When to retire, even if you like your job

One of the top regrets of retirees is that they wish they'd retired sooner. This poses a conundrum for people who enjoy their jobs, particularly when they have the financial resources to retire at any time.

Ironically, because these folks can walk out the door and be just fine, they enjoy their jobs even more!

Yet, no one lives forever. I've noticed a startling difference in vitality between a person's early 60s and late 60s. At 60, many people are comparably healthy to when they were at 55, and they implicitly expect the next 5 years to be similar, with minimal decline. That usually isn't the case. Usually, we tend to slow down exponentially starting in our 60s, and it really only goes downhill from there.

My dad's older tennis friend summarized it this way, "your 60s are where it gets tough, and your 70s will hit you over the head with a hammer." You won't appreciate your youth until it's too late.

Roughly half of the people I know in the 67+ crowd have some health issue that would limit their ability to hop on a plane and visit Europe.

That's important to consider if you're debating when to retire. For you, it may or may not be traveling to Europe that matters, but the same logic applies. Maybe you've always wanted to do a triathlon. Or play a few of the famous golf courses. Or take an RV trip.

Rich experiences like these take time, dedication, and energy. When we have all three, it's important not to take them for granted. That's why, when my clients are on the fence about retirement but are financially ready, I tell them something like this,

"We've discussed that you're safe to retire and that you're working for fun at this point. I have no problems with that. I think that's really cool. But my question for you isn't 'do you want to quit your job?' Instead, I'll ask you to consider, 'if you only had 5 years left where you could still do everything you wanted, are there things that you might wish you'd done, that you're currently not making time for because of work?'"

Whatever the answer is, I'll support it. But it's worth making a conscious choice.