What Will You Do When You’re Retired?

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“If all the year were playing holidays, To sport would be as tedious as to work.” –Shakespeare

Mention “retirement” at the office. Most people will be conjuring visions of sun-drenched beaches, lush golf courses, soaring mountains, or shimmering pool sides. Everybody knows that retirement has to be awesome, because vacations are awesome, and retirement will be just like a vacation — only longer. Right?

Not exactly, in my experience. A satisfying retirement, I’ve found, is ultimately a new mixture or a re-purposing of the same ingredients that were in your working life.

What will be the right mixture for you? It’s worth thinking this through a bit before you actually pull the plug on your job. Leaving a career behind is a serious decision, so it’s only sensible to plan ahead. But, be realistic. Expect the unexpected. This is a big life change. Did graduation, marriage, kids, work, ever go exactly as you planned?

For some people, retirement might just mean bigger helpings of the usual leisure activities. And perhaps for some, as an antidote to years of stressful work life, that will be good enough. After decades of getting up to an alarm clock, commuting, dealing with schedules, agendas, priorities, goals and objectives — all set by somebody else, you might need a good long break, with nothing much to think about. But, in my experience, that period of unadulterated leisure eventually ends.

In truth, most people will need more out of retirement than pure leisure. Here, then, are the elements I believe make for a truly happy and satisfying retirement:

Fun — without question, retirement is a reward of sorts, for having worked long and hard, and been a wise steward of your money. You ought to get to do something now that is genuinely luxurious and fun, by your own standards. Otherwise you’re likely to feel cheated. The older generation in my own family did things like move to the beach, or build a homestead in a rural setting. For myself, I bought a small RV, relocated to our dream retirement town, upgraded all my outdoor gear, and spent even more time hiking, biking, and climbing.

Staying busy — in a satisfying job, most of us require a minimum of useful assignments to perform — reasonable tasks that interest us and match our skills. Retirement should be no different. The difference is that you are now 100% in charge of your assignments! And it makes no sense to be bored when you finally have the time and freedom to do whatever you want. Most people, given the opportunity, find meaningful activities. They travel, join, connect, learn, study — to get a fresh perspective on life. If that doesn’t work for you, you can always go back to work, on your own terms. Above all, don’t let yourself lose interest in life: what a waste!

Creativity — whether it be taking photographs, painting watercolors, blogging, writing that novel, or starting a small business, it is hard to envision a satisfying retirement that doesn’t involve an element of creativity. At last you are free to invest your time as you see best, beyond the strict rules of the workplace. Retirement is the perfect occasion to try your hand at expressing your individuality in something new in the world. Maybe you do it for the sheer joy of self-expression, or perhaps you have an eye on leaving a legacy that informs others. Either way, you are older and wiser, and can care less about measuring up to any standards other than your own now.

Productivity — just because you are no longer tied to a job, doesn’t mean you can no longer be, or won’t want to be, “productive.” What do we mean by that word? One dictionary definition reads “yielding results, benefits, or profits.” In the traditional work world, that usually means getting paid. But that may or may not be true in retirement. Making money is surely one useful measure of productivity: You create something of value for others, and they trade you money for it. But that’s not the only measure of productivity. Volunteer work or community activity can yield genuine results and benefits for others, that does not involve a profit. The main point may be to have goals, and make progress towards them. The psychology classic Flow: The Psychology of Optimal Experience, reports on research showing that people are actually happier at work — stronger and more satisfied, less dull and apathetic — than in leisure! At work we are usually challenged to use our skills in achieving certain specific goals. And, in retirement, we don’t have to give up that satisfaction — but we do get to choose our own goals!

Service — the satisfying retirement lifestyles that I’ve observed, include some element of service. It just makes sense. We all know, deep down, that helping others is one of the most satisfying ways to spend our time. But in the hectic career and family years, we may not have as many opportunities for service outside the home. In retirement, at last you have the time and freedom to find your own best route to improving the world. Ideally that will be a path that truly leverages your own talents and passions. For some that might mean volunteering in the community. For others it might be signing on to political causes. For others it might be creating something of value and beauty.

