Year Five

The average lifespan for a software engineering job is 4 years. Okay, I've never actually seen proof (or contradiction), but that's the general feeling in the groups I associate with. Perhaps that's selection bias - my employer has generally changed on year 3 or 4. Perhaps this is the exception and not the rule, in that case feel free to simply read this as an experience report. However, I do think it's somewhat common for developers to leave around year 3 or 4. This entry contains speculation on why they leave, and offers one idea on what employers can do to break that cycle.

My 4 year employment cycle generally looks like this

• Year One: "I'm in over my head. My semi-bluff was in-fact a bluff. They're going to fire me any day."
• Year Two: "It's nice to feel like a productive team member"
• Year Three: "This is fun, and I'm not bad at it. It's satisfying to pass on knowledge to teammates."
• Year Four: "This feels repetitive, that grass over there sure looks greener"

I expect that I, like many programmers, probably undervalue my contribution in the early days and overvalue my contribution in the latter days.

In Year Three and Four at DRW I spent some time thinking about how I felt, and observing the behavior of some colleagues that were also on year three and four. A few things stood out to me.

• A company you don't work at always seems to have infinite possibilities; however, after a few years with an employer, it's extremely clear what your options are. More importantly, it's very clear what limitations will likely always be there.
• A company you don't work at contains no code you're responsible for. Conversely, any company you've been with for 4 years probably has plenty of code you're not proud of. If you're responsible for that code, it's a constant reminder of your previous limitations. If you're not responsible for it, your co-workers aren't likely to let you forget about it anytime soon.
• There's always someone willing to pay you more than you're worth. After several years with a company it's likely that they're going to pay you what you're worth, but not what some other company thinks you're worth. I'm surprised that more companies don't pay (the employees they want to keep) what their "flawless market value" would be. In other words, what would you pay them if they interviewed, you determined what they knew, you determined what value they would bring, and you were completely ignorant of their flaws? That's what your competition is likely doing. That's what you're fighting against if you want to keep them around.
• A new job often offers a new challenge. Once you feel like you've given that challenge your best shot, what remains? If you did a great job, it's likely that you'll have plenty of other options. However, if you've done a good job, you may be stuck in a spot where there aren't as many open doors and challenges to choose from - not nearly as many as a position at another company will appear to offer.

I was recently in Punta Cana for wedding, and I was on the beach - working on my laptop. My wife asked: don't you want some time off? My response was short and immediate: no. Later that evening my wife and I discussed my work situation. I observed that I'm in Year Five at DRW and I'm happy, happier than ever, strange - given my previous experiences. She asked if I thought that I was working too much, and if I thought that I would burn out. I remarked: I'd rather have a job that I love, that I don't like to be away from, than a job where I feel like I need a week or two off.

I hear you, nice work if you can get it. I don't have a general recipe for getting there, but I know how I got there.

Back in 2009 I interviewed at DRW. At the time I was working for ThoughtWorks, and my client was Forward. I considered the founder of Forward to be a friend and someone I would gladly work for. I decided it was time to leave ThoughtWorks (after 3.5 years), and I was sure that Forward would be my future home. I remarked to my DRW recruiter "H" (who also happened to be a friend from my ThoughtWorks days) that one of the best things about Forward was knowing that I liked and trusted the man who ran Forward. H said nothing, but made a brilliant move.

In my interview I was grilled, killed even, and then things turned. I met with a guy who asked me a few questions and then told me about the company: the vision, the people, and where I could fit in. He was smart, easy to talk to, and someone I related to. We discussed things casually, it didn't feel like a company pitch in any way at all, it felt like small-talk - something I was very grateful for after the beating I'd taken previously in of the day. After everything concluded I hit the bar with my friends, including H. At that point they revealed to me that the guy I'd met was the partner at the firm that was (among other things) responsible for the firm's technology. I'd also met the CTO, and various other people responsible for technology in the firm. H had shown me that DRW, just like Forward, had what I like to call Awesome All the Way Up.**

Awesome All the Way Up has served me very well at DRW. To this day I remain in fairly common contact with the CTO and several of DRW's partners. About 6 months ago I asked 3 favors. First of all, I asked for enough money to pay someone's salary for 6 months. I identified a project that I wanted to undertake, and I needed help to complete it. Then things got unconventional, I asked if I could create a contract-to-hire situation. Even more unconventional, I pursued a friend and previous colleague who lived in Austin, Texas. DRW rarely uses contractors, and has no other remote employees that I'm aware of. An appropriate amount of questions were asked, but in the end my request was granted.

The experiment is on-going, but I'm very happy with our progress so far. That's all well-and-good, but the support of DRW is the important aspect of the story. I'm confident that their support of my unconventional requests was a major factor in ensuring my happiness in Year Five. We recently hired John Hume, thus declaring success at some level already. However, if things had gone poorly, both parties could have gone their separate ways with little lost and lessons learned. More importantly to me, DRW would have continued to give me confidence that they were willing to take chances to provide me with opportunities and ensure my continued happiness at the firm.

There's a similar discussion around DRW allowing me to use Clojure as my primary development language. I'll spare you the long version. tl; dr: They gave me a reasonable amount of space to try something new, and supported me appropriately as we found more and more success.

Not all of my experiments are green-lighted, and I've also had unsuccessful outcomes. DRW has done a good job of not setting me up to fail; my ideas that have a low probability of succeeding are fleshed out and appropriately shot down. All experiments have risk measures put in place, limited downside, and are reassessed constantly. It's great to have support when things are going well, and it's essential to have support when things don't go as planned.

For me, that's been the secret for keeping me around more than 4 years: An appropriate amount of trust and a willingness to experiment.

A foreign thought also recently came to mind. For the first time in my life I can say that I see myself happy and successful at my current employer in 10 years. This is a question I've asked many people since it occurred to me. To date, +AdeOshineye (http://www.oshineye.com/) is the only person who's responded affirmatively. The results aren't surprising to me, but I do wonder why more employees and employers aren't looking for ways to extend relationships.

Perhaps the secret for keeping me around isn't more broadly applicable; however, simply asking what will keep an individual around is probably the more important message in this entry. It's good to know what will make someone happy now, but it seems like it's equally important to know what will make them happy in the long term. I suspect the answers will be at least a little, if not very different.

The way things currently stand, I'm looking forward to writing about Year Six.

** DRW became my home in the end; however, Forward continues to do well. I suspect Awesome All the Way Up would have ensured happy and gainful employment at either destination. I remain in regular contact with my friends at Forward.