Stumbling Towards Retirement

The last thing I expected at age 50, after 30 years of full-time employment, was to find myself preparing to attend tractor trailer school. It was a surprising journey. I was a partner at a large private equity firm. I really enjoyed my work and my colleagues. Why was I feeling increasingly unsettled? I finally came to terms with the fact that I wanted to start a new phase of life, so I made the difficult decision to retire.

My hope was that I could put my technical experience to use helping others. I envisioned that retirement meant no longer ceding control of my time and personal priorities to the inevitable demands of a full-time job. At the same time, I was scared by such a radical change with so little certainty about the outcome. My greatest fear was that I would become irrelevant. At the request of my partners, I deferred acting on my decision for a year. I was secretly relieved when they delayed me from actually taking the leap.

During that time I spoke to a number of friends, acquaintances, and strangers who retired after long and successful careers. I figured I could learn much from their experiences to help me prepare for my own transition. I was surprised and disheartened by what I discovered. Little did I know that they would add to my trepidation as I struggled to put every piece in place before leaving my job. The pieces weren’t connecting and too many seemed to be missing. It felt like I was preparing for a trip and couldn’t figure out what to pack. It took me too long to realize that retirement entailed embarking with empty luggage and figuring out what to pack along the way.

Some people I spoke to were at peace with their decision, but a disheartening number of retired professionals were adrift and unhappy. They craved the fulfillment, recognition, and rewards enjoyed during active employment. They added to my own fears because I did not expect to find them so desperately trying to recreate the same external structure during retirement. Most disturbingly, many admitted to being lonely as they gradually lost the cohort that anchored them during their working career.

While many people retire by choice, an increasing number of productive professionals are forced to retire prematurely because of ageism, buyouts or layoffs. Even though I retired under different circumstances, I am acutely sensitive to the pain, frustration and financial hardship that can accompany such a brutal and unwanted transition. I have also been humbled by the experience of those who chose retirement to take on the role of primary caregiver for aging parents. That is such a challenging circumstance that I do not feel I have standing to offer any observations, just deep respect.

A friend recently asked me how I shaped my retirement in light of the many retired professionals he knows who are unmoored. To paraphrase him, “They were at the top of their game and now they are confused and cannot figure out what to do with their lives. They feel like no one returns their calls”. My friend was intrigued by my own stumbles and subsequent discoveries over the past decade. He suggested I write up an account of my experience so others might find it easier to chart a course that can work for them.

Looking back over the past 10 years, I now realize that my own mis-steps paved the way for a more enjoyable and balanced future. Those often harsh lessons informed a framework that evolved to start working for me. The frustrations of the first few years “out of work” eventually gave way to a more fun and interesting phase of life. With that in mind, I hope that you might benefit from what I learned during the twisting journey from employment to retirement.

Of course, anyone contemplating retirement will have to frame an approach that works for them. For what it is worth, here is mine.

Constructing an internal resume

Many people who have enjoyed a successful career have been rewarded with relevance. Unfortunately, some have not. Relevance comes in many forms: public accolades, respect from colleagues, deep and unique expertise, financial success, assistance to others, a fancy office, a beautiful home. You get the idea.

Some of these accomplishments are universally lauded and admired. Others are usually deemed to be superficial and self-indulgent. Regardless, they all shape our own perception of personal relevance. I’m sure you know countless “successful” people who try to impress by convincing themselves that what they can buy and what they can control makes them relevant. I learned the hard way that relevance purchased is not relevance earned. 

When I was struggling with “how to retire”, the most impactful insight came from Tom Gilovich, a leading psychologist and former chair of the Cornell Psychology Department. He told me that I was more likely to find fulfillment and balance in retirement if I focused on my “internal resume” and stopped worrying about my external resume. He observed that many successful people have dense external resumes and surprisingly sparse internal resumes. 

Our external resumes are chock full of degrees, accomplishments, and other validating signals of success. I assume many of you are justifiably proud of your external resume. At the same time, our external resumes rarely reveal much about our values, passions, commitments outside of work or the relationships that matter most to us. That’s where the internal resume comes into play. Our internal resumes are focused on personal values and the focus we bring to activities that exclusively nurture our inner sense of purpose, or the impact we have on others. Most importantly, no one else will see your internal resume. You only write it for yourself and you are the only person who edits it. 

