Generalise or Specialise?

Generalise or Specialise?
Photo by Alexander Schimmeck / Unsplash

I think it is worth it to try to figure out if you're happier being a generalist or happier specialising in something. Some initial thoughts here. It's been on my mind for quite a few years now.

Some of the main arguments:

"Generalists are flexible!"

  • You can switch quickly and respond better to changes.
  • You are able to make unexpected connections between fields.
  • In an uncertain world, it is less costly to invest it all in one field, if the bet does not pay off.
  • You can take advantage of our tendency to favour new things and have enthusiasm for new things to push your progress forward.
  • You can pick up new fields easily because you are used to the process.
  • You are able to explore fully what the world can offer.

"Specialists are valuable!"

  • Most companies want specialists who are good at what they do. They hire for a specific role.
  • It is efficient that way - adding on and deepening one skill is much, much easier than learning many disparate skills.
  • You don't have to do what you love - as you deepen your skills you would grow to love it and have it become your passion.
  • You build valuable patience to really get good and get the full rewards of learning a skill. Fewer people have the patience to wait it out; you get results more at the end than at the beginning. It is also more useful. We'd rather have an accurate calculator than one that can do everything.
  • Stronger branding; you're easier to recognise.
  • It is impossible to truly be a generalist in everything; we tend to specialise in a few things at the end of our lives.


If you tend to be more of a generalist, you'll like working in startups where you get to touch a little bit of everything. If you tend to specialise, then you'll find that being in large companies may suit you better.

Income streams

You can make money as a generalist, but you would deal with complexity. It will likely look like small income streams from many different sources. For example, running many small sites instead of one big one, on totally unrelated topics. Doing multiple part time jobs instead of one high-paying one.

Specialists will tend to earn more in a main job that they have rare skills for - few people will be at their level, and so they can charge a premium for their skills. This value is also more easily recognised by others. It's simpler to be known for one specific thing than many vague things.


Apart from extroversion and introversion, being a generalist and specialist will bring you into different social circles. Generalists will tend to have a lot of disparate circles and know a lot of people from everywhere. Specialists will tend to build deeper relationships with those in their field, eventually becoming more well-known and a thought leader in that field.

Reaping the benefits of both

So how do you get the most out of both, and hit the sweet spot? I've found a few suggested solutions to this problem.

Generalise in your personal life, specialise in your professional life

One way people balance it is by honing one career skill, and then exploring many hobbies on the side. It doesn't have to be all or nothing. This way, you can get the variety while still performing at work. For example, making music in your spare time without expecting it to make money. Not crossing streams can take the pressure off of art.

But, that may not be enough. Work may get boring, since you'll be spending a large part of your day on it. Some people don't mind it though. It is a gift to be able to explore what you like in your free time.

Specialise in many different things over time

Derek Sivers has an article on being too much of a donkey, whereby you try to pursue many different things at once. He proposes deep dives into them, one at a time. Of course, some things can't be done in a deep-dive style. For example, you could obsess over optimising your diet, but you'd still need to maintain it after to continue reaping the benefits.

If you do this with a career, you'd end up having to start over many times, sometimes with a corresponding income dip.

Don’t be a donkey | Derek Sivers

Personal observations

I've noticed that for specialists, their hobbies tend to be the same as their work - reading up extra on work-related issues. Putting in extra time because they are dedicated and committed and just enjoy working. Building up skills in that particular field.

I've found that I am more of a generalist - I like the initial learning curve so much that specialisation starts to bore me and, whenever I remove a commitment, a new one comes up to replace it. It does not come to me naturally to deepen my skills. My hobbies tend to be completely unrelated to work. Even the topics I talk about on this blog tend to be all over the place, just because life is complex and I enjoy exploring all the different things it has to offer.

Yet I've also specialised - I used to play the piano almost every day for 12 years, attended art classes weekly for about 5, and have been doing parkour for about 5. I finished a bachelor's degree in an engineering subject, too. So I know the value of specialisation and consistency, and the results it can bring. And given how much specialist skills are valued in the working world, I feel a lot of pressure to specialise. Imagine if I spent all those extra hours spent on art on the piano, or on studying theory - how much farther could I have gone, then? Not everyone is interested in everything. If I focused the blog on certain topics, won't I get more revenue? I am sacrificing depth for the thrill of doing something new.

But being a specialist makes me unhappy. I had to suppress urges to work on other things, and wasted time on social media instead because I didn't feel motivated to do anything at all. Keeping myself busy with variety has instead cut down on unproductive time for myself.

In the end, I think it may boil down to observing how you are normally without guidance. Derek's deep-dive model can suit patient generalists, but at this point for me, the variety of working on different projects is fulfilling in itself. Trading away mastery of a skill for this variety is worth it, right now. And by keeping this blog varied, it can grow with me.


Explore and play with the models. Find one that suits you and one you like, or come up with something new entirely.