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.

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