Ok Boomer: Older People React to My Early Retirement

In my 40’s, I retired early, sold almost everything I owned, to slow travel the world. Sharing this with people elicits a fascinating mix of responses, often varying by generation. While it’s hip to dismiss the ‘Boomers’ lately, I’ve found that they are my favorite group when it comes to their reactions.

3 Types of Responses

Regardless of age, the first and most common response tends to be a somewhat indifferent acknowledgment. A simple, “good for you,” is often the extent of the reaction. It’s a reminder that, in general, most people are preoccupied with their own lives and are not particularly interested in what others are doing. Especially when it falls outside the conventional norms.

The next most common sentiments expressed are along these lines:

“That’s soooo amazing! If I could go back in time, I would do something like that. Knowing what I know now, I would have traveled more when I was younger.”

This validation from the older generation reinforces my conviction that I’ve made the right choice. Their Acknowledgment that regrets are real, helps me know that I would have been one of those who lamented not taking the opportunity to travel. I’ve been traveling as far as I could from home as soon as I could walk!

Then, there’s a small but inspiring minority of Boomers who share things like this:

“I did something like that when I was younger. It was great. And then I want on to…..(followed by a captivating list of remarkable experiences)”

These are the stories I cherish from Boomers! Those who dared to take the road less traveled, survived, even thrived!

Thanks Boomer!

Their tales give me hope that my life choices are not the worst. Someone’s done it before me and it turned out well for them.

Some successfully navigated a return to a conventional life with a job, a house, a pet. Some ventured down obscure and unimaginable life paths. It demonstrates to me that going off to do something a little different doesn’t have to be forever. But if you do, the possibilities of where you might go are boundless.


Remarkably, I’ve never encountered a Boomer who regretted taking a break from work to explore the world. Even when they recount stories that weren’t exclusive full of rainbows and sunshine. Of course, it’s likely that survivorship bias plays a role in their overwhelmingly positive responses. Or, perhaps societal norms prevent them from admitting otherwise.

I’m not conducting actual research, of course. I’ll leave that to people smarter than me! However, the anecdotal evidence I’ve collected offers a persuasive argument that taking a calculated risk to leave work and travel often yields great rewards. At least, taking the risk is seldom a fatal error from which there is no return!

In Conclusion

These stories provide encouragement, affirming that the pursuit of adventure and exploration is a life choice that holds immense value. Particularly for those who yearn for it.

Having examples, people to talk to who have done things we hope to do, but are a little further down the path we want to go, is extremely helpful. I am profoundly grateful to those who’ve paved the way ahead of me, which is why I am compelled to share my own journey.

In the end, we are all travelers on our own unique journeys. Towards the end of yours, do you want to be burdened by regrets or enriched with tales to tell?

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