You Are Worth More Than You Think

Someone’s going to ask: “What do you expect to earn?”

Imposter syndrome makes you negotiate against yourself before employers speak. Learn why you are worth more than you think and how to anchor compensation confidently.

This Substack isn’t my day job. It barely covers caffeine expenses. Like you, I need actual income and somewhere to keep my brain engaged.

For fifteen years, I made a living traveling the world, delivering keynotes, running workshops. I built a reputation inside what became the agile industrial complex—contributed to it in ways I’m proud of and, let’s be honest, in ways I’m not. That whole ecosystem has mostly imploded. I’m not mourning it. I had my run. Now I’m hunting for whatever comes next.

The search is wide open.

Teaching at a university? Running a regional startup hub? Working with a boutique consultancy? Taking an executive role somewhere that won’t waste my time? Joining a non-profit with actual teeth? Collecting advisory board positions? Some Frankensteinian combination of all of the above? Different contexts, different shapes, same underlying compulsion to do something that matters.

One thing became obvious fast: wherever I land, I need my own domain. My own territory. I need sole accountability for an outcome people actually care about. I don’t function as a component in someone else’s machine. I do my best work as a Solo Chief. And when you own the outcome, negotiation isn’t ceremony. It’s structural.

Which brings us back to that question.

“What do you expect to earn?”

That question lands harder than it should.

After fifteen years as a contractor and entrepreneur, I don’t really expect anything. Some years I cleared more than half a million euros. Other years—the Covid stretch, last year’s trainwreck—delivered a fraction of that. Volatility isn’t a bug in entrepreneurial life. It’s the entire operating system.

On top of that, I’m terrible at negotiating. I see an interesting role and immediately think, “Well, that pays significantly less than what I used to make. I should probably lower my ask.” You see what I just did? I negotiated against myself before anyone else got a word in.

And then there’s the voice that never fully shuts up: imposter syndrome.

Doesn’t matter what I’ve done, written, built, or sold. There’s always that quiet hum underneath: “Don’t ask for too much. They’ll figure out you’ve been improvising this whole time.”

That’s exactly the wrong approach.

So I did what any reasonable Solo Chief does when their own instincts are clearly sabotaging them. I consulted my team of advisors. In my case, that team consists of four AIs: ChatGPT, Gemini, Claude, and Grok. I gave them my CV, described the wildly different roles I was considering, and asked a straightforward question:

You are my career coach and negotiation advisor.

I have been self-employed for years and am now exploring a wide range of roles, from executive leadership and consulting to teaching or advisory positions. I’m sharing my CV for context.

When potential employers ask about my expected annual compensation, what should I say?

Please give me:

• a realistic but strong anchor number for gross annual compensation

• tailored to my experience and the Dutch market

• plus the reasoning behind that number and how to use it in negotiations

The answers were illuminating.

ChatGPT:

“Anchor at €180,000. You’re not pricing labor hours anymore, you’re pricing judgment. Your CV reads like C-level and board-level impact: founder who scaled and exited, ex-CIO with a 100-person org, global IP and credibility. An anchor in the high executive band signals ‘strategic hire’ and gives you room to negotiate structure (bonus, equity, autonomy) without downgrading yourself before talks begin.”

Gemini:

“Drop €225,000 with a straight face. You’re trying to put one price tag on four products, so anchor to the highest relevant market: executive transformation roles. If they can’t meet cash, fine: bridge the gap with equity, IP ownership, reduced workweek, or freedom. The point isn’t that every employer will pay €225k. The point is that anchoring high makes any lower number feel like you’re granting a discount.”

Claude:

“Use a range of €180k–€220k, with €200k as the anchor. The case is simple: decades of leadership, proven ability to create scalable intellectual property, measurable global reach, and demonstrated enterprise execution. The risk isn’t overpricing yourself, it’s looking unfocused because your options span academia to enterprise. Anchor in the executive market, then flex the package based on scope, equity, and role design.”

Grok:

“Anchor at €200,000 and deflect slightly: ‘I’m targeting around €200k depending on scope and total package, what’s the range budgeted for this role?’ That keeps you senior, invites them to reveal budget, and shifts the discussion toward full compensation (bonus, 13th month, holiday allowance, pension, mobility, equity). Your brand and track record justify being above the median for Dutch digital/AI transformation leadership.”

Different voices, same fundamental message: I wasn’t being priced as a pair of hands. None of them positioned me as ‘senior’ or ‘experienced’ in the way those terms usually function—as polite euphemisms for “competent but fundamentally interchangeable.” They benchmarked me as executive-scale leverage: someone you hire to reconfigure systems, not to occupy a box on an org chart.

I had to sit with that for a minute.

Two hundred thousand euros annually? Who’s going to pay that?

That reaction is precisely why it’s the correct anchor.

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