It’s been over a year since we sold our startup and it’s been an interesting time returning back to normal life. Whether it was the chaotic fun of running a team or the fact that we were the sole dictators of our fate, I definitely miss it — and at the same time, glad it is a chapter closed.
Not many people talk about it but running a company gets pretty lonely. The feeling of guilt followed me on the daily. The idea that every individual’s fate on the team was dependent on the decisions I made was something that ate at me constantly. Being a founder comes with the expectation of being the leader that steers the rest of the cohort to success. There’s a degree of accountability of a founder to be able to produce results which include monetary results for their team. When there is a question, there is an expectation that you will have or do your job to get the right answer. When there is a problem, the requirement of a leader is that you will be the one with the best solution. You’re the one who is expected to align everyone from the chaos and direct everyone with the vision — regardless if you’re ready.
As time went on, the fatigue got to me and there were days where I just didn’t want to get out of bed. There were days I just couldn’t make a decision on the next steps but convinced myself it was only temporary. In the grand scheme of things, a lot of stress and worries might’ve not mattered but at that point of time, it felt like the weight of the world was on my shoulders. But like many first-time founders, I just had to cope with it.
Fast forward a little over a year of running the startup with a 14 person team, we decide to exit with a company in Seattle and that was it.
Some can say that was somewhat of a happy ending but for me, it was shadowed by a large cloud of disappointment that the business couldn’t scale to be bigger and greater like we all wanted. Even till this day, the feeling of guilt that I didn’t lead my team to a bigger exit or be a sustainable company for their hard work lingers inside of me. In many ways, as the one who was supposed to lead everyone to succeed, I ultimately fell through on that promise.
After the exit, I decided to go back to school and finish up. I took a co-op job in Florida for a few months, drove around the East Coast, did a road trip in the Maritimes and had an incredible time meeting new people and going through new experiences. During all of that, I bought a new car and a new house in Canada for my family.
So what am I doing now?
Well, I am proud to say that I’m coasting.
Life after has been relaxing. In some ways, I’ve been trying to do a lot of unscalable activities. I think what ultimately burned me out, in the end, was my need to control and plan for the future. Whether it was trying to strategize my professional life or plan for my personal relationships, I tried to dictate and think of everything in detail… and it was very much pointless and draining.
So yeah, I’ve been doing a lot of unscalable things. What are unscalable activities? Well, I’m glad you asked. When I say “unscalable” activities, it’s referring to things that I do that don’t necessarily (or directly) produce a practical outcome — such as going to comedy shows, doing hikes, attempting to sing (not as badly) and walking on the beach. Unscalable things are any activities done for purely fun. On the other hand, examples of scalable activities would be working on longterm projects in hopes it’ll turn into a business or networking to further one’s career. Those things are done with a purpose and unscalable things don’t and shouldn’t have one.
So yeah, I’m coasting. I don’t have a masterplan. I don’t have anything I’m really working towards.
For now, I just want to sit back and actively listen. I’m trying to ask more questions and unfold more about what I don’t know. I think one of the key lessons I took from running an early startup was the fact that I don’t know nearly as much as I thought I knew. Whether it is how to be a better product manager or simply how to be a better leader in general, I’ve always had the expectation that I will develop those skills and traits as I grew — and that’s still somewhat true. It just turns out that a lot of that development is dependent on asking and learning from others.
And I’ve been taking this coasting period to recover. I was burned out and was pretty depleted of energy after all the hustle and bustle. Doing something with so much instability and pressure takes a toll on you mentally and physically. Being close to family and travelling has definitely helped me get back on my feet.
I’m also a huge lone-wolf kind of guy. I enjoy going to movies, doing hikes and sitting in local comedy shows alone. Something that I didn’t really get a chance to do with so much going on in the past. It’s like meditating…but not really.
But don’t get me wrong, I enjoy good company and actually thrive around groups of smart and interesting individuals. I think of my alone time as detoxing after eating fried chicken. Fried chicken to me is like socializing. Like fried chicken, it’s something I’ll probably never get sick of and will generally make me pretty happy but similarly, it’s never good to have too much of one thing. Sometimes, you got to eat some veggies and slurp down a fibre-packed detox drink for a few days to balance things out. That fibre-packed detox drink is my alone time. Please let me know if this analogy doesn’t make sense.
Now that I’m freed up with a lot of time, I started investing my energy in fun side projects and actively getting to know interesting people and learning how they think. Obviously, there’s a ton of subjectivity when it comes to defining who is interesting and who is not but in general, I’ve allocated a lot of my attention and time to meeting and learning about people’s stories. It’s really intriguing what you can learn about someone over coffee and that’s probably something I suggest everyone try out. I’ll write my next piece about this topic haha.
I’m not sure how long I’m planning to coast for but I’m already feeling the itch to do something.
But for now, I’ll keep learning and being a sponge.