Mike Carlson
Aug 17 · 4 min read

Monday I’m getting on a plane and flying to Connecticut for a job interview

Who’s crazy enough to go to this much fuss to talk to me in-person? (say my self-doubting synapses)

I have had a weird career track. It’s been more of a career shamble, punctuated with increasingly tenacious self-talk (and associated actions taken) that I’m worth more than I’m making, that I’m never going to get anywhere waiting around for piddling little cost-of-living adjustments and infrequent merit-based increases, and so it’s time for a change. I have observed that this is a common pattern in the tech sector, as I see many of my peers jumping jobs every few years in order to make forward progress.

Briefly, I have a humanities degree, and my entry into tech — professional amplification of a passion I’ve had since I first stepped into a Radio Shack in the late '70s — was unusual. Fell in love during last year of college, finished college, followed love to Seattle, did AmeriCorps because it was a way to pay off student loans that was less likely to suck than 9-to-5 servitude, did second AmeriCorps year at a non-profit that was (unbeknownst to me) the serious community endeavor of a quirky and progressive local ISP, applied to said ISP at end of AmeriCorp service, got hired.

It stayed weird. I worked at Speakeasy for two years before the Dot-Bomb dropped and I ended up collateral damage. The convergence of already freelancing for some AmeriCorps-involved folks, getting a fat severance, and qualifying for at least 9 months of very comfortable unemployment benefits prompted me to try my hand at running my own show, as a consultant. It was touch-and-go around the one-year mark as my safety net disintegrated, but after teetering for a couple of months, I had enough coming in to pay the rent and not starve to death. This situation improved modestly over the next 5 years.

“Dammit, Jim — I’m a problem-solver, not a salesman!”

I got nearly all of my new business as referrals from my truly awesome clients. I’m not a sales guy or a marketer, and while I tried to be inventive with my advertising, all that effort resulted in just a few nibbles. New business slowly outpaced turnover, but Seattle was getting more expensive, too. By the time Terra and I had been a stable domestic unit for a couple of years, which was 2008, consulting had plateaued and I was supplementing with a part-time retail job. Our gross monthly resources of $3k were survivable, but with no health insurance, no nest egg, and accounts run to empty every month, something had to give. I also wanted to be more financially supportive to my three charges, and that further prompted the change.

After 6 years as my own boss, I went to work as a help desk tech for vastly less than I was worth, but still about twice what I’d been bringing in from the solo gig. Initially, my lack of solid corporate track-record and technical certifications worked against me. I spent 2 years at Classmates, 3 years at Apptio, a year and a half at SEI, and have now been at Oracle for nearing four and a half years. All the while I have invested heavily in cultivating a professional network via LinkedIn, which has not been in vain, and used each new position as an opportunity to move away from internal support and toward operations and engineering. The resulting track-record is expansive, with multiple areas of depth, which turns out to be a rare and precious combination in the era of “The Cloud”.

A few months ago, a former colleague who I never worked with directly at Oracle, but who served as my in-person technical interviewer for reasons of 'Montana’, pinged me with an opportunity. I like this colleague, would enjoy working with him again, and have deep respect for his technical depth, so I decided to look into it.

Let me frame this. Flying places for job interviews, having companies spend $1000+ just to talk face-to-face — this is something that happens… to other people. Up to now, I may have daydreamed about this, but it seemed unlikely to happen to me. Now that I think about it, as my experience has broadened, and my job prospects expanded, the distances related to interviews seem to have gone up as well. Of course, moving to — from an urban coastal perspective — the middle of nowhere in Montana magnified this tendency. I had to drive 200 miles from Missoula to Bozeman for the Oracle interview. More accurately, my wife had to chauffeur me 200 miles, as I was not yet a licensed driver at that point. For this new opportunity, I have to fly 2500 miles for the interview.

When I moved to Montana, one of my biggest worries was getting trapped in some career cul-de-sac, some small company with modest aims and no advancement opportunities, but which allowed me and mine a stable existence in this amazing state. I am excited to say this has not been the case, and an aim I’ve had for at least 7 years — to work 100% remote, and make good money — looks to be well within reach.

Mike Carlson

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I'm an atypical middle-aged white mountain-man with a strong interest in social justice. I answer to 'intellectual', 'introvert', and 'INFP'.

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