I Want You To Fail

Commencement Address to the 2015 graduating class of Harbor Springs High School

I was asked to give the commencement address at my alma mater 11 years after I graduated. At first I didn’t know what I could possibly offered them so I decided to try and give them some practical advice about the next ten years of their life.

This should be interesting.

In the summer of 2008 I got a call that would change my life. I was sitting not far from here on the steps of my front porch here in Harbor Springs.

Months earlier, I had sent in a resume to work on then Senator Barack Obama’s 2008 Presidental Campaign. I was young and full of hope and wanted to be apart of something big.

That call was an impromtu interview for an internship role on the targeting and analytics team — basically the team that ended up changing how modern campaigns are run. I don’t remember the interview except for one question at the end.

“If I asked you to start tomorrow morning what would you say?”

Without hesitation — “I’ll see you tomorrow”

And just like that I packed up my life and moved to Chicago to join the Obama campaign as an unpaid intern. I lived in a rat infested basement apartment and worked 18 hour days.

Because I had taken two years off after graduating from this high school to unsuccessfully chase my Olympic ski racing dream, I had yet to finish my college degree, so on top of not getting paid and working crazy hours I was taking two night classes to finish up my degree — and to make my parents happy.

One Sunday while working at campaign hq I ran to use the restroom. In an office of 300 people I was excited to find it empty.

I’m standing there following the unspoken rule of staring at the wall. When out of the corner of my eye I see someone step into the urinal next to me.

Suddenly I realize that I’m standing next to Barack Obama. Just me and him. And this overwhelming anxiety hits me as I keep saying in my head “don’t look, don’t look”

Then all of a sudden he says something like “Thanks for coming in on a Sunday, I appreciate it”

The moral of the story is this. If you fail at becoming a professional athlete, drop out of college for an unpaid internship, live in a rat infested apartment, work crazy long hours, maybe someday you will be lucky enough to be thanked by a president while using the restroom.

The answer to the question that you are all thinking is yes, I did wash my hands.

I’m not your traditional commencement speaker, so I’m not going to give you a traditional commencement address filled with banal platitudes about the world that you won’t remember or won’t fully understand until years from now.

I know the truth about this speech. You don’t care what I have to say. You’re probably thinking what does this guys crazy story about peeing next to Barack Obama have to do with anything.

So if you will indulge me for a few short mins to listen to my self reverential speech on what I wish i had known 11 years ago when I was sitting in your shoes — I’d appreciate it.

I recently turned 29. That means two things. That I have one more year to get on one of those 30 under 30 lists.

It also means that I have one foot in the world of youth — full of hope, optimism, a fully functioning metabolism, and the unwavering belief that I’m always right and that anything is possible.

The other foot stands in the world of the old and decrepit — your parents and teachers — with debt, ungodly amounts of stress, and a hefty dose of cynicism.

What this means is that I can’t tell you how to live your life, but I can give you a few bits of advice on how to handle the next 10 years of it.

There are four things I want you to take away from today.

I want you to fail.

Old people are stupid.

You are annoying.


Let’s touch a bit on each of these topics individually.

# 1 Failing — For me one of the fundamental challenges of growing up in an incredibly supportive community like Harbor Springs is that it’s nearly impossible for you to fail. The community just simply won’t let you. It’s the safest, cleanest, least diverse place in world. It’s an amazing little bubble that is a great place to grow up.

If I could hope for one thing for each of you in the next 10 years is that you need to fail. I want you to fail in everything that you do. I want you to fail at relationships, I want you to fail at school, I want you to fail at your career.

Failure is not something you should fear. It’s not something you should avoid. It is something we all should embrace and celebrate. Because the only way to grow, the only way to truly understand who you are is do something hard enough that failure is a likely outcome.

The key to failing is to fail fast. You need to be able to quickly learn from your mistakes and never do them again. Failure is like licking a chairlift in February, you quickly realize you’ve made a mistake and you’ll never want to do it again.

#2 Old people are stupid — Yes, I’m here to confirm that what you have been saying under your breath for your entire life is true. Your parents, your teachers, your aunts, uncles, and grandparents are stupid.

They are cynical and slow moving. They will try to protect you from making “mistakes.” They will ignore you, they will do things that will frustrate you. Sometimes you will wish they just go away, and let you clean up their mess.

But and this is an important but. They — for all of their many many faults have wisdom. They’ve been through it all. They understand that our world — as much as it has changed — is still fundamentally about relationships.

So seek out an old person or two and bring them into your inner circle. Cultivate mentors. Constantly seek their advice and counsel, because while I want you to fail I also want you to succeed and trust me there will come a time where the advice of an old person will mean the difference between success and failure.

However, As an ambassador sent here by the old people I’ve come to talk to you about something really important.

#3 You are annoying — I can’t stress this enough. You think you know everything. You are impatient and stubborn. You challenge authority and ask lots of questions. You’ve annoyed your parents and your teachers for 18 years. They can’t believe that at long last you will leave and go annoy someone else.

Oh that reminds me Congratulation Parents!

The world is changing rapidly. From how we work — how we live — how we consume information — to who we can, and cannot love.

It is scary to us old people. We don’t like change. You should just get a good white collar job, shut up, work you way up, and retire. This is the way the world works kids, don’t you know that?

At my first “real” corporate job, I was 23, had just been through an incredible 2 years in the Obama Administration. I had help elect the first black president. So naturally, I thought I knew everything, and I walked into this company and immediately started blowing things up. I pushed and pushed and pushed for things to change, I butted heads with the longtime CEO on a daily basis. Basically I was a bull in a china shop.

4 months in I was fired. It didn’t matter how right I was, or that everything that I was pushing for turned out to be true. I was too annoying.

The challenge then is to keep being your annoying self without being so annoying that you are kicked out of the room. You have to thread the nettle, find a way to challenge assumptions without being challenging. Find a way to push the envelope without getting pushed out of the way.

Unfortunately their is no easy answer for how to do this — but it does help to be very charming. What I can say, is that when I was your age I thought that experience was overrated, and that at my ripe old age of 18 I knew everything there was to know.

I learned the hard way that there were in fact things that you could only learn through experience. That instincts, adrenaline, an inteligence could only get you so far.

But its important to remain authentic to who you are, learn how to communicate, learn how to listen, learn when to be patient and remember that while old people may be stupid that eventually you will too be an old person some day and some young punk will stand on a stage and call you stupid.

So this is your time to take chances, push the envelope, lead, and teach us old people a thing or two. It’s your time to fail, and screw things up.

#4 Leave — As I said earlier. Harbor Springs is an incredible place to grow up. But at some point you need to leave. Leave Michigan. Get out of the midwest. Live in another country. Travel. See the world. Take the next ten years and live because at some point you will become old.

Yes, Go to college. Get a degree, get a second and third one if you really want to. It will make your parents and teachers happy, and they’ve put up with you for the last 18 years so that is the least you could do.

But take a year or two off. Go do something crazy. Join the peace corp. Go work on a farm in Australia. Join a startup. Volunteer. Back back through Europe. Experience different cultures and different ways of life.

Harbor Springs will always be your home. It will always hold a special place in your heart, and if your life leads you back here like me, you will bring your experiences and perspective back with you because this place desperately needs that

The reality is. Everything I’ve said here today means nothing. They are quite literally just words. You graduates get to now go figure it all out on your own, and when it comes down to it, that is what the next 10 years will be all about. Trying and failing to figure this thing we call life out.

There is incredible joy to be had in it. Go forth. Always move forward, and in 10 years you can ask me what new things I wish I had known when I was your age.

Congratulations and good luck!

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