Redefining “Luck” In the Entrepreneurial Economy

Growing up, I was a good student, at least on paper. By no means the poster child for good behavior, following the rules, or respecting my elders, I nevertheless managed to eek out A’s on my report cards in high school.

When I got into the University of Michigan – an academic powerhouse and ‘public ivy’ school – my friends told me I was lucky for getting in. At the time, I didn’t feel super lucky nor did I feel prepared for school, but went ahead anyway.

At Michigan, my interest in school continued to wane, but I still managed to survive a gauntlet of math, science and physics classes and get my diploma. When I graduated and found a post-bacc research job at Harvard Medical School, my friends and family said that I was lucky. A strong feeling of unease continued to grow in my gut, but with so much positive external reinforcement, I took the job.

At Harvard, my interest in my work reached an all time low. Eventually I quit the job, and in doing so, waved goodbye to any notions of going to a top tier medical school.

What happened next?

Thereafter, my career took a 180 degree turn (or perhaps 540 or 900). I spent nights and weekends selling internet marketing services online as a freelance SEO and took a job at an internet marketing agency in Chicago. Most of my friends, family, and professional colleagues thought I was insane.

How did things turn out?

A year later, I quit that job too and now work for myself. My time is spent traveling, seeing and experiencing the world (I write this from the island town of Bol, Croatia), and connecting with other badass entrepreneurs.

working from the balcony in bol croatia

Not exactly a cubicle. A lot can change in a year.

In the year since quitting my job, I’ve launched 2 profitable online businesses: a digital marketing agency selling outsourced services to local businesses and an Ecommerce business selling horse riding pants.

My life, up until the point I started a business and quit my job, was simply spinning wheels. It had almost zero effect on what and who I know and relate to now, and was perhaps harmful to my long-term growth and happiness.

Looking back, all the things that other people called “lucky” were in fact the opposite. The apparent “wins” of getting A’s in high school, getting into a good college, getting a great job – all successful accomplishments viewed from within society’s traditional job script – only delayed my switch to entrepreneurship.

Luck is contextual

When does “luck” actually mean the opposite – a step back? From the little picture perspective of comfort, security, and sticking to the script, a good school and good job both appear lucky. This is a limited perspective, though.

If we’re looking at those from the bigger picture, then they were in fact unlucky events that reinforced bad habits and got in the way of necessary growth. What is lucky or unlucky then, is context-specific.

In the book The End of Jobs, author Taylor Pearson hints on this idea with an anecdote:

“Angie graduated from law school in 2013. It wasn’t a so-called top tier law school, but it was well-respected. I was sitting with her in a hamburger joint while she related to me that she spent a year waiting tables before she got enough connections to finally “get lucky” and land a job at a law firm.”

In “getting lucky”, Angie made the same error I had: relying on a broken system that overemphasizes the importance of credentials. In the context of the little picture, Angie’s “luck” saved her the drudgery of waiting tables. In the bigger picture, waiting tables could be the superior job, allowing her the free time and energy to build a business on the side.

This sounds harsh. You may be thinking: it’s easy for you to sit there and tell Angie that landing a job is bad for her. Well, that may be the case. But the reality is that not getting the job would be better for Angie in the long run, as she would be forced to think for herself and create a path to success.

This is, evidently, the path to success taken by many entrepreneurs. In his now-famous commencement speech at Stanford, Steve Jobs describes his on-and-off relationship at Apple:

“I didn’t see it then, but it turned out that getting fired from Apple was the best thing that could have ever happened to me. The heaviness of being successful was replaced by the lightness of being a beginner again, less sure about everything. It freed me to enter one of the most creative periods of my life. … It was awful tasting medicine, but I guess the patient needed it. Sometimes life hits you in the head with a brick. Don’t lose faith. I’m convinced that the only thing that kept me going was that I loved what I did. You’ve got to find what you love.”

Had Jobs “gotten lucky” and stayed on at Apple, it’s quite possible that we wouldn’t have devices like the iPhone or MacBook. Failure in one context is luck in another.

No one likes getting fired. Or losing, or failing. No one likes getting rejected from law firms while waiting tables. But the truth is, these challenges represent an opportunity to think differently.

Echoing Jobs’ experience, Conan O’Brien tells the story of his getting fired from NBC in a commencement speech at Dartmouth:

“[The year after getting fired] was the most satisfying and fascinating year of my professional life. To this day, I still don’t understand exactly what happened. But I’ve never had more fun, been more challenged, and…had more conviction about what I was doing. How could this be true? Well it’s simple: there are few things more liberating in this life than having your worst fear realized. …The point is this: it is our failure to become our perceived ideal that ultimately defines us. It’s not easy – but if you accept your misfortune and handle it right, your perceived failure can become a catalyst for profound reinvention. … Whether you fear it or not, disappointment will come. The beauty is that through disappoint comes clarity, and with clarity, conviction and originality.

Had Conan stayed on at NBC, it’s likely that his comedy wouldn’t be where it is today.

Not getting hired by a law firm would’ve forced Angie to find a solution, possibly build a business, work for herself, and find new meaning and joy in her working life.

Not reaching the ideal of “getting into a good medical school” allowed me to transition into some of the most exciting, creative and fun years of my life – and it’s only going to get better from here.

It’s not easy

Don’t get me wrong – taking the path less-traveled is hard. Not withstanding the anxiety and uncertainty that we face in without a comfortable script to follow, it’s a lot of work. That is, in fact, precisely why events in our lives seem unlucky (at first), but very lucky when we connect the dots in retrospect. But if we can consciously choose to accept misfortunes as opportunities rather than setbacks, we set the stage for reinvention and growth.

Next time you hear about someone “getting lucky”, ask yourself – is this true? Is he or she really getting lucky? Why or why not? Answers to these questions will help frame luck in the right context.