One Risk That Really Paid Off

Failure, uncertainty, and serendipity.

We all face uncertainties in life, and risk taking is the key to growth and success. But what are the important ingredients that enable us to take those risks?

I remember the conversation clearly, “Mom, I can’t go home. I can’t work a normal job. I’ll never be happy.”

She was as supportive as she could be. But my parents didn’t have a lot of extra money and I was now hundreds of miles away. I just scraped by a few credits from my second year in college, and had only a few dollars to my name.

I knew there wasn’t a future back in Wisconsin and that was even more clear now that I had met a girl.

I had the first important ingredient for taking risks: motivation.

But, with my freelance design work now all dried up, staying in Tennessee had a lot of uncertainties.

For starters, I had to figure out a place to stay.

I plead with the school student housing office to let me stay in my dorm for the summer and put the bill on my next semester’s tab. I had no idea how I’d pay for that, perhaps with more foolish student debt. But that was months away.

Now I needed a job and fast. I hopped in my ‘99 Jeep to make a trip to the employment agency in the next town.

The gas gauge read 1/8th of a tank. Close, but enough to drive there and back.

I remember the feeling walking in. A sense of hopelessness filled that room. I knew I had a family I could turn to if I was in real trouble. How many of the others in the unemployment line weren’t so fortunate?

I told the lady at the counter that I knew graphic design. She was going to queue up the test on the computer and after a short wait, I began the assessment to determine my ability.

I’ve never been good at test taking. My memory, even today, is pretty poor.

Immediately I knew I was in trouble. The program showed images of Adobe Illustrator (the standard for graphic design software) alongside multiple choice questions asking what the names of certain tools were. I had no idea. I was self taught. I could use the “direct select” or the “lasso” tools but never learned (or could remember) what they were called.

I failed. Much like I was failing out of college. Why did I fail so much?

I only learned well into adulthood it’s common for kids with ADD to struggle in some areas of function (like memory) while being quite capable in others (like art).

I still vividly recall the shame I felt leaving that room. The lady at the counter informing me that “they’d be in touch.” I felt so vulnerable walking in there — in need and running out of options. Now I was leaving empty handed. I felt a judgement…likely my own.

And as I rounded a steep and high incline that cut across the Tennessee foothills, the power from my gas peddle began to sputter. I pushed it down in a panic several more times, with each push the Jeep lurched more and more until the incline defeated it (and me). I put my flashers on and pulled over along highway 75, a busy artery that connects the eastern portion of the country. Each semi that flew by shook the Jeep.

I didn’t know who else to call so I called my mom again. Through eyes welling I let her know my predicament. I was out of gas, no money to spare, and no job prospects.

Now, made more real than ever, I experienced the second ingredient to taking risks: support.

My mom was yet again gracious and compassionate. I don’t remember exactly what she said but if you can imagine a Wisconsin accent with “ohh honey” you’ll get the picture. She called me a tow truck to bring a few gallons of gas, enough to get me back to campus and then some.

I got home, opened the only food I had…Lucky Charms, and plopped down on the futon my older brother had given me.

As Charles Eames, one of my hero’s in design once said, “Design depends largely on constraints.” I felt the ticking clock of those constraints about to sound.

The next day I woke up with my mind racing. I’ve always been resourceful. In art classes especially. I could always turn whatever I had into something.

Then I recalled a small advertising agency next to a laundromat that I’d often pass on Walmart grocery runs. I had the idea that if I couldn’t pass a test, I could perhaps pass an interview.

Later, as I built my company, I’d come to fully appreciate the creative power of constraints.

I put on a button up and khakis and drove there. There was no sign that said they were hiring. No indication at all that they needed any help. I sat in the parking lot working up the courage to walk in.

What other choice did I have?

I stumbled through a pitch to the receptionist about how I could design things and asked who could I speak to about a job.

I waited again and eventually the owner came out. This proud small-town Southern lady said if I could do some sales part-time I could also have a part-time design gig.

I had secured the final important piece to taking risks: a skill to fall back on. I had a job.

I enthusiastically said yes and started the next day. We made lists of prospects I’d drop in on, mostly mom and pop shops needing flyers or business cards.

I roped in a few local clients for her. I also became quite good at cutting thousands of business cards by hand with only a small paper trimmer. I worked alongside a very talented photographer named Grant (who we still work with today). He lent me some of the knowledge from his formal education in design. And rest assured I figured out all the tools in Adobe Illustrator.

Through that experience I uncovered what I’ve come to believe are the three key ingredients required for people to take risks in life.

They’re motivation, a skill, and support.

Motivation to face the challenges that come with risk-taking has to come from within. It can’t be given. Skills can be learned and they provide the much needed security to take any leaps forward. And support for those moments when we don’t know where else to turn, and are struggling to believe in ourselves.

Choosing uncertainty over being unhappy was worth it. Taking risks that summer kept me on the path to paving my own way. I kept dating the beautiful woman who’d become my wife and mother of my three boys. And I honed two vital skills that would help me in building Legacybox: sales and design.

Serendipity is defined as the development of events by chance in a happy or beneficial way.

But that is only possible if you take the chance.