Reflections on pivoting to entrepreneurship
Recently, I bought a small business called The Print Authority. I left behind a great career in corporate America to pursue entrepreneurship full-time and chart my own path. I’ve learned a tremendous amount about myself, business, and life in the process. I’ve boiled it down to three key lessons that I’d like to share here in the hope that it can be helpful.
Lesson 1 – “The best time to plant a tree was 20 years ago, the second-best time is right now.”
This has always been one of my favorite quotes, and it’s a constant reminder for myself to “get busy living or get busy dying” as the saying goes.
Like many who pursue acquisition entrepreneurship, I was introduced to the concept in business school. I thought it sounded exciting, but figured I could always do it later in my career. Then, as cliché as it sounds, becoming a parent changed everything for me. It made me realize that life is not going to get any less complicated anytime soon. I decided that there is no “right time.” The right time is right now.
I’m also struck by this quote as it applies to parenthood in the context of what I’m hoping to build for our family through my work over the long term. Corporate America is great: it provides rewarding career opportunities with amazing people. But I couldn’t help starting to feel like the work I was doing was supporting other families’ dreams, not ours.
Once I began to see my work in a way where I was constantly wondering who the ultimate beneficiary of enterprise profitability was, it was impossible to un-see. I wondered why my family shouldn’t have its own little engine of profitability that I was directly responsible for taking care of.
Lesson 2 – “You get sober with your feet, not your head.”
This is a saying we have in the recovery community that has always resonated with me. It applies to so many other areas of my life and has perhaps no better application than to entrepreneurship. On this journey, I have decided to try to worry less about outcomes and to just do the next thing in front of me and see where that takes me. It is much easier than trying to figure out everything all at once. I need to constantly remind myself to do more and think less.
This sounds so painfully obvious to write, but I’ve learned that you need to take action for opportunities to come your way. Opportunities don’t come knocking on your door while you’re sitting on the couch thinking about how to unlock the secrets of the universe – believe me, I’ve tried. Opportunities flow to those who take action.
My unsolicited advice: if you’re considering something you think you’ll regret not trying, I challenge you to just go do it. Start taking action now and figure the rest out later. Right now. Seriously. Make that phone call you’re afraid to make by picking up the phone and dialing the number. Send that email you’re afraid to send by typing it up and clicking send. Walk up to the girl or guy you’re attracted to and ask them out. The worst thing that can happen is you are told “no” or get no response at all. Funnily enough, neither of these worst-case scenarios is actually a bad outcome since it provides valuable information about what action to take next. I cannot stress enough how big of an asymmetric risk/reward profile an action-first approach has in the world of business and relationships.
In getting past my fear of rejection and taking more action I have realized two important things about rejection:
It happens a lot less often than I think it will.
When it does happen, it hurts a lot less than I think it will.
Once I started taking more action and started getting over my fear of rejection, I have realized that just getting the ball rolling is more than half the battle.
Lesson 3 – Know what you know, know what you don’t know, and most importantly, know that some things are unknowable.
I had a professor in business school that said one of his greatest skills was knowing what he knows, but more importantly, knowing what he doesn’t know. This is a fantastic insight, but it is incomplete. One must also remember that many things in life are simply unknowable. Whether or not I’ll be successful as an entrepreneur is one of those things. This is where my personal risk tolerance and my faith came in.
Regarding my perception of risk, candidly, my personal experience with addiction and recovery shapes my perspective in a big way. I genuinely feel lucky just to be alive and healthy. On top of that, I have a great relationship with my family. Anything beyond that is just icing on the cake. With that perspective, taking a big career risk has been a lot easier mentally and, perhaps more importantly, emotionally.
Ultimately, however, entrepreneurship is a leap of faith. And my faith in a Higher Power has led me to (and gotten me through) this big life change. I believe deep down that God has a plan for me and that my duty and obligation is to be of maximum service to His will. I feel called to entrepreneurship as the best way for me to fulfill my duties and obligations in my professional endeavors. And not in an “I’m destined for greatness” kind of way or anything, but because I just believe that my unique combination of skills and experiences make entrepreneurship the right fit. This is not an aspect of my decision-making process that could be modeled in Excel, but it had a major impact on my ultimate decision to pursue entrepreneurship full-time.
Finally, while I haven’t gone into much detail about my investment thesis or business strategy (reach out to hear more on this part!), hopefully I’ve given you a view into why I’m doing what I’m doing and that it can be helpful to you on your journey, whatever that may be.