The one thing I’d tell my 20 year old self…still applies

The old lesson still applies.

I’m going in for my third acting class tonight.  I have no ambitions to be a stage actor, but rather to learn to read people better. What better way than stage?

Unfortunately, I’m quite terrible at emoting or reading others’ emotions so far.  No one else seems to be having trouble with this.  I think I’m actually getting *worse*. is there any point to this?

On days like this, I need to re-read the letter I wrote my 20 year old self on the ONE LESSON I wish I’d learned earlier.

Still applies.


Hey there champ:

This is you from the future paying you a little visit from 2018. Slightly creepy but you’ll want to hear this.

Okay, so you’re plagued with doubt that you can do this whole software engineer thing. You’re barely graduating after that spectacular C- in Operating Systems,your LAST CompSci class at UMich, “Who needs Operating Systems anyway, I’ll never work on one.”

Done laughing now. You’ll see why later.

You have a vague-sounding job offer from the Goodyear tire factory in Akron, Ohio that you’re seriously considering because it’s close to home and you think you can probably do it. The other option is a highly paid job at Siebel Systems in Seattle, Washington that you’re afraid of since you don’t know anyone there. Also what is CRM anyway? Whoever needed software to track their customers? Why did they offer you a job again?

Your family’s slightly petrified of letting their little girl move to the mysterious west coast. What if you decide to give up software engineering after 6 months and have to return home, a laughingstock and embarrassment?

You also have a million words in your head that you’re thinking you should write into a book someday.

You’re looking for a role model, a mentor, a guide to share with you some words of wisdom.

You found none. BUT get this: in a decade, you’ll BE that role model, mentor, guide for many people just like you today. This is not because you had it easy or always made good choices or were super-good at everything. In fact, it’s because you were SUPER TERRIBLE at pretty much everything you did the first time.

That first software engineering job? Failed. Did not love. In fact, you started studying for the LSATs because you were going to be a lawyer after that first year. You. A lawyer. Reading long texts and memorizing them isn’t your core strength there, champ.

Everyday you were afraid of and hopeful that you were going to be laid off. You watched your mentor, your co-workers and your boss get laid off and then a few weeks later, find jobs where they truly seemed happy. You learned that the end of something means the beginning of something else. You got your second software engineering job at Microsoft on the Windows team—you know, the operating system. Definitely worked out better. You discovered a love of creating products for billions of people with passionate, close-knit mission driven teams. You learned that failure in class does not actually mean failure at life.

I would tell you what else you work on, but I don’t want to ruin the surprise. You’ll love it, trust me. It’ll take many years to get there, but it will so be worth it.

First novel you wrote (yes, you finally wrote it)? No plot, but pretty fun characters. You wrote a second book and got an agent. You wrote a third and got glimmer of interest from the publishing industry. You wrote a fourth and got a LOT of interest from the industry…but no book contract. You cringed when everyone asked where they could find your book. In my head, mostly was an answer you were tired of giving.

You wrote a fifth and FINALLY got published.

Many years later, your most successful book was the one you published yourself–about honest career and life advice from your journey for young people.

Remember that Poetry class in college where you had to read something out loud in front of 20 people and you were hyperventilating with nervousness? Well, many years later, you realized you needed to get over your fear of public speaking and decided to spent the year accepting every speaking gig that came your way.

One day someone in college recruiting at Microsoft put out a call for someone to travel to University of Iowa to do a talk to college students on working at Microsoft. You raised your trembling hand for that. Beforehand, you spent one hour lecturing at the cornfields to practice. Unfortunately, when you stood on stage staring at the audience…you froze and stumbled through words that made no sense.

You got feedback that you’re not very good and maybe you should stop. Happily you decided to give yourself another shot. If you listened to that kind of advice you’d still be contemplating life in the now-closed Goodyear tire factory.

The second time you spoke at a university, you did not freeze, but stumbled through the words. The third time you said the words without stumbling, but shook violently the whole time. The fourth time, you said the words decently, the shaking definitely less. The fifth time you started to enjoy it and realized your nervousness was coming off as energy.

At the end of that year, people were hitting you up for advice on how to speak in public. Now you speak to the public for a living and are able to say words to 5,000 people with only excitement and the desire to share stories.

For all of these things, you followed one simple formula:

1. Do the thing. Don’t overthink it, just go for it.

2. If that didn’t work (and 99% of the time, it did not) you did the thing AGAIN. That led to actual progress.

It’ll take a few tries. Sometimes two, three, four tries, but usually five. Five seems to be your magic number for when you really “get” something. Took you five software jobs to find the one where you’re most “you”. Took you five books to get published. Five speeches to stop stammering. Oh yeah, and you went to fashion school (I know, I know, YOU REALLY?) and it took making five garments to create something wearable in public.

No matter what, though, you never sat around waiting for the hero to show up. You always picked up the damn sword and went for it, even when you had zero clue as to what you were doing.

In fact you have no idea what you’re doing RIGHT NOW in 2018 even though you just wrote a book to help people do the thing.

You need to get over finding your calling tomorrow. It’s not going to happen. It’ll take an decade for you to even have a clue. It’s also an ongoing process. That’s cool though. Who let a 21 year old decide what they should do for the next 80 years anyway?

If you listen to one thing, let it be this: people are not going to like you because you’re great at things. People are going to like you because you’re TERRIBLE, then bad, then decent, then good…and you’re willing to share how you did it. Be open, be honest, be vulnerable. No one is going to like you because you’re perfect. People will like you because you are relatable.

Every chance you get to make someone do the thing they’re scared of, make them do it. They’ll be mad at you at first, but it’ll be something they’ll be happy they did.

Also, for the love of god, stop plucking your eyebrows and SMILE more!

Do the thing. We got this.


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