I have always considered myself an outsider to the business community. Ironically I felt this most acutely in the financial world in which I operated. Even though I played the part, there was always a mismatch between me and the traditional business landscape.
I still remember an elevator ride in which this played out in real time. The contrast of my black trading jacket and Cubs tie was stark compared to the nattily-attired Chicago bankers next to me. One banker sniffed to the other about the indignity of having to do business with so many traders who wore smocks rather than three-piece suits.
The bias went, and still goes, beyond attire. And while the private equity world may be a bit more lenient on wardrobe selection, the exclusivity of access granted to only those with a certain pedigree is the same. So while it’s easy to now feel part of the club because of a few past wins, let the record show: I would have had zero chance of getting an interview at the firm I started twenty-five years ago.
The road to my success in private equity came from an entrepreneurial leap, not a traditional trajectory of right degree, prestigious internship, and predictable ladder climbing. Hey, it’s all I knew.
Every grounded person who has walked the path of an entrepreneur believes in their heart that the journey is attainable for the next person. The “if I can do it, you can do it” ethos will always come with a hearty warning of the many challenges and difficulties, and seasoned entrepreneurs will forewarn that the journey requires everything you’ve got, lots of luck, and tons of grit. But they will also attest that if you maintain the hope about the worthiness of your idea, it can absolutely be done.
Now, here’s the secret: The best part of the entrepreneurial adventure is not the wealth you create or the benefit you give the world from your business idea, these things are all fleeting. Money is only satisfying to a degree and has the deceptive, creeping nature of being never enough. And even if your idea is a huge success, it will almost certainly be replaced by another, better idea that comes from the next entrepreneur who iterates on what you started.
I don’t say this to discourage you, it is simply the way that the game works. It is also likely the reason that opportunity exists today for you. Businesses create jobs and opportunities for a specific period—some longer and some shorter. Then, a new business replaces it and the cycle goes on. Being innovative in the face of change is the only way to stay consistently relevant, and being motivated by something deeper than money is essential.
The biggest secret of the entrepreneurial journey isn’t about what it produces externally, but rather about the person it requires you to become along the way. When the financial success normalizes and the public affirmations and accolades fade, what you are left with is the personal culmination of what the journey has created in you.
Successful entrepreneurs must also make peace with the fact that a part of the journey is never complete. No matter how great the bigger purpose that undergirds your mission, it will inevitably have limits. If you feed millions of people, there still will be some who remain hungry. If you build schools for thousands, there will always be some who get left out and struggle with illiteracy. And the narwhals? While their numbers may go up from your temporary efforts, they may later decrease in number for reasons unknown.
Like our businesses, our philanthropy isn’t likely to change the course of history, at least on a glamorous, widely-visible scale. Jesus said a blessing exists for those who give merely a cup of cold water in his name to a weary stranger, and sometimes the smallness and invisibility of our work feels like just that.
Having humility and perspective about how our work and our gifts affect the world will allow us to enjoy them both immensely more. It enables us to wake up each morning to do what we can, accept what we cannot, and keep trying tomorrow.
Frontiersmen learned about this kind of inner resilience when they engaged the ferocity of nature for the first time. Blazing a new trail, they encountered very real challenges that tested them to the limit physically, mentally, spiritually, and beyond.
While starting a business will not require you to cross a mountain pass barefoot and ill-prepared, there is a shared fierce rawness in undertaking the entrepreneurial adventure. You will undoubtedly be forced to summon something from inside yourself that you didn’t know existed, and your belief will be tested to the limit.
When you are done– win, lose, or draw–you will be a stronger and better person if you endured.
For me personally, I’m grateful that the three-piece suit was a bad fit because it catalyzed my trajectory toward a different path and an accidental discovery. Looking back, I set off with such minimal ideas and intent, and the journey was so much wilder. It made me who I am today and made it all worth it.
Good luck to you on your journey.
