Retirement is Obsolete

Midjourney AI: "an empty rocking chair on a porch with an elderly man running through a field in the distance"
Midjourney AI: “an empty rocking chair on a porch with an elderly man running through a field in the distance”

I “retired” in 2001 at 44, after an 18-year career at Microsoft.

There was a spreadsheet (in Excel, of course) that calculated I was done. The meteoric rise of the Microsoft stock price and the serendipitous timing of my joining came together to give me options (including literally stock options), for which I am forever grateful.


I was recently reading some articles discussing the traditional transition from the work-a-day world — aka a “job” — to a world of leisure and choice — aka “retirement”.

I was getting increasingly uncomfortable with the assumptions and preconceptions of what it means to retire.

For many retirement means no longer doing productive work.

I don’t mean to imply that’s bad. It’s definitely one option: a retirement full of leisure travel, personal experiences, and more.

Especially at 44, that certainly wasn’t me. Besides, I had long before decided I would never truly retire. At least, not by the get the gold watch and go home definition.

But regardless of age I now believe the concept of retirement, especially at some arbitrary point in life, is simply outdated. There’s no scenario where we should expect anyone to retire at some pre-defined age.

There are two important aspects to this outdated mode of thinking.

Society’s expectations

Agism is rampant, and retirement expectation is one common way it manifests.

Retirement is, in part, built around the assumption that as we age we can no longer be productive members of society. The arbitrary number seems to be 65, but that’s an artifact of how the United States set up its Social Security payout system. AARP (formerly the American Association of Retired People) seems to think 50 is when they should start collecting members to join their ranks.

I won’t claim that abilities don’t change as we age; they do. I see it in myself.

I won’t even claim that some abilities don’t degrade. Just ask my knees. I was tempted to say “just ask my memory”, but honestly, that’s never been one of my strengths.

And that’s one problem. We are all a complex collection of strengths and weakness throughout our lives. That those strengths and weakness might change over time is also nothing new.

But approaching “retirement age” seems to be an invitation for society to focus on one: our weaknesses. The resulting expectation is that it’s time we stepped back from whatever it is we’ve been doing, regardless of our actual ability to do it, or something else productive.

Our personal expectations

I knew from an early age that my chosen profession would see me not just through to “retirement”, but to my deathbed. I realized, and continue to expect, that I’ll be playing with this stuff until some actual physical or mental limitation rears its ugly head.

My assumption is full speed ahead until I kick the bucket.

Not everyone makes that assumption. It’s unfortunate, but I hear from too many people who not only make that assumption — “I’m too old” — but end up using it as an excuse well before there’s any tangible reason to assume decrepitude.

It’s frustrating.

But society has taught us how we’re supposed to set our expectations, and many dutifully do so.

So. Many. Options.

Life provides an ever-changing array of opportunities, regardless of our age. Technology has only increased the number of doors open to us.

When I turned 44, I didn’t retire by any classic definition of the term. I was privileged to be able to focus two years on aging parents, and then I started my entrepreneurial journey. In a sense, I went back to work.

It was a choice.

I needed to stay busy. I need to do something. And I had a passion for technology. My “retirement” would allow me to continue to pursue that.

It wasn’t a retirement as much as a choice to keep doing.

Keep doing

I’ve commented before that traditional retirement — sit on your ass and watch TV all day retirement — is a death sentence. Premature death after this style of retirement is not uncommon.

This, too, is frustrating, as it doesn’t have to be this way. So many options. So many choices.

We all have the choice to keep doing something; to continue to have a purpose and meaning in our life, and a reason to get up in the morning. It doesn’t have to be world altering, it simply has to be meaningful to us.

That’s not retirement. That’s simply changing and choosing to follow a different passion.

Whether that’s at 44, 65, or 86, it doesn’t matter. Age is irrelevant. It’s our desire, our passion, our abilities, and our situation that combine to offer us choices at any age.

The changes throughout life aren’t about retirement but about transitioning from one collection of needs and opportunities to another.


In an ideal world, our ability to make a living aligns with our passion. I was very fortunate that this was the case for me when I discovered computing. But for many, perhaps even most, the alignment between earning a living and fulfilling your passion isn’t necessarily as straightforward as we might want.

