Is too much of our focus on the last gate ?

We sleepwalk through a dozen career gates and obsess over one.

I’ve been playing around with this idea of “Career Gates” for a couple of weeks now. I want to be honest that my thoughts aren’t fully formed but part of why I write is to think out loud with people who might be wrestling with the same thing. So bear with me here.

This thought came to me when I was attending Sunday Mass a couple of weeks ago. I don’t go every week as life gets hectic with two young kids. But a few weeks ago, the priest was talking about the final gate to heaven. The moment of reckoning at the end of this journey we’re on and how we are shepherded through this journey throughout our lives without really thinking about it daily. He went on to talk about how all of our daily choices in life lead to this one moment. Do we treat people with kindness? Do we hold true to our values? Do we forgive? Do we practice our faith, whatever that faith may be?

After mass, I started thinking about how this applies to our careers, and something nagged at me. We have this entire infrastructure built around one gate, the last one, being retirement. Financial planners, calculators, endless content telling you exactly how to prepare for the moment you stop working. You sit there with all of these resources, mapping out a scenario that’s decades away, you make a plan, and then life happens. You forget about it until it sneaks back into your head ten years later, asking yourself, “How the fuck did ten years go by?”

The point I’m questioning is: Why do we put all of our energy towards planning and thinking about the last gate - when we retire? There surely must be other gates along the way that we should reflect on and even better, know they are coming.

When I look back at the first half of my career, there were probably a dozen gates I blew right through without even knowing. Finishing school at Northeastern University with some half-formed idea of what I wanted. First real job. Getting materially better at it. Getting promoted. Building something that looked, from the outside, like a career. I realize now each of those moments was a gate. I didn’t really celebrate any of them. I just kept hustling. Not really thinking and all the while, being shepherded through by….society? We’re almost on autopilot through all of this.

I’m 45. I spent twenty years doing what we’re supposed to do. Worked hard. Read the books. Logged a lot of hours.

And then, without much warning, a major gate recently appeared for me and it feels like a substantial one that I should have been thinking about a decade ago. It isn’t as clear as the retirement gate: moving from work to no longer working. Perhaps that’s why nobody talks about it.

It’s the gate where I’m realizing the next chapter isn’t necessarily about proving anything. Instead, it’s more about relying on the last two decades of practicing my craft, honing my skill and wanting to genuinely help others with all of this knowledge.

I think a lot of people in their forties are at or approaching a gate like this, and don’t quite know it. The Greek poet Cavafy wrote about this a century ago in Ithaka. The idea that we spend our lives focused on the destination without realizing the journey was always the point. Our careers aren’t much different. But for some reason, we always seem to be running hard, rushing to get to the end without wondering what exactly we’re running toward.

I don’t have a clean answer for any of this. I told you my thoughts weren’t fully formed. But I think the starting point is simpler than we make it: just look up. Not to overhaul everything, not to panic. Just to notice where you are on the path, and whether there’s a gate ahead that should get more of your attention. Each juncture or gate on our journey matters.

Would love to know if this resonates. Are you approaching a gate right now? Have you already walked through one and not realized it until after? If anybody wants to collaborate with me on a second piece about this, reach out and let’s talk.

Dave