I pride myself on my ability to see the big picture at work. I can look out six months, understand what needs to happen today on my team, and make the necessary course corrections. Intuition, gut feel, and experience—that’s how I’ve always run.
Whenever I’ve started a new job in a different “swim lane,” I’ve trusted my gut to judge the situation and implement changes. I don’t wait long. I don’t take 90 days to “onboard” and understand every tiny detail. I take it all in quickly, look for the proper timing, and act.
It’s shocking how I don’t even think about it. It’s almost automatic.
As I’ve gotten older, I trust my gut more and more in work settings. Most of the time, it’s right.

his instincts didn’t work out so well
I need to remember this for the other parts of my life. Wisdom builds, hopefully, over the years. Deep down, we all likely know what we should do logically; it’s the emotion that holds us back when its personal. The Dark Side.
Trusting what I know is the path. Only then will I become one with retirement.
I admit that with the decision to retire, I’ve stayed in my head too much. I analyze from every angle, over and over. Any new piece of information feels like a reason to start over.
Money questions? Let’s move the goalposts.
Inflation? Let’s overthink it.
Padme’s job anxiety? Better reopen the timelines.
Boredom for a single day? I quickly break out the violins and worry about what I’ll do with all this time.
I hope most soon-to-be retirees don’t go through this much hand-wringing, navel-gazing, procrastinating, and avoidance. It’s painful. Frozen in carbonite am I

maybe get a friend to finally push you out
I need to take away the targeting computer (the spreadsheet), shut my eyes, and just do it. Take the shot. The worst that happens is I make a mistake and retire too early. I can always take a second pass if I miss the mark. That is the benefit of retiring young-ish; if I’m wrong, I can just find a new role. One thing I’m good at is finding a new job.
But wait a second…
There’s this AI thing. Not only does it make pretty pictures, but it’s starting to impact jobs. When you dig into it, it’s already impressively good. My basic functions are to run various back end organizations. Like managing the logistics of a Star Destroyer (Warehousing) or overseeing Trash compactor services ( Quality Engineering). My skills are replaceable.
Maybe finding another job won’t be so easy next time. Great, a new fear. Another thing to worry about.
It’s easy to get lost in the “math” of the jump to lightspeed away from work. I can twist the numbers, the assumptions, the spreadsheets, the inflation rates, and the AI threats hundreds of ways to avoid making the decision . But I have to remember who else is on this ride with me. Retiring isn’t just about me hanging up the cape; it’s about the people I’ve been working to “provide” for while I was busy conquering galaxies.
The spreadsheets are just numbers; they aren’t the destination. The destination is time with my family and to define what is next.
So….
Trust my gut. I’ve done it for my career; now it’s time to do it for my life. It’s time to make the call. Set the date or the dollar amount, and let that be it. Set the path. Is it a hard date? Do I work three or four days a week to “glide” into it? Better yet, I should set big plans with my kids and wife regardless of work. If work gets in the way—emphatically, fuck it—and just go.
Sit back. Put the gut in charge.
Today, my gut says I should work for 17 months, with a reduced four-day work week for the final year. This gets me through to Padme’s possible retirement date. On top of that, I should take as many extra unpaid weeks off for vacations as I want—seven weeks or more to “test drive” a normal year of retirement travel and special events.
Tomorrow, my gut might say six months. Don’t let the door hit me on the way out.
One of these days, my gut will settle down. If I talk about it enough, I’ll eventually get tired of the back-and-forth and just pick one. I don’t know how cows do it with four stomachs to follow; my two are hard enough. They’ll figure it out.
Whether it takes 5 months or 17, I am finally ready to “stop conquering galaxies” and start becoming one with retirement









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