The tortured entrepreneur

posted by Jeff | Wednesday, January 18, 2012, 12:44 PM | comments: 2

In all of the excitement lately, and particularly the forthcoming transition to a new job, I had the strange realization that I've become a little unbalanced in my professional endeavors. By that, I mean I've concentrated heavily on the primary paycheck without thinking about everything else that I care about, specifically my own business and ideas.

There is actually a strong and repetitious pattern around my behavior, and I can see it in my blog posts over the years. I get swept up in a new job, become disappointed with it over the course of a few years (assuming the company doesn't choke and start ditching people first), then I get energized over things I want to do on my own time, then forget about them when the cycle repeats. This has been going on for about a dozen years.

So what exactly does this mean? At times, I've mistakenly thought that it means I hate working for The Man. That's completely untrue. Working for others is exactly the thing that has enabled me to raise my skills to where they are today. Do I struggle with figuring out how to fit my skills and interests to a specific company? At times, sure, and I'm sure everyone does. But really, I'm thankful for every opportunity I've had, and what I've come away with in every case.

What I have developed, to some degree, is some level of contempt for the conditions surrounding working for someone else. In other words, I've always had an entrepreneurial itch to scratch, and sometimes the day job has anti-itch lotioned over the desire to the point it was completely obscured. Then, later, I realize that I had these ideas that I never did act on, because I was too busy with other things.

This brings me to the self-assessment stage of my realization, to take inventory. Things I'm good at include product design, software architecture, writing code, managing the process of development, marketing to customers, setting goals and deliverables, relationship building, etc. Conversely, I'm not good at accepting risk, starting up something or believing that what I want to do has enough value to overcome the risk. The things I'm not good at tend to be largely emotional issues rooted in fear and doubt.

When I put on my process management hat, I immediately think that next step is to reduce fear and doubt. Duh. Since the fear is largely rooted in risk, I've already started steps to reduce risk. Unfortunately, those steps will take probably two years to be fruitful, so there's a lot of expectation management on my own part that I'll have to do in that time. I think that the most important thing to do in that time is remember 1999 and 2000, when I very successfully managed to start a business and work a day job, with the two endeavors coexisting easily, and not interfering with my social life.

The most obvious change in my life is that my actions now dramatically affect my family, which I didn't have before. There's no changing that. What I've learned in the last three months is that I can manage those effects as well.

In other words, I'm figuring it out. As I'm blessed (or cursed) with a professional soul as part of my overall self, being happy in that part of my life means navigating a combination of corporate work and entrepreneurial efforts. Maybe the question that I've never asked, or developed a plan for, is, "Do I want to get to a point where I'm self-sufficient, or is the mix the best way?" If I try to intellectualize it, then the combination world is obviously the best (not to mention easiest and safest) way to go. If I root the question in my own ego and pride, then a strictly entrepreneurial outcome is best. Maybe that's what holds me back the most. I'm just not ready to risk the ultimate failure, or maybe I'm not willing to make a decision rooted in my pride.

As is often the case, you only go after what you want the most. Hopefully I'll stop dicking around and figure out what that is.


Comments

tigellinus

January 18, 2012, 11:24 PM #

So what's your opinion on the Seattle blizzard??

Jeff

January 18, 2012, 11:42 PM #

It's hilarious.


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