The PE earlier today has left me way too much in my head. I find myself questioning my value to the company I work for, to other people and to myself even. My new manager put it best that if you're spending a third of your life working, you might as well figure out how to make that a positive experience.
But after a soak in the hot tub before the freezing death rolls in tonight, I took a little stock and realized that I'm in a very good place in terms of a relationship, I have a wonderful group of core friends, I'm not entirely unhealthy, and in the general sense life is treating me pretty well.
So in order to figure out how to roll in terms of my professional life, I think it's best to look at where I've been, and my relative state of contentment along the way.
My first career job, technically came in high school working for the city's cable TV office. I got to use professional gear and learn the (analog) craft of television production and basic engineering. It gave the dorky kid something to do.
My next "real" job was as a part-time jock at a radio station in Mansfield. That ambition quickly moved me into what was then market #23, Cleveland, and I learned quickly that it was a shitty business. The divide between sales and marketing and everyone else was huge, and there were starfuckers everywhere on our side of the building. Deregulation was in progress and Clear Channel started moving in. Getting laid-off was good for me.
1996 brought my longest running gig to date, running the city and school cable TV operation in Medina. I was there for three years. When I started, they had a bulletin board channel, and that was basically it. I got to use my business sense, some marketing, engineering and creative energy. I got off to a rough start because I "took" the secretary's job doing bulletin board stuff, but eventually the people I was working with around town saw me as a valuable asset. While every job has politics, I answered to a board of politicians though, and they didn't like me saying no to their special interests. That may have doomed the salary alterations to get me to a pay grade like that of my peers, but that Internet thing was taking off. It was media on the cheap, and I liked that.
So in 1999 I moved to Penton Media, as Webmaster for a group of magazines. It wasn't a true development position, but it introduced me to enough technology that I started to learn how to use it myself. That was an exciting gig because people around me trusted me to be an expert at what we were doing. I was soon sitting in meetings with executives, wearing jeans, as the hip late-20's guy who understood the broad potential beyond brochureware Web sites. The golf/sales culture wasn't my scene, but I was bridging the gap between sales and editorial and the techies, and I loved it. I was making meaningful progress when the bubble burst, and the company quickly started to tank. When they cut the development staff, I saw the writing on the wall and jumped ship in 2001 because I couldn't afford to be unemployed with a wife in grad school and having just bought a house. Leaving made me sad.
Onward to a small start-up B2B publisher, I was finally hired into an actual development role. Back then we had to use ASP, which like all scripting languages is messy and cumbersome, but I was starting to learn about the data more than anything else. That job deteriorated quickly because what they really needed was three developers. Then 9/11 caused them to cancel a trade show and they were in danger of dying entirely, so out I went.
I was out of work for six months, which really fucked with my self-esteem. Eventually I landed at a local family-owned payroll processing firm that wanted to build a Web interface to their app. Only they never really facilitated an architecture that would let me build that. They were using FoxPro, so I don't know why I was surprised. But I hung out and had nothing to do every day, until they finally laid me off after a year and a half. They did me a favor because I was getting brain rot and didn't even realize I was miserable.
That gets me to early 2004, when I started working as a consultant at Progressive, out of work for only a couple of months. They paid me astronomical amounts, but it was more like a retainer because they weren't ramped up for the project I was on. In the time there, I did learn a great deal about giant enterprise architecture though, working with some brilliant architects. Before the payroll processor dumped me, I was already talking to a publisher about writing a book, and finally got the contract.
In May of 2004, I declared my independence. I'm not exactly sure what happened after that, except to say that I did in fact write my book. On one hand, I have a lot of great memories of writing, and researching the as yet unreleased .NET v2.0. It was even the year I started to rewrite POP Forums (ouch!) the first time. Sunny afternoons on the deck, random trips to Cedar Point and a smile every morning. What was difficult was that Stephanie was at school most of the time, and I started to feel a bit isolated. I wasn't sure if, as a developer, I could really learn as much as I could if I were working with other people.
By the time 2005 started, I started working for a local development consulting firm, on a project for a student aid calculating firm. It was exciting at first, and I liked the client, but it was being project managed to death and despite my prodding, I couldn't get us moving toward actually developing product. That was frustrating. Then I discovered they were billing $90 an hour and paying me $55, which felt dirty. Then the separation happened and none of it seemed important.
I quit that job in the late part of summer and spent the rest of the year up to October focusing on coaching at Our Lady of The Elms. While a handful of asshole parents could've easily ruined the experience, it ended up being one of the most rewarding things I've ever done. Desire and heart go a long way toward making up for a lack of skill, and when those kids had the desire, they were awesome. In the last quarter of 2005, I didn't do much of anything except be pathetic.
With the start of 2006, Insurance.com found me online somewhere and made an offer I couldn't refuse. The time was right too, because I was bored out of my skull, not learning anything and desperately needed something to keep my mind off the fact that my marriage wasn't coming back. The first year was tough making adjustments, and then last year was easier, but I wasn't sure where I fit. That gets me to where I am today. Where Progressive schooled me in enterprise architecture, this job has taught me a great deal about frameworks and design. Most of the time I like it.
During all of that time, it's clear that my time at Penton was probably my favorite of all jobs. It was sad to see it end, and the company only fell apart more after my departure. We were really on to some great things there, but the timing sucked, and the executives were too clueless to empower the Internet product (they treated it as "value added" instead of "replacement for your dead trees"). But I loved that place between the technologists, sales and editorial staff. You could see the money potential, and it was obvious even with the overall decrease in ad spending.
I saw a story on the news about how people hit their most unhappy times in their 40's, because they feel like they failed to achieve everything they set out to do in the excitement of their youth. But really, if you look at how you've changed as a person, how the world has changed, I think the ultimate conclusion is that you've necessarily adapted, and you've changed too. I never want to work in radio again, and it doesn't mean I failed, it just means my needs changed.
And that, ultimately, is the thing that makes me happy. I can always change if I can't make things work. Maybe a year from now I'll be an all-star where I work. Maybe I'll have moved on to something else. Maybe I'll come up with that great idea and be the next Zuckerberg. More likely, I'll be some combination of those things, and perhaps realizing that is a true measure of success and happiness.