From the blog.

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“What Might Have Been?” Is The Wrong Question

768 Words. Plan about 5 minute(s) to read this.

A friend sent me a picture of an ink stamp from a company we started back in 1999 or so. It was a little consulting & hosting company that delivered for our customers things that we were good at: web hosting, e-mail services with spam protection, and a variety of SMB IT services. A little Novell. A little Microsoft. A little Linux. A little Cisco. You get the idea. We had a small customer base, and our customers loved us. We weren’t making much money because we simply didn’t have enough volume. And so, we never both dove in and just went for it. Or should I say, I never did. I had a family, a mortgage, a car payment, and not a lot of room for financial error.

On the other hand, my partner did dive in, billing most of the hours and making almost all the money, which made sense. The business was closer to supporting one person than two, and he was the one most in need. I worked the business a little bit on the side, chipping in when I could. I handled the web & email hosting, which was mostly a hands-off exercise anyway once customers were set up. I didn’t work on the consulting side of things, choosing instead to remain focused on my day job. Over time, I took yet another job with a larger organization than where I had been, rather than join my business partner in trying to build up the consultancy. Why? The larger organization was a sure bet. The small consulting business was not. With the larger organization, I had benefits and a steady paycheck. With the small consulting business, I had risk and responsibility.

Seeing the picture of that ink stamp brought back all of these memories, and made me wonder.

What might have been?

It’s hard to say. I didn’t get deeply enough involved in that specific business to see where things could have headed. My business partner did okay with it, maintaining a small customer base, and then selling to a larger consulting firm for a bit of money. Nothing spectacular, but enough to at least be able to say, “I built this thing, made it worth some money, and then sold it.” If he and I had gone for it as a unified force, could it have been epic? Hard to say, as consulting is a highly competitive business with fickle customers. Anyone that makes a go of it in consulting has my admiration.

Upon further reflection, “What might have been?” is probably the wrong question. That question is really a proxy for yet another question which is, “What do I want from life that I am unable to get?” That’s not a materialistic question, at least not directly. Rather, it’s a lifestyle question. Like marriage, children, mortgages, and car payments, choices regarding employment are tied to obligations such as showing up, doing your job, being reliable, contributing to the team, etc. Those obligations are what help you get from life what you need in the form of a hopefully steady paycheck, but might prevent you from getting what you desire.

My career has been a struggle between the need for security and the desire for independence. Security has always won out. In that context, “what might have been” doesn’t matter, at least not enough. Yes, I want independence. The lifestyle that independence affords greatly appeals to me. But if I have to give up the security of a predictable income to gain that independence, I am unlikely to convince my family that the risk is worthwhile. Of course, that’s another big part of the equation — family. Making the decision to go after your wants vs. your needs is more complicated when other people are affected by the decision. I never make a family-impacting decision on my own. My wife and I are comfortable with the decision together, or it doesn’t happen. And I mean genuinely comfortable. I don’t mean I browbeat her into agreeing with me, so that I can go ahead and do what I want.

So for me, what might have been or perhaps what could be isn’t nearly as important as what is. If your current state is meeting your needs, then is meeting your wants worth upsetting your life with a new job or new independent venture? Maybe it is. Maybe it isn’t. The decision is complex, and varies for everyone. While I’m sure I don’t know exactly what I might do in the future, I do know that I’m not going to keep going over the past.