Generalists 🎨

How to navigate your skills and career as a generalist.

Sep 16, 2021

My longest professional experience has been as co-founder and CTO of a VC-backed startup.

As a co-founder you rarely stay in your lane. Over time I had frequent forays into product, operations, marketing — basically anything about our company life.

When this experience ended last year, I reflected on my strange set of skills and I struggled to see what my next act should look like.

Looking at various roles I could apply for, I often felt uncomfortable for two reasons:

I felt unprepared — I knew what these roles were about, but in the past they had been only part of my job, or just briefly.
By working full-time on a specific role I wouldn't leverage other skills I had acquired and genuinely loved.

Talking with some friends it turned out to be a common feeling, and the diagnosis was clear: I had turned into a generalist.

Generalists

The separation between specialists and generalists is not clear-cut. My personal definition is:

🔍 Specialists — focus on a specific domain that has a clear career and professional growth path.
🎨 Generalists — have had a wide array of experiences that do not all contribute to a single professional path.

Specialists are usually intentional about their careers, while generalists are born out of founders, unexpected career shifts, early startup employees, and a long tail of unorthodox situations.

People rarely decide to become generalists. It just happens.

So, just like they don't come from conventional journeys, generalists may have a hard time fitting conventional companies. Large, structured orgs tend to have most roles carved for specific skills, which is reasonable as you get to scale teams and processes.

They expect people with T-shaped skills, while generalists may have more of a..."rake" shape?

Nevertheless, your generalist career can be amazing if you navigate it properly.

Let's figure out how 👇

Generalists’ superpowers

Generalists have several strengths, and they all come down from a major one: they are open. If you look for an edge you may have over specialists, it isn't in your skills, but more in the way you think.

When you specialize in something, you slowly become biased. Your toolbox is made of some specific tech and processes, and you risk to become overly attached to them because you feel your career depends on them.

In other words, you risk to shift from the "choose the right tool for the job" mode, to the "when you only have a hammer, everything looks like a nail" mode.

This is not inevitable, of course. The best specialists I know keep themselves updated and jump timely on new trends. It's just not always easy — you may find yourself stuck in local optima that are uncomfortable to leave.

By developing a wide array of skills, instead, you keep optionality and get three major strengths for free:

📚 Learn fast — generalists are learners. They are used to pick up new things fast and they don't see them as a threat to what they already know.
🏃 Get things done — they look for the best way to deliver value, instead of trying to fit a specific skill to the task.
👁️ Systems thinking — they develop a wide perspective that helps them to create strategies, find bottlenecks and help with processes.

How can you use these strengths in your career? 👇

Generalists’ careers

Career options for generalists are just like their skills: diverse, unusual and interesting. It would be impossible to list them all, so here are the three directions I have seen applied the most, with success:

🚀 Join a high-growth, early stage startup

In a high-growth environment your ability to wear multiple hats is invaluable.

Startups always have more things to do than people who can do them, so you will find plenty of ways to apply what you know, take responsibility, and keep growing yourself.

As the startup gets larger it will also give you the opportunity to take a more specialized role, should you want one.

💼 Go for a management / operations track

Systems thinking is critical for managers and all people working on processes.

In these roles you often don’t need super specific credentials to excel — even more so, your broad experience is an asset.

As a manager you need the end-to-end vision to guide your reports, the curiosity to learn from them, and the right amount of knowledge to challenge them when needed. As a generalist you may have all of these.

📈 Leverage your experience in an industry

If you had multiple roles but mostly in a single industry, you can go for specific roles in that industry, compensating your lack of experience in the role with your experience in the industry.

Many companies are willing to take this trade off, especially in industries that have non-trivial learning curves (e.g. crypto).

📚 Resources

📑 When Generalists Are Better Than Specialists, and Vice Versa — this fascinating study by HBR compares specialists and generalists performance in fast-evolving and slow-evolving fields.
📑 Don't Underestimate Generalists — fantastic interview with David Epstein, who wrote the Range book about generalists. Filled with insights and examples. I haven't read the book — but the interview convinced me to.
🌀 The Three Stages of Engineering Teams — generalists and specialists are both useful in engineering teams, only with different roles and in different stages. This article contains a simple framework for structuring your engineering team, inspired by the Instagram team story.

📣 INTERACT Conference

I am really happy to promote the INTERACT event that will take place on September 30th.

INTERACT is a free, community-driven conference, built by engineering leaders for engineering leaders. It will include interactive sessions and stellar speakers, such as Twitter’s VP of Engineering Maria Gutierrez.

I will also join as a speaker, so stay tuned for a funny — and hopefully insightful! — engineering story.

If you are interested in learning how other leaders are scaling, improving, and solving problems, you can reserve your free spot to the virtual event below 👇

Learn more

⭐ Weekly Featured Jobs

Here are the remote engineering jobs featured this week! They are all from great companies and I personally review them one by one.

Haven — Founding Engineer — platform to enable users to engage with health and wellness providers
Commit — Tech Lead / Senior Engineer Fellowship — the remote-first community for software engineers.
Paperstreet — Full Stack Javascript Developer — the easiest way to share your startup's progress with anyone.
Coinbase — Senior Software Engineer, Enterprise Integrations — the easiest place to buy and sell cryptocurrency.