You should probably give up. - Kristen Kalp

You should probably give up.

You’re going to fail. Hard.

You’re going to fall flat on your face, like the 13-month-old kid who’s learning to walk and then WHAM! catches a lip on the coffee table and screams for the next 40 minutes.

You’re going to wish you had never, ever started a business.

You’re going to compare yourself to others’ highlight reels. The victorious tales. The entrepreneur who started with a peanut, a paper clip and thirty cents and then sold the company for $1.2 billion. The woman who made cookie treats in her basement and then started the world’s largest cookie franchise. Tale after tale, like stark-raving success porn, lavished upon you via the interwebs and in all the business magazines available at your local bookstore.

Only sometimes, the tales aren’t victorious. Sometimes you biff really hard, like that time you were trying to do a wheelie on your bike to impress your friends but instead you ran into the ditch and you still have the scars.

Last year, I held a real-life summer camp for entrepreneurs called Brand Camp. I anticipated sold-out crowds of peeps swarming the place. I hired the best speakers money can buy. I lined up treats and delights galore.

I went all in.

I got the ice cream truck and the Ferris wheel and the yoga teacher I love best. I put my whole heart into the event, every last bit of what I had to give. My best friend quit her six-figure corporate job to help me pull it all off. (She was all in, too.)

Some attendees called it the best days of their lives — people who are married, who have kids, who have hit those milestones that you’re supposed to give the “best days” titles.

The event was pure magic. From a monetary standpoint, though, things didn’t go exactly as planned. I sold less than 25 percent of the seats available.

You should probably give up. (A backwards pep talk for entrepreneurs.)

I could buy a house in my hometown with what I owe. (Not even exaggerating, friend.)

Following camp, I crumpled. I cried in bed, on the couch, driving around, at the grocery store and right in the middle of Target. Then I started eating my feelings and gained ten pounds. Oh, pizza and beers. Why do you taste so good!?

It took me a month to leave the five miles surrounding my house. I ordered in, I freaked out about money, I sat on the couch and couldn’t face any numbers. The number of attendees, the debts, the invoices. The FAILURE of it all.

It took me a few more weeks to love even my most trusted business clients. I spent much of a retreat I led in Costa Rica waiting for my lovely peeps to turn on me or tell me how disappointed they were in me or demand their investment in my services back because WHATDIDIKNOWANYWAYI’DJUSTLOSTABUNCHOFMONEY.

It took me a few months to start showering regularly (Because depression). I had separated from my husband a few weeks before the event, and untangling my heartstrings from my purse strings was nearly impossible. I made my very best effort to sink into the couch cushions and disappear.

It took me ten months to be able to look at the photos from camp without crying because a few people didn’t have the best days of their lives. In fact, they wanted refunds and were vocal about it, and I never did quite figure out how to make them happy. The thought of even ONE UNHAPPY CUSTOMER still looms over me.

Nearly one year later, I’m coming up with ways to dip my toes in the waters of risk.

How can I give you everything I’ve got without holding some back, because 10 percent of income goes to paying the venue, 5 percent to speakers, 8 percent to debts accrued during planning?

How can I try again, this time in ways that guarantee success? (HA! Guaranteed success!)

It’s murky water at best.

I should probably give up, right? I should be ashamed of myself, hang up my hat and never set foot into the world as an entrepreneur again.

Only, if you shame me for losing money, you would have to argue that I shouldn’t take the big risks in life — and by extension, you shouldn’t, either.

I gave some people their best days on this planet — and in the process, I got some bruised knees and a banged-up lip, metaphorically speaking.

You should probably give up. (A backwards pep talk for entrepreneurs.)

That’s what happens when you go all in: you risk losing pretty much everything.

Your money, your reputation, your confidence. Your sense of well being and purpose.

You put who you are and what you stand for on the line when you introduce something new to the world through your business.

You’ll naturally want to back down, to halve the costs, to double the odds of succeeding by watering down your work to appeal to the most people possible.

People will say you should give up.

You should play it safe.

You should round your edges, soften your corners or refuse to put the f-word three inches high in your website’s header.

Don’t, don’t, and … well, I did, but you probably shouldn’t.

Even if it’s strategic or makes the most sense or is guaranteed to take your business to the next level.

They’ll tell you to hightail it out of there, to minimize your risks, to open up channels of revenue that don’t feel quite right. They’ll paralyze you with stories of credit card debt, invoices owed, and all the times it didn’t work for them, or their brother-in-law, or that one kid from your graduating class who lost everything and now lives in a box under the bridge.

Only they’re not you, bringing your distinctive blend of gifts and weirdo talents and loves and hates and knowledge and products and services to the world. They can’t know which lessons life has in store on the other side of that dance you’re doing with your purpose this lifetime.

Go all in.

Maybe you’ll be sorely disappointed.

Maybe it will end up better than you ever imagined.

Maybe you’ll be able to buy a small house in your hometown, or maybe you’ll just owe that much money.

Maybe you’ll give people some of the best moments of their lives.

Maybe you’ll do all these things and more, all at once, in a life-jumble that you can’t clearly define as good or bad.

Who knows what will happen? I can’t tell you how it will go.

I can only tell you to follow the bits that make you more alive, that make you feel like you’re somewhere between on fire and holding onto an electric fence. Even with knowing how it went, and how it played out and how swiftly it struck me down, I’ve never felt more in tune with my sense of why I’m on this planet than I did during those days.

You should probably give up the questions, forgo the advice…

and go all in.

That’s the art of it, when the numbers are put away, the debts are paid, the e-mails are answered, and the event is long gone.

The art of going all in is the art of getting more alive.

Success, failure, BIG LOOMING TERRIBLE THOUGHTS and magical minutes all lead to being more alive as a business owner, as a human, as a citizen of the planet.

Now go, get more alive.

P.S.  For when it all falls apart.

Photos // Jon Canlas