Some things are worth doing, even if you fail: How a failed startup changed my life.

“If we knew each other’s secrets, what comforts we should find.”?— John Churton

In 2012, I had an idea.

It was one of those ideas that came to you in a flash and you know immediately that it’s a good one.?

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At the time, I worked at a health insurance company as an RFP writer, about as cliched as an office job as you can imagine: I spent all day in a cubicle, sending out emails requesting information from various departments and writing reports. There was very little that was satisfying about that job, other than when we would win a contract and the sales team take us to the bar to celebrate.

At one such celebration, one of my colleagues mentioned that her female boss was going on vacation (it feels weird to have to write “female boss” in this day and age, but I need you to know the boss was a lady). For some reason, I asked where she was going on vacation — and I’m not even sure why I asked, because I didn’t much care.?

“Oh, she’s going backpacking in the Porcupine Mountains with her sister and her best friend.”

I nodded silently but inside I was taken aback;?you can go camping without your family??This seemed both preposterous and revolutionary. Camping? With just women? No kids, no husbands, no one to take care of but yourself? No shopping for coolers full of food, making sandwiches for everyone, then you clean up while your family abandons you for the lake?

I could hardly imagine what camping exclusively with grown-ass, responsible adult women who were my friends was like, but it sounded exactly like something I needed.?

(To be clear, I was NOT an outdoorsy person at that time; I had only been camping a handful of times as a kid with my parents in a popup camper with our church group.)

Driving home from happy hour, the more I thought about it, the more I loved it.?

Now it happens that at this exact time in my life I was trying to come up with a really killer business idea. A few weeks earlier I’d attended a program for wannabe women veterans entrepreneurs in Chicago, and was immediately hooked. I loved the thought of owning my own business, and it just so happened that the organizers announced a $50,000 business plan competition only for women who had graduated from the program.

I knew right away I had to win that competition.

I just didn’t have a business idea,?yet. I had a vague concept about writing a series of books for newly-divorced women who were trying to rebuild their lives, but I wasn’t super excited about it.?

So I began to wonder if women camping together would be my idea, but I worried that the idea wasn’t creative enough. Creativity to me was bringing two ideas together that had never been brought together before.?

Hmmm. What was I passionate about, and would be willing to make a business out of? Women, camping and…nachos? Hmm, I do love nachos, but no. Chuck Norris jokes? That’s a pretty small target audience. What else, what else…

Wait, what about books? I LOVED books, always had. My mother tells me I could read pretty much by the time I was three years old. What if we took women and books outside? WHAT IF THERE WAS AN OUTDOOR BOOK CLUB??

The idea blew up in my chest. It was amazing. Profound. This was clearly my idea.?

But then immediately I shut down the thought because if it was so amazing, then surely someone else had already thought of it. Boo.?

But I went home and googled it anyway, and try as I might, I could not find one single thing on the internet about a book club that met outdoors. Nothing. (Remember, this was 2012, before all the good ideas were taken, haha.)

So Outdoor Book Club (or OBC) became my obsession. I dug into drafting my business plan, spending every waking hour researching market size, creating spreadsheets, writing soaring social media plans, and reaching out to anyone whom I thought might be able to help.?

I decided the business model (how I would make money) would be via all-inclusive adventure tours that I designed around books. We’d go kayaking, biking, backpacking for a weekend, all designed around a book. At night, we’d sit around the campfire and dive deep into the themes of the book, but also discuss the bigger things in life, like how we were struggling with motherhood and how we didn’t feel good enough to pursue our dreams.?

I imagined all the deep conversations we would have under the stars in front of a roaring fire, clutching a sippy cup of wine in our hands.?

I submitted my final business plan just under the deadline, and when I got the call that my business plan made it into the top 30, it was literally the best day of my life. (I know I should say that the best day of my life was the birth of my kids or my wedding day or even the day I got out of the Army, but no, it was the day I found out I had a shot at winning a $25,000 (op prize to pursue my dreams.)

I remember so clearly how I was driving by myself in my car on the highway over the river and I screamed and pounded on the steering wheel like a goddamn Masai warrior.?I did it.

I worked my ass off for something I really, really wanted and it fucking paid off.?

That day was a turning point for me. I became a different person after that day, a more confident woman, a more competitive woman, a woman who knew she could do anything she really put her mind to. I still think of that day whenever I drive over the river today.

The competition organizers flew me out to Long Beach, CA to compete in the semi-finals, where I had to first give a 20-minute pitch in a small room with 3-4 judges (20 minutes seems CRAZY long today, but this was the early days of startup culture). At the last minute I ditched my $200 Ann Taylor suit and walked several blocks from my hotel to a sporting goods store where I bought a hiking outfit and an internal frame backpack. I did my pitch in braids and hiking boots.?

