The Case For Work

“Two roads diverged in a yellow wood,

And sorry I could not travel both

And be one traveler, long I stood

And looked down one as far as I could

To where it bent in the undergrowth …”

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So begins my favorite poem, “The Road Not Taken,” by Robert Frost. It has always been a defining metaphor for my life.

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Context

I recently celebrated a milestone birthday, my 65th. At least, the Social Security Administration recognizes it as a milestone; it’s the age at which one qualifies for Medicare. (Pretty much every insurance company in the country apparently recognizes it, too, because my mailbox began filling up with Medicare-related recycling fodder several months before the big day, and the mail continues to roll in a couple of months later.)

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At my age, many of my contemporaries are retiring, or have already retired. I see the notes of congratulations to them on LinkedIn and Facebook, and to those I add my own congratulations.

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A teacher once explained the stages of life as thus: Not Old Enough to Know Better; Old Enough to Know Better; Not Old Enough to Know; Old Enough to Know; Not Old Enough To; Old Enough To; Not Old Enough; Old Enough; Not Old; Old; and Not.

More seriously, for Americans, the traditional stages have been simpler: pre-school; school; career; and retirement (let’s not think about the “Not” stage at this point). But there’s a case to be made for either delaying retirement past the traditional retirement age, or even not retiring at all. Before I make that case, let me describe my path.

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My Journey

For most of my career as an investment analyst, investment advisor, and economist, I did quantitative analytical work: heavy doses of statistics, stochastic calculus – the stuff of most people’s nightmares. And I loved every minute of it. Later, as a CEO, my focus was on strategic problem-solving. I had to out-think not only the threats and opportunities that the market presented, but my competitors, regulators, and sometimes, lawyers and even my own board of directors.

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My brain needs those kinds of cognitive challenges to not atrophy. It’s just how I’m wired. I need to be doing some kind of quantitative work, or I’d be counting the ceiling tiles and multiplying them together. And I need to have complex problems to solve – but I’d prefer that they’re not my problems, like they were when I was a CEO.

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When I left my CEO role, I never wanted to be in that role again. In fact, I never wanted to manage people again. I wanted to get back to what I did as an investment advisor: helping clients solve their problems. I was fortunate to land a consulting job that allows me to do just that. I work from home, and have since well before the pandemic. I control my own schedule. And since the pandemic, I only travel about 15 days a year for work.

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The Case for Work

I could retire today. We have more than enough saved for retirement, and I’m eligible to begin Social Security withdrawals. Some of my friends question why I continue to work; others almost act as though they feel sorry for me because I’m still working. So why am I working?

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First and foremost, I love what I do. I love solving problems, and more specifically, helping clients solve their problems. I believe that’s why some people are so ready to retire: they’re doing work they have to do to make a living, but they’re not necessarily doing work they love.

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Second, I’d get bored. I don’t really have any hobbies: I don’t play golf, I don’t fish, I’m not a gardener or a painter. I don’t like playing board games or doing crossword puzzles or sudoku. I gave up serious cycling a decade ago. I do work out nearly every day, but my job affords me the flexibility to work that into my schedule. I also walk my dogs whenever the weather allows. And I’m a voracious reader, but I can do that in the evenings or when I’m traveling.

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If I retired, what would I do? How would I spend my days? Walk the dogs, work out, read – all things that I do today. But what then? I don’t want to spend my time watching TV (especially the news) or getting sucked into social media. My wife, nine years my junior, still works part-time. She loves what she does, and isn’t interested in retiring yet. So it’s not like we’d be doing things together – I’d have to entertain myself all day.

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There’s travel, but I have the flexibility to do that now. My company doesn’t really limit PTO within reason, as long as the work gets done. And I can do my job from anywhere. In 2023, I took about five weeks’ vacation time for travel, though I did some work on a few of those trips. This year’s plan is similar. If we retired, I doubt that we’d travel much more than that, at least as long as our dogs are around.

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I know people who are retired who don’t travel more than that. I also know people who are retired who are on the go constantly, and that’s wonderful. Of course, it’s hard to do with pets, and it takes you away from your grandkids, if you have them. We’re blessed that our kids and grandkids are only about 20 minutes away. I wouldn’t want to be away from them constantly.

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In addition to having flexibility to travel and work from anywhere, I also have flexibility in planning my daily schedule. Most of my work consists of webex meetings with clients. I provide them with my availability, but I can set parameters around that. I can block off days that I want to reserve to get other work done. I can make sure I have open time during the day. With clients on both coasts, I can make sure that my day doesn’t stretch to unreasonable hours in my time zone.

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I work on weekends occasionally. But that allows me more flexibility during the week. And often it’s by choice, because again, I enjoy what I do, and it keeps me from what could otherwise be a boring weekend day with nothing to do.

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In short, my work essentially is my hobby. It keeps my brain active; I enjoy the engagement with my clients and helping them meet the challenges they face. I often use the graphic below to describe the ideal balance of one’s work:

?I’m fortunate to have found work that’s aligned with my purpose. Now, let’s look at the financial side of things.

