Two forks I think about.

In high school, was accepted to Art Center College of Design in L.A. (where lots of auto design was being done then, this was mid 70s) and to an art school in Paris.

I think about what would have happened if I’d gone to art school. I was really into cars (not wrenching, but drawing them), maybe I’d have gotten into the car industry, or product design. The French comic scene was exploding then (remember “Heavy Metal” - that was “Metal Hurlant”) and I was super into sci-fi and drawing, maybe I’d have gotten into comics, or animation, or pop art.

Instead, I decided to go to UCLA and study physics. Edit: this thread isn't about regrets, unless you want it to be. Anyway I can't know if I would regret that decision. I'd be a totally different person in a different world, that I know nothing about. Maybe I'd be dead of a drug overdose by now.

After 13 years of lawyering, I was a young partner in a big L.A. firm, a couple solid clients of my own, bringing in $2MM/yr fees but seeing less than 10% of it after overhead and senior partners, and I was burned out. Four other young partners, all my friends (we’d all come up the ranks together, worked together for years), asked me to join them in starting a law firm that would be All Indian No Chief, meaning low overhead, everyone takes home as much as possible of what they bring in.

Maybe I’d have been re-invigorated at lawyering, or made enough money that it wouldn’t have mattered.

Instead, my wife and I quit law, sold our house, took our 6 mo daughter and went traveling around the world for a year, then I went back to grad school to change careers. Edit: This one is a fairly easy "regret/not" analysis. I'd have slapped golden handcuffs on myself, locked myself into a career that had burned me out in a city that I was done with. Trading money for life, not great.

Edit #2: Apologies to the still-lawyers, but what happened to me was that after 10 years doing it, I realized that if you have a certain personality you think that if something is demanding it must be interesting. Eventually you (I) realize that things can be demanding without being interesting. I got scared of dying behind my desk as an old lawyer. Took me three more years to extricate myself from law.

I should have never got married x 3.
Thinking with the wrong head.

two years after college i left a good corp job near DC to be back home on the Md shore. probably earn about 1/2 what i'd be getting on the other (wrong) side of the Chesapeake but my kids have grown up in a conservative thinking environment and i get to enjoy my hobbies virtually any day of the week instead of being a zombie living only for a few hours of fun on the weekend.

Not certain but being self employed has helped me grow up in a professional sense. I'm sure i would've done well in the old corp job but i'm not sure i'd be doing my own thinking vs just mimicking what those around and above me say and do. I suspect i'd be a much better corp employee now with my experience and confidence however i'd likely be fired in a few weeks for not owning a suit/tie and showing up 2hrs late during duck season.

lol..
well one of the other fork's showed up last week..
She & friend came to visit my Mom..
after 30 some years she still had that smile..
and I fond memories of Paris..
t'was interesting..


Rika

Another fork, should have saved more when I started in aerospace 37 yrs ago. Doing fine now, but would have been far better off if I was more disciplined.

My buddy laments regularly how we “could have made it” in the world of playing rock and roll.

I don’t regret anything. Best case would be playing crap county fairs and a string of rehabs.

Lucky I missed.

My fork in the road happened when I was working as a machinist at TRW and they offered an aptitude testing by a pro. My foreman recommended I take it to see what was up.
Turned out I scored a lot like the actual person doing the evaluations, or so she said. When she asked me to describe a typical day, when I finished, she told me I was working in a 'shadow' type of situation and that I'd better switch jobs as it was dangerous. I was literally turning off my brain to cope with the tedium of machining.
I ended up getting a job as a planner, which was good for my 'writing' desire/skills. That led to manufacturing engineering and the rest is history, so they say.

With hindsight, I can see many things I could have done better. But isn't a big part of life making mistakes and learning from them? The silliest regret I have is how I came into this world. The product of an unplanned pregnancy. Given up for adoption. My birthfather's life literally ruined and ending in suicide. Certainly not something I had any part in or control over. I know that, but still regret my part in it.

Leaving race car mechanic/pit crew for construction. I'm sure I did the right thing. Being on the road is a tough life. So is construction, but those were the choices.

I think it is true for everyone their life would have been totally different with different choices.

