Rediscovering the known: being a generalist

I often joke that I can do everything, but I’m good at nothing.

This joke is less of a joke if you measure it by how easy it is to find a classic job.

I am rediscovering being a generalist.

The Eierlegende Wollmilchsau

There’s a German phrase for this:

Eierlegende Wollmilchsau. The egg-laying-wool-and-milk-producing-pig.

Eierlegende Wollmilchsau: egg, wool, milk, pig — all in one.

A mythical creature that does everything.

I think I am that animal.

How you end up here

In hindsight, it’s clear. I was jumping all around, never quite specialising.

I started in the SAP area and grew into range rather than depth: solution architect, development consultant, always switching between business and technology.

When you realise you like connecting the dots across tech, people, and business more than staying in one lane, starting something yourself feels like a logical next step.

So I started a business. Starting a business is pretty much exactly what a generalist does, or should be doing. Ambiguity, no clear playbook, figuring it out, selling, building, talking to customers.

After that, the business got acquired, and I worked as a CTO, then started something new.

A few bootstrapped apps later, I’ve been paying the bills myself for about a year and a half, dipping into savings, but not breaking even.

Since I left the corporate world, I always had this backup plan in the back of my head:

If startups don’t work, I can always go and find a job.

What the market looks like

I’ve been looking for jobs for a few months now.

Result? Not a lot of interviews. Not a lot of replies. Not much progress.

If I look at classic roles - backend engineer, enterprise architect, staff engineer - I’m unlikely going to win those. Not because I have no experience, but because I don’t have the depth.

A company looking for a hardcore backend engineer with 15 years of experience will prefer the person with 12 years of exactly that over the person with 20 years of “I can figure it out.”

They don’t need a pioneer; they need someone who has depth.

The roles that do get a reply are rare.

It will include something like this: Startup founder mentality, zero-to-one, build a new capacity inside a larger business.

In other words: the Eierlegende Wollmilchsau.

There just aren’t many of those listings. And there is no clean job description that says: we’re looking for a software generalist with 20 years of experience.

Three CVs

The clearest sign of the problem, for me, is that I maintain three different CVs.

One geared toward solution architecture.

One toward forward-deployed engineering.

One toward technology leadership.

I use them separately depending on what I’m applying for.

Ideally I’d have one CV - “I’m a generalist” - and apply to generalist roles, but those roles don’t exist as a category.

Detours look different depending on who’s reading

For a generalist, detours acquire range. In a specialist hiring process, detours are what you have to explain.

Solution architect/development consultant. Startup founder. CTO. Consultant. Software builder. Forward-deployed engineer.

All of these are different pathways I could have individually specialised into. But you can’t have both.

To me, my profile reads something like: adaptable, can operate in different environments, can figure things out, not scared of undefined problems.

For the majority of classic roles, however, it will look like I can’t decide what to do and therefore can’t master a topic.

They want progressive depth in one lane.

It’s not only that they won’t hire me, however.

It’s also that I don’t like these roles.

I like being pulled into different problems.

I like things that aren’t fully scoped. I like to experiment, drive something forward, and figure out uncertainty.

The roles that would be easy to map onto a job board aren’t really the work I want.

The work I want doesn’t show up as a normal title with a normal hiring funnel.

What this leaves you with

This doesn’t mean generalists are stranded. It just means the standard “Plan B” of submitting CVs to traditional job boards was the wrong tool for the job.

Hunting for non-standard roles using a standard hiring funnel doesn’t work well.

It changes how I look at the options going forward:

• Double down on building: Keep working on products and bootstrapped projects. Zero-to-one progress takes time.

• Sell range directly: Lean into consulting or fractional work, where clients hire you specifically to handle cross-functional ambiguity rather than fit into a fixed org chart.

• Target the rare frontier roles: Focus exclusively on those rare positions that explicitly need an Eierlegende Wollmilchsau to build something new from scratch inside a larger company.

Being a generalist is great; plan B just doesn’t come neatly packaged on a job board.

Realising that doesn’t make the path easy, but it changes how to navigate it.