A Hill I’m Willing to Die On

Messy Middle Mondays
June 29, 2026

It's Messy Middle Monday!

And Corporate baddies... this one is for you.

If you skim my résumé too quickly, you might miss the most impressive thing I’ve ever done: I invested in myself.

Yes, I’m proud of the titles, promotions, and boardrooms. I worked hard for every one of them. But somewhere along the way, I realized something uncomfortable: my employer could decide tomorrow that my chapter there was over.

And they would still owe me nothing.

Not because they’re bad employers. Because that’s business.

A hill I’m willing to die on? Never put all your income eggs in one 9-to-5 basket.

For years, I watched brilliant women wait. Wait for the promotion. Wait for leadership to notice them. Wait for permission to explore something beyond their job title.

Meanwhile, their ambition was quietly outgrowing the box they were in.

Your professional development is your responsibility. Your legacy is too.

I’m not telling you to quit your job. In fact, I’m probably the last person who would. But I am telling you that building something alongside your career can be one of the greatest investments you make in yourself.

My practical tool: ask yourself, “If my job disappeared tomorrow, what part of me would still feel fully expressed?”

Sit with that answer.

If this resonates, I’d love for you to watch my conversation with Hadriana Leo on Catalyst Conversations: Stop Waiting for Promotion: How to Build Parallel Paths and Reclaim Agency. I think you’ll see yourself in it.


Register for this free live virtual session hosted by Measure on July 16th, 2026 from 1:00pm to 2:30pm EST.

New York, NY
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