From Side Quest to Main Quest

The start of a new journey

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    Ten years ago, I had an idea

    Ten years ago, I had an idea for The Next Big Thing. It was going to be huge. Sprawling. Touching everything on the Internet. It would change the world! Even better, a really cool domain name was available that matched the concept.

    The details of that thing are not important, right now, but I had a vision and a product name and enough talent to put together a prototype. So, I set to work.

    I lived the startup prep life for 18 months as a side quest

    I had a full time job supporting a family of four, one of which wasn’t quite a toddler. I set aside 2 hours every morning before work and 2 hours each morning on weekends to work on the project. Family and my paying job were the main quest. Building the prototype and a business plan were the side quest.

    My idea was too ambitious…

    The more I worked on the business plan, the more I wanted this idea to cram into this idea that I was building. It started out big and complex, and it was only getting bigger and complexier (that could be a word!) over time. After 12 months, my prototype could have possibly been finished except that my scope creep had gone unchecked. It was nowhere near finished by my own standards. So, I shifted my focus to creating my pitch deck to try to get some investment.

    … and I made a terrible pitch deck

    I should have started with the pitch deck in the beginning. It would have given me better direction and would have kept my scope creep in check. Putting this together after a year of adding stuff to the mix was not easy. Predictably, the attempt to get everything I wanted to do within a few slides on a presentation war a horrible failure. I broke every pitch deck rule. I ended up with 20 slides. I didn’t have any numbers to back me up. I didn’t have a partner. I just had a sprawling, messy, really cool idea that I couldn’t communicate clearly.

    An investor gave me a reality check

    A friend connected me with an investor. I think he got the gist of the idea, despite me being terrible at making the pitch. I think he understood what I was trying to do, because he told me three things: my idea was too ambitious; I would be taking on major established competitors; I had no reputation.

    Ouch.

    I put the idea on a shelf

    I took a week to think about the conversation. Ultimately, I agreed. He was right. I started out trying to design and launch something with the scales and complexity of Facebook on day one. The most significant point he made, though, is that I had no reputation. I couldn’t point to something in the public space and say “I did that from start to finish”. I also didn’t have connections to anyone else who had done so. I needed connections and a reputation, more than anything. I took all the documents, and the code I had written, and zipped them up and put them in a digital shelf.

    But I didn’t lose my vision

    I gave myself permission to slow down and to sleep past 5 AM. But I didn’t lose the drive to start something new. I started collecting ideas. I started reading books on business and startups. I listened to podcasts. And, I didn’t let this failure get to me. I just needed to be smarter, more prepared, and maybe more realistic the next time.

    More ideas, more experience

    Over the next few years, I kept accumulating ideas for myself while my responsibilities grew at work. I pursued opportunities to take on big projects from start to finish. I talked to executives and other business leaders. I changed jobs, built more products, and got some management and then executive experience for myself.

    Then a mid-life crisis

    COVID happened. Once it felt like it was no longer disrupting every aspect of our lives, I started to get the itch to strike out on my own. I had success after success in my career, building new things for other people, supporting their visions. I had been praised repeatedly at work for being a strong leader and a strong visionary on many levels. When I turned 50, I couldn’t stop thinking that it’s now or never. I needed to start down my own path or forever follow others.

    So, I did the unthinkable (for some)

    Once I made my decision, I had an honest discussion with my boss and the owner of the company I worked for: I had to strike out on my own. I had waited too long, and I had too many things I wanted to do that were not related to the industry or clients the company served. I wanted to put together a transition and exit plan.

    This was not the first time I had approached management and the owner of a company that I was working for to tell them I felt the need to move on. This was, in fact, the fourth time in my career that I had a discussion like this.

    Opportunity for investment

    Immediately after that, without going into specific details, I was presented with the opportunity to create one more thing for someone else in exchange for what amounted to an investment in me: enough resources that if carefully managed would give me at least one year to get established and start earning revenue.

    Side quest becomes main quest

    Here I am, 3 months into my journey. That side quest to start my own company has finally become the main quest. I can focus 100% of my energy and resources into building something new. Will it succeed? I am giving myself a year from now to find out. I have many ideas, and I’m going to try a few over the next year to see which ones get traction. What shape will all of this take? Let’s find out together.

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