In my own case, I’ve been able to combine my long-term interests in personal finance and writing, into a retirement avocation through my blog. Yes this is a business, and it makes a small profit on the side. But once you figure in the time I spend maintaining software, researching and writing posts, replying to comments and emails — I’m making a little above minimum wage! So it’s a labor of love that helps people and the world, and that’s what really matters to me.

Freedom — lastly, retirement should have an element of freedom, right? You are retiring from a workplace that somebody else created and structured, so that you can spend the rest of your life following your own passions on your own timetable. Sounds good. But, if you wind up locked into a web of social, service, or family obligations, you may not feel that retirement has accomplished much. You could just wind up trading one over-scheduled, over-committed life for another. Alas, I think this might be the greatest danger in most retirements — missing the sense of ‘space’ that this stage of life deserves and requires. Some people like being over-scheduled, but for me it squeezes out the taste of true personal freedom that ought to accompany financial freedom.

So, what’s my biggest challenge in retirement to date? Boredom is nowhere in sight for me. I’m constantly busy with creative, productive activities that are often of some service to others. And I’m generally having great fun doing it.

I’m embarrassed to admit, but I’ll be honest: My biggest challenge now is stress! Not that dismal, grinding stress of an unwanted job or work environment that drones on day after day. No, I’m talking about the stress of being pulled in a dozen different directions by people, activities, places that you all love.

Once there are no longer obstacles to pursing your dreams, you take on new interests and deepen old ones. The activities, projects, and goals that were impossible when you were working, now become possible, even necessary.

So I often feel like there isn’t enough time in the day to capitalize on every opportunity for fun, creativity, learning, service, experience, or connection. Thus I’ve had to cultivate a finely-tuned ability to say ‘NO,’ even when it’s uncomfortable or unprofitable, just to keep my sanity. (Apologies if you’ve been the recipient of one of those ‘NO’s — but now you understand why.)

And I’m still too busy in retirement! This is one of those problems that most people would love to have. So I’m not going to complain about it further. But, if you’re nearing retirement — You’ve been warned!

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  1. Great article – I feel the same way, juggling a bunch of things while “retired,” but doing what I want to do. Well done, Dan Bowling

  2. Hi Darrow,

    I think I signed up for your blog a couple of months ago , Just read the one this month and do appreciate the suggestions. I am an orthodontist and have been for 42 years coming up on 72 in August. Still not in a big hurry to retire as have been absolutely blessed with a great professional career. I wanted to fly and be a fighter pilot but this has really been a lot better and I never had to shoot at anybody. I got to fly some really neat airplanes privately

    I saw your small RV post also, What are the 20 mpg diesels that are out now?? I drive a Prius and really like the high mileage cars. I used to drive Audi Diesels for great mileage but really slow little devils.

    • Hey Clark, good to hear from you. Those who love their careers (and have some freedom in them) are very fortunate in my opinion. Not getting shot at is a bonus, as well.

      The RV’s I’d look at right now, if I was in the market, would be the Sprinter-based units. They were brand new when we got our E350-based rig used in 2009, otherwise I’d have been shopping for a used Sprinter. (Used is the only way to buy an RV, for my money.)

  3. Darrow,

    This is the issue I am grappling with. I certainly have enough money to be financially independent but I cannot get my mind to be independent.

    I could stop work tomorrow but I cannot get my head around what I would do all day. I have spent too many years working 12 hours a day with the result that I have few hobbies and activities. I enjoy travel – but still have a child at school so travel time is limited.

    Your article was great – just need to get my head around it all.

    • Hi Philip, thanks for that. A certain percent of people are in this camp, so you’re not alone. Hope my article will trigger some ideas. Perhaps you don’t need to retire — but sounds like you have the freedom to “fix” anything about your work that you don’t like.

      • Darrow,

        You are right that I do have the freedom to fix things. I have been a self employed consultant for the past 6 years with the freedom to work as little as I want but still work as long and as hard as I did before.

        There seem to be 2 aspects – financial freedom (which I have achieved) and mental freedom (which I am grappling with).

  4. My greatest need in retirement is that I must be productive. This need has been met with a part-time job at my church and helping out some friends with a severely disabled child.
    My best days are when I come home after a chunk of time being helpful/serving.

