retirement is an important question. We should strive to answer it as accurately as possible. But how we’ll spend our time in retirement deserves equal, if not greater, attention.

Unlike the financial question, this one defies ready analysis. Perhaps that’s why we tend to give it short shrift.

Saying Goodbye to Work

In our zeal to achieve financial independence, it is easy to overlook what we’ll leave behind in the workplace.

Adulation, purpose, routine, camaraderie. Do you get one or more of these from your career? They will all but disappear when you quit your job for good. Unless you are a Zen master—one of those who can be truly happy eschewing all things ego—you will feel their loss.

Either we must learn to let go of these things gracefully, or find a way to replace them (hint: it’ll likely be the former).

What about intellectual stimulation? If we got it at all from our jobs, it is one of the few benefits we needn’t leave behind.

I am fortunate. I am stimulated by physical and intellectual pursuits alike. I take solace knowing that when I can no longer do the former, I can lean into the latter. I also realize this may not work for everyone.

What will you lean into when your physical mobility falters?

From Strength to Strength

There is a wonderful book that treats these (and other) aspects of life after work. It was written by Arthur C. Brooks, and its title is From Strength to Strength: Finding Success, Happiness and Deep Purpose in the Second Half of Life.

I read and found this book incredibly useful, and plan to write about it more extensively in a future post. It offers a novel and credible approach to dealing with post-career letdown.

Related: Becoming a Beginner in Retirement

Related: Why You Should Never Retire

Reaching the Mountaintop

About a year ago I was hiking out of a remote canyon in Capitol Reef National Park. I had just spent several nights in the wilderness. It was before dawn, and the gathering light cast the cliffs in dazzling colors.

I reflected approvingly on my first years of retirement. Should I stumble and fall from a cliff at that instant, I mused, I could imagine no more perfect a state in which to depart the world.

For better or for worse, I did not walk off a cliff. I knew even then that such moments of intense fulfillment are fleeting and elusive (if we are lucky enough to experience them at all). They may even portend trouble.

Cracks Begin to Form

Last winter, mere months after that sublime moment in the wilderness, I began to experience something I had not known since childhood: boredom.

I manufactured ways to stay busy; to keep from lingering too long in my own head. I reassured myself that it’s probably normal for a retiree to get bored from time to time.

All the same, the feeling frightened me, and served as a wake-up call. It was time to ask myself what I want the next five years of my life to look like; to construct a plan worthy of the one that propelled me into retirement in the first place.

Past Performance and Future Success

The old investing adage warns us that past performance is no guarantee of future success. The same can be said of life after work.

My first five years were indeed magnificent, and I have zero regrets. But they are behind me now. To sing as rosy a tune on the ten-year anniversary of my retirement will require planning, effort and more than a little luck.

I’d love to know what others think. Did retirement turn out the way you envisioned? Has it been mostly good, bad or somewhere in between? What were (or are) your challenges, and how did (or will) you navigate them?

I invite you to share your experiences, insights and/or observations in the comments below.

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[I’m David Champion. I retired from a career in software development in March 2019, just shy of my 53rd birthday. To position myself for 40+ years of worry-free retirement, I consumed all manner of early-retirement resources. Notable among these was CanIRetireYet, whose newsletters I have received in my inbox every Monday morning for the last ten years. CanIRetireYet is one of exactly two personal finance newsletters I subscribe to. Why? Because of the practical, no-nonsense advice I find here. I attribute my financial success in no small part to what I have learned from Darrow and Chris. In sharing some of my own observations on the early-retirement journey, I aim to maintain the high standard of value readers of CanIRetireYet have come to expect.]

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