Thoughts on Working at the Same Company for 10+ Years

Baby chowing down on birthday cake

I've been working for AlumnIQ since March 2nd 2012. Today is my 10 year work anniversary.

In 2020 on the occasion of my work anniversary – just a few days before the pandemic got real here in the U.S.! 😬 – I wrote about how the most common advice in tech is to quit your job every couple of years to get a significant salary raise, but that somehow I had managed to stay in the same place for 8 years. I attributed that to finding success in products, and the new and interesting challenges that brings with it.

Two years on and not much has changed, perspective-wise. I still love what I get to do every day because my job isn't, "Design and implement another CRUD form for another database table;" it's, "This feature has been so popular that the naive initial design is becoming a problem. Make it more resilient."

These types of challenges are great opportunities to think creatively, and they're hard problems to solve.

We continue to have all of the best problems you could hope for. Our products and services are selling well, our customers are the right mix of happy and demanding of new features, and we all enjoy working together. Occasionally users push the limits of what the software is capable of, and this is an opportunity to design and build something even more capable, or to help them fall into the pit of success.

This is exactly the kind of work I most enjoy: Avoid premature optimization (see also: design naïvely), and then when the seams start to buckle, make that part of the system more complex to support its increased demand.

The team is really small, and even that has its benefits. I've worked at organizations that had 10 people just on my team. AlumnIQ is 5 full time employees plus a few seasonal helpers for on-site operations when we do in-person events.[1]

Just 3 of those 5 people are on what I would consider "my team" and 1 of those 3 is me. It means we're all on-call every 3 weeks, which is a little bit of a bummer to be honest, but it's also in large part responsible for the fact that most of the time we go from a need, to coded, to reviewed, to shipped in hours or days, rather than weeks or god forbid, months. Meetings are kept to an absolute minimum because you're not just wasting 2-3 people's time, every added person attending that meeting is burning an additional 20% of our ability to be productive in that moment.

It's kind of a point of pride that we make a big impact with a small team.

I had to schedule a meeting with a couple of customers to discuss a change we'd like to make, and even just the knowledge that I'm going to have to wait a business-day or two (weekends, ugh!) to get some face time and my questions answered is more friction than I'm used to, and it was startling how odd it felt.

The idea of having more people to share the workload (and the on-call schedule!) with is appealing, but the idea of the bureaucracy and politics and red tape and ... that comes with working in a big company again makes my stomach turn.

I've been working from home full time for 10 years. It took some getting used to (as you all now probably know), but it's become so normal that I can't imagine going back to an office full time. If I did, I might need to bring my dog, cats, and my fireplace with me. I don't think that work-from-home really works without actual trust from the top of the company, so that's been another fringe benefit, too.

Could I have doubled my salary by now by taking jobs I'd be less interested in and moved my family around the country a few times? Probably.

Would I be as happy as I am with my house, my neighborhood, the school my kids attend, my hobbies, my access to entertainment, and so on? There's no way to know for sure, but I can say that I'm quite happy with what I've got and I wouldn't gamble it.

I like to think of it as investing in whole-family happiness. We're close to family and friends here. My kids have a good chance at having a few friends that they know for effectively their entire lives. That's not an opportunity I had, but it's one I'm glad I can give to my children.[2]

Not only that, but I now have 10 years experience building a single product from scratch and all of the really good, and really bad decisions made along the way. That's a pretty unique and really valuable experience.

If this article has a take-away, I guess this is it: It's ok to settle down.

Change jobs early in your career when you feel like you've leveled up and your salary doesn't reflect that. If you like where you work at that time, ask for a promotion first. It'll be easier to do this when you're umarried or early on in your family, than after you have school-aged children and established support networks.

But if and when you land a job that challenges you the right amount, where you like the people, and you like the work, and there are lots of little benefits that you couldn't or wouldn't get elsewhere, it's ok to plant roots.

Cheers to ten more years. 🍻

  1. Remember in-person events? Those were the days! ↩︎

  2. This is not said to disparage my parents. They were pretty good ancestors – they traded one thing for another. Giving up geographical stability to gain financial stability is an easy decision to make, and I benefitted greatly from their sacrifices. ↩︎


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