During my late 20s, I took the time to reassess how much money I had lost out on because of ego and hubris; whether it was ego preventing me from asking for help, ego preventing me from accurately assessing the gaps in my skill or knowledge, or hubris leading me to believe that I already possessed sufficient information and need not inquire more. This radical reassessment of my past behavior led me to declare that “Naija boy would rather win than stay broke by unnecessarily protecting ego”. Here are some of the specific instances that I had in mind at that time – all together I believe these mistakes have cost me conservatively more than a million USD in potential career earnings.

1. High School: There were students who possessed academic & life skills that I should have desired to possess. I should have gotten close to them and humbly begged them to allow me to learn from them.
2. Law School: There were law students who possessed specific knowledge on how to do well in law school. Rather than studying by myself, I should have begged them to tell me their secrets.
3. China: I used to hold hackathons where I would teach people the basics of web development. One time in Beijing, I was teaching a group of friends and acquaintances basic HTML & CSS. I mentioned that a career as a programmer was lucrative and one of my friends agreed and mentioned that her boyfriend currently makes $300k as a software engineer in the USA. Y’all, let me tell you - I was floored! Shocked! Flabbergasted! Speechless! My internal dialogue went something like “WTH! People make THAT much money!?” Next came a flood of embarrassment at the thought of her knowing a real software engineer, while I was here teaching her simple HTML & CSS. I was embarrassed that I had no idea that “real” engineers made that much money. Rather than being honest with the group and stating the true contents of my internal dialogue and begging her to introduce me to her boyfriend so that I may learn how to similarly make such money, I let my pride get the best of me and remained silent. After a few seconds of being flustered at this new revelation, I found some way to change to subject and continued teaching the class. I should have instead stopped everything that I was doing, and humbly begged her to put me on. A wasted opportunity.

All these instances of not seeking out information because of the temporary pain of feeling inadequate left me broke. The follies of my younger self were clear when contrasted with the harsh realities of being a broke black man. Being broke and not being able to support my family was far too costly of a trade-off just to avoid the temporary feeling of vulnerability. I knew then that couldn’t change my past behavior, but I could change my future behavior.

I promised myself to go as far in the opposite direction as I could and master the art of BEGGING people to put me on. I committed to being able to recognize that familiar feeling of embarrassment that led me to remain silent back in Beijing, instead of sharing my internal dialogue. I ruminated incessantly about all other previous instances in my life where I chose to avoid feeling vulnerable over seeking information or help that could potentially lead me to financial freedom.

I made it a conscious goal to proactively seek situations where I would have previous avoided. I practiced telling everyone and anyone who had some skill or status that I desired, “You’re where I want to be in life, how can I be like you”. I’ve said this so much that it barely effects my sense of self. With time and practice I learned to lean in whenever I felt inadequate about my salary, position, or skills, and instead open to others, and myself, in a non-judgmental exploration on how I could improve the current situation. Put simply, I needed to <Naija accent> make money </Naija accent>, and if I had to feel temporarily uncomfortable when revealing some gap between my current state and desired state, so be it.

Had I humbled myself years earlier, I would be a much richer man than I am now. I would have started my career years earlier and would be comfortably making $500k a year at this point. See the cost of my hubris.