You Are Worth More Than You Think

How to deal with imposter syndrome and confidently enter negotiations

Jan 12, 2026

Imposter syndrome in salary negotiation — solo chief anchoring compensation confidently

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

Imposter syndrome made me negotiate against myself for years. Then I asked four AI advisors what I was actually worth. The answer changed how I think about compensation.

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.

What Four AI Advisors Told Me

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.

I’m a seasoned founder, intrapreneur, and former CIO who builds maps and models for Solo Chiefs navigating sole accountability in the age of AI—informed by plenty of scar tissue. All posts are free, always. Paying supporters keep it that way (and get a full-color PDF of Human Robot Agent plus other monthly extras as a thank-you)—for just one café latte per month. Subscribe or upgrade.

You can only negotiate down. Never up.

What shifted my thinking wasn’t just the number itself. It was the frame around it. Salary is not the same as value. Compensation is not synonymous with the sum deposited into your account each month.

I don’t exclusively value cash. I value autonomy, ownership, and time. Hybrid work arrangements. Minimal commuting friction. Equity in something worth building. Control over my intellectual property so I can reuse and resell what I create. These aren’t perks. They’re compensation components.

Once you recognize compensation as value attributed to a work-life structure instead of a single figure, negotiation stops being confrontational. It becomes design work.

For example, I don’t expect a university to wire €200,000 annually for a lecturer role. That would be absurd. But that doesn’t mean the conversation ends there. They pay what their budget allows, and we engineer the difference. Fewer days. More autonomy. Ownership of course materials. Space to build parallel projects alongside teaching. Suddenly the total value approaches my fixed mental anchor. The anchor stays constant. Only the components shift.

“Once you recognize compensation as value attributed to a work-life structure instead of a single figure, negotiation stops being confrontational. It becomes design work.”
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The same logic applies to startups, consultancies, NGOs, and enterprises. Cash down, equity up. Salary down, autonomy up. Different levers, same outcome.

What I found most useful wasn’t just the number. It was how each advisor reframed the narrative I’d been running on autopilot.

ChatGPT:

“You’re negotiating too early. Imposter syndrome isn’t telling you that you lack value. It’s telling you that you’re pricing yourself before the other side has shown their hand. Anchoring high isn’t arrogance. It’s refusing to negotiate against yourself in private.”

That landed because it was accurate.

Gemini:

“If a number feels uncomfortably high to you, that’s usually a sign it’s finally calibrated to the market instead of your fear. Executives don’t start negotiations by asking what’s reasonable. They start by defining the frame in which ‘reasonable’ will later be discussed.”

Claude:

“Your income volatility doesn’t make you risky. It means you’ve already absorbed the risk personally. Employers often mistake entrepreneurial scar tissue for instability, when it’s actually evidence that you can operate without safety nets. That justifies a premium, not a discount.”

That one flipped a belief I’d been carrying for years without examining it.

Grok:

“Breadth isn’t lack of focus if you can clearly name the problem you solve. Imposter syndrome shows up when you compare yourself to narrow specialists. Negotiation becomes easier when you anchor to outcomes and impact, not to job titles or years in a role.”

In the age of AI, you are not pricing hours. You are pricing judgment.

That applies to all Solo Chiefs.

Most of us systematically undervalue ourselves. We anchor to historical salaries. We preemptively adjust our ask to what we assume the organization can afford. We let imposter syndrome conduct the negotiation for us—quietly, efficiently, against our own interests.

If I hadn’t asked for external perspectives, I would have done exactly that. I would have minimized my track record. I would have adjusted my number downward for each organization before any actual negotiation even started.

Instead, I now have a clear anchor. A number I never would have arrived at independently. And, counterintuitively, that anchor makes me more flexible, not less. I’m confident about the value I bring, which makes me creative about how that value gets compensated.

I also found it useful to ask multiple advisors. Not because they agreed on everything—they didn’t—but because they couldn’t collude. Independent perspectives converging on the same range is a strong signal, especially when your own internal voice is demonstrably unreliable.

So here I am. Better prepared. Better anchored. Still human. Still prone to doubt. But no longer negotiating against myself before the conversation even starts.

If you’re a Solo Chief wrestling with similar dynamics, take this as permission to ask for help, to anchor higher than feels comfortable, and to remember that you are probably worth more than you think.

Ten Key Takeaways for Solo Chiefs

Do not negotiate against yourself in advance.
Imposter syndrome does its most effective work in private. Anchoring early prevents you from quietly discounting your own value before anyone else speaks.
Anchor to value, not to fear.
If a number feels uncomfortably high, that’s often a sign it’s calibrated to the market instead of your self-doubt.
You are not pricing hours. You are pricing judgment.
Especially in the age of AI, experience isn’t about execution speed. It’s about decision quality, pattern recognition, and accountability.
Entrepreneurial volatility is a premium, not a liability.
Years of uneven income mean you’ve already absorbed risk personally. That’s evidence of resilience, not instability.
Fix the anchor, then engineer flexibility.
The number in your head stays constant. What changes are the components: cash, equity, autonomy, time, intellectual property, scope.
Compensation is a system, not a salary.
Money deposited into your account is only one lever. Freedom, ownership, and optionality are part of the deal.
Breadth is not lack of focus if you can name the problem you solve.
Stop comparing yourself to narrow specialists. Anchor to outcomes and impact, not job titles.
Discomfort is not a warning sign. It’s signal.
Executives don’t start negotiations by asking what’s reasonable. They define the frame in which “reasonable” will later be discussed.
Ask for outside perspectives when your internal voice is unreliable.
Multiple independent advisors converging on the same range is a stronger signal than anything your imposter syndrome tells you.
You are probably worth more than you think.
Not because you’re special. But because most people systematically undervalue themselves.