Two years into this experiment, I’ve accumulated some early lessons about the process of retirement There’s an emphasis on “process” here, because that’s what this really is. Think less in terms of crossing a bridge to a destination, like the famous Bixby Bridge on Highway 1 in Big Sur, pictured above. But a process. You may be surprised where the process leads you. For me, it led to a relocation from Houston to the mountains and lakes of Coeur d’Alene, Idaho.

Why I Don’t Like the Word “Retirement”

Conventional wisdom says that once you leave an extended career, you’ve “retired.” If you do it younger than the traditional age, you’ve “early retired.” I don’t love either term, because I don’t feel like I’ve done what they describe.

When I looked up the meaning of retirement, I found words like “giving up work”, “ceasing to do something”, “retreat”, “withdrawal”. One definition even included the phrase “because you are old.” Wow.

None of that matches my experience. If anything, it’s the opposite. To me, this stage is about designing your day on your own terms and doing what you actually want to do. I’ve stopped fighting the word when other people use it to describe my situation — I just own it. But privately, I think of it as my post-corporate life, not a retirement.

For simplicity, I’ll keep using the conventional word throughout this post. Just know I don’t fully agree with it. So what have I actually learned?

How Do I Explain What Retirement Is Now?

Short answer: I don’t, really — not anymore. I let what I do speak for itself. Some days that’s writing a book. Other days it’s building community, spending more time with friends and family, exploring new hobbies, traveling, playing sports, or volunteering. Sometimes it’s simply not rushing through the mundane parts of life.

One of the best parts? No more Sunday-night anxiety as a weekend, holiday, or vacation winds down. That alone might be worth the whole transition.

Retirement Happens in Stages

There are recognizable stages to the retirement process. They vary somewhat from person to person, but they generally fall into common phases. One of the better breakdowns I’ve come across is a TED Talk called *The Four Phases of Retirement— worth watching if you’re in the early planning stages.

Is It Okay to Second-Guess the Decision?

Once you’ve made the decision and it’s official, can you still look back and question it? Or is it time to burn the boats?

From my own experience: yes, it’s okay to look back. In my case, I did that for a while, then eventually grew comfortable enough with the decision to remove the rear-view mirror for good. Reconsidering is a natural part of the process — but eventually you’ll know when it’s time to stop looking back and just move forward.

My Number One Piece of Retirement Advice

If you’re within a year of your official retirement date, start a list of everything you plan to do once you get there — and then start doing those things now, not later. You likely won’t have time to pick up every new activity at once once you retire, but getting a head start matters. There are two reasons why.

1. New activities take time to build momentum.

Whether it’s joining a community group or starting to volunteer, most new pursuits have a runway. Get things moving before your retirement date so they’re already in motion when you arrive.

2. You might discover you don’t actually like it.

Say you played tennis years ago but gave it up for work or family reasons. You plan to pick it back up once you retire. But when you finally get on the court again, you realize it’s not for you after all — and now you’re starting from zero with no backup plan.

Start now, to whatever extent you can. Don’t wait for the date on the calendar.

Why Building a Retirement Around Travel Might Not Work

This one may not land well with everyone, but it’s worth considering. When I ask people what they plan to do in retirement, “travel” is often the first answer. That might work for some — I don’t think it will work for me.

I enjoy traveling now that I have the time for it. But I don’t see it as a sustainable foundation for retirement long-term. Every trip ends, and you come home to the same retirement process waiting for you. For me, travel will stay a part of the picture, but I’m building my retirement around other things — community, friendships, staying active, volunteering, and writing.

If your retirement plan is built primarily around travel, it’s worth really thinking that through before you get there.

Final Thoughts

This is a process, and everything above reflects lessons from my own journey through it. Your path will look different, but I’d guess there’s some overlap with what I’ve learned along the way.