As we live circumstances change. Opportunities make themselves available to us at any point, and at any age. And sometimes we’re able to take advantage, or at least make a choice.

“Retirement” — the traditional cessation of productive work at some pre-defined age or age range is an outdated concept.

It’s simply wrong.

There’s no reason we shouldn’t be able to continue to pursue our passion as long as we’re cognitively and physically able, or to pursue something that calls to us and that fits our skills and abilities.

Isn’t that the definition of contribution at any age, anyway?

Make choices. So-called retirement need not be so much an end to a work life but a change or a retargeting of our efforts into something that perhaps more closely aligns with our passions and our circumstances. Something allowing us to continue to be productive, for whatever that might mean to us.

Don’t assume you’ll “retire”.

In fact, stop using the word.

Instead, expect that throughout your life you’ll have opportunities to transition into new careers, if that’s what you want, new lifestyles, if they call to you, or just spend your time more closely aligned with your needs, your values, and your dreams.

But never, ever, stop living. And for too many, that’s exactly what “retirement” means.

23 thoughts on “Retirement is Obsolete”

  1. Hear hear.

    When I worked at NASA’s Jet Propulsion Laboratory (and I left there more than a quarter-century ago!), I definitely noticed that many co-workers were well beyond 65 years old. They were encouraged to continue working if they wanted to and were capable of doing their jobs without regard to their age. One classic case is Ed Stone, the project scientist for the Voyager missions, which started in 1972. He was still the project scientist when I visited JPL in 2017 and had the opportunity to chat with him. He was 81 years old, still sharp as a tack. He only retired last year, after 50 years in that role.

    It’s one of the reasons I wanted to be a writer (and the publisher of my own work): I might slow down. I might change focus. But as long as my brain works, I can still explore the topics that interest me.

  2. Thanks so much for your thoughts on this subject! I am 72 and work fulltime. I get so many questions about retiring with most of them implying that it’s past time to go just because of my age. I even kept telling myself, “okay, I’ll retire this year.” I realized I was following the same line of thinking, that it was time to go.

  3. In 2018, a job I had been doing for 27 years, in human resources for a small company, came to an end. I was 57. I decided that I simply had no use for the 40-hour workweek any longer, and I also had no use for New Jersey winters. With no family to tie me down, and a decent 401(k) balance and the proceeds of a house sale to sustain me, I picked up and moved to Florida, intending to watch a lot of baseball and supplement my income with Uber driving. Well, that turned into a continuation of my previous side hustle of public address announcing. I’m now working for the Phillies at their spring complex in Clearwater, doing the PA for the minor league team that plays there. More than one person has told me that I’m living my dream. I feel healthy and I can probably do this for another 20 years as long as my eyes and voice hold out. It was the best change of scenery that I could have imagined.

  4. The first 17 years of my computer career were mostly on the constructive side with occasional investigation of destructive activities. The last 27 years have been on the destructive side of computers. Most of that has been figuring out how someone might abuse computer systems in order to forestall such actions. Occasionally I have gone fully to the dark side I tell people that I will not retire because if I do I would lose the get out of jail free card.

  5. I’ve failed what was supposed to be retirement five times. Now I fail it every day The day I don’t fail retirement will be the day after I die!

  6. I am a 72 year old software engineer. My retirement plan is that my wife will pry the mouse from my dead fingers, then call my boss to ask, “Where do you want me to send his computer?”

  7. You are 44. you may change your mind as you age…

    When I was 50, I told friends that I would only retire when I no longer loved my job, and that I loved it so much I could not imagine retiring. By 62, I was tired of work, finding it repetitive (I was a software developer), and realized that in a group of 50 developers, nobody else was born yet the year I was married…

    At 63 I retired and moved to Ecuador. I was afraid it might be rash and a problem in the future… My boss asked me to consult in retirement on a project the following year, and I took that lifeline and said yes.

    The next year, he told me that Xmas sales had been poor and he had been ordered not to use consultants. I made the “oh, sorry” noises to him, but privately I was pumping my fist and shouting YES! I had made a commitment and would have followed through, but I discovered I did not want to “work” any more.

