Letter to my 23 Year Old Self #Startup

I was talking to a young entrepreneur recently, and the things that he was saying reminded me of what I used to think when I was 23, and just starting NextDrop.  I went home and looked through my old journals and, well yes.  Those were almost exactly the same words I’ve used (we probably read the same articles).  But I also realized how far I’ve come since then.  I’ve grown so much and man, so many things I wish I knew back then.  Would have saved me a lot of pain and anguish.  If I could go back in time and digitally deliver a letter, this is what it would read:

Dear Anurag,

Yes, first of all, I’m not going to call you Anu, your name is Anurag, I know you wonder every day why your mother gave it to you (it IS a boy’s name no matter how much she denies it), and yes, all the airport security guards still laugh at it when you walk through security, but you know what? It’s actually a really great ice breaker, and it’s really funny when you see grown men in uniforms laugh.  You’ll usually be really stressed or rushed and when you hit the security check, it’s comic relief.  Reminds you to not take life too seriously. So don’t hate on it too much, ok?

Moving on.  You sort of think you’re the shit.  You’re afraid to say it so you couch it in self deprecating humor, but deep down you’re really thinking you can make your company into the next Google or Facebook, and you can kick ass like Michael Jordan.  You’re working your butt off, you’re reading all the right things, talking to the right people, you’re on track.  But you’re afraid to look like a cocky prick about it because you don’t want to turn into one of THOSE douchebags. But really?  They’re actually still a step ahead because they are at least being authentic.  And the sooner you do that, (be authentic I mean) the sooner you can get on with your life.  Being a cocky asshole is sort of part of the young entrepreneur process, so don’t worry, just be real about it and move on.

Which brings me to the next part.  As soon as you start trying to be the shit, and executing on this grand goal that you have, life will throw all hell at you.  And you are going to fail.  A lot.  And very often.  Everything you thought would take 3 months has now taken 1 year.  Nothing is as you think it is.  All the spreadsheets and the books you read and the advice you got can’t prepare you for what you are doing.  Because what you are doing isn’t written in books.  What you are doing is creating a new market that nobody has touched before, because guess what, you’re creating it right now.  After the first year and a half, you’ll realize that you need to stop reading things and listening to other people, because what you need to be doing is paying attention to what is happening right in front of your face.  And using your gut to make decisions.  Which is just as scary as it sounds.  You thought you had a map but you realize it’s not taking you where you want to go.  So you have to chuck the map, and navigate in the dark.  Sans GPS.  Hurrah.

And it gets better (and by better I mean worse).  You’ll start comparing yourself to other startups and other companies and you’ll feel like a failure.  You’ll make unfair comparisons in your head with other founders and startups in completely different industries.  This gets worse when you go out and try to raise money because that’s what potential investors will do in their heads.  They’ll tell you all the reasons why you are going to fail. Why you will fail. How you’re doing it all wrong.

And it continues.  You’ll realize (the hard way) that there are different kinds of entrepreneurs.  There’s one who goes for the in and out, work like hell for two years, get acquired, and bounce.  The work 24×7 365 and then sell.  But you’ll compare yourself to people like that and think you’re not working hard enough.  And it will just amplify your own insecurities, so then you’ll try to work harder, not take vacations, not see friends, not have a life.  Because isn’t that what all successful entrepreneurs do?

And then the moment will come when you will break.  Emotionally, mentally, physically.  Break.  You don’t realize it, but that is the turning point in your life.  That is the moment. And what you do at that moment changes the trajectory of your entire history.  You’ll realize at this point, you have 3 options: You can quit, you can keep doing what you are doing/keep pushing through, or you can try and reassess your entire life.  We both know you will never choose option 1 because you’re way too competitive for that.  But we also know that in the past, you would have chosen option two.  It’s the most obvious choice, right? I mean isn’t that what we’re supposed to do- push through the pain, and persevere? That’s what everyone in the startup world tells us to do right? Because if we can’t do that, maybe we don’t have what it takes to be an entrepreneur? Which is what secretly, deep down, you’ve been struggling with? That people will find out you’re a fake? You don’t deserve to be here? You shouldn’t be doing this?

But then you’ll hear this really tiny voice, coming from deep within you, that makes you consider option 3.  And you think it’s completely crazy, and you think you should ignore it.  Don’t ignore it.  That’s when you decide to reconnect with your family and friends. Your support network.  And they make you realize that option 3, though the scary choice, may be worth taking.  What the hell.

And soon, you’ll realize it’s the best decision that you’ve ever made.  You learn about life in all it’s amazing glory. You learn that yes you are the shit, but not in the way in which you thought.  And the things that make you amazing are not what you initially thought they were.  It’s not your intellect, but your ability to be humble that makes you successful.  Your ability to listen, put ego aside and get the right things done when they need to get done, even if it’s the most unsexy work on the planet (which it usually is btw).  It’s your ability to not just read spreadsheets, but get people to understand what those numbers mean, and build a team to make that dream happen.

You learn that the most successful people listen attentively to everything (wherever and whoever it comes from), but they have the acumen to know when it makes sense and when it doesn’t.  When to listen and when not to.  The most successful people have the emotional fortitude to make really tough decisions,  and most importantly, live with them.   You realize that success isn’t defined by numbers.  It’s a very human thing.  The human connection is what makes it all happen.  Making spreadsheets, numbers and dreams come alive.

Finally, you come to realize that this is the reason you exist (or at least part of it). You realize that this is your dream, and you want to keep living that dream.  To create things in this world that never existed before.  You finally realize why you really do what you do.  Not because it’s sexy or cool or en vogue, but because…you want to work with smart people to take what’s on paper and make it into reality.  That’s why you get up in the morning.  And you’ll realize that…you’re hooked.  You love startups.  Not because you love money, but because you love creating.  You’ll finally come to realize that you and startups are intrinsically tied together, and this is your calling in life.  Not many people can do what you do, so you may as well put it to use.  And enjoy it in the process.

You’ll also realize that work (and yes, startups, though they are a calling, are, at the end of the day work) is only a part of who you are as a human.  There are so many other parts to you, parts that you’ve ignored, that you realize you should start getting to know.

You’ll feel blessed because not only do you love what you do, you have so many other things in life to look forward to.  Life.  LIFE.  That insanity which is life.  After this experience in the startup world, you’ll realize just how much you don’t know about…literally everything else. And you’re pumped to grow in those ways too.

So Anurag, what I’m trying to say is…at the end of the day, please believe that everything is going to be ok.  Remember that it’s not about trying to be perfect, it’s about trying to grow.  That is the entire point. And as long as you’re growing, every day, you’re winning.  You have a lot to look forward to in life.  Always remember that.

Lots of love,

Your 28 year old self.

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