Choosing work wisely at 65

A job seeker “of a certain age” recently told me two things that seem related. 1) That she just applied for Medicare and 2) that she’s choosing her next work carefully because she doesn’t have time to waste on jobs that don’t work out.

You could ask me what Medicare has to do with job choice and I’d have to admit, I don’t know. They just seem like related points. Maybe because starting Social Security benefits is a generational marker, like graduating from high school. Once you’ve made this leap, you’ve entered a new chapter of your life.

In the case of a 65-yearold, the sense that time is limited can be acute. This is the point where people start saying, “My next car will be my last” and, “I think we can get one last puppy before we stop having pets.”

I understand the logic behind these thoughts – I just wish they were framed a little differently. Instead of “one last” this or that, it would be nice to hear someone talk about “leaving behind the inconvenience of having pets” or graduating from driving to being driven.

Clearly, I have issues. I don’t like seeing the world as a shrinking pool of diminishing options. I prefer to think in terms of ‘curated,’ as in: “I’m now choosing the elements of my life more carefully, to ensure each part fits my goals and interests and abilities.”

Never mind that the act of curating might be the forced response to an unwelcome choice; I still prefer to think I am choosing.

Which brings me back to job selection and trying to ensure you “get it right” so you don’t have to endure false starts at an advanced age. I think this is the right idea, but I also think the execution of the idea can be a bear. For one thing, it’s devilishly difficult to discern the reality of any situation from the outside. People can seem nice and the work can look interesting right up until the people become your colleagues and the work becomes your obligation.

What to do? I can’t solve this problem for you – or for myself, for that matter – but I can provide process to help with your decision making. Although I’m framing the following tips for people at mid-life and beyond, they can be converted for any age group or career stage.

Start with a self-inventory. It’s no good looking for work at 65 with the same criteria you used at 45, as too much has changed. You have different goals and needs than you did then, and you want different things from your work life. Instead of revising an old plan, start fresh by asking yourself: What parts of working are most important to me – the paycheck? The chance to contribute my skills? Social aspects? Structure to the day?

Review past experiences. This will take some time, so grab a cup of coffee. I want you to go all the way back to high school or earlier to remember each and every work experience you’ve had. Now think: Which were the most fun, and why? Which did you truly regret leaving? Which would you do again in a heartbeat? Even if you don’t intend to replicate the jobs, it’s useful to identify patterns such as working with a small team or having a lot of client contact.

Identify the skills you want to use. At your age, you’ve accumulated enough skills that you’ll need to downplay the ones you don’t enjoy using. For example, even if you have excellent telephone skills, if you don’t want to work on the phone then leave this off the list. Think instead about five skills, or ten at the most, that you truly enjoy using.

Throw it all at the wall to see what sticks. That doesn’t sound very scientific but it’s a pretty good description of what happens next. Now that you know what you need from a job, the experience you want to have at the job, and the skills you’re willing to give to a job, it’s time to play Mr. Potato Head – that is, put things together in different combinations until something resembles an actual job. Try to come up with three to five job titles or ideas that appeal to you, which you can then research in pursuit of actual opportunities.

Talk to people. This step is best applied throughout the process, as you’ll need feedback and ideas from others.

This is also the best way to get the insider’s view of an organization, to help you feel as reassured as possible that specific opportunities are the actual fit that you’re seeking.