The Generalist Spectrum [#79]

"What's better, being a generalist or a specialist?” 

If you follow this newsletter, you know my answer and I know yours. 

But being a generalist or a specialist isn’t black and white – it’s a spectrum from the true “jack of all trades” to the PhD that has researched the same topic for his entire career. And the space in the middle is equally interesting. 

Today, let’s talk about the generalist spectrum, and how that spectrum explains which company size you should be working in. 

Let’s dive in. 

Let’s say you have four people of equal experience, and they all have the same amount of expertise units that they can allocate to different disciplines. 

• The purple guy is a true generalist and allocates all units equally. 
• The red guy is a true specialist and allocates all units to one discipline. 
• The green and blue guys recognize that it pays to be a bit better in some fields at the cost of being worse in others, but that broad education is important as well.

Think of it like a video game where you allocate "skill points".

The way you allocate these points defines where you stand on the spectrum. With every new year of experience, you level up, and get to allocate new skill points. 

The allocation of time spent on activities in real life is equal to distributing these skill points.

For example, when planning the new year, you have to make a decision: do you want to become super proficient in sales, or become generally better at building a business? 

Based on this decision, you can plan out your time and activities for the year, and make the necessary adjustments (ie moving into a sales role, starting online courses, etc). 

For 2025, my decision was to continue building a business while getting better at recruiting and copywriting. 

• 60% of my time is allocated to generally running the business, doing sales, building processes etc; but I’m not actively investing into getting better at these things
• 20% of my time (roughly, not exact) is allocated to writing and getting better at writing (by taking courses, reading books, getting coaching)
• 20% of my time is allocated to recruiting and getting better at recruiting 

This way, I’m slowly making my way towards an E-shaped expertise – broad foundations with spikes in a few disciplines. 

Next year, I can decide whether I want to double down on these abilities or if I’m happy with the increase in skills and want to raise the baseline elsewhere. 

Fun fact: the “generalism” seems to have foreshadowed a lot in my life – in role playing video games, I’d almost always build out a broadly balanced character, never a highly specialized one. 

There is no right or wrong way to allocate your points, but it does inform what roles and company sizes are open to you. ⬇️ 

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Specialization and Team’s Maturity 

This graphic explains why I’ve always had the urge to leave companies with >200 employees: 

In an early-stage company, there are a lot of jobs to be done but only limited resources (with the most extreme case being the solo founder, where you literally have to do everything yourself). 

This is great, as generalists bring: 

• a lot of versatility, and can adapt quickly to changing business needs 
• a higher growth mindset, and will grow with the company
• Leadership ability, so they can eventually become managers 

In a late-stage company, there are enough resources, so that for every job to be done, there is at least one person dedicated to only doing that job. 

The scale-up stage is somewhere in the middle, where you want people with higher expertise in a given field who can still adapt relatively quickly and translate between functions. 

That being said, it’s not impossible to grow with a company as long as you grow in seniority: you can still remain a true generalist by leading teams.

In fact, the higher the seniority, the broader the skillset tends to be: 

• CEO = true generalist
• VP = E-shaped generalist (ie. a VP of revenue would have spikes in Sales, Marketing, RevOps, but an overall broad skillset)
• Head of = T-shaped generalist (deeper expertise in one discipline, but still broad enough to communicate with other teams and see synergies)
• IC = specialist (only does one thing) 

But I’d argue that at a later stage, it’s almost impossible to be an IC (= individual contributor) and to be a true generalist. 

With this framework, planning out your next career move becomes easier: 

→ Want to work in an early-stage company? Broaden your skillset hard.

→ Want to work in a scale-up? Deepen your expertise in 2-3 disciplines. 

→ Want to become a manager? Broaden your skillset, while retaining your spike in one discipline. 

→ Want to have a corporate job? Go super deep on one thing. 

Conversely, this informs how you should hire depending on your company stage:

• Corporate = specialists
• Scaleups = T-/E-shaped 
• Startups = generalists 

Which is precisely why I mostly work with early-stage companies at Generalyst, the platform for A+ generalist talent in the EU. 

In short: 

1. Identify your next career step 
2. Decide where on the generalist spectrum you need to be
3. Allocate skill points accordingly 
4. Execute 

That’s all. Hope you have a fantastic week.

LFG. 🔥

PS: Remember how I adjusted my approach to making the national team after being cut from the roster in 2023 and 2024? Well … it worked.

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[2] Hire your next Founder's Associate or other business generalist position with my startup, Generalyst Recruiting.

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