I’d been a first-level manager in the software industry for 15 years, leading testers and technical writers, when I was passed over for a promotion to Director. It pissed me off. I was a good manager who had accomplished a lot for that company, and I was ready to stretch into the next level. I thought I deserved the chance. I don’t think it’s just my ego talking when I say I would have done a better job than the man they brought in and for whom I had to work.
Then I got a call from a startup software company: was I interested in being a Director for them?
Why yes. Yes I was!
I don’t know where my ambition came from, as I’d had little of it before then. Since I was a teen I had wanted only to work in the software industry. For a long time I was perfectly happy writing technical documentation and testing software to make sure it worked as intended. I didn’t seek to move up the ladder; my first management job fell into my lap.
Yet through my early 40s I felt pangs of discontent. I could see ways to do things better, but as a manager I lacked the authority to do much about it. I itched to have more clout and make a bigger impact. Also, as my kids were headed toward their college years, the extra money of the Director level appealed to me.
I got the job and dived belly first into boiling water. What a mess things were there. Not only did I build their test team from scratch, but I also turned around their broken software delivery system. I wasn’t able to fix the company’s fatal flaw, however: the product was a hard sell, and we kept widely missing our sales goals. We rolled and pitched as upper leadership had us build this and then that into the software hoping something would catch on in the marketplace. Nothing ever did, not enough to make a dent in the market, not enough to satisfy investors. Sales became frightfully poor for six months and it became clear they’d have to cut staff. They showed me the door.
I moved on surprisingly quickly to another young company, beyond its startup stage but not yet mature. I built a couple functions from the ground up as a Director there — another testing team, and a program management team. It was great fun and I liked it there a lot.
Yet I’d started dreaming of being a Director of Engineering. Testing had become old hat for me, and because of changes in the industry opportunities were drying up. But also, I knew that quality starts at the top — you have to build it in. To deliver software as well as I knew it could be done, I’d have to do it by leading the software developers.
My chance came two years ago. An executive I knew and admired wanted me to lead engineering at his startup. I jumped at the chance.
I proved there what I wanted to prove all along: that building a product well from the start is better and faster all around. Our product had few bugs, it held up under load, and it scaled with the business.
But after we built the core product, there were internal disagreements about what to build next. It undermined everything. The executive who hired me had ideas, but he didn’t win over the rest of the execs and in the end he resigned. The person they brought in to replace him treated me badly, and as you know if you’ve been reading this blog for the last six months she fired me with neither explanation nor warning.
I had proved to myself that I could do all the things I wanted to do — but so what? It didn’t save these companies, it didn’t give me the feelings of accomplishment I wanted, and it sure as hell didn’t bring me the respect and admiration I was secretly looking for. Instead, I wound up on the street.
The job I was able to get before my family’s finances got rough is as a first-level manager. It stings a lot to have been essentially demoted.
At least I’m still in engineering. Also, I’m a deeply experienced first-level manager; this is a job I can do well. Even better, I’m in an organization that, while not perfect, functions reasonably well. As in all companies there are business challenges, but there are agreed-upon plans to work through them. If you’ve ever worked for me, you’ve heard me say it: even a mediocre plan will work if everybody follows it. Also, because the company is mature it pays market rate, something startups don’t do. I make the same money I did before as Director of Engineering.
I’m dancing on a fine line. To accept where I am feels like giving up on my dream. Even though I found out my dream isn’t all it’s cracked up to be, a part of me wants to double down on it to prove it was good all along. Maybe I should get a new dream. Or maybe I should stop dreaming and be content with what I have, because it is objectively good.
Last updated on 2 March 2020 by Jim Grey