Never Retire - When You Don't Live The Life Your Parents Wanted

A lot of what we discuss in this newsletter boils down to expectations.

Throughout your life you often choose between satisfying somebody else’s expectations or doing what you really want to do.

It’s difficult to do both, particularly because people tend not to budge on the expectations they set for you.

When you do what you really want to do, you give yourself flexibility. For many of us, flexibility is the prime motivation behind the life-work-money choices we make.

For living the life you wanna live now and for the duration.

When you live up to other people’s expectations, you might give up flexibility.

Case in point—I love my parents. I know they love me. They’re proud of the things I have done in life. In fact, they tend to overblow my so-called accomplishments.

I’m just out here living life.

But I’m just out here living life the way I wanna live it (now and for the duration) because I chose to pretty much do the opposite of what they—at one point—expected and—all along—definitely wanted.

Where I’m from, a majority of people never leave home. In fact, quite a few of my high school friends live down the street, a few blocks from, or in the city or two next to where their parents live. Quite a few who leave end up coming back. They couldn’t be away from family.

They buy and build houses. They decorate them—over the top—for every holiday. They have kids—usually more than one—that grow up with and around their parents. While there’s nothing wrong with this, it was never for me.

I have lived in eight different cities in my adult life, including where I am today (Los Angeles). Before it’s all said and done, my partner and I plan on living in at least one more.

As a result of my choices, my parents didn’t get to see my now 19-year old daughter grow up. My daughter and I each live roughly 2,500 miles away from my parents.

Maybe I’ll regret this one day, but it was never a difficult decision for me.

By a similar token, I have never expected or even desired proximity from my daughter. She lives a few hundred miles away from her parents now. Honestly, I wouldn’t have it any other way.

If she stayed in Los Angeles after high school—particularly living at home—she would have done herself a disservice. She would have robbed herself of the flexibility being truly on your own makes possible. If we encouraged her to stay, we would have been doing her a disservice.

As a parent, I encouraged her to go. In fact, when she struggled in her first few days away from home, I administered tough love. So far, so good. It has worked out well. She’s thriving.

When I left home, my mother cried for weeks. Maybe longer. As a 19-year old, I felt guilty leaving her. But I still did it. Because I knew it was the best decision for my present and future. Moving away changed who I am and allowed me to experience people, places, and things I absolutely would not have experienced if I stayed put.

So many people succumb to the pressure other people, especially their parents, put on them. In fact, they often look to mom and dad for approval. If they don’t get it, they often scrap their plans.

Along these lines, there’s a stigma around Never Retiring, especially if you embrace it as a choice.

Because when you accept it as your reality and embrace it as a choice, you often—

• Don’t hold a traditional full-time job. Some people, especially older parents, don’t understand or aren’t cool with freelancing.

• Work less now, so you can work less longer. The idea of living evenly across the lifespan also stumps more people than you might expect.

• Come off as lazy. I spent years working my ass off. People admired my work ethic. One day, I said no more.

• Earn less than you otherwise could. Self-explanatory when combined with the other points.

• Focus on a low cost of living, not material rites of passage. When you buy your first home, people recognize the “achievement.” Same for a shiny, expensive new car. When these things aren’t part of your life—when they don’t matter much to you—people get confused.

The list goes on.

If you kick and scream into relative old knowing you’ll Never Retire, it’s not the same.

However, if after acknowledging and accepting it as your reality, you embrace and recognize it as superior to traditional retirement, you have made a choice.

A choice others often will not understand. A lifestyle others often will not understand.

Everything from the low cost of living to calling yourself semi-retired. It just doesn’t make sense.

All that matters is that it makes sense to you. That if it’s calling you, you go for it.

To this day, I really don’t think my parents understand what I’m doing with my life—professionally or otherwise. So they hang onto conceptions of what they expected and work them into their perception of what I’m actually doing.

This is actually what—in part—makes them good parents.

We don’t get it, but we’ll support it even if we don’t fully understand it. Even if it’s not what we wanted or—when you were a little guy—expected.

Bottom line—I gave them no choice.

If you’re looking to make a big move—even if it’s different from what we outlined here—don’t check in with people you don’t need to check in with. Particularly if they have self-centered expectations for what you should (they want you to) be doing.

Make your moves. Embrace your lifestyle. Give them no choice.