Kay Yoon
Choices That Matter

Looking Back at 50: Five Things Worth Doing in Your Late Thirties

The job of your late thirties isn't to find life's right answer. It's to remain someone who still has choices.

My mid-to-late thirties were fairly eventful.

At thirty-four I left my company and went independent. At thirty-six I started law school at Cambridge. And when I was almost forty, I had a child.

Thinking about it now, that was a lot.

That doesn't mean I had life meticulously planned. If anything, I changed direction as things changed and made many decisions as they came.

Looking back at 50, there are things I'm glad I did in those years.

1. Take the challenge you've long had in mind and look into it concretely.

I went back to university at thirty-six.

Of course you can study something new or take on a challenge in your forties or fifties too. But it's true that the older you get, the more variables you have to consider.

I'm not saying you have to do it now. But if there's something you want to do, at least find out the time, the cost and the possible ways of doing it.

Vaguely dreaming about something is different from making it a real option.

2. Try explaining your expertise without your company name or title.

By your late thirties you've built up quite a lot of experience. Yet when it comes to explaining what you're actually good at, it can be surprisingly hard.

Take the time to work out which problems you can solve and which of your experiences are unlike other people's.

I studied engineering, business and law, and worked across several fields. There was a time when I struggled to explain all of that as one thing. Now I think that combination is what sets me apart.

3. Check whether your value holds up outside your company.

I went independent at thirty-four. That doesn't mean I recommend starting a business or going solo to everyone.

But it's worth asking what value you can offer once your company's name and your title are taken away. You could connect with people in your industry, look at opportunities at other companies, or find out how your expertise is valued from the outside.

Being recognized by your company and being recognized by the market aren't necessarily the same thing.

4. Don't let your living costs rise as fast as your income.

The late thirties are often when a career settles in and income grows. But once you raise your standard of living, lowering it again is harder than you'd think.

I'm not saying don't have a nice home or a nice car. But it's worth thinking about how much today's spending may limit tomorrow's choices.

I think one of the greatest benefits money gives you is choice.

5. Leave room for life not to go according to plan.

Independent at thirty-four, law school at thirty-six, and pregnancy, birth and a baby at forty, ha.

I didn't plan all of this from the start.

As you live, your thinking changes, unexpected opportunities appear, and priorities shift.

The same goes for career and family plans.

That's why I think that in your late thirties, leaving room to choose differently when plans change matters more than perfectly designing the next ten years.

Sometimes being able to change direction is itself a great asset.


In your late thirties you may feel you're still young, and at the same time feel it's too late to start something new.

But looking back at 50, that was an age when far more could be changed than I realized. And the choices I made then had a big effect on the life that followed.

I don't think the thing to do in your late thirties is to find the right answer to life. I think it's to remain a person who can keep making different choices. That's what lays the groundwork for those kinds of forties and fifties.

For those of you already past your forties, how about you? Is there something you're glad you did in your late thirties?

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