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Questions to Ask if You’re Thinking about Working after You Retire

Questions to Ask if You’re Thinking about Working after You Retire

Is it looking like you might have to work for your entire life?  That may be better than you can imagine. The trick is to stop thinking that the current rat race is your only option.

If you do it right, including some amount of paid work as part of your retirement lifestyle is likely to result in a more satisfying retired life overall.  The key is figuring out how you can do what you love for money.  And how you can do it for as much of the time as you choose instead of letting your work life blot out the rest of your life as it often does in prime career years.

As you consider how this might look for you, there are six important questions to ask:

  1. What do I love to do?  Quite often we end up in our life’s work by default.  Some of us come to love it and some of us just keep doing it because it’s easier than starting in a new direction.  If what you are doing now (assuming you aren’t yet retired), doesn’t make you smile anymore, it’s wise to start figuring out what will before you retire.  Maybe it’s a hobby you are already pursuing.  Maybe it’s something entirely new.  The only way you are going to find out is to start thinking about it.
  2. How can I make money doing what I love?  There are ways, regardless of what it is.  If you love golf, work at a course…or a golf megastore…or write freelance articles about golf.  If you love to shop, find a slot in retail that’s fun or offer your services as a personal shopper.  If you love making sausage in the middle of the night, there’s probably a way to parlay that into an income. An essential piece of getting this to work is to stop thinking that everything has to be done between 8 and 5 on weekdays.  You may want to keep that time for other things and work nights and weekends to keep the checkbook fat.
  3. Is there only one thing that I love to do?  If you’ve done a lot of different things while you were working full time, expect to do so for retirement income as well.  A retired elementary school teacher I know makes great money as a Santa in November and December but is also a tour guide for a travel company in the summer.
  4. How much do I want to work?  Half time?  A third of the year on specific projects?  Only with customers X, Y, and Z?  A piece of that answer is going to be about how much money you need to continue to make, but an even bigger piece is what else you want to have time for.  (Hint:  Don’t worry about lying on some tropical beach with a cold drink in your hand.  That’s called vacation, and it doesn’t work as a longterm lifestyle in retirement.)
  5. What shape do I want my work to take?  When you love what you do, you find ways to get to do it.  The most traditional would be regularly scheduled work—full- or part-time–but there’s a long list of other options.  You can work on a contract basis for a limited period.  You can work piece rate.  You can work project by project.  You can work in a “performance only” company where you can do your work whenever you want as long as it’s done on time.
  6. How can I get to do what I love the way I’d like to do it? It takes time to get to where you can pull this off.  No one is going to see that as a wise move unless you are already really good at what you want to do and the world knows it.  You need to build your reputation.  A guy I met recently drives a high-performance dune buggy for tourists as a retirement job.  He worked for the utility company for decades, but he’s been driving dune buggies since he was nine.  His driving skills were so well known that a total stranger approached him in line at the grocery store about working for him as a sand rail driver.

His story is the magic we’d all like to rely on–where what we need just comes to us.  He wasn’t even thinking about working, but the offer was too much fun to pass up.  On the surface, it looks like it “just happened.”  But that isn’t the case.  He had a longstanding reputation for doing that work well.

Figure out what you want to do.  Get involved with others who are doing it.  Achieve a reputation for doing it well.  The more of that you can do before you retire, the easier it will be to walk into your dream retirement job when you get that far.

5 Big Reasons NOT to Retire

5 Big Reasons NOT to Retire


I’m not going to bother you with how you working longer benefits the nation and brings you more money.  I’m not going to remind you that staying employed usually means  better health care coverage.  Here are five other reasons why staying in the workforce may be better.

Not retiring is better for your physical health. People who continue to work stay healthier than people who retire to a life of leisure.  Working gives you a sense of purpose.  And purpose is good for you.

In a study of 900 aging religious, those with a strong sense of purpose lived life to the end with no sign of Alzheimer’s disease even though posthumous brain studies found the lesions characteristic of it.  A study of 12,460 middle-aged Hungarians found those who believed their lives had meaning had lower rates of both cancer and heart disease.  A retirement of drifting from thing to thing at leisure isn’t an automatic ticket to good health.

Not retiring maintains  your emotional health. Work is one of the best sources of self-esteem available.  If you are good enough at something to get paid to do it, that’s strong evidence of your worth.  Most of us don’t realize that’s important until after we let go of it.  Then we struggle to figure out why we are feeling “empty.”  We need to work.  If not for pay, then in some other context.

Not retiring gives you less incentive to hang onto a job you hate. If you are going to work for a long time and don’t plan to rely on your current company’s benefits for retirement, it makes perfect sense to find a better job, no matter how old you are.  But it’s tempting to tolerate a bad job fit or a boss that is literally making you sick in the name of “making it to retirement.”

If your job sucks and you’re going to have to work for as long as you live, for heaven’s sake go out and find one you like.  It might take some time to pull it off, but you still won’t be in your current unhappy place as long as if you hung on until you could retire.

Not retiring gives you more room to find your dream job. Let’s face it.  When it comes to work, it takes most of us some time to figure out what we like.  I know at lot more now than I did when I was forty.  As you learn what lights your fire, you can move toward that kind of work if you aren’t telling yourself that you’ll be “done” soon and that it’s too late to even thing about that.

There are people in their eighties who attribute their good health to the fact that they have to work.  A local lawyer is 99 and still goes to the office–but on a reduced workday.  That’s a piece of the dream job, too.  Maybe yours can be done from home or in alternate weeks, or using a WiFi connection from Maui.   If you know you’re going to have to work forever, finding something you love is essential.  Also more exciting.

Not retiring reduces your vulnerability Not working can leave you vulnerable a lot of ways.  You’re vulnerable to becoming isolated.  You’re vulnerable to having your income streams dry up.  You’re vulnerable to having way too much time on your hands if you lose a spouse or companion prematurely.

It’s easier to get a few more hours–or take on a second job for a while–if you’re already employed.   People need people, and the work setting is full of them.

The biggest lie of the traditional approach is that retirees are privileged to not be able to work.  That’s not how it started and not why it continues.  It’s a quiet, effective application of ageism.  “Here’s some money.  Now get out of the way.”  Nobody cares what you do or if you do it after you retire.  You’ve rendered yourself irrelevant.  Arghh!

Instead, find a way to work that’s fun.  Work at something you believe in.  And find a workstyle and employer that make you feel you have a life not just a job.   Retirement isn’t the only alternative.  If you find what you love can can thrive while employed.