Ask Me Anything

I too am a generalist and completely empathize with your situation.

I can't speak to your specific situation without a lot more context, but I'll make some general observations around the trade-offs with being a generalist versus being a specialist.

• As a gross oversimplification, large companies appreciate specialists, whilst tiny companies appreciate generalists. This is because once a company gets small enough, you don't have enough specialized work to spend an entire person's full-time salary on. You need everybody to be fractional on everything.

• Generalists tend to do better when environments change quickly because the thing a specialist is good at sometimes becomes worthless if a company changes direction significantly.

• To be compensated well requires that you have a skill that is both valuable and rare. Specialists can often be valuable because they are rare, by definition. That rarity, of course, comes with the risk that the thing they have invested their life in becoming good at may one day be useless. At the extreme, you can imagine a general manager of a Fortune 500 company likely has valuable skills that can survive many industry changes.

I suspect the key question is to know whether you ultimately enjoy the work of being a generalist or you want to invest in becoming a specialist. People's dispositions are very different here, and I think an attempt to become the type you are not is unlikely to lead to long-term happiness.

I am a generalist. I could, in theory, choose to specialize, but I tire of things easily if I'm in a domain for too long. Acknowledging that I am a generalist, I do better in situations where:

• the company is very small, so that generalists are more valued, or

• things are changing very dynamically, such that a generalist is obviously more capable of dealing with whatever needs arise

Lastly, I'll leave you with this thought: almost every company, once you get senior enough, requires a generalist. The man operating artillery is definitely a consummate specialist, but his General is called a "general" because that much larger scoped job requires the ability to handle everything.

Opinions on where this is going vary a lot, understandably, because we're going through a time of unusually rapid change. If you even consider how much opinions have changed within the last three years alone, you'll see that any guess of mine is equally likely to have huge error bars. But I'll make a few observations.

The cost of producing software is definitely going down. The speed of producing software is definitely going up. What's unknown is how far these two things have yet to go, and in what time frame. There is a lot of talk recently about Jevons Paradox because it's unclear whether the decreased cost and time of software will lead to much greater demand or whether it'll shrink the workforce. I don't have an informed opinion here, but I'll observe that in my own life, I have been building far more software now, a lot of it custom for my own use, simply because the cost of building has gone down. I've also been building more prototypes that could become useful tools for other people. At the same time, I canceled my contract with a Brazilian programmer with whom I had been working for the past two years building software together because the state of AI has gotten to the point where his salary became way too high in comparison. So, in my own life, both things are going on: I am building more software because its cost has gone down, and I have eliminated the job.

I'm not sure if it will all end up in just taste and judgment, though. If AI building software really is like everyone having a word processor, then it's true that all that remains are the thoughts of the people who know what to write on a page. But I wonder if it's more like a carpenter with a nail gun (something I've personally used before). While it's true that even amateurs can use a nail gun (and occasionally might even hurt themselves seriously), a professional carpenter is going to be much better at using the same tool. Professional carpenters continue to be employed; they're just each personally more efficient than they were before nail guns were invented.

I don't know which direction all of this goes. I will say, however, that the last two decades in software will likely come to be viewed as the halcyon days of software development as an amazing job from a compensation perspective. My intuition, given this uncertainty, is that people should only get into software, as they did in the 80s and 90s, because they truly love the creativity of it, not because they feel like there's some sort of guaranteed awesome job at the other end.

This is hard to answer without knowing specifics about you or the team. But here are some general thoughts that I feel help in most situations:

• Take time to understand the full context before making big changes to what the team is doing. Someone at your level is expected to lead initiatives on the team, which you will absolutely do in due time, but it's important to only make moves once you understand enough context. A lot of the first weeks is about learning that context.

• Relatedly, teams have very different interaction expectations with how they collaborate with each other. Some teams favor strong, independent action: shoot first, ask questions later. Other teams can be very committee-oriented when it comes to making changes on the team. There are many ways other than these two to work, and so fitting in well is often about shaping your natural inclinations toward how the team prefers to work.

• In your first weeks and months, it's especially important to get feedback that helps you quickly attune to expectations of your manager and of your team. You should get this feedback both by asking your manager explicitly, but also by asking key members of the team that will know your work well. The frequency of feedback can go down as you're in the job longer because you'll increasingly be vectored in the right direction. In your first few weeks, especially, it's easy to go off course if you don't get corrected early.

It's exciting that you're starting a new job! Wishing you all the best.

Most people who ask me something are actually trying to sell me something. For instance, when they try to sell me leads, I often respond that I'm only interested if they're "the Glengarry leads." This is how I've come to know that most of these outreaches on LinkedIn are likely driven by AI, because their responses to me show that they're definitely not human beings paying attention.

Occasionally, people ask whether I'm looking for employment. Sometimes a startup will ask whether I might be able to join them for a while. In truth, I think most jobs, at least for me, come through asking friends who've joined interesting companies whether they have roles open. I rarely get a cold offer, which frankly would be weird if people haven't interviewed me.

I have often considered being a CTO of an early-stage startup. It's probably not the right thing for me, at least for now, unless I know the existing founders or I have very high confidence in them. What's far more important for me these days is the people I work with.

I don't think much about terms and evaluation, but I would love to join something that is strongly purpose-driven for everyday users. I tend to be less interested in enterprise-type products.