You are so busy thinking about what you might lose, that you don’t stop to think about what you could gain.
Recently I had coffee with a young man who follows my work. We’ll call him Daniel for the sake of anonymity. My inbox is usually flooded, but Daniel emailed me a thoughtful message and I happened to see it. One of my favorite things about writing, is that I hear from people with fascinating backgrounds. I especially enjoy meeting inspiring people who have overcome the odds and taken uncommon risks in life. Daniel had one of the most powerful origin stories I had come across, so I knew I had to meet him.
Daniel grew up raised by his mother and absentee father who immigrated from from South Korea. He had to bail his father out of jail twice and he was rarely around. His mother worked as an esthetician in Southern California. No one in his family had ever graduated from high school, so he didn’t have high hopes. Despite exceptional grades and test scores, his school counselor told him that he should consider a career as a sanitation engineer. He assumed he’d be going to community college, because there was no way he could afford college tuition on his mother’s income. Daniel ended up applying to a few colleges and went to the one that supported him the most financially. He moved across the country to the east coast to attend a private university.
While Daniel was in college, he worked different jobs to help pay for his education. During these jobs he was exposed to the world of venture capital and technology. He decided at some point that he wanted to apply to law school, but he couldn’t afford expensive LSAT prep courses. He ended up studying for the LSAT using books available in the public library. His LSAT score and grades were exceptional, and he was accepted to Harvard Law School. It was expensive, but his mother wouldn’t let him turn the opportunity to attend the top law school in the world down.
At Harvard Law School, Daniel was very active in the university’s student government. During the rise of anti-Asian hate crimes in the early 2020s, he became vocal about what was happening to his community. Ironically, his AAPI peers and classmates who had much more privileged upbringings and attended fancy private boarding schools like Hotchkiss and Exeter, were much more guarded and reticent about what was happening. They were afraid to risk their reputations by speaking out.
After spending his summers as an intern at big law firms, Daniel decided that law wasn’t necessarily for him. He was still drawn back to the venture world and wanted to learn more about business. He thought the best way to do that was via management consulting, but the top firms don’t recruit from the law school, only the business school. So he showed up at the career fair and acted like he belonged with the other b-school students. He ended up landing interviews and offers from the top consulting firms: Bain, BCG and McKinsey.
Daniel ended up taking a job with one of the big three firms in San Francisco to be closer to the tech industry. During a round of layoffs in the pandemic, he was the only consultant from his associate class to survive. The firm offered to send him to business school and pay for it, but he wanted to start his career in venture capital. Venture firms don’t hire management consultants with law degrees. But if you haven’t noticed the pattern, those odds never stopped Daniel before.
After much persistence, a venture firm gave him a four month trial period at a massive pay cut. It didn’t deter him, because he was confident he could prove himself. He ended up getting a full-time offer and is now an associate.
From a kid who was told he wouldn’t amount to much in life, because he started from so little, Daniel graduated from college, got his law school degree from the best law school in the world, worked for one of the top consulting firms in the world, and is now working at a venture capitalist in Silicon Valley. Time and time again, he defied the odds and wouldn’t allow conventional norms to stand in his way. Unlike many people, his name wasn’t on the guest list, he had to find a way in through another door.
Daniel’s story is one of resilience and perseverance, that comes from a deep sense of self-belief, but one that is not riddled with self-doubt as well. He could have easily settled for a high-paying career at a big law firm with his Harvard degree, but that’s not what he wanted. Many people told him it made no sense for him to take such unorthodox risks, but that didn’t deter him, because he grew up with nothing to lose. Meanwhile, the children of privilege were scared to even speak up, much less take a chance with their perfectly engineered and manicured resumes.
It’s unfortunate that the ones who have the most, are the least willing to take risks, because in their minds, they have more to lose. In reality, the abundance they have is in fact a safety net and cushion for them to be more bold. It is all about how they frame that abundance and whose approval they seek. Some people are afraid that they will fail, and somehow disappoint the people who provided those opportunities for them. Other people take advantage of their privilege and leverage it to take big swings, even if they miss. Knowing that they can take multiple swings and still be just fine.
When you grow up in a culture of scarcity, you become wired with risk aversion that holds you back. When you are raised in a culture of abundance and growth, you become wired with a boldness and arrogance that makes you believe you’re superhuman.
I grew up in a scarcity culture. I was held back by a self-preservation mindset that I had for so long. Even though I had a stellar resume, I was afraid to take any risks to tarnish it. Failure was never an option, because it would look bad. It wasn’t until I thought about who I was afraid of looking bad to, that I realized that I was just rationalizing to myself. I was finding any and every excuse to avoid failure or making any mistakes, because that was how I was raised. The burden of my parents sacrifice paralyzed me from taking any chances. So I told myself that I would take bigger risks when I reached a VP level. I knew full well that I was just kicking the can down the road to avoid making any scary decisions. I was the prisoner of a perfect resume.
The irony is that I had built up this stellar resume with an Ivy League degree, Stanford MBA, big name consulting and fancy corporate brands, and I was terrified of taking a single step off that track. My whole life I was programmed to stay on this narrow staircase to nowhere. The thought of not staying on that path was debilitating. It was not like any of those things I had achieved would suddenly disappear if I took a risk. I would still be the same person, even if I veered off the path.
When I finally took the leap to start my first company, it was humbling to not have my life preserver of identity from a big brand name. I realized that I had to stand on my own, and my self-worth was no longer tied to my resume. That’s when things started shifting internally for me. I went from seeking external validation through attaining merit badges to building internal validation through building up my own companies or serving others in the community.
Ultimately, the shift in mindset from scarcity to abundance is a choice. It’s a choice between what is safe and predictable, but capped, and an alternative that is uncertain but has no ceiling. But if you have all of the talent in the world to build up that fancy resume, it becomes a lot less risky, not more. You have what it takes to do even bigger and better things. Why waste it making someone else more successful or wealthy?
You are so busy thinking about what you might lose, that you don’t stop to think about what you could gain. Daniel started with nothing and has continued to put himself in positions where he could open new doors and enter exclusive rooms. Most of us have no excuses not to do the same.
There is no better bet than the one you make on yourself. Stop kicking the can down the road, and start making those bets.
The perfect resume is just a very expensive comfort zone.