What's the First Thing You'd Do When You Retire?

Author

Matt Viera
March 12, 2024

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I hope this finds you well.

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What would you do if you no longer had to trade your time for money?

More precisely, what’s the first thing you’d do?

You no longer have to wake up to an alarm clock, go to an office, and do the same daily work tasks you’ve been doing for the past few decades.

You now have the time and the financial resources to do anything you want; what’s the first thing you do?

Me personally?

On the first day, or sometime during the first week of retirement, I’d go somewhere (Wyoming, Barcelona, Berlin) for a few weeks and figure out how I’d want to live the rest of my days.

But that’s me.

I’m reminded of a powerful piece of advice someone once told me before I had my first summer vacation in 2012: have a plan to travel somewhere on your first day of summer vacation.

And not just anywhere; travel somewhere completely different, somewhere you’ve never been to, or somewhere you have been to and feel comfortable staying in for a few weeks.

This immediate change will help your transition from work mode to relaxation mode.

Truth be told, it wasn’t until 2016 that I took that advice and rented a car on my first day of summer vacation to drive from New York City to Montana.

I’m sharing this because I met my good friend this past Friday at one of our favorite bars in Brooklyn to catch up.

He recently retired, no longer has to trade his time for money, and has a passion for traveling (he’s traveled worldwide).

So, during our first drink, I asked him: what’ve you been doing since you retired?

I was surprised by his answer.

Aside from pursuing one of his passions, acting, he hasn’t done much.

Or rather, he hasn’t done anything I thought that he would do, like travel.

I asked him why. And this is what he told me (I’m paraphrasing):

We are programmed early in life to do the following: go to school and college, get a job, find a partner, buy a house, get a dog, have children, etc.

When you work for most of your life, you are conditioned to that Groundhog Day-esque nature of existence.

You have a set schedule every day.

Then, one day, you wake up and no longer have to work; you no longer have to trade your time for money.

Transitioning from working a 9-5 career for decades to unlearn the aforementioned programming and conditioning is necessary.

You’ve been doing something so long that any drastic change is challenging.

My friend has been working for decades.

It’s not an easy transition for anyone working for decades to not working at all.

It can be daunting.

It reminds me of Brooks in The Shawshank Redemption - you become institutionalized.

So I told him that one thing he may need to do is travel somewhere.

His reply was, “I’m planning on it.”

I shook my head and told him:

“Nah man, you have the time and financial resources to go home right now, buy a ticket to Paris, and spend a week or more there doing anything you want. You can fly anywhere in the world. Go somewhere in Europe you’ve been to before. Enjoy your morning coffee at a sidewalk cafe every morning. Or jump in your car and start driving west. Go to Montana, go to Wyoming, and spend some time in a cabin. Explore. Get lost. Find yourself. You didn’t retire to spend most of your time in Brooklyn.”

And then I asked him, “Tell me in one word, what’s stopping you?”

His reply was, “Fear.” Fear of traveling alone.

And I get it.

Traveling with someone else or a group of people is one thing.

Traveling alone is an entirely different beast to tame.

Then I reminded him of one of my favorite quotes, “Everything you ever wanted is sitting on the other side of fear.”

We continued our conversation of me trying to encourage him to travel somewhere.

I believe he appreciated my encouragement.

As to whether he’ll take my advice, that remains to be seen. I’m a gambling man; I’ll bet money he does. I just don’t know when.

It may take a few more conversations.

Which is entirely reasonable. What works for one person may not work for anyone else. Especially when it comes to traveling alone.

But, I am adamant about the fact that life is entirely too short.

And if traveling alone is stopping you from experiencing life in a different place, I urge you to overcome that fear.

If traveling alone sounds overwhelming to you, travel somewhere familiar. Somewhere you’ve been to before. Find your footing.

When you’re ready, travel alone somewhere you’ve never been.

And while it’s easier said than done, I speak from experience.

In 2016, I rented a car and drove from New York City to Montana. Alone.

It was one of the best experiences of my life.

And I won’t lie. I was definitely afraid. I had no idea what to expect.

But, it was such a powerful, positive experience for me that a cross-country road trip is now one of my annual non-negotiables.

So, consider traveling alone. Start somewhere familiar. Then, broaden your horizons.

It may be one of the best experiences of your life.

Then, when you no longer have to trade your time for money, you’ll know exactly what to do.

Interesting reads:

You can find the collection of financial tools & resources that helped me grow from a 6-figure debt to a 6-figure net worth by clicking here.

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