There’s an old saying that history doesn’t repeat itself, but it often rhymes. Lately, I’ve been feeling the rhythm of a past life. I’m currently staring down a career situation that is almost identical to a crossroads I hit twenty-five years ago when I was running my own consulting firm. Both times handed me the exact same variables—minimal work, maximum downtime, and no immediate financial worries—but checking under the hood of my mental state today reveals just how much has changed.

My workdays back in 1999–2000 consisted of going to an office every day with absolutely nothing to do and very few people to interact with. I deeply struggled with the forced presence of being “at work” without a task. I felt like I had to be in the office 9 to 5 just to put in the face time to get paid—to be seen as getting the job done.

Back then, it was a massive transition from being a day-to-day doer to a senior manager who delegated and made decisions. The work I used to do was no longer being done by me.

I owned a niche consulting business with eight people, specializing in transferring manufacturing operations between factories. It was a one-year contract, and because I had pitched the idea and landed it myself, I was making six years of salary in one. Let’s hear it for business ownership.

For the first time in my life, money wasn’t a concern. And because of the hands-off nature of the role, I had a massive amount of downtime to let my mind wander.

Mentally, I struggled. I felt like I wasn’t adding value, and I had no plan for what came next. I didn’t feel productive, and worse, I didn’t understand that directing work was actually work. I was lost in a way, after having worked hard for the first six years of my career. With time on my hands and plenty of resources, I had infinite choices in front of me.

The Paradox of Choice hit me for the first time. Too much choice can be crippling.

What to do, what to do? Not easy

2026: The View from the Death Star

Fast forward 25 years, and I find myself in a remarkably similar situation. At work, my day-to-day responsibilities are minimal. There are days where I literally do nothing, and it doesn’t matter. My Emperor is entirely corporate, absent, and uninvolved. The metrics that matter are my team’s results, not my personal output—and because the team is executing well, I can choose to do very little. Once again, money isn’t a concern; my financial goalposts are about to be passed, and retirement is not far away, with endless possibilities ahead of me.

I have maximum time on my hands to just think. In fact, I’ve basically authored a full-length book on my thoughts while sitting at this Death Star. The infinite choices have returned.

The similarities between these two eras are striking. The main structural difference is that I have a family now, but otherwise, the landscape is almost identical—just with a 25-year age gap.

Today, I wanted to check under the hood of my mental state to see how the two periods actually compare.

1999–2000: The Weight of Infinite Choice

Looking back, that year was one of the lowest emotional periods of my life. In many ways, it was self-inflicted. I tortured myself over my “life plan.” Because I had no clear path ahead of me and money didn’t matter, the world was wide open. I could play. I could go back to school. I could travel.

Instead, it brought me down to a mild depression. Because I lacked clear desires and a concrete plan for what was next, I mentally shut down. That paralysis triggered the end of an on-again, off-again six-year relationship and prevented me from fully leveraging my financial good fortune.

Looking back, any decision would have been better than the stagnation of shutting down. It’s still surprising to remember how dark that year felt. Money didn’t fix it; in fact, the lack of financial pressure made the void feel wider.

2026: The View from 54

Today, I am still somewhat paralyzed by the question of what comes next. In that sense, it’s not too dissimilar to 1999. There is no set path ahead because I could choose to walk away tomorrow. I still face close to infinite choices (bounded slightly by geography because of family). I could go back to school, start a “play” business, or take a low-stress job just to pass the time. I could sit on the couch and eat bonbons. The indecision is the same, and it still impacts my mood—but the emotional gravity is entirely different.

I am anxious about the next chapter, but I am not scared. This time, the infinite choice carries a sense of excitement. I’m looking forward to being more social, meeting new people, and taking ownership of exploring the world. Instead of bringing me down, it actually has an upside that comes with little to no expectations.

My anxiety today stems from simpler questions:

• Will I fall into boredom?
• Am I walking away from easy money just to do nothing?
• What if retirement isn’t as fun as it looks?

But here is why it feels different this time. I know a few things now that I didn’t know then:

• The Erasure of “Next”: At 54, there doesn’t need to be a next big thing. It would be nice to stumble into a new passion, but it’s completely okay if I don’t. At 29, that was an unthinkable concept. I was trying to live up to societal expectations; at 54, I don’t care about them.
• A Solid Foundation: I am giving myself permission to explore without tying my worth to money. At 29, money carried too much weight. More importantly, I am happy at home. I love my wife, and I have great kids. In 1999, I was in a status-quo relationship that wasn’t working for either of us; I couldn’t rely on it to lift me up. Now, I have a rock-solid foundation, which removes the underlying stress of navigating a transition alone.
• Effort vs. Value: I have far more confidence in my abilities now. I’m the veteran in the room, using decades of experience to make decisions effortlessly. At 29, I may have had more raw brainpower, but punching above my weight class left me insecure. I used to equate value with grueling effort, carrying immense guilt when the work felt too easy. I now know that value isn’t about face time or sweat equity—it’s about solving problems efficiently.
• The Safety Net of Experience: I’ve proven to myself that I can land a job easily if I choose to. Combined with financial independence, I know I can walk away and return to the workforce on my own terms. At 29, felt like I was riding a once-in-a-lifetime wave with a ticking clock, terrified of what would happen when the clock ran out.

When I add it all up, I am in a vastly better place mentally than I was 25 years ago, despite the circumstances being almost identical. I attribute that to wisdom, confidence, and a willingness to judge myself less.

Because I judge myself less, I don’t need a massive, earth-shattering mission to validate my existence when I finally leave this Death Star. The vital difference is that infinite choice now contains excitement, not terror. At 29, the blank canvas was an interrogation; at 54, it’s an invitation.

I am ready for the next adventure. What will the next 25 years bring?

I’m much more relaxed at work now