What I've learned in the last year--the hard way

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On March 26, 2008, I was dismissed from a job I held for seven years, where I did good work with good people and had a lot of fun and earned a decent living. If I hadn't been shown the door, I'd probably still be there. Instead, I've spent the last year squarely outside my comfort zone, for good or ill, and learned a great deal about myself. These facts include:

• Management is harder than it looks. During this past year, I was placed in an upper management position for around eight months. I was "the boss" in a very real sense for the first time. I'm rather introverted by nature, and my usual work flow is give me a task and let me go off alone and grind on it for a while. Being a leader required me to develop new skills that I had never touched on before. It was gratifying, but far harder than any actual "work" I've had to do before.
• Entrepreneurship requires passion, which I'm not known for. GameJabs, the software start-up I helped get going, has stopped going. Our funding got held up, we missed our window in the product space (others have started building products similar to those we planned, and we can't beat the head start), and my partner who fronted the money is auctioning off the codebase to recoup some of his losses. We tried, it failed, and it sucks. I liked the product, and would have used it, but I didn't live and die by its success. None of us did, and I think that played a large part in its undoing. I'm an even keel guy, and I don't rush headlong into much, and that's not the mindset that makes for a successful entrepreneur. I'm going to think long and hard before I undertake another start-up opportunity again.
• I hate sales, which makes me a lousy consultant. I've dabbled in consulting since December, when Vupal (my last day job with a different startup) folded. I've done okay, mostly on referrals from friends who had consulting work they didn't want or couldn't do. I've learned I'm lousy at chasing work, and selling myself. This, quite frankly, is the more important skill set for a consultant than actual competence at the work being done. I'm not a good consultant, and I don't like the lifestyle. I crave structure and certainty, and the freelance life offers neither. That's an important thing to know as I plan my next move.
• I'm a great souce of ideas, but passion is necessary for execution. Every company, partner, or client I've worked for or with in the last year has benefitted from my ideas. That's not hubris; that's what I've been told by these other parties, and the evidence I've seen of it. I've got a knack for coming up with viable options for almost any venture. The problem is I lack the passion to push most of them past the goal line. Like my friend Michelle (another person I've come to know and appreciate in the last year) says, your work is to discover your work. That's what 2008 has been about for me. I'm done chasing things I don't care about.
• I need to learn to say no. Lot's of people want me to help with lots of stuff (usually for free). I spread myself way too thin, and I don't like it. I missed evenings with my daughter, and weekends with my friends, and time at all with my wife, because I chased too many commitments and tried to please too many people. "No" needs to be an acceptable answer, even for people I know and like and want to see succeed. I can't do everything for everyone, even when I want to. This has been hard to accept.
• I don't want to leave Louisville. My easiest career move would have been to relocate to New York, LA, San Francisco, Chicago, DC or Austin. The kind of Web work I've done is in high demand in those cities, though the relative cost of living would have meant a rather drastic step back in lifestyle for a year or three. That's not why I stayed. I have friends and family here. My wife and I have friends in this town we practically consider family, we've known them so long and so well. I want my daughter to grow up spending at least one evening a week with her grandparents. I'm willing to sacrifice employment opportunity--and it's a serious sacrifice, because as much as I love my hometown, it is designed against innovation in almost every way--to make sure I can keep close these friends and family, in every way possible. They've gotten me through this year.
• I actually like working at home. Time was, I had trouble working from home because I had trouble separating work tasks (deadlines) from home tasks (laundry). In the last year, I've learned how to strike that balance, mostly through time management, and I've found I like--even prefer--working from home. I can get the car's oil changed and write up five blog posts in the same day if I manage my task list correctly, and I like that flexibility. If I land a day job that affords telecommuting, I plan to take extensive advantage of it.
• I'm good at writing, and I miss it. In this whole mess of insanity that has been 2008, I've done almost no fiction writing. My skills have waned. My art has been optional as I've chased work. This has bothered me, more than I expected. When I finally get settled--hopefully with a new day job--I plan to carve out a lot more regular time to write.
• I know what my dream job is now. When I was doing six things, chasing consulting work, trying to build a startup, helping a friend with her event-planning business, and had ten other balls in the air, I followed a whole host of people on Twitter: CEOs, social media experts, local ad agency people, technology experts, entrepreneurs, Web comic artists, and sci-fi writers. Only the last two groups ever really interested me. I relate more to the creatives, to the dreamers, to the folks that make ideas for a living. When all is said in done, that's what I want to do. I'm a writer, and I want to write. I'll need a day job for a while as I ramp up that line of income--and it may never be full time (Web work pays too well, and has benefits)--but that's what I want to do. I think I'm done with any other game.

I've been very lucky this last year, for all the jobs lost and stress endured. I've learned a great deal, and been pushed out of my comfortable niche to finally make some choices that I'd been putting off. My goals now: Get a day job, get my wife and daughter into a bigger house (as we're outgrowing this one), and get cracking on a writing career that has been stalled too long.

Depressed I'm not going to South by Southwest,

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For most of 2008, I had plans to attend South by Southwest Interactive for the first time. Initially as an employee of CNET, then as an employee of VuPal, then as a co-founder of GameJabs. (It's been an eventful year, employment-wise.) For various business and economic reasons, all those plans fell through, and as I search for my next day-job, I have to be more conservative with my discretionary funds.

Theoretically, I could go to SXSWi on the pretense of finding a day-job, but I'm not truly convinced that any job I'd find there would be different from most of the other jobs I've already found for which I'm qualified. As to why I'm having trouble getting one of those jobs? I don't want to take a drastic hit to my standard of living. As a Web content/product/social media guy, most of the work for me is in New York, Los Angeles or San Francisco. Thus, I'd either need to telecommute from Louisville (where my wife, family, and insanely affordable 3-bedroom house are employed and/or located) or I'd need to be paid far more than anyone is willing to pay me.

Paying several hundred dollars to attend an event that help me discover jobs I can't accept is bad business, which is a shame, because I'd very much benefit from the educational and networking opportunities to be found there. I'll just live vicariously through the 15 or so friends and colleagues that are attending, and hope that if any of them find out someone is looking for a kickass, SEO-savvy writer/editor/strategist, that they think of me.

Alas.

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