I often reflect on Tom’s observations because they stood out then and still do today. As a result, I reframed my approach to retirement. Instead of prioritizing activities and relationships that were vital during my working career, I now find myself focusing on developing new relationships, new skills to serve others and maximizing autonomy from unwanted obligations.

Even though I am often asked to describe my internal resume in detail, that’s not how it works. Suffice it to say that a few concrete examples are the best I can offer. I started teaching, asked three coaches to help guide me in learning new skills, fulfilled a long held dream to go to tractor-trailer school, lent my technical skills to some national security challenges, and sought out non-profit entrepreneurs who are gearing-up to tackle unmet needs. It might take longer than you are comfortable with to refine your priorities to the point where you no longer feel like you are grasping to find purpose. It’s worth the wait…

You’ll be surprised how many apparently relevant activities suggested by others don’t deserve an entry on your internal resume. You’ll be liberated when you say “no” to suggestions that you might have jumped at in the past because they enhanced your external resume. The shift from “yes” to “no” will liberate you as it starts to feel comfortable and justified. It didn’t exactly start off that way…

The perils of overcommitment

I was scared by the disturbing conversations I had with those who were adrift. I was scared that my phone would stop ringing. I was scared that my hard-earned professional expertise would be deemed obsolete. I was scared that I would not be invited to engage in professional activities. I was scared that I would become irrelevant as my external resume stagnated. I was scared to retire.

Because of this self-perceived void, I committed too early and too often to activities that, in hindsight, were unjustified. Looking from the outside, you probably would have endorsed most of my choices. Looking from the inside, I was increasingly unhappy with the prospect of what retirement was offering. My wife was also critical of my choices. My misallocation of time was a painful stumble. The worst part is that my most valued mentors (you know who you are) strongly advised me against over-commitment during my initial transition. I ignored their advice and paid the price for doing so. You’ve been warned. If you choose to make the same mistake, don’t blame me.

It took me several years to unwind those premature decisions and ill-advised commitments. I regret the wasted time, dissipated resources, and strained relationships. I strongly recommend you not commit to anything until you are sure that it deserves a place on your internal resume. Three months of recognizing my fear for what it was, and sidelining myself to reflect on how to reframe relevance, would have saved a lot of frustration and regret.

Time is NOT money

I got lucky in my professional career. Undoubtedly many of you did too. As a result, you may have freedom to spend time on activities that are not necessarily focused on personal earnings or profit. I am especially mindful that many people still need to generate income in retirement. I hope my experience is helpful, regardless of individual economic circumstances.

You won’t be surprised to learn that when you value your time at $0/hour, there will be unlimited demand to consume it. Most of my early commitments were made as a “favor” to someone to whom I felt obligated. A few of these activities were fulfilling. Most were not. All took more of my time than I expected…and too much time to conclude or unwind. 

I hope you are wiser than I was and do not over-commit, but that’s only half the battle. Any time devoted to others, whether it is compensated or not, has to earn a place on your internal resume. If you don’t want it there…then you’ll be much better off by saying no.

But as usual, it’s never that easy. We all have obligations that can’t be ignored, regardless of whether we are retired or not. What’s less obvious is how people, including people you really care about, will react when you say no to their request for a commitment of your time. I’m still taken aback by some of the responses I get when I say no to requests for “a short meeting”, “a quick phone call”, “an urgent email”, “a chance to mentor a promising young professional”, “the opportunity to engage with a deserving non-profit” or “a compelling investment opportunity”.

Suffice it to say that “no” does not bring out the best in people. If it sounds selfish, that’s only because I spent too much time responding affirmatively to other people’s priorities. My poor triage for the first few years after retiring was a waste on many levels. The converse is so much better. When you do say yes, it will be with genuine commitment and a sense of deep satisfaction when your impact is positive and meaningful. Empty time is a privilege and a reservoir of power and potential that you should not squander. You’ll fill it when the time is right, and feel good about it when you do. 

When you come to a fork in the road…take it!

Some people retire to bring renewed focus to a primary activity or passion that is important to them. I completely understand and celebrate that choice. I eventually came to understand that I needed to travel a different path. 

