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One Year Bossiversary

One year ago today, I threw away my business cards.

They were fine business cards, really, but they came with one huge caveat: they represented the fact that I was hired to work on someone else’s dream, in a windowless room on an uncomfortable ergonomic chair, for nine hours a day.

So I left.

Turned in my two week’s notice.

And bought my own damn business cards. (Plus a bottle of wine.)

Calling yourself “boss” is a lot like setting yourself on fire while simultaneously trying to invent water. You’re ALL out there. There’s no backup. No accounting team to double check the numbers, no boss to ask permission, no one to tell you to reign it back in.

So, in lieu of my One Year Bossiversary, I wrote this letter to myself.

Hi you!

When you leave for work that one April morning and walk out the front door saying to Joe, “We should start that business together sometime,” you should act on that instinct. Your intuition will NOT fail you this year. Your intuition is the boss of you, so learn to love it, nourish it, and listen to it as often as possible.

Your intuition will tell you to fire your first big-deal client. It’ll tell you to pivot and sign these incredible new clients that feel good in your soul. It’ll tell you who in the creative community is ‘good people’ and who to befriend. Your intuition has never been sharper, my dear, so make the most of it this year.

A lot of people will come out of the woodwork just to see you fail. People who you thought were your biggest supporters will show you their true colors. They’ll launch vendetta campaigns against you, they’ll sic people on your back, and they’ll try to poke holes in your self-esteem. Don’t waste your time worrying about it. It won’t work. You’re stronger than that. You’ll learn that silence is sharper than small minds, so try to let these things go and be the bigger person. Oh, and keep that lawyer’s number on speed dial. She’s a badass.

In your first few months of business you won’t sleep much. You’ll wake up before sunrise and question everything. You’ll wonder if you should just chalk all of this up as an experiment – there’s no way you can keep yourself afloat – and who are you to even try? But deep down inside, you’ll know that’s a coward’s choice and you’ve never backed down from a challenge. You’ll write a Post-It note on your mirror that says “just try”. Some days, you’ll look at this with tears in your eyes. Some days, things will feel so crushing that you’ll stay in bed under the covers. It’ll be hard. But if you never try, you’ll never know, won’t you?

A year later, you’ll have signed well over six figures.

You’ll realize, for the first time ever, that you co-founded your six figure plus business at 23.

You’ll poop a little.

(That’s okay. You can afford new pants.)

You'll soon learn that money is just a scoreboard for the number of people you've served.

You’ll live without a car for a long time. You’ll carry home groceries in the depths of winter, and the heatwaves of summer. It’ll feel like a heavy burden, but it’ll actually turn out to be a blessing in disguise. You'll log 1,342 miles on your own two feet. You’ll decide that bosses need to be fit for the job – mind, body, and soul, so you’ll get rid of some weight in your life. You’ll start lifting and lose 25 lbs. You’ll eat better. The new pants you bought will continue getting looser.

Oh, and by next summer you’ll have bought a car – in cash.

Sometimes you'll get discouraged because it seems like lots of people are getting married and having babies and buying houses. And then you realize that you will, too. But you'll have a strong, debt-free foundation AND the ability to go hike a mountain on any given Tuesday. Give it time. Let it happen.

When you have that meeting that goes really well, keep everyone’s business card. You’ll have to be persistent, but it’ll pay off one morning in late summer. When you get the good news in your inbox on a morning you began to send out resumes – as a backup plan – you’ll run and tell Joe about it. He’ll be in the bathroom, which was serendipitous given the reaction.

You’ll be scared a lot of the time. Even when things are going well, you’ll wonder if you’re doing any of this right. And then there will be moments that shine through the cracks, like when you look across your desk and see your handsome co-founder working on the same dream with you. Or, like that time you learn a client is launching a non-profit because of the workbook you created for her. You’ll be called on as a creative partner to someone you consider your idol and role model. People will get emotional when they tell you how much the process transformed their business – their life – and that they have you to thank for turning an idea into a story they can own. They’ll tell you that you ask better questions than they’ve ever been asked in 20 years in business. Trust the process. Trust yourself. Because you might not know it yet, but people trust you.

When you order that used book on Amazon one winter’s night and a nonprofit’s bookmark floats to your feet, email them. You’ll play a small role in changing the story of AIDS. And when your grandmother passes away and you want to make a contribution in her name, skip the Donate page and ask what you can do to help instead. You just might help some people live through what she suffered through.

More than anything, enjoy yourself. You left that cold, dark office for a reason. Buy the $300 Katy Perry tickets. Get away from your desk and fire up your hotspot. Sleep in ’til noon and still get your work done. Book a massage after that killer deadline. You deserve your success because you worked for it.

You invented your own version of water.

Congratulations, you, on your first year as CEO.

You not only survived your first year in business – you became a firestarter.

To this year, and many more.

Love, The You Who's One Year Wiser