Have you ever said to yourself, “If I can do this, get this, have this – I will be set for life?” I have. Many times, over the past 30 years.

When I took some time off in 2024, I did some reflecting on the chasing of that feeling and why I was hellbent on trying to be “set for life.” The decisions I made, the jobs that I evaluated or the dreams I wanted to fulfill.  I saw this pattern and wanted to learn from it. I worked with a coach, and after a few sessions and analyzing various examples, the lightbulb went off. It was a simple idea, almost annoyingly obvious once you hear it out loud: there’s no such thing as being “set for life.”

Most of us grow up believing this mythical moment exists—a number in the bank, a title, a business sale, a finish line we think will deliver permanent ease or certainty. We imagine that once we reach it, we’ll exhale for the rest of our lives. No stress, no questions, no doubts.

But that moment isn’t real, and more importantly, the pursuit of this carries a cost.

The key takeaways after my coaching sessions could be summarized with “When people say they want to be set for life, they’re not chasing a reality—they’re chasing a feeling.” It’s the imagined feeling of safety, love, validation, or completion. The idea that one day we can say, “I made it,” and everything after that will be easy.

Here’s the problem: because the target is a feeling, not a fact, it moves.
Every time you get close, it shifts.
Every win is discounted because it isn’t the win.
Every milestone is dismissed because it isn’t that milestone.

While we search for being “set for life,” and that big bang validation, we missed out on the real tangible validations that were sitting right in front of us. The wins we earned, the progress we made, the risks and challenges we survived, the people we helped, and the complex problems we solved. The worst of all – we overlooked the proof that we were already building something meaningful.

Now for the fun part …

Assuming you were the fortunate one to achieve that large goal – the money, title, business sale, whatever your version is—you likely felt underwhelmed and probably reset for the next big “set for life” milestone.  Because the moment you reached that mythical goal, it didn’t come with the fireworks you imagined. It didn’t fix everything. Life still has challenges and is not frictionless, and in the end, we start asking ourselves, “Was it really about the milestone?” I believe it’s about the feeling we hoped we would feel upon reaching the “set for life” milestone.

All that said, I am still focused on short-term and long-term personal and professional goals. I am still driven by the idea of building success with the company I recently acquired. I still dream about what retirement could look like in the next chapter of life. However, it’s not tied to a set dollar amount, a timeframe for an exit strategy, or a set date in the future to stop working. As my wife says from time to time, “Let the universe do its thing,” which I fully subscribe to now. I am more in touch with what is happening today, and I have a greater appreciation for what is happening around me, my family, friends, and colleagues. I am no longer waiting for some final moment to feel complete.

To summarize,  being “set for life” isn’t a finish line—it’s a mindset.

We become “set for life” by realizing we’re already living it, one earned win at a time.