My priorities are to get on the steepest learning curve possible, to avoid interactions with toxic people and to refocus on individuals rather than on institutions. This led me to construct a “portfolio” of loosely related activities in four areas that are relevant to me. These are entirely personal choices that I could not choose in the prior 30 years of working for an employer. My approach is no better or worse than the alternative of a more unified focus. All I know is that regardless of which fork you choose on the path to retirement, there is one path that is almost certainly going to end in tears.

Past has to be context for our future, but you’ll likely join the ranks of the unmoored if you strive to recreate your professional past in retirement. Many struggling professionals think that they’ll regain their sense of purpose and externally validating structure by joining boards, focusing on non-profit activities, and investing in small companies to counsel entrepreneurs. All of these activities can be fun and fulfilling, but not if they are an attempt to continue filling in your external resume. 

I learned the hard way that public boards can be a major hassle and create too much stress for too little return. Hopefully you’ll find more fulfillment on that audit committee than I did. Many non-profits are looking only for a checkbook and have little interest in operational engagement from board members/donors. And sadly, many young entrepreneurs are not really interested in advice from a well meaning, retired expert who wants to “coach” them.

At the risk of sounding overly prescriptive, file your external resume away with all those lucite tombstones that no one cares about but you and your cleaning person. Only you can definitively decide if you want to create a new portfolio of activities or primarily focus on a personal passion. Either path can be more balanced and satisfying than you expect…and might unnecessarily fear.

We’re in this together

Although it might seem obvious, retirement really does require a challenging re-definition of your relationship with your spouse/partner/significant other. We’ve all heard funny stories of the retiree who re-organizes the spice drawer. I was much more enlightened…I reorganized the book shelf on my first day of retirement (no joke).

Seriously though, because I over-committed so early I did not leave room for the inevitable partnership rebalancing that must come when you retire. I’m lucky that my wife, who was already retired, called me out and insisted that I stop trying to recreate my past. She’s the one who recognized my unjustified fear of irrelevance for what it was. She kept insisting I would still be relevant in a different way. I refused to believe her. She was right. I was wrong. Who knew marriage could be so complicated?

If you allow for it, you’ll eventually find a new steady state that leaves room to spend time together in ways that were not possible when working full-time. Of course, synchronizing with a working partner poses a whole other set of issues I’m not qualified to address. Fortunately, my wife and I finally figured out what works for us, but I have to admit that she has no interest in spending all her time with me. Who can blame her?

The biggest surprise

I spent the first stage of retirement trawling my contacts for lunch dates, coffee and other activities with people I knew. It filled my time. It was sometimes interesting. It was no different than when I was working. I already knew these people and felt a little desperate trying to catch-up on professional lives and situations I had formerly been part of. I was taking a misguided approach to stave off the loneliness that afflicts so many middle-aged retirees. I came to realize that, along with focus on my internal resume, I needed to find a new cohort populated by people I did not already know. I gave priority to those who were doing things that had nothing to do with my prior career. As I write this, I am smiling because I just got an email from an expert woodworker who has become a friend. We never would have met if I didn’t spot his work and make the effort to seek him out. I can count many other interactions like this. I’ve serendipitously met soldiers, academics, magicians, physicians, poker players, entrepreneurs, and especially truck driving instructors, who have enriched my life since I stopped working. Many of these people don’t share much in common with my former colleagues, but they sure are fun, often humbling, and personally enriching to hang out with. I know you are never supposed to eat lunch alone, but it gets even better when you eat lunch with someone you don’t know. It takes work and some chutzpah, but you’ll have more time to get used to it when you retire.

The Bottom Line

Every retirement looks different and what works for me may not even be close to what works for you. I do know for sure that you will be stuck in a holding pattern if you wait until every piece is lined up before taking the plunge. Don't worry about packing your bags. You’ll be off to a good start if you focus on enhancing your internal resume, protecting empty time, redefining your relationship with your life partner, engaging with a new cohort, and choosing a primary focus or a portfolio of activities. You’ll discover that you’re relevant in new and surprising ways. Your calls will be returned. You’ll learn a lot about life that you don’t already know and, if you really want to have some fun, you can always learn how to parallel park a 70 foot tractor trailer.

Good luck writing your next chapter. I hope we get to share discoveries over lunch.