They freaking?loved?it.

Later that day when I found out I made it to the top 3 — which ensured I would walk home with some amount of money — I nearly hyperventilated in my hotel room. The next day I would have three minutes to stand up in front of the entire conference and make my pitch in front of a crowd of over 100 women veterans, and they would vote on the winner.?

I had 15 hours to figure out how I would convince them to give me that money.?

I went down to the hotel bar and ordered a scotch, neat. There were a bunch of people in the bar from the conference and they were all laughing and having a great time and circumstances were different, I would’ve been one of them. But fate had other plans for me. So I stared into my scotch and thought real hard about my best course of action.

And I decided I would just speak from my heart. I would get up in front of the whole audience and just let all the passion I had about Outdoor Book Club pour out of me and let everyone see how amazing I was. I had a vague idea of using Oprah’s schtick about “You win a car, and you win a car, and you win a car!” (one of the judges said my pitch reminded them of Oprah’s book club) but other than that, I would wing it. Jesus, take the wheel! I tossed down the rest of my scotch and turned in early, deciding to get a good night’s sleep before my big day.

If you’ve ever done any public speaking, you can probably guess what happened: because I had done zero preparation,?I choked. HARD. I got up in front of that crowd and looked at the timer and totally panicked. I started babbling about people winning trips. It was awful. People looked confused. I realized “Past Me” had made a terrible mistake by thinking I could just wing it. All that hard work I put into my business plan went down the drain as I whispered weakly into the microphone.?

I ran off the stage with a full minute left on the timer and headed straight to the bathroom. I ugly cried for a few minutes before I forced myself to walk back into the ballroom, trudge up the stairs and get my picture taken with a giant third (last) place check for $10,000.

Now I know that $10k is a LOT of money, but at the time I couldn’t see it as anything but a complete and utter failure. I had let down everyone who was cheering me on back home, I’d let myself down, and it cost me $15,000.

It took me a long time to get over that failure, but I couldn’t very well come back with all that money and not start the company. Plus I still believed in the idea of Outdoor Book Club, even though I was scared of failing again and took a huge hit to my confidence.?

But I kept telling myself,?“Some things are worth doing, even if you fail.”And I truly believed that.

I quit my job and created meetups and workshops and more than a few women came. I hosted one or two weekend trips, but frankly, I was terrible at the whole thing (I am not a details person) and I didn’t have insurance, which was a DUMB move, so eventually I just let the business go. It became more of a hobby or social club, and I went on to other jobs, started another company and simply moved on with my overall successful life.

Fast forward nine years — this past December — when I threw myself a birthday party.?

I do this every year, bringing people from all over my life together just before the holidays so I can drink them all in and have them meet each other and just bask in the warm, glorious glow that is the people I love most in this world.?It’s my birthday gift to myself.

Dozens of people stood in a big circle in my kitchen and introduced themselves and how they knew me, and a crazy thing happened: so, so many of them knew me, and each other, through Outdoor Book Club. After a meetup or a weekend trip,?they had gone on to hike the entire Appalachian Trail, to backpack by themselves, basically embarking on all sorts of brave and amazing adventures that they never had the courage to do before they met me.?

The failed experiment known as Outdoor Book Club changed my life in so many ways that I couldn’t have possibly seen, crying in that hotel bathroom in Long Beach.?

Because I was willing to take a risk and reach out to connect with others over shared experiences and passions, I put myself on a whole new path.?

Without it, I might still be working in that cubicle, still sending emails and writing reports, still lonely and frustrated and still wishing my life was bigger than it was.

Now I don’t expect you to go start a business (but if it’s something you’ve been dreaming about, I’m 100% cheering you on). However, I do expect and encourage you to do something to connect with other people. Find your tribe. Let them make you laugh, give you inspiration, help you through the rough times.?And then give it right back to them.?

Life is too short, and we are too strongly wired for connection to sit at home and isolate ourselves.?

Look, I’m legally blind. Navigating a world that’s full of trip hazards and speeding cars and people who might laugh at me or steal my wallet is scary and HARD. I could stay at home, read my books and play with my dog and never make the effort to meet my friends or have new adventures. But I would be miserable. I would miss my friends and family; heck, I’d probably even miss strangers. So I make the effort to connect, even when I really don’t want to. Because I know how important social connections are to living a life I love.?

We are wired for love and connection. Don’t miss out on your best life, and don’t deprive people who need the light of your presence, your personality, your dreams, because you’re scared. There’s too much at stake.?

Some things are worth doing, even if you fail.