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The Retirement Prison No One Plans For

I think one of the more interesting things about retirement is that two people can retire with roughly the same amount of money, in roughly the same health, at roughly the same age, and end up with completely different retirements.

For the sake of making this a little more fun, let’s call them George Jetson and Homer Simpson.

George is our planner. Always thinking about what comes next.

Homer is our cold turkey retiree. Very capable of getting comfortable on the couch.

George Starts Building Retirement Before He Gets There

George gets to within a few years of retirement and starts thinking pretty seriously about what life is actually going to look like when work is no longer taking up most of it. Not just whether he has enough money to retire, but what he is retiring to.

He makes a conscious decision to start phasing out.

Maybe he cuts back to four days a week. Then three. Maybe he intentionally gives up some responsibility at work. At the same time, he starts building up the other parts of life. He volunteers somewhere. Spends more time with the grandkids. Picks golf back up. Starts gardening. Travels a little more.

The specifics really don’t matter. What matters is that he is doing it on purpose.

He isn’t just retiring from something. He is actively building what he is retiring to.

Eventually George fully retires, but by then he has had a few years to figure some of this stuff out. He knows what he enjoys. He has relationships outside of work. He has a hobby or two. He has some things he is working on and some places he still wants to go.

Retirement isn’t this massive empty block of time that suddenly shows up one Monday morning.

Golfer taking a swing on a sunny day, showcasing leisure and sport on a lush golf course.

Homer Goes Cold Turkey

Now take Homer.

Same basic career. Same long hours. Same excitement about retirement.

Except for him, retirement comes all at once. We’ll call this the Cold Turkey Retirement.

Friday he is working. Monday he isn’t.

And for a while, I’m sure that is awesome. Sleep in. Drink coffee. Play some golf. Watch a little TV. Go to lunch with somebody. Take a nap in the middle of the afternoon because you can.

I mean, that sounds pretty good.

One of the biggest appeals of retirement is the comfort of time freedom. You get to wake up when you want to wake up. Nobody is telling you where to be or what needs to be done next. After 30 or 40 years of working, that sounds pretty darn appealing.

And there is nothing wrong with enjoying it.

The problem is that you can only sleep so late and play so much golf. Eventually there are still a whole bunch of hours left in the day. And if you haven’t intentionally decided what is going to fill those hours, something will.

The TV stays on a little longer. The phone comes out more often. An hour of scrolling turns into two or three or four. You still play golf a couple of times a week, maybe go out to eat, run a few errands, and before long that is more or less the routine.

Nobody intentionally plans to spend the last third of their life watching TV and scrolling Facebook four hours a day.

It just fills the space.

When Freedom Starts Feeling Like a Prison

A few years pass and something that was supposed to feel like complete freedom can start to feel a whole lot more like a prison.

You have all the time in the world, but not much pulling you anywhere.

The relationships from work have faded and not many new ones have taken their place. There isn’t much you are working toward. There aren’t many new experiences on the calendar. The days are comfortable, but they also start looking an awful lot alike.

The really scary part is that after a few years of that, breaking out of it may not be so easy.

Then health takes a turn. Nothing catastrophic necessarily. Walking gets harder. Energy drops. Travel sounds like more work than it used to. Maybe you start worrying about being a burden on your kids.

And some of those things you were always going to do “someday” suddenly become a whole lot harder to do.

The difference between George and Homer isn’t really golf or gardening or volunteering.

It’s intentionality.

George intentionally built a life. Homer assumed a life would simply appear once work was gone. That is a pretty big gamble.

A detailed view of a locked prison cell door with a bed inside.

Lifelong Learning Is Really About Growth

I think this is also where lifelong learning fits into the conversation, although probably not in the way most people think about it.

Retirement doesn’t mean you need to go back to school, collect another degree or spend your mornings reading textbooks.

Most things done with intention are going to require some amount of learning anyway.

If George decides to garden, eventually something is going to kill his tomatoes and he is going to figure out how to keep it from happening again.

If he golfs and actually wants to lower his handicap, he is going to have to learn something.

If he travels, half the fun can be learning about a new part of the country or the world, figuring out what is worth seeing and learning how to plan a bomb trip.

If he is spending more time with his grandkids, he is going to learn about them. Maybe he teaches them their letters. Maybe they learn to make sourdough together. Maybe he discovers that something that worked perfectly with his own kids 30 years ago doesn’t work at all with this particular grandchild.

Maybe he volunteers. Maybe he takes on an encore career. Maybe a hobby eventually turns into a little business.

Where there is growth, there is learning. And I think we need some of that. If you’re not learning, you’re dying. Why would you want to atrophy?

We Need a Few Rainclouds to keep us out of Prison

A good retirement should have plenty of comfort, but I don’t think all comfort all the time is much of a goal.

If everything is sunshine and rainbows, eventually the sunshine isn’t going to feel quite as sweet.

We need a few rainclouds.

We need the garden that doesn’t work. The golf swing that falls apart. The trip that doesn’t go quite as planned. Something we aren’t very good at yet. Something that makes us think, adjust and try again.

Those things keep us engaged. They also tend to keep us connected to other people.

Interesting people are usually interested people.

They ask questions. They try things. They learn about other people. They have experiences. They have something going on besides whatever happened to be on television last night.

Work gives us a surprising amount of that without us really noticing. Coworkers, customers, meetings, problems to solve, people asking for our help.

Then retirement comes and much of it disappears.

If you don’t intentionally replace some of those relationships, challenges and reasons to engage, your world can get pretty small.

bridge, forest, trees, leaves, foliage, umbrella, person, nature, bridge, bridge, bridge, bridge, bridge, umbrella, umbrella

“Can I Retire?” Is Only Half the Question

This is why I don’t think a retirement plan is complete if all it answers is, “Can I retire?”

Obviously, that is an important question. A lot of what happens in my office revolves around the money side of retirement.

How much can I spend? When should I take Social Security? What about taxes? How should my investments be structured?

We need to answer those questions.

But a retirement plan that only solves “Can I retire?” is boring. And who wants boring?

What you are retiring to is what gives the retirement plan life.

The money piece should be built around your life, your goals, your relationships, your hobbies and the things you actually want to do with all of this time you have worked so hard to create.

Why I Like George’s Approach Better

That is also why I am not and probably never will be a big fan of Cold Turkey Retirement.

A phased or hybrid retirement gives you a chance to build some of this before you need it.

Maybe George discovers he loves volunteering. Maybe he doesn’t.

Maybe he thinks he is going to golf five days a week and discovers that after three months he doesn’t actually like golf that much.

Maybe the thing he thought would fill retirement doesn’t, and he has time to figure out what does.

That seems like a pretty useful thing to know before retirement becomes your full-time job.

The Goal Isn’t to Stay Busy Every Minute

None of this means every hour needs to be productive. Sleep in. Play golf. Watch the Chiefs. Sit on the porch. Take the nap.

One of the rewards of retirement should absolutely be the ability to do absolutely nothing once in a while simply because you can. Homer has that part figured out pretty well.

Just don’t confuse the freedom to do nothing with a plan to do nothing.

You worked too long and saved too much to finally earn control of your time and then accidentally waste it.

The question isn’t just whether you can retire. It is what you are going to retire to.

That is the part that makes retirement worth planning for. That’s the part that will keep retirement from feeling like a prison.

This post is for education and entertainment purposes only. Nothing should be construed as investment, tax, or legal advice.

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