I have talked to a lot of smart old guys and they generally tell me you do not regret anything you did. You regret the things you did not do.

I am very happy with who and where I am now, a day does not go by that I am not struck by how fortunate I am. There have been a number of times where I sort of doubted it, but then something implausible happens and I land in tall cotton. If you go back and take a different path, it changes everything after. Even given the impossible opportunity to go back and make some crucial change, no way I do it.

I would goon that shiite up, no doubt.

Luckiest thing for me was choice of parents.

So many interesting perspectives...

For me, the first big hurdle in my life was getting hit by a car in college...I was on an athletic ride that rode away after the injury.

I wallowed for a month or so (woe is me, I'm domed [sic], etc.) until my Mom just wore me out: "Enough. Start moving forward in your life or I will...you did not die so act like it."

So I did.

I was always a good student but I pored my anger and emotions into school and I am a far better person for that opportunity, changed my life.

Brevity is the soul of wit, adversity is the soul of accomplishment.

An even earlier fork for me was back living in Hawaii in the 9th grade and pickling up my dad's Miranda viewfinder camera and loading in some Tri-X and taking some photos. I pedaled my bike to the Hickam AFB photo hobby shop. Joe R. was the manager there. For 25 cents, I was handed a film reel, and a car to process the film myself. I had no idea what to do so the manager there showed me the steps, and I processed the film with his help. I picked out a few negatives to print, and he showed me how in the print darkroom.

Watching the image appear like magic was a life changing thing for me. I was hooked.

That manager was just working part time as a second job at the hobby shop. He was a black man and a Sergent in the Air Force. Joe and I became good friends. My officer dad had to get written permission from the base commander for Joe to get to come over and socialize at our house. Officers and enlisted are not supposed to fraternize, and it was never more than a handshake, and hello to each other. Joe of course had a car, and he would drive my to the nearly endless beaches in Hawaii. For some reason as a teenage boy the endless supply of girls in bikinis held a real interest for me.

Since then the only thing I have ever done for money, to this day involves photography.
Joe was my first teacher and set me on the path of doing for a living what millions of people do as a hobby.

So that act of picking up a $25 camera my dad had set me on a career path.

According to Dan Pink in his book, "The Power of Regret", there are four types of regret.

Foundation Regret - things that could set you up for life - school, family, parenting, etc. No regrets here on choices I've made.

Moral Regret - nothing here.

Connection Regret - nothing here.

Boldness Regret - "could've would've should've" on that big chance. Maybe going after the girl. But in hindsight, I'm probably better off for not doing it. On the flip side, it may have been bold to migrate to another country and leave family behind, but then, my kids don't have relationships with cousins or grandparents, but I would be grinding with very little to show for it.

… Yes, there were times, I'm sure you knew
When I bit off more than I could chew
But through it all, when there was doubt
I ate it up and spit it out
I faced it all, and I stood tall
And did it my way

… I've loved, I've laughed and cried
I've had my fill, my share of losing
And now, as tears subside
I find it all so amusing
To think I did all that
And may I say, not in a shy way
Oh, no, oh, no, not me
I did it my way

… For what is a man, what has he got?
If not himself, then he has naught
To say the things he truly feels
And not the words of one who kneels
The record shows I took the blows
And did it my way

no regerts

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Yeas ago I was at some bar with live music. Some scrawny young 20 something was singing that, and I almost choked.

It means something when a man like Elvis or Sinatra sings it, but with some young kid it just seems funny.

Scrummy or backfield? I was many years a hooker then wised up and went to loose forward.

If you dwell on that you will be miserable. There are more than enough barriers to make it practical for one to do everything they think they ought to do. Plus it takes enormous dedication and effort to do anything quite well. I could do a lot of things in mediocracy.

And if I told myself I was going to be a singer, every minute of that effort would have been a waste of precious time.

Life is like that.

Every second thing I've done has been a mistake, and every other thing I've done has turned out to be twice as good as I expected.

So it kind of evens out.

I wish I'd married Debbie Holden.

No regret; but I do wonder if I'd put the skill at being a race driver I had to full use chasing pro how that would have gone.
I'd rather be building and designing, so I am.

No regerts.
Somebody had to say it.