If you’re in your 40s or older, you should be thinking about your jobby

At age 57, I voluntarily left a good job to do something I thought would be better. Are you ready to do the same?

I know there are lots of you who are at the beginnings of your careers. You may want to stick with the company you work for, or the gigs you are doing, or you may want to try to move up. Good for you.

There are lots of you in the heart of your careers. You have made some transitions and you are hitting your stride. Keep it up!

And there are some of you who don’t have the economic security to stop what you’re doing, no matter what age you are. You might find that security is an illusion, but by all means, if you have to cling to that position to survive, I salute your hard work.

But no matter who you are, you are going to get to a point where through forced retirement, boredom, or layoff (um, sorry, “rightsizing”), you may want to — or have to — do something different.

That’s not an easy thing for people over 55 to consider. But what are you going to do when you reach that point? Stop avoiding thinking about it and think about it.

I did.

Some questions to ask yourself

As I contemplated the possible paths for me at the end of a long career, these are the things I considered, and you should, too.

• What are your financial needs? I have a child who is a recent college graduate and one more kid in college now, but their educations were funded already from money I made when I was working in companies. I have a house to maintain, but I paid the mortgage off with stock from my company a while ago. This gave me more freedom than many. But if you have less freedom, figure out what you really need to live on. Would you be happier living somewhere smaller or cheaper? You cannot estimate what you can do until you know what you need to bring in.
• What are your social needs? I thought I would miss having other people around when I worked — that turned out not to be the case. Online connections are a godsend for me (including the one you’re reading right now). And you could always work in a shared office space — they’re everywhere now. You probably don’t want to sit in a chair by yourself all day. What will you do to connect with people?
• What kind of work makes you feel fulfilled? I like figuring things out and writing. As I learned, I like writing and editing just about anything — the sense of flow that creates makes me feel great. If you could do something all day long, what would it be? You should at least dream about what work could make you happy, and strive for that.
• How are you going to handle the overhead? If you are on your own, you will need an online presence. How will you create that? How will you let people know it is there? Who will do your accounting, book your travel, take care of your insurance, set up your company, and maintain your computers? If you can do that stuff yourself, great; you can also pay people to do it, but someone has to take care of it. If you hate these things and can’t pay for them, you’re probably better off in a company.
• How will you avoid the things you hate? You might hate bosses. I hate excessive amounts of travel away from my family. Some people hate sending bills, or marketing themselves, or writing emails. If you are thinking of something new, how will you reduce the time you spend on things you hate?
• How will you launch yourself? New beginnings are hard. They take energy, whether that means finding a new company or launching your own. Do beginnings excite you, or terrify you? You’d better plan your launch either way.
• How will you take care of health insurance? This might seem like something much smaller than the other things. It’s not — it’s the one thing that can determine whether you need a company that provides insurance or can do work that doesn’t provide it. Can you get it through your spouse? Can you pay for it on your own? (If you live in Canada or Europe or Australia or Japan or China, good for you, this won’t be a problem for you.)

Who needs this worry?

If you are in your 40s or older, you should be planning for this sort of transition. Because sooner or later, you’re going to retire. Better to do it on your own terms. Before that happens, you might lose your job — and find that getting hired is harder when you are older. Or you might decide, as I did, to leap into the abyss when the finances permit it.

You could, of course, just keep doing what you are doing. You could assume there will always be a job for you, just like the one you have, and that if you need it, you’ll find it.

But where’s the fun in that?

Or, you could consider what the next adventure for you could be, the one that will sustain you in your 50s, your 60s, and beyond.

It’s going to pay, so it’s not a hobby. But it’s going to be just what you love to do, so it’s not a job. Call it a jobby.

What’s yours going to be?