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The Most Important Lesson for an Entrepreneur is To Learn How to Forgive Yourself

Usually we become entrepreneurs because we are naive.

When you declare that you’ve made the leap and you’ve struck out on your own people will often say, “wow, you’re so brave,” and while that may be true, a voice in the back of our head tells us that if we knew in the beginning what we know now 6-12 or 18 months later, it’s highly unlikely we would have started. Naivety is that fun-loving friend who says, “come on, one more drink!” and when you wake up the next day in a strange place sporting a new tattoo, naivety is no place to be found. Instead, naivety’s cousin anxiety has moved in and she’s sleeping on your couch. Indefinitely.

The trials and tribulations of the entrepreneur are well-documented and almost a cliché. The truth of the matter is that as an entrepreneur you will reach new personal lows, and it’s best, in the beginning, not to know how low those lows can be.

I thought I had reached a new low the first time a client fired me. Then I thought I had reached a new low the first time I was late paying salaries. Then I thought I had reached a new low the time that my business lost $30,000 in a single month. Then I thought I had reached a new low the time I had to lay-off four people. They hated me. Then I thought I had reached a new low when I had to ask my wife’s cousin’s husband to lend me a ginormous amount of money to keep my business afloat. Then I thought I had reached a new low the time I had to fire my accountant and I discovered thousands of dollars lost or owed due to mismanagement. I realized I had reached a new low when my wife and I suffered a personal tragedy and I couldn’t completely disconnect from work in order to grieve. That’s still my lowest low up till now.

If someone had offered me money for my business at any of those moments I would have taken it. So long as I could pay my cab-ride home, I likely would have accepted the deal even in the payment was in a cryptocurrency named after a dog meme I’d never heard of. After each incident I thought to myself, “why the <expletive> am I doing this? Is going through this really worth it?”. In each case I saw myself as a victim both of circumstance and my own naivety.

Nowadays my management team and I have the great privilege to work with an executive coach based out of Toronto, Hina Khan. Hina often says, “if it’s on your plate it is because you ordered it”, and she’s right. We remind each other of that saying all the time because it keeps us from slipping into that victimhood mindset. Did I provoke the aforementioned events? No. Was I still the architect of the context in which they took place? Absolutely. To give one example, after 3 years of running a business I still hadn’t created a structure that would enable me to be absent from my business. Everything ran through me. I had created a Matthew-dependent organization. In other cases I had hired too quickly. I had taken on the wrong type of clients. I had not done sufficient financial planning to foresee and forestall downturns. Did a lot of self-loathing come as a result of owning my mistakes? Absolutely.

Here’s the plot twist: If someone asked to buy my business today I would most likely say No. Despite all of the aforementioned stress, I dream of my business becoming 4-5 times bigger than it is right now, and I think I can achieve that goal in 4-5 years. I know the path. I know how to execute. The road is full of potholes, and I expect to discover some new lows along the way. The reason why I am still determined to move forward is because at some point I learned the most important lesson of all for an entrepreneur: to forgive oneself.

Many entrepreneurs are at war with themselves. I am reminded of something else Hina says: “if we spoke to others the way we allow our internal voice to speak to ourselves, we’d get fired or worse.” Whereas some people see over-achievement as the product of some higher mental and spiritual state, often times what’s pushing us forward is a voice of doubt and self-conflagration that we are trying to silence through achievement, like we’re living some sort of weird mix between Fight Club and Whiplash. We are Edward Norton punching ourselves in the face while whispering into our own ear, “not my tempo”.

Entrepreneurship amplifies our demons because we we spend a lot of time alone. Though I have business partners, I never really had a co-founder per say; as such, most of hard times were a bag of rocks I carried on my own. My wife, also an entrepreneur, lent me a sympathetic ear and lived it all with me while also managing her own mini-crisis from day to day. I knew that to survive in this journey I would need to work on myself. I started meditating and that helped me better deal with the ebbs and flows of daily life as an entrepreneur. I began seeing a psychologist in order to become more self-aware. My team and I started working with Hina, our executive coach, and she revolutionized everything about how we operate as individuals and as a team. I took action. I changed the context.

The reason I didn’t give up is because I always knew that I was learning. I knew that if I just made it over the hill I could implement the lessons each crisis was teaching me and my business would be more stable and prosperous. Of course I was motivated by other things. I was motivated by not wanting to let down the people who put their faith in me, including my partners and my employees. I was motivated by the shame of failure and walking away. I was motivated by not being quite sure how I would feed myself without my business, but my purest motivation was faith in the idea that even when I was moving backwards I was somehow moving forwards.

A big part of being able to embrace my own failings was learning to forgive myself. Forgive myself for each client & employee that left against my will. Forgive myself for not knowing beforehand the thing each crisis was teaching me. Forgive myself for not sensing urgency early enough to prevent certain incidents from taking place. Forgive myself for all the things I am not. I even have to forgive myself for over-learning lessons from the past.

4 years after naivety bought me a drink, I am still here and my business is still here. We achieved our first goal: to be sustainable. Now we’re setting new goals. We’re looking up. We’re experiencing change, and we’re creating rather than resisting it. We’re taking hard decisions. We’re pushing ourselves out of our comfort zone. Who knows? We may be drawing up plans for our own demise, but even after all that we’ve been through, we’re still winking at naivety across the bar. We’re doing things differently. We own everything that happens to us. We mess up, but most importantly we forgive ourselves for messing up. “No-one ever regrets being brave,” said the manager of Luis Miguel, one of Latin America’s most well-known 80s teenage heart-throb singers as documented in the Netflix series that bears his name, and starting a business is often the product of a deadly cocktail of naivety and bravery. Being successful as a businessperson, on the other hand, often requires the bravery to look deep into the mirror and say the words, “I forgive you,” and treating yourself with the compassion and empathy required of someone with good intentions trying to do something he or she has never done before. That, to me, is the most important lesson entrepreneurship can teach you, because it makes every other lesson more manageable. The business will come and go. You as a person will never be the same. Allow yourself to find the best version you in the process by discovering how to be kind to the one person in your life who deserves it the most: you.

Matthew Carpenter-Arévalo is part of the Maritime diaspora. After working at Google and Twitter, he founded Centrico Digital, a managed marketing services company with operations in Canada, The United States, and Latin America. He can be reached at mca@centricodigital.com.