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You Are Paid for It

Again, we’ve saved and invested well, and I’m eligible for Social Security (SSA) withdrawals. However, I hate leaving money on the table. If I work just five more years, until I’m 70, my monthly SSA benefits will increase by more than 45%. That’s my money; shouldn’t I maximize it for my benefit, instead of giving some of it to the government?

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Look at it from an investment perspective. Waiting to withdraw SSA benefits until I reach full retirement age – 66 years and 8 months in my case – earns me a guaranteed 6% rate of return for that 18-month horizon. That’s about a percentage point higher than the current yield on a similar maturity Treasury security, with the same full faith and credit government guarantee. And if I defer withdrawals from my full retirement age until age 70, the guaranteed annual return on my benefits increases to 8%. That’s approaching long-term historical stock market returns, but without the risk of the stock market.

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Working also allows me to delay applying for Medicare until my wife is eligible. We’re currently covered under my employer’s health care plan. If I went on Medicare, she’d either have to work full-time to qualify for benefits through her job, or we’d have to purchase insurance for her on the Affordable Care Act exchange, which at our income level would be anything but affordable.

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Then there’s the fact that I’m also continuing to defer part of my compensation into my company’s 401(k). My firm offers a generous match, effectively providing a guaranteed percentage of my salary on top of the money I defer, even if I invested it in a money market fund. That match is also money that I’d be leaving on the table if I retired today. And it’s a Roth 401(k), so the money that I ultimately withdraw from it – including investment earnings – won’t be subject to taxes.

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Will I need that much additional money to live on after I retire if I work until I’m 70? Probably not. But we can live much more comfortably. We can travel more. My wife can continue to live well and travel after I’m gone. And we can leave a legacy to our children, our grandchildren, and charitable causes we believe in. Also, we don’t get nervous every time the market drops.

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As would be the case if I were retired, I’m living on a (slightly) reduced income vs. my previous earnings as a CEO. I’m traveling about as much as I would if I were retired. My work is like a hobby to me. I have the flexibility to pursue the activities that I enjoy. At the same time, I’m keeping my brain active and challenged, I’m doing something rewarding with my time, I’m adding value to an industry that I believe in, and I’m building additional wealth for the future: mine, my family’s, and causes we believe in. It’s like being “retired with a paycheck.”

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A Final Consideration: The Alternative

Several retirees I know now serve on boards of directors. I’ve served on various boards throughout my career. While I was a CEO, I was on my company’s board for thirteen years. The benefits to be gained from serving on a board are no different from the benefits of my work. Plus, I prefer a more hands-on approach. And I’ve seen too many boards become bogged down in inertia and political dysfunction, which is frustrating.

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Some of the commonly cited advantages of serving on a board are exposure to other companies’ operations; networking; leveraging one’s experience for the benefit of the organization being served; a sense of accomplishment in seeing others succeed based on one’s counsel; building one’s reputation/credibility/expertise; learning, building new skill sets, and professional development; and compensation and other perks.

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As a consultant, my work provides all of that. I have a variety of clients with varied operations, sizes, and structures, from coast to coast. I continue to build a network of professional contacts as I work with new clients and take on speaking engagements. I’m able to leverage my skills and experience to my clients’ benefit, and to see them succeed as a result. I’ve largely built my personal brand in the industry, but I do have the opportunity to increase my reputation further. I’m constantly learning - I work in an industry that is continually evolving, in a marketplace that is rapidly changing, surrounded by some of the best talent I’ve ever had the pleasure of working with. And my compensation and benefits far exceed anything I’d receive as a board member for any but the largest organizations.

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Summing it Up

One of my favorite authors, Brad Thor, defines happiness this way: “Being happy boils down to three things: Something to do. Someone to love. And something to look forward to.”

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My work gives me something to do. It’s something I enjoy, it’s meaningful, and it adds value to my clients, their members, and the industry. I have a wonderful family (including our pups) that I love with all my heart. And I have much to look forward to – that includes my work, but also travel, and eventually, probably retirement. I don’t know exactly what that will look like. I may continue to do a scaled-down version of what I do now, perhaps on a contract basis. Work is vital to me, and it keeps me vital. It gives me energy and keeps my brain active and engaged.

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There is nothing wrong with the traditional path of school; career; and retirement. Certainly, if you have hobbies about which you’re passionate, or are able to travel extensively, or just don’t need the mental stimulus (or have other outlets for it), you should retire when possible, especially if your work isn’t enjoyable. But if you have the flexibility to travel and pursue your interests while enjoying a career that you love and has purpose, and if that work provides the challenge and cognitive stimulus that feeds your vitality, there’s a strong case to be made for continuing to work, even if you don’t have to.

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Robert Frost’s poem ends this way, and neatly sums up my journey:

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“I shall be telling this with a sigh

Somewhere ages and ages hence:

Two roads diverged in a wood, and I –

I took the one less traveled by,

And that has made all the difference.”