The context

Marcus, a longtime council member, had built a successful AI consulting business and was working on his own AI startup. Then a PE-backed software company offered him a Chief Product Officer role, to help reinvent a roughly $30M ARR business into an AI-first company.

On paper, it didn’t look great. The company was struggling, he wasn’t impressed with the technology, and the compensation didn’t stand out. Talking it through with Phyl, he admitted what he was really after: permission to turn down money.

The advice

Marcus worked through the decision with Phyl Terry, CG’s founder, over text and calls as things unfolded.

• Calm down first. The first conversation helped Marcus settle and think clearly instead of reacting. With a clearer head, he realized he didn’t know enough to say no yet.
• Get the facts before deciding. He spent several hours on the phone with the CTO and learned that the company was further along with AI than he’d thought, that the CTO would own technical debt so he could focus on AI transformation and monetization, and that the Board was considering spinning the AI work into a separate business he could run.
• Negotiate for what you need to succeed. Before saying yes, he went back for the resources and support to do the job well. He got the budget he wanted, plus a larger bonus and more equity.
• Look at the people, not just the offer. He saw firsthand how the CEO lived his values, and the leader he was replacing was staying on to help him succeed.
• Notice when one worry replaces another. When he worried about giving up his entrepreneurial dreams, Phyl reminded him he’d negotiated permission to keep building his AI side project. When FOMO about missing a “rocketship” startup crept in, Phyl asked whether he actually wanted the life that comes with one, and the pressure it puts on marriages, health, and family. His answer was no.

The outcome

Marcus took the job, with a clearer mandate, more resources, better terms, and room to keep building on the side. He made the decision from a place of clarity, not fear of leaving money on the table or of missing out.

Why it worked

Support met him where he was, through a fast-moving decision, over text and calls.

The first goal wasn’t an answer. It was helping him think clearly enough to ask better questions.

Phyl knew Marcus, his career, and his family well enough to push back on worries that didn’t fit the life he wanted.

The broader point

Big career decisions aren’t math problems. Once one worry fades, another tends to pop up. That’s the inner game of career management. Having someone who knows you help separate real concerns from noise is what turns a reflexive no, or a fearful yes, into a decision you can stand behind.

The advice might seem obvious now. Having peers to act on it with is what made the difference.

I guess I’m just looking for permission to turn down money.