On regret, in life and business.
Examining an incredibly dis-empowering word
Part of my work with 1517 involves meeting with early-stage founders and helping them understand venture capital, our fund or simply troubleshooting issues in their business. Every so often, I have a conversation that takes me a little by surprise.
A founder had taken the time to read another one of my posts about the journey of my time as a founder and leader of my last company. After sharing this with me during the first 5 mins of our call, she then asked me, “Do you regret anything?”
After a brief pause, I realized something that I have thought often about but have never had an opportunity to speak on directly. I realized that I do not believe in regret.
Regret: noun
a feeling of sadness, repentance, or disappointment over an occurrence or something that one has done or failed to do.
Let me explain.
The basic principle that I now adhere to is that regret, or the feeling of regret, or the emotional charge that surrounds a certain event that could trend towards sadness or disappointment, as the definition above suggests, is my opinion simply unprocessed experience. An experience that has not been critically examined for its lessons - inside of which wisdom can be harvested. What I am describing here is a process that does require conscious work and an investment of time, but the reward of this work is a deeper capacity for skillful navigation of life and each of our relationships.
Every experience often comes as a package deal. There is the experience itself, what happened, and then there is the emotion, or how we felt about it. It’s often quite challenging to realize at first that the emotion, or how we feel about something, is carefully overlaid on top of the objective perception of what happened. Realizing and accepting this is the first step towards harvesting wisdom.
How we feel about something is completely subjective. That is two people can witness the same experience and come away with feeling two completely different and sometimes opposite things. It therefore follows that how we feel about something is a perception, which luckily, falls under our control in our ability to change. When we experience something undesirable, consider the first emotion to be a reaction to that experience, nothing more. If we adopt that emotional reaction as truth and fail to update it later through reflection then we truly are at the mercy of life, we are a victim to our circumstance. For example, we have all had experiences that didn’t go to plan or conversations where we didn’t like the version of us who was speaking. Sure, it’s possible to look back on an experience like that and feel disappointment in an outcome or a behavior but this leads us very close to the line of wallowing in self-pity.
What is the point of having life experience at all? What is the point of action, reaction, cause and effect, choice and consequence? I would suggest that it is simply to provide the raw materials for us to grow. Change, as we know, is constant. Circumstances change, those changes create new experiences and those new experiences allow us to experience ourselves differently. They create emotion and awareness that work together to show us more about who we are at that moment. The contrast between the person we were before the experience and the person we are after presents a unique opportunity for personal reflection. A moment to realize that we are not the same person now and if we are paying attention, for us to update this understanding of ourselves. To realize that what we were feeling back then doesn’t have to be what we are feeling now. While we may feel disappointment or sadness in the moment at witnessing how we lost what we wanted or missed the mark around expectation, the bigger tragedy is not realizing that we can learn something profound about ourselves. This is the opportunity to convert raw emotion and experience into wisdom.
For the sake of this thought experiment let’s define wisdom as the ability to update one’s perceptions of self, other, or circumstance to a more close approximation of truth. A truth of knowing oneself more deeply and thus being able to more skillfully and gracefully navigate the vast multitude of life events.
Perhaps it would be helpful for me to share a personal experience. I started my first company at twenty-two. Over the next eight years, I was able to find product-market fit, raise around 8MM dollars, and scale our business to around $250K/mo in revenue. We had our best quarter one month before COVID hit the US and new regulations severely impacted our company’s top-line revenues. I spent the next year and a half trying to sell off a business that was bleeding cash and while ultimately successful, the proceeds barely covered legal costs.
At the time this was all happening, I was devastated. Emotionally I was numb, psychologically I was terrified but the reason I want to share this story with you is because I was watching all of my hard work and years of late nights go to zero. When the dust settled, I barely had any personal funds remaining and I was far from the dream of being financially independent and free.
While it took quite some time to process this experience and realize the wisdom contained herein, I ultimately found peace. I realized two extremely critical things that will stay with me for the rest of my life. First, I got a chance to see who I was under pressure. Up to that point, I didn’t know myself in the face of extreme circumstances but coming out of the experience, I realized that I am someone who can weather storms. This has subsequently made other challenging experiences in my life easier to handle. Second, while I was hoping for a big payday, I think having a significant amount of money at that time would have been harmful rather than helpful. I honestly don’t think I was mature enough to be handling a life-changing amount of money, furthermore, I was not a very emotionally secure individual and I think I would have just started throwing money at my problems and fears instead of having to do the hard work of understanding how to skillfully handle them.
And so what started as a challenging and emotionally charged experience and one that I originally was deeply disappointed by has since turned into one of the most powerful teaching moments of my life. One that has changed the trajectory of my life in the most amazing and unexpected ways. I no longer feel any negativity or charge around what happened to me back then and because of this, I have come to the belief that regret has no place in our vocabulary. Regret is giving up. Regret is an excuse to not do the work to understand how an experience affected us the way it did. Regret is a luxury that will make you a victim of your own life. And the worst part is, regret would have you believe that you cannot do anything about it.
Do yourself a favor, forget regret. You won’t regret it.