My client was scrolling through his friends’ updates again on his way to work.
His friends were sharing about their work at “real” AI companies. The agents they were building. The apps they were creating using Claude Code and Codex. It felt like they were moving forward and leaving him behind.
My client was using AI to automate clinical supply chain workflows at a top tier biotech company. His manager trusted him, giving him new projects to encourage his AI use and development. His team valued him and wanted to learn from his experience.
The work was strategic and important. His company’s efforts ensure that drugs reach patients who need them.
And he was miserable.
No one thing ever defines us. Even when we know this to be true, it’s easy to get so caught up in our emotions that we lose sight of reality. - Lew Frankfort, Bag Man: The Story Behind the Improbable Rise of Coach
I recognized the pattern from his description. I’ve heard and lived the story. That self-doubt mixed with FOMO from doing meaningful work no one is posting about.
I asked my client, “Have you fully leveraged what you already have?”
He started by referencing his friends and their “cooler” jobs. I waited. He tried again. I reframed the question. The honest answer finally came back “no”.
He’d lurked in internal AI channels but never contributed. He’d spotted senior people doing advanced work but never reached out. A mentor he’d wanted for months but didn’t contact as he wasn’t sure what to offer in return. An AI project approved by his manager was waiting for him.
He was so busy wanting what his friends had that he overlooked he could water his own garden and watch it grow.
When someone uses “the grass is greener” on you, the typical response is an eye roll.
There’s typically a judgment lurking about whether you’ve done the hard work you’re capable of. Not because of laziness, but because reaching our full potential in our current role is harder than leaving and blaming someone or something else. It requires you to be seen. To ask for things before you feel ready or worthy.
The urge to leave is loudest right before you talk yourself into doing the hard thing.
I know this because I have my own version of the story. For years, I made myself small by not eating, not speaking up, and not taking up space. Then I’d go on a work trip and feel like a different person. Energized. Seen. Capable of more than I’d allowed myself to believe.
When I returned to the office, I felt defeated and deflated. It was terrible.
It took me longer to understand that I hadn’t discovered a new version of myself on those trips. I’d just stepped outside the work setting convincing me I was less.
The problem wasn’t the environment. It was what I wasn’t doing.
The discomfort of becoming more than you are feels almost identical to the discomfort of being in the wrong place.
Same Sunday night dread and heaviness. But the source is completely different.
I’ve created the following model, building on my Positive Psychology coursework with Dr. Jonathan Aronoff and insights from neuroscientist Lisa Feldman Barrett on emotions as signals:
Stretch discomfort is internal (growth zone). It eases when you feel appreciated or do the hard thing and recognize you were capable of it all along. Your values stay intact even when your confidence doesn’t.
Values discomfort is structural (warning zone). It doesn’t ease over time because the problem isn’t you, it’s the fit.
The current uncertainty makes it harder to tell the difference. When everything outside feels unstable, it’s tempting to believe internal discomfort is the new normal.
Sometimes it is. Other times you’re using it to avoid the hard thing you need to do.
The world’s uncertainty is real. It’s also a convenient place to hide.
After months with a difficult manager, a client stopped trusting his judgment. He thought it was values discomfort and time to leave. We did a whiteboarding session, listing all the areas under his control. He had internal contacts he wasn’t utilizing. He pushed out of his comfort zone and built a network of champions. It took months for the work to pay off. He realized the discomfort was stretch, not values. He’s on a stronger path now.
Another client watched a new leader restructure her organization into a centralized, top-down approach. She shared, “Everything has to generate immediate revenue. No questions. Just execute.” She looked for where she could still make an impact. But doing so meant becoming smaller. She left. It was the right call.
What’s the difference between these two? Both did the hard thing. Both looked inward. One discovered he was avoiding growth. The other discovered the environment was asking her to abandon her values.
Same internal work. Different outcomes.
Before deciding to stay or go, reflect on two questions long enough to feel the answer.
Can you name one thing that would change how you feel? Not a fantasy. If there’s something within your control that would change how you feel, it’s worth trying before you walk away. For example, asking a senior leader to be your mentor.
When did you last feel like yourself at work? If you can answer quickly, you have something to fight for. If years ago come to mind and nothing in the last year, that gap is telling you something.
You don’t have to take today’s answers as final. Applying for jobs takes effort. My challenge to you is to focus that energy towards these questions first.
The questions are the work. What they reveal, or don’t, is the answer you’ve been seeking.
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Reach out over LinkedIn: Diana Stepner
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