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What’s your biggest regret in life so far?

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Spending the first two years of my career doing not particularly much and neglecting my development. Fully admit I got it all wrong. Good environment to make inexpensive mistakes in that would otherwise have been really bad, but set myself back two years by having the wrong sort of ambition.

Didn’t even do anything cool like travel or lose myself on the road, just blew two years in a dead end job I was, frankly, a lot better than.

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Two things:

I got started mining Bitcoin back in 2013 in college but didn’t have enough money as a college student to properly get into it.

Also wish I had bought a home the second I graduated and rented out a room to a roommate. Feel like I threw away money renting for far too long.

Both are a case of hindsight being 20/20.

Otherwise I’m a pretty happy guy

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Accepting an offer from Deloitte

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Not taking my own mental health seriously.

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Not actively working to maintain contact and strong connections with more of my high school and college friends. The older I get, the more I regret this as I see others with true life-long friendships. Seems like I have small groups of friends which represent segments of my life…friends from work, parents of kid’s friends, neighbors…they are good, but not the same as the ones who knew you before you knew yourself.

Make the call, send the email, drop by when you are in town….it will be more important than you think as you approach retirement.

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Professionally: not studying business or computer science in undergrad

Personally: not realizing I was trans 🏳️‍⚧️ until I was almost 30

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Had a full ride to college and I studied accounting and finance. It has worked out thus far and I have a well paying job in consulting but now feel pressure to get another masters that will cost me a ton. I should have just studied computer science or computer engineering.

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Agreed and a majority of the CS people only have undergrad degrees. These kids are making crazy amounts. They do live in expensive cities though

Not applying for MBB internships during college because I was too intimidated and thought I dont have what it takes…

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Bitcoin

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Not buying a house in my home country that was dirt cheap years ago.

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Not having a plan. Under estimating small talk. Selling my cheap house in DC.

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Going into consulting after the military

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If you are interested in consulting for defense companies, feel free to pm me!

In the realm of stuff I could have foreseen: moving to Chicago for a couple of years as an adult.

In the realm of stuff I probably couldn’t have foreseen: deciding Bitcoin was dumb back in 2009/2010 and then ignoring it until it was worth a lot.

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To be fair, most people who would have invested in bitcoin early, would have taken profits early as well.

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Deloitte.

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Not divorcing my husband earlier. The years of therapy and trying to make it work were a waste.

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Coming from the other end, wishing I had seeked professional help before ending a LTR.

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Screwing up McKinsey, Bain and OW interviews for MBA summer internship

Tech. But not as a core techie so I don’t make those astronomical figures you hear about

Damn. I can’t think of any so far…

Not getting a dog before I got married

Professionally: Chasing a career to earn my Dad’s affection instead of being myself.

Personally: Not getting professional mental help for myself and my ex-gf. Like hamsters on a treadmill stuck in the same place for 8 years.

Any period in my life where I know I was wasting time.
Not mistakes, or taking time to reset, or learn, these are all important at various times....but where I know, I spent the only currency that I can't make more of, with 0 deliberate purpose

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