    That was a decade ago (in 2013). Since then, we have moved to Honolulu and now have homes both here and in Ecuador. I can barely remember being in an office, and cringe at the thought of it now. When people want to hire me (and I have gotten half a dozen offers in the decade since retiring) I state emphatically that I no longer work for money. If they convince me that their goal is valid and of interest to me, I will do it for free, but I am no longer shackled to cash and paying the bills.

    If you have the money you imply from your stock, you may find a decade or two from now that your opinion changes significantly…

  8. After working as a software engineer for 28 years at HP (and 10 years with other companies prior to that), HP decided it was time to cut me loose. It was the best thing that ever happened to me because I’m now an education assistant (teacher’s aide) at an amazing K-8 school where I get to help kids at all grade levels with math, English, science, PE, courtesy, kindness, friendship, trust, etc. My mom turned 100 last year and is still going strong, finding and making purpose every day. I’ll be 65 this June and I figure I’ve got an easy dozen years ahead of me in my new ‘career’. I tell people, “I had great fun working at HP making stuff… and now I’m having even more fun making a difference in the lives of the kids at school.”

  9. I retired from a public school district at age 65 because it didn’t make financial sense to continue working with the structure of our state’s retirement system. And truth be told, I could no longer work (IT work with the school information system) 8 – 10 hours a day and get anything else done at home like mow the lawn. But as many persons, after a year of “vacation” and traveling”, I itched to go back to work. Substitute teaching in a vocational school for me was the ticket. I learned lots of new skills, worked when I wanted to, and was always appreciated when I did my job. Now at 76 I can not imagine giving up the my work. The best coffee and conversation in the morning is still in the IT office!

  10. I find it interesting that the comments all seem to be from people involved software/ IT – not seeing how people who work in public safety, medical field, highway construction might feel about keeping on working past a particular age…

    Look, I get it – if you love what you are doing, software is one of those things that you can do without much stress on your body; assuming your mind stays sharp you can keep on doing it.

    Me? I’m in the software business. I was working for a company where they announced that a prominent employee had died at the age of 87, still working; and I thought “that’s terrible!” Now obviously I was project my state of mind onto him. Also, that company was not fun to work for (in my opinion) so the thought he was stuck there till he died appalled me. Again – he probably loved it like so many of you on this thread. I’m now at a partner of that awful company, and have to watch what they are doing to their s/w products and act like it’s a good thing; but looking for another job at another company is not what I want to do at this age. I want to retire – just let me get to Medicare age and then I hope to be out of here.

    Call it whatever you want. But there are many of us who don’t want to be still working for a company after a certain period of time. We don’t want to put up with the BS (I had to do a self-evaluation this year – really? at my age, after all these years, really? We got bought by another company that has them… ugh). I want to read. Maybe go on some easy hikes. Watch TV. Enjoy days where I don’t have to toe the line and do what the company wants me to do.

    Guess I don’t have the passion for software, IT, teaching, that so many on this thread have.

    So just a grumpy counter-opinion from someone who thinks we work to afford a house, food, car, entertainment; we don’t work to feed our souls. I think it’s great that Leo and the others are so passionate about it and don’t even call it working. Great! but remember others feel differently and that’s great too.

    • I think you’re missing the point. I’m not suggesting you need ot keep a J-O-B, or work for some employer. What I am saying is that the concept forced retirement is bad, and that we’re all better off if we do something, anything productive until the day we die. Doing nothing (traditional “retirement”) merely hastens that day’s arrival.

      To use your terminology: we should never stop feeding our souls, whatever that means for us individually.

  11. I was needlessly retired, medically from the US Army , at the age of 36 (in 1986.) I understood the Army’s need for physically fit warriors,” but I wasn’t in a “warrior” field; I was an enlisted nurse (LVN or LPN depending on the State that give the license.)

    In a darker financial time while on Active Duty (AD) I worked, as I could for a Nursing Agency, they staff hospitals that find themselves short of workers. When I was retired, I went right back into Agency work. Along with my Military Retirement pay, what I earned at the Agencies allowed me to feed, and all the other stuff, a wife and two children (teens), and buy a nice home. The AD Army’s loss was my gain.

