The forward journey

A question asked from time to time in every career is, “Where do I go from here?” I’m confronting it now.

The view to the rear

I’ve been blessed. I started working in CPU hardware design, with the good fortune to work for “the” company at the high point of its existence.  I then worked for start-ups, as either an early employee or founder.  Regardless of their success or failure, all were educational.   Every job you hold should improve your toolkit and broaden your outlook, and I’ve been fortunate to have learned something from every experience along the way.

My greatest success was Singingfish, which was a bona fide home run. We sold it in 2000, after the dot-com crash, in a very profitable cash transaction.  Seattle start-up pantheons rarely list it, which has always puzzled me, since it was far more successful than some oft-mentioned local companies.

I’ve occupied VP or Director level positions for the past 12 years, except for a brief manager stint at Motorola.  I enjoy building and leading teams to do great things.  And individuals from my teams have told me they would gladly report to me again, which is nice. Start-up and small-company VP Engineering jobs have an interesting set of stresses that I’ll write about in the future, but on balance VPE jobs can be very rewarding.

My technical interests gravitate toward the back-end — web server development, relevancy, data relations, and so forth — but they take a back seat to the joy of simply getting things done.

The last tick

I’ve been working on TrenchMice since leaving DocuSign.  It’s been fun on multiple levels.

Python and Django. I was an avid Lisp coder long ago. (I’m old enough to recall when Lisp was LISP.) I found functional programming inherently elegant and more productive than procedural programming. But other career carrots captured my interest, and so I filed my LISP neurons away…

After leaving DocuSign, my good friend Joe Heck suggested I take a look at Python and Django. (This was after he suggested Ruby and Rails, but that’s another story.) I fell in love. Others have written about them with orders of magnitude more eloquence than I ever could. My summary: They ROCK.

Creating value. One day, there’s nothing. The next day, there’s a service that people use. That’s great.

Not dealing with undesirables. Working in a small team on a common vision is more enjoyable than, say, striving to Do The Right Thing in a poorly managed company that’s an Alaskan oil taker with a drunk incompetent skipper at the helm.

Working at home. What’s not to like?  I can get more done at home than at an office.  I roll out of bed and get right to work, and I can work right until I turn in at night.   She-who-must-be-obeyed isn’t entirely happy with this situation, however.

Now what?

TrenchMice isn’t yet yet delivering enough revenue to even be a lifestyle business. So Quicken, my wife, and my internal clock all tell me it’s time to move on to a new adventure.

There’s at least three paths from here.

Full-time engineering leader

A VP Engineering or Director position in a start-up or small company would appear to be the most natural direction, based on my resume.

I’m formulating a future blog post about the nature of engineering management. That’s an involved topic all by itself. For now, I’ll just say that while this position as significant pros, it also has a few cons:

• With corporate growth can come distance from the technology, and from the work being done
• Companies sometimes have a less-than-ideal delineation between the CTO and the VPE
• Non-technical founders often think they understand software and software engineering, and need careful attention lest they bite you
• Monday morning SMT meetings, PowerPoint presentations on long-range plans, annual budget cycles, etc., are necessary chores

Full-time developer

TrenchMice has been a great vehicle for getting hands-on with some of the latest open-source web technologies. And as I’ve said I’ve here and in other posts, I’ve thoroughly enjoyed it. So it’s appealing to consider becoming a full-time developer.

This kind of quasi-career switch is not without its perils. The most notable one being, companies pay more for management positions than for individual contributors. That’s wrong, but changing the nature of work in America is way beyond my capabilities.

Contract Python+Django developer

Another option is Python and Django contract work. I’ve always worked full-time, so this offers the additional excitement of mastering a new work mode. The major problem here is, again, money.

The way ahead

I’m now evaluating contract and full-time positions, and thinking about what would make me happiest.   I’m having a particularly hard time deciding what will best position me for the adventure after this next adventure. Believing every job should enhance your toolkit begs the question of what toolkit to have.

The Seek Nuance LLC is in place for freelancing, and maintaining it costs little. So now all I have to do is decide what I want to do. Having multiple paths from which to choose is a “good problem to have” — there are worse alternatives — but that doesn’t mean I don’t have a lot to ponder.  And I do have to get off the dime, at some point.

I’ll blog about my continuing process on this. Even if nobody reads it, writing it helps organize my thoughts. 🙂