'Climbing Higher' no more

tl;dr In November of 2013, through a chance conversation with a casual acquaintance, I happened across what would turn out to be a pretty significant shift in my career path. After two years as the CTO of iTrellis, it’s time to move on.

When my first startup partnership dissolved, I was hunting around for a new gig, but I didn’t want to go back and take up being an individual contributor again; I’d had a taste of what it was like to be a CTO, and although it was just a very small taste (I’m sorry, but being the CTO of a two-person company is basically like being the “5-star General” over an “army” of you, a bottle of wine, and a one-legged housecat), it was something I felt I definitely wanted to do again.

An acquaintance heard about my search, and said, “We should talk.” Turned out he was currently the CTO of a fledgling consulting company, but he had just been offered a tremendous opportunity to go do his dream job (he wasn’t really keen on the whole consulting company thing). He wanted to know if I was interested in either joining him at his dream job, or in taking his place as the CTO.

Me, I’ve always really enjoyed the consulting thing, so I said “Sure, why not?”

Thus was I introduced to iTrellis.

Now, two years, seven clients, and 20 hires (and a few departures) later, it’s time to move on.

It’s with mixed feelings that I write this. We accomplished a lot. We grew the company from just the three of us founders to a consulting company of 20 people, occupying three offices in a co-working space in Seattle, working with a half-dozen clients on a variety of projects across several platforms (JVM, .NET/CLR, and NodeJS), and using some really interesting tools (Scala/Akka/Spray, for one, Azure for others, some DevOps stuff as well).

I have great faith in what I’m leaving behind—the teams are solid, the path forward is clear, and they have the tools they need to grow without me. I won’t leave them entirely—in fact, now that we don’t have that employer/employee relationship in place, I’m looking forward to being able to connect with them on a more informal, collegial basis. Go grab lunch and talk about something that has nothing to do with work. Toss back a Scotch or two. Gripe about our coworkers (without worrying whether it’s going to result in HR actions when that’s not really what we were trying to do). That sort of thing.

They’re good people, and they’ve been great to have along on this particular ride.

And what a ride.

Moving from what I knew (coding, architecting, advising around technical issues, advising around development process, and so on) to what I didn’t know was a breathy mix of challenging and scary and exciting and all these other emotions. I mean, what, exactly, do you talk about in a one-on-one with your staff? How, exactly, do you tell somebody, “Dude, stop doing that or I might have to fire you”? (Fortunately, I never had to fire anybody over stupid disciplinary stuff.) What qualities make up a good developer, and how do I test for them in an interview setting? Where is that line between “too removed to know what’s going on” and “micromanagement”? How much freedom do you give your team if they’re getting ready to go down a technical direction you’re not sure will actually work out in the long run?

What else do I need to do to make sure that these people all have a job tomorrow? And the next day? And the day after that? They’re counting on me—am I doing enough? Am I doing too much? Am I doing the right things, the wrong things, irrelevant things, things that will be useful later but entirely a waste of time now?

Oh, the questions. Finding the answers—talking to friends in management, reading management book after book, including a few Harvard Business Review ones—was a challenge all in of itself. For the first time, I was acting in a capacity in which I’d never participated, but always observed with a critical eye. A US Navy chaplain for whom I once worked (in high school, at the local YMCA) once told me, “You never know how you’re going to react once you’ve been given the Captain’s Chair”, and damn if he wasn’t right. I dunno if I did it right, or really wrong—that’s for my (former) employees to tell me, now, and I hope they will. I know there are things I could’ve done better—but I’m not sure I know yet what they were.

Challenges galore.

Inevitably, the question of “Why are you leaving?” will come up; in fact, it already has, from several quarters, and frankly, I don’t really want to say. It’s kind of like when you’re in that relaionship with that really great significant other, the one that isn’t a bad person, isn’t an abuser, certainly isn’t perfect, but also just isn’t perfect “for you”. You try to figure out why you’re feeling this way, and you just come back to, “They’re great, but I’m just not ‘in’ to them anymore.” All you really know is, it’s just time.

It’s time to move on.