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You know what you’ve lost. But can you name your wins?
Most people in a career transition can recite their losses on demand. The VP title. The 401K contribution. The Friday happy hours with the work family. The satisfaction of knowing what the job is and how to do it.
Ask them to name their wins? Awkward silence then a short, apologetic list they immediately start walking back. “I mean, it wasn’t that big a deal.” “Anyone could have done that.”
This isn’t humility. It’s your brain doing exactly what it was designed to do.
Your Brain Thinks It’s Helping - It’s Not
Your brain tracks threats and losses with far more energy than it tracks wins. It’s called negativity bias and a lot has been written about it. Essentially, as humans we’re wired to look for what’s not working as a way to protect ourselves.
During a career transition, exactly when you need a clear and accurate picture of your professional story, your brain is actively over-indexing on the negative. The losses stay top of mind while the wins get tucked into a bankers box and put into the back of a storage container.
Over time, negative bias feels like the truth. And once it does, it starts calling the shots on every decision you make — what you apply for, how you talk about yourself, what you believe you’re capable of next.
I learned this the hard way. And what made it worse is that my brain wasn’t the only thing working against me. I was also using the wrong measuring stick.
Another Reason Your Wins Go Missing
Several years ago, when I was pivoting out of independent film and TV producing, I went after three corporate opportunities, hard. Made it to the final round for all three. Got none of them.
When I dug into why, the feedback was consistent: the candidates who were hired had more recent, measurable wins. Box office numbers. Emmy nominations. Projects that crossed the finish line in ways the industry recognized.
Ouch. I knew how hard I’d been working. And I knew that a lot of the gap wasn’t about effort — it was about circumstance. COVID. The lockdowns. The writers’ and actors’ strikes. An industry that had slowed down so much, we could count the number of greenlit productions on one hand.
Turns out my wins weren’t missing. They just didn’t fit the industry’s scoreboard.
I’d spent years making sure the people on my projects felt respected. I knew this because they kept wanting to work together on new projects. I took great pride in responding to submissions when most people didn’t bother. Timely passes built relationships with agents, managers and other producers who understood that most of the time, the answer is no. Nobody was measuring those things that fell under the emotional intelligence category. They weren’t measurable in the same way the industry looks at ROI or KPIs. They were about humanity.
I wasn’t winless. In fact, I was quite victorious. But me and the industry were using different measuring sticks so I felt less than.
Finding The Wins Hiding In Your Story
If your career story feels heavier on losses right now, here’s an exercise worth sitting with that includes the parts that haven’t made it onto your résumé yet.
Start with the most obvious place: external recognition. Awards, nominations, acknowledgments — any moment where someone outside your own head said yes, this. Write them down without editing or qualifying.
Then go a little deeper. What do people thank you for, come to you for, refer others to you for? This one matters more than it might seem. When something comes naturally to you, it stops feeling like a win — it just feels like any other day. But the fact that people consistently seek you out for it says a lot about you.
Then ask yourself about the goals you hit without fireworks going off. The ones you set, achieved, and moved on from without a big victory dance. Those count too.
Now here’s where it gets more interesting. We tend to define victory as coming in first, getting the public recognition, beating the competition. But that’s only one definition — and for many people, it’s not even the one that matters most.
Think about a time you made a decision that honored your values, even when it went against what others expected. Or a time you went so far outside your comfort zone to make something happen that it surprised even you — even if the outcome wasn’t perfect, even if it wasn’t work-related at all. The stretch itself is a win. The integrity itself is a win. These moments are the most accurate picture of who you actually are.
And then the really big question: what measuring stick have you been using? Did you choose it? Or did someone hand it to you a long time ago and you just never put it down?
When you sit with that question — really sit with it — does your current definition of a win feel energizing? Or does it feel like a bar you can never quite clear? Where did it come from? A parent, an industry, a company culture, a moment early in your career when you decided what success had to look like?
You get to choose whether to keep it.
Mine shifted when I stopped measuring my career solely against greenlights and started asking: did the people around me feel respected? Did I show up with integrity? Did I make something better because I was there? Those wins were real because process matters to me.
Why This Matters Right Now
If you’re in a hard career moment, your brain is going to keep handing you the losses. That’s what it does. You have to actively go looking for the other side of the story — not to paper over what’s hard, but because your professional story is the foundation you build from. And if it’s missing its best chapters, you’re building on incomplete ground.
This is the work we do inside Solid Ground, my paid membership community. During the month of April we’re mapping the highs and lows of your career to see the full picture, not just the parts your brain defaulted to. Every month I send a short lesson and worksheet to work through before we get on a live coaching call together. It’s one of my favorite things I do. If that sounds like what you need right now, becoming a paid subscriber gets you in.
Bottom Line
Your brain was built to remember the losses. It’s doing its job. But that means your career story has probably been edited — wins minimized, qualified, or left out entirely.
Start with what people thank you for. Move toward the decisions you’re proud of, the stretches that surprised you, the moments you showed up with integrity even when no one was watching. Then ask the harder question: whose measuring stick have you been using, and is it actually yours?
The answers might change what you think is true about yourself.
If someone came to mind while you were reading this—please send it their way. You never know the impact a well-timed message can have.
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Longing To Feel Lighter?
Professional heartbreak can leave you spinning. You replay what happened, question your judgment, get stuck in indecision, and worry you’ll never get your mojo back.
Solid Ground is the paid member program inside the Moonshot Mentor Substack community that helps you move from spinning to forward motion.
Paid members tell me they feel less weighed down. Empowered. Relaxed for the first time in a long time. Here’s the thing. It’s not because they got a pep talk. It’s because they finally got an accurate explanation for what’s happening and a way through it.
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Journal Prompts
Here are 5 journal prompts for paid Solid Ground members. Studies have shown how spending time with your thoughts and feelings through journaling increases your ability to problem solve and calms your nervous system. These prompts will help you identify your wins.
