How To Grow (Up) In 5 Years

You convince somebody who knows you know nothing that you know something, or more likely that one day you might know something.

You finish classes, say goodbye to people you’ll never see again, and celebrate with those that you’ll always see. You’ll later realize that at some point most of these people you’ll never see again too.

You start your job and are blown away by the intelligence of those around you. You envision your future, map out your next 10 years, and start thinking about how to walk that path.

The exit that was going to change your career is called off and you realize you need to make a move. You now understand that all of those times your boss would smile at the naivety of your life plan is because of moments like these. You feel like the world is against you and that your whole life has been unfairly de-railed. You wake up months later and realize life goes on. You learn that whatever plans you have for yourself will undoubtedly change, but you still don’t fully understand why.

You join a startup. You realize quickly that you don’t have all the answers despite being 23. You feel what it’s like to disappoint your boss. You feel what it’s like to have your boss push you to be great. You work in an overcrowded room on 37th street. You see what believing in a mission looks like.

The startup is now ~5x bigger. You move offices. One late night with your CEO you look at the massive empty office and ask “Do you ever just look at all of this and think ‘holy shit’?” With a smile on his face he says “every day.” You learn what it’s like to experience growth.

But what you really learn is what it’s like to experience growing pains. You learn that culture can make or break a company. You learn about fixing culture the hard way.

You learn what personal growth looks like. Not from yourself, but you look at your first-time CEO and see how far a combination of intelligence, arrogance, drive, and conviction can get you. You learn the type of people you respect most.

Somewhere in the middle of this you’ve been seeing someone. She’s older. You took a break 2 years in because everything felt too serious and you were too young. You realized 2 months later that it’s easier to be 75% committed and have something than be 100% free but have nothing. You reconcile your differences but never break that 75% commitment level again. Now, 4 years in, you learn how much people change, and how much they don’t.

You learn resentment builds and that it will eat away at any relationship. You comprehend that people are fragile and you have to be honest and fair to yourself and the ones you love. Things end one night walking down Hudson Street. You learn that the most important decisions are often the hardest.

Your next year is split into work and honesty. You realize relationships, non-relationships, and fun nights out are easiest when you’re brutally honest. You don’t quite know it yet, but you’ve established one of the pillars of your short life that honesty is indeed the best policy.

Months later, you get a job offer. You have 48 hours. You remember that important decisions are the hardest. You meet with your friend in Madison Square Park at 7:30AM on a cold November morning to talk it out. You learn that the chances you don’t take are the ones you’ll regret. (He also tells you that 6 months is nothing. You will highly dispute that fact 7 months later.)

You move to San Francisco for 6 months. Your last day at your startup is on a Friday, your first day at the new gig is 3000 miles West on the following Monday. You realize how easy and difficult it is to toss your life across the country.

You get to SF and feel what it’s like to be lonely in a new city. You’re the most friendly you’ve ever been because you’re living with 5 strangers, in a shitty neighborhood, in a city filled with a few people who are “sort of” friends. You learn how your home really affects you.

You start your job and find out what peer mentorship feels like. He teaches you how the power of being a human can give you an edge. You eventually learn that humanity and friendship can take away your edge as much as give you one if you don’t manage it correctly.

You finally feel like you’re doing exactly what you’re supposed to be doing. You meet tons of smart people. You meet tons of dumb people. You learn that there are situations in the world that make smart people dumb and dumb people smart.

You take too many meetings. You know just how important networking is, so you network a lot, constantly balancing quantity and quality. You learn that what people call networking isn’t how you build a network, friendship is.

You make more friends. Despite that, sometimes you still spend weekends leaving the house at 8am and coming home at 9 pm. You learn how to be with yourself.

You fly back and forth between SF and NYC every month. You now have people you care about in both. You begin to wonder which is the right place for you. This scares you. You learn that doubt can creep into any situation, no matter how great, when you’re not fully in either one.

You look at the calendar and you only have two months left in SF. You realize you’ve been putting off important things. You remember the importance of taking chances. For the first time you really live in the moment. You have one of the best months of your life. You learn how an entire city becomes tolerable.

You move back to NYC and remember how much home affects you. You had never fully admitted to yourself that NYC was home, but now it feels perfect to say it.

Your life plans are de-railed once again. You remember that whatever plans you have for yourself will undoubtedly change. This time you understand why. You learn that life is messy and its complexities are what make it worth living.

You take too many meetings again. You get a lot of advice. Most of the advice frustrates you for its simplicity. You already know everything will work out. You promise yourself you’ll never be the type of person to give average advice.

You look at the calendar again and see it’s almost October. You write 1000 words on a Sunday about growing up. You probably could have written 5000 words. You learn that growth comes from outliers and happens in step functions.

You’re still learning that there are so many step functions left.




My mostly random thoughts and experiences as I make my way through life.

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Michael Dempsey

Michael Dempsey

Want to live in a better future so investing in Frontier Technology @compoundvc. Learn more @

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