    Looking back at that time, the Army was not in conflict, and I could have been assigned to a teaching position (after all, good nurses spend a great deal of their time teaching patients how to better take care of themselves) and I was always most comfortable teaching my subordinates new techniques. And, the kicker was my size. I’m 6’5″ tall, and even with the disabilities listed in my Medical and Physical Boards, I was still capable of leading a squad or platoon in the field (proven a month before I was retired during a Field Training Exercise. Not actual battle, but as close as we could come.)

    I continue to say this: if the Army had allowed me to stay, I would still be in uniform today, at age (almost) 73. I love the job! But in looking back over the past 36 years, I have to say that I have also loved working in the civilian workforce.

  12. What concerns me is the increasing difficulty of finding employment. I haven’t been able to pile up money like the OP and many of the commenters: if I can’t go on getting J-O-B-S, I’ll end up living on the street and eating cat food from cans. I can get consulting work for a year or two, but then I need to persuade someone to hire me again, and the fact that I can do the work will become simply irrelevant if employers continue to take a traditional view of my employability. It’s pretty frightening.

    • I’ve thought about that a lot. My take is that now is an excellent time for individual entrepreneurship. The internet has SO MANY OPPORTUNITIES — from freelance work, to publishing opportunities, to creating and running your own business. There’ve never been so many opportunities. Not all are for everyone, but particularly if backed into a corner, that’s where I’d be investing my energy.

  13. I am a Line Cook. I am 62 years old. I have been in the restaurant industry since I was 25, with a 7 year break as a Houseman at a Holiday Inn. These jobs are physically taxing. Luckily, I have been in good health. The bending, stooping, walking, standing in one place has kept me in pretty good shape. I also love working with food, whether prepping, or working the cook’s line. Cooking is one of my favorite hobbies at home. I have found my passion.
    Although working in my favorite career field is satisfying, the mental challenges of working in a restaurant are the reason I am counting the months until I am 65. My schedule is not set in stone. Most restaurants are under staffed, so being called in on a day off is common. The hours range from 40-60/week. Making plans is impossible. I frequently miss family events, since most people with
    “real jobs” are off on the weekend. Unless I give at least one month’s notice, I cannot attend these events. These facts are normal at any restaurant you work.
    I can cook anywhere, and jobs are plentiful. I want to cook at a place maybe 2 or 3 days a week. I can also volunteer more at my American Legion post. I miss monthly meetings and post events. I can arrange my work schedule around family and Legion events, and indeed set my own schedule. I want to be in charge of my life instead of waiting for the phone to ring.
    That is why I am “retiring”. On my own terms. No one is forcing me to retire except me.

  14. First off: Shameless plug for Randy Cassingham (responder #1) for pointing me at this. Like many of you, I’ve worked most of my life in one form or another: part-time while in school (back in the day) and then a succession of jobs until I found my “sweet spot.” Vietnam Era US Navy for a 26 year stretch (general Electronics Technician) then got into computing with MS-DOS and haven’t looked back since. IT work since military retirement; private and Government contracting doing Unix System Adminstration and now “Cloud” and IT Security based work. Didn’t file for Social Security until the SS local office called me to inform me I would be leaving money on the table if I didn’t sign up by 70 years old. Still working as “that old fart who seems to have all the answers, and if he doesn’t know it, he’ll MacGyver it.” Turned 74 last October and have no intention of “retiring” as long as I find it interesting/fulfilling and the wife doesn’t mind. Keeps my mind sharp the ticker ticking and my butt out of the wife’s way.

  15. I have “retired” from three “careers” in my book. First was the military, second was post secondary education in traditional settings. Then I retired from being an itinerant world-wandering college teacher (yeah, I made that up; it’s kinda hard to describe). Now I joke with folks that I have “retired from retiring.” I’m not gonna do it any more. We have been so blessed we are able to have me working (cough, cough) full time for a ministry agency. Guess what? we use computers and the Internet to conduct training around the world. I really enjoy saying, “I’m a missionary to cyberspace.” Has kind of a neat ring to it. We were made to work. Stopping working is just the first step toward an early death. (P.S. notice how many of the commentees here work in software somehow [I taught Computer Science and Software Engineering].)

  16. And today they had a riot in France because the retirement age is being raise from 62 to 64.

Comments are closed.