Photo courtesy of Luis Rodrigues

Setbacks and Self-Belief

Five years ago was the worst birthday I’ve ever had. I got up that morning knowing that at 9am I would find out if years of hard work and dedication towards a clear and singular goal would pay off. At 8:45 I ducked out of a meeting and started preparing myself mentally, taking deep breaths and pacing around the block. Finally, at the stroke of 9:00, I refreshed my phone and read the first few words of a rejection letter. I was alone, leaning against a mailbox on Pine Street, having been punched in the gut. It was the biggest setback of my life.

Some people pursue an MBA to change paths, others for a break from the grind. Since high school I wanted to go to business school for an experience that I believed would change my life for the better. Having grown up as the son of two professors who met while getting their PhD I viewed it as a connection of my interests and my roots, and the key to discovering my passion.

When in senior year of college my peers who had secured jobs started checking out, I kept pushing to improve my grades. When friends headed for Europe and Asia the last day of exams I stayed on campus for another three weeks to study for and take the GMAT. I spent the first five years of my career trying to reverse-engineer a path to the school of my dreams: the right private equity firm, the right community leadership, the right letters of recommendation. I had no plan for post-school or what I would do if I didn’t get in — I had absolute tunnel vision and I thought the odds were stacked in my favor.

Then all of a sudden it was 9:01am and the odds didn’t matter anymore. After a few painful texts and calls to loved ones to break the news (some of whom initially thought it was a practical joke) I went back inside and started coping. I told myself that I wouldn’t show weakness, so I spent the day telling my mentors that I was okay, that I would figure it out, and that I would never in the future look back on this moment and think “that’s when everything went wrong”. Wise words, maybe — I didn’t believe them yet. Then I left the office, skipped a birthday celebration, flew home for the holidays and settled into a period of depression.

It took months for me to understand and years for me to truly feel that my own self-belief mattered more than the admissions department’s belief in me. Long before then I needed to decide what to do next, no longer comforted by the blanket of a five year plan.

Thankfully that business school had given me a nudge in the right direction: by forcing me to dream big in my admissions essay they got me thinking (and writing) about how one day I wanted to start a firm that would invest in early stage companies. At the time it was a pipe dream, not a goal, but it was all I had so I started learning about it. I needed progress and forward momentum — even if only small steps, I couldn’t get stuck.

To get started I set a goal for myself to meet a new interesting person every week outside of my existing profession, just to ask them about their lives and careers. Were they happy? If so, how did they figure it out? That exercise eventually led me to a small technology company called CircleUp that was trying to invest in early stage food and beverage brands. Investing in these brands turned out to be perfect for me and I didn’t even know that such a job existed in December; then in May I signed up to join. It was a leap I probably never would have taken before that setback, but at that point I no longer felt like I had something to lose.

There’s nothing like a clean slate to discover who you really are and what you care about. My first realization was that business school would not have given me all of the answers about how I should spend the rest of my life afterwards. My second was that all of the hard work I had put into getting into business school wasn’t a waste — the pursuit was actually worth more than the destination, and I never could have grown so much if I didn’t have something important to pursue. My third was the most important: as deep as the pain was, things did start feeling better and amazingly I became much less afraid of another setback. I now knew that I could survive it.

Our society has a fascinating captivation with linear and flawless career trajectories. People go to extreme lengths to avoid failing, and that often comes at the expense of ever trying at all. When faced with the choice of staying in the same prestigious job they don’t like or failing at a startup they would pick the former; now, if you asked me which of those two backgrounds I would prefer when investing in a founder or hiring a teammate I’d pick the latter all day.

Setbacks are an inevitability when you push yourself hard enough, but positive responses to adversity are not. Investing in somebody who has never failed feels like rolling the dice on a critical lever of success: how will this person respond to difficult challenges? Will they break or emerge even stronger?

At some point, years after that fateful rejection letter, I began to understand the difference between self-confidence and self-belief. I realized that I had been defining myself by a series of credentials rather than abilities and traits. The result was plenty of self-confidence, but an accompanying fragility that came with needing the next external win.

It was not until I had failed in my pursuit that I was forced to ask: if I am not my credentials then who am I? Not knowing yet was a painful realization, but a necessary one in the process of discovering who I actually was. It’s impossible to achieve self-belief if you don’t know who you are, and it’s impossible to build something special without self-belief.

It has been five years and I have a lot to be grateful for. Five years ago what was a naïve idea in an admissions essay is now a two year old investment firm that I launched with a big dream, built on new found self-belief. Five years ago I was about 100 days into a relationship whose foundation was not yet built for long-distance; this past summer we got married — she’s my best friend.

I can’t say that I appreciate the rejection — admittedly I still have a bit of a chip on my shoulder — but it’s been a long time since I wondered or cared what it was they didn’t see in me. What I am grateful for is the experience of failing and growing. It is that growth that I now appreciate as a powerful asset in the people around me who have had setbacks of their own: rejections, layoffs, losses and breakups that hurt at least as bad as mine did.

I now look back on my “wise words” that my setback “would not be where everything went wrong”, and believe: maybe it was necessary for everything to eventually go right.



Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store
Kiva Dickinson

Consumer Investor / Founder of Selva Ventures / Proud Canadian Living in San Francisco