Life As An Accidental Entrepreneur

This story was submitted anonymously to the Work it! Working to Live and Living to Work collection as part of the October SEEQ sessions.

I’ve had “career transitions” before. About 8 years ago, I pivoted from a career track in Enterprise IT Management to Corporate Innovation Leadership. It was not a difficult decision, and frankly, it sort of just fell in my lap. I didn’t have to change companies, I got promoted to the new role, and I had spent the 6 months prior on “special assignment” to the team I would be joining and learned I had a passion for this work of solving corporate innovation challenges. The stakes were not high. I did not have to think about my relationship with my work in relation to the rest of my life. Most things would stay the same. Paycheck every two weeks. Vacation when I want it. Four kids in dance class with ridiculous fees for recital outfits and everything else? Well, make it work. Then earlier this year everything shifted. The big company I worked at for 20 years, for my entire life, was going through another round of cuts, and this time, I was out the door. But I saw it coming. And I had already begun creating optionality for my future. For one path, I worked with a colleague to lay the foundation for a small consulting practice, where we could continue to work on the types of challenges I enjoyed solving, but for lots of companies, not just one. The consulting business got a strong lead right out of the gate. I thought things looked pretty good, and it was still so early. And then, as quickly as things had appeared, they evaporated. The lead went cold and other large opportunities weren’t coming in fast enough. I thought, “It’s just a numbers game though…”. But it turns out that the numbers game takes a lot of time to play out. Building a business from scratch is a very different type of work than filling a role in an established company. For one thing, its a lot harder to turn on and off, like you might with a 9-5. I began to feel like I was getting less quality time with my family. At the same time, I began seriously worrying about my ability to provide for them. I started to realize I had built a life, no I had built 6 lives, around a very specific kind of work. The kind where you get two paychecks a month, health benefits and respectable work-life balance. As this new business startup got tougher to get off the ground, I started questioning whether I have what it takes to be an entrepreneur. I realized I wasn’t actually doing any of the work I wanted to do and instead I was spending all my time trying to sell the work I could do… I started asking myself why I work? I think for as long as I can remember, it was just to provide a good life for my family. My interest in work had little to do with its intrinsic value. It was a means to an end. I worked to live, not the other way around. It didn’t matter if I was “fulfilled” by my work, because I find fulfillment in my relationships at home. And now my family has grown to a size that needs stable work to sustain it. Or so I think, because I don’t really know any other way and don’t have a lot of entrepreneurial role models to follow. So right now I’m wrestling with what I want work to be, or what role it should play in my life. The entrepreneurial work I find myself doing right now is not able to provide for my family and it’s demanding more attention away from them. Right now, work is running counter to the role I’ve always thought it should play in my life. It’s confusing, frustrating, and terrifying. And if I lived to work, I would probably feel very differently about it. Because for all the uncertainty, it’s one hell of an adventure.