Coaching Toolkit: The Stories We Tell Ourselves

How to reframe the stories that hold you back at work

About the Coaching Toolkit

I’m trying something new with paid subscriptions to Tech and Tea. I’ll be building an evergreen library of tools — exercises, reflections, and downloadable resources — to help you navigate tricky work situations, align your career with your values, and move through transitions with more clarity and confidence.

Each Toolkit post includes a personal essay or story (free for everyone), and a deeper practice or resource — like a worksheet, set of journaling prompts, or audio note — just for paid subscribers.

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Our brains are master storytellers. Faced with incomplete information, they’ll fill in the gaps with a narrative that makes sense—to us. But just because a story makes sense doesn’t mean it’s true.

And often, those stories are harsh. They tend to center around us, highlight our insecurities, and paint us in a less-than-flattering light. We assume someone’s silence means they disapprove of us. A curt Slack message means they’re annoyed. A tepid response in a meeting? A sure sign that everyone thinks your idea is stupid.

Because these stories poke at our insecurities, they often lead us to pull back—to isolate and protect ourselves. When you imagine that someone is annoyed with you, you might avoid them. When you assume someone is dissatisfied with your work, you might hesitate to ask for help.

A story like this can take on a life of its own.

Here’s one of mine:

Many years ago, when I was a new grad at Google, I got a slightly critical email from a senior engineer who was pulled into a code review. I was trying to merge some hacky JavaScript into his codebase, and he pushed back — reasonably, honestly.

Years later, I saw his name again — this time during the hiring process at Medium. I remembered that moment at Google and assumed he would too. He joined the team, and I made up an elaborate story: that he thought I was a bad engineer, and even that he wished he’d joined earlier so he could have screened me out.

We ended up working on the same small team. And for a while, that story persisted. I thought he still saw me as inexperienced, that he questioned why I was even on the team. I avoided him. I was overly guarded about feedback. I didn’t ask for help because I didn’t want to confirm what I feared was true.

Over time, the story unraveled. Someone mentioned that he’d wanted me on his team and that he had spoken positively of me. Eventually, he became my manager, advocated for me over and over again as I transitioned into engineering leadership, and supported me through a second maternity leave. A few years later, he hired me as his VP of Engineering at his startup. We’ve now worked closely together across three different companies.

I missed out on so many learning opportunities during that first year we worked together — all because of a story that wasn’t true. But it held power over me until I finally examined it.

In coaching, I’ve seen how often people carry stories like these — quiet, heavy, and unchallenged. So here’s a simple but powerful practice to help you take a closer look at the narratives that might be holding you back.

🛠️ The rest of this post includes the Five Stories practice, a bonus AI-assisted version, advanced tips, and ideas for using it in 1:1s or with your team.

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