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Sean Cooper

The Value of Being Uncomfortable

As I write this, I am uncomfortable. I have not had employment for over three months and I don't know when that will change. I have to move in two months and I don't have a new place for my family and I to live. My income from unemployment insurance is far less than my family needs to survive. I am deeply uncomfortable.


This is not a new feeling for me. This is the third time I've been laid off in a career that spans over 20 years. The first time, I spent most of a year unemployed and was days away from being homeless. The second time, I spent most of a year working for the bare minimum needed to pay rent and buy a bit of food. This time is going a bit better but time will tell what the outcome looks like.


I don't share this to paint a grim picture and ask for pity. I share this for context because each previous instance of being very uncomfortable resulted in growth that has served me later.


Layoff 1 - Building a Foundation

I was laid off at the end of 2004. In early 2005, as I came to grips with my diminished job prospects, I decided to teach myself a new programming language. Microsoft had released .NET in 2002 and, by 2005, it was looking like it had some real traction. I had no money for classes but I had time, the internet, and a stubborn streak. I threw myself into learning this new programming platform. I built a property management system that I tried, and failed, to sell. I spent hours upon hours bashing my head against various coding challenges.


By the end of 2005, I had a decent handle on a good portion of the .NET framework and understood the principles that underpinned the entire system. This allowed me to land a software development job in 2006. That position turned into my first management position. And the people I met at that job became some of the people that I partnered with when, in 2009, we all got laid off.


Layoff 2 - Building a Company

Shortly after getting notice that we were being laid off, a couple of coworkers and I got together to discuss what we were going to do. Over the last three years of working together, we created some exciting and innovative software that had a transformative effect on the industry where our soon-to-be-former employer operated. We weren't interested in heading out to find "real" jobs working for other companies. After some discussion, we agree to start our own company to try and take these ideas and solutions to other players in the industry.


In February of 2009, our company was officially born. That started my next period of being uncomfortable. As we were winding down our time with our employer, we would work from 8 am to 5 pm then relocate and work till midnight or 1am on stuff for the new company. This continued for months until our time with our employer was officially done. After that, we were working 12 and 13-hour days doing all the things that were needed to start and grow a new business.


This time was exhilarating and challenging. I learned to write contracts. I handled sales duties. I did marketing. I even fired a customer! I was introduced to new facets of business that I'd not been exposed to before. I stumbled. I succeeded. I learned. By the time I left in 2011, I had a much clearer understanding of what was needed to make a successful software business.


Layoff 3 - Building for the Future

In January of 2024, I joined around 70K other people in losing their jobs. Unlike my first two layoffs, I was not given any advance notice. I woke up one morning with a job and during my drive home from dropping a kid off at a school, I found out that by the time I got home, I would no longer have a job. A small severance would come my way but that was it. Unlike the previous times, I now have people counting on me. I have a family. I am extremely uncomfortable, especially given the slowness of the job market.


After some reflection and discussion with friends, I have elected to embark on a two-pronged approach. First, I will continue to look for new employment. However, I am also building a new company. I'm taking the learnings from my entire career and using them to try and deliver something of value to others. Already, I am learning and growing. The world of SaaS startups is a very interesting place. My new company will be leveraging AI. This is a rapidly evolving space.


My goal with this new company is to build something large enough that I can ensure my family's future. I'm not looking to make enough money to buy a private island. I'd be happy with enough money to buy a house and ensure our ability to retire later. If I can generate enough revenue to hire others and help them towards their goals, I'll be extremely happy.


Conclusion

Muscles don't grow unless they are stressed. We don't get fit without working up a sweat. Knowledge must be earned through hard experience or diligent study. Skills are only earned through constant, deliberate practice. Stressors are what drive species and individuals to evolve.


In this time of deep uncertainty, many of us are feeling very uncomfortable about our futures, our place in society, and even our viability in our chosen careers. I have felt every one of those feelings. However, I am choosing to use this time of being uncomfortable to evolve into the next version of me.


If you're reading this and any of this resonates, I urge you to embrace the discomfort and recognize that you're positioned to grow.


My journey summary:

Retail Manager -> Help Desk Associate -> Software Developer -> Software Development Lead-> Co-Founder/Marketer/Architect -> Software Development Manager -> CEO?

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