  5. “My biggest challenge now is stress! Not that dismal, grinding stress of an unwanted job or work environment that drones on day after day. No, I’m talking about the stress of being pulled in a dozen different directions by people, activities, places that you all love.”

    I SOOOO understand that statement. It was powerful to read that you experience some of the same. I have been filling my days with all that I love most and working more…and feeling guilty when I’m not creating something, blogging, reading to learn, decluttering, etc. I’m back to where I started a few years ago when I left the office. It looks like I have to review what I’m doing and let some activities go. I just want to do so much!

  6. Hi Darrow,

    Very interesting and thoughtful post. I quite my career job almost three months ago, am 58, and have the financial independence to do what we want within reason. We can’t rent a private jet or buy a Bentley, if you know what I mean. I am doing some consulting for an off-shore electronics distributor (my career is/was in semiconductor marketing) which is kinda fun, and not that I need the money per se, I like to see it coming in.

    I’m also pursuing an avocation I’ve long wanted to do, which is software development. I seem to recall that was your career, so I imagine you’re laughing, wondering why anyone would want to do such a thing. Suffice it to say that even way back in the day learning Basic on a timeshare TTY I was hooked. Probably should have dove fully in, but always chose what I thought was the safer approach, which was electrical engineering, then marketing and business. So, I’ve been studying Objective-C and iOS, and developing a prototype app that I think people learning this stuff (which is pretty challenging) will appreciate. Then last week at WWDC, Apple announced that it’s coming out with a new language called Swift which, while “compatible” with Objective-C will be their focus. Like Sisyphus, Apple shoved the rock back down the hill and I’m starting over. It’s not all that bad. Swift looks like a remarkable achievement and language, and with almost 400K downloads of their reference book in less than a week, the market for apps such as mine is confirmed! So, why am I writing?

    I suppose it’s mostly about community. Your post reminded me of what I was grappling with in the months and years before quitting my day job. I think what’s really needed is “purpose,” which was recently written about in the NY Times, “Living On Purpose.” So I have some of that, and that’s good. And, I can (and do) grab a cup of coffee at the local shop, or hang out at the library when needed for a bit of down time. I’m very lucky indeed. So, beyond purpose, what am I missing? I think there’s a few things:
    1. The team: as much as me and my co-workers had issues and problems which I remember all too well, we were also a family (dysfunctional in many ways). It was fun to socialize with some of them, and I miss them. Without the common bond of the job there’s not much there for us.
    2. The travel: I used to travel internationally on business perhaps 25-35% of the time, and while it was stressful being the point man on why we weren’t all that bad, and why they should stick it out with us, and all that… I miss it. Here again, there was a social aspect of dealing with the customers and field people. I think they liked my dedication and we worked well together. Notably, my wife also misses my traveling, as she enjoyed some of her own down time when I was away!
    3. I might say that I also miss some of the stress. Yes, I still feel some these days as I struggle back up the hill with my development. But, it is fun to have to face challenges, risk in front of colleagues and customers, and navigate those shoals.

    All in all I’m very happy where I’m at now. Indeed, I have several professional friends who may call to see if I’d like to join them in their newer ventures. And if they do I’m not sure what I’ll say. On the one hand I may very well toss my hat back in the ring if only to see if the past few months have taught me something that I can use to enjoy the work life again. But on the other I’d be disappointed to postpone (again) my nascent software experiences for later.

    Like I said, I’m very fortunate for having these “problems” to consider. But I’m very appreciative to have the Internet and small communities like this one to participate in and learn from.

    • Hi Barry, good to hear from you. And congratulations on your recent retirement! Software development is great fun. If I hadn’t spent my career doing it, and didn’t have a full plate of other interests, I’d probably still be doing it myself. Purpose + downtime sounds like a good starting recipe for retirement. I agree about teamwork: it’s nice to find a way to replace that if possible. I think challenge is always available, for those who seek it. Great to hear your thoughts from your new perspective — thanks!

  7. I doubt I will do much different when I am retired from what I do now. A large part of my job includes writing programs to model dynamic behavior of engineering materials. I may continue working on that with the goal of publishing a paper or two, or I may go off and work on some open source programs. Then again, I might just say forget this engineering stuff and instead work longer and harder at learning to play the piano. That’s the nice thing about retirement that I am looking forward to.