Description

Episode 70: Ego Off, Value First with Jill Trimmel
Hosted by Katelyn Calhoun

In November 2023, I was a brand-new solopreneur with more debt than I knew what to do with and just enough in the gas tank to get to Muncie. My friend Brittany Scott of GROW had gifted me a ticket to her very first women’s leadership conference, and I wandered into a breakout session on failure... and how to make a fail plan. That’s where I met Jill Trimmel. I’ve held on to her as a mentor ever since.

Jill is the CEO of Elevate Claim Solutions. She came up through the corporate insurance world, often as the first woman in the role and the only woman at the table. She knows her numbers in a way that’s honestly a little dazzling. But underneath all of that, she’s a people person through and through. We recorded this conversation back in the spring, and it’s actually the one that sparked this whole fall series.

We talk about choosing experience over the bigger paycheck, how to hold onto your value when it’s time to negotiate, and why sometimes the goal is just to still be in business at the end of the year. Then Jill gets really honest about her own burnout, and about Margaret, the business partner who wouldn’t accept her resignation.

In this episode, we talk about:

• Jill’s path from Enterprise Rent-A-Car to Manhattan’s financial district and back home to the Midwest
• Why she took pay cuts on purpose, more than once, and usually came out ahead
• Keeping a “kudos folder” and tracking the numbers that prove your impact
• Negotiating for the value you’ve created, including asking for that six-month review
• Why mentors don’t always have the full picture, and why the consequences are yours to own
• Finding your “Margaret,” the person who’s strong where you’re not
• Scaling an eight-figure company on a $25,000 line of credit, through multiple lawsuits
• Hiring slow, firing fast, and leading without your ego in the driver’s seat

A few moments that stood out:

• The story of an adjuster asked what you do first at a total loss fire. His answer: you give out hugs.
• Jill saying her value comes from seeing the value in others. That one stuck with me.
• “Your ego is not your amigo.” I laughed, and then I thought about it for a week.
• Hearing her name the voice that kept saying “you need to do more,” and admitting she wishes she’d learned to be easier on herself sooner.

If you’ve been keeping score against yourself lately, I hope this one feels like permission to ease up a little. You’re doing better than you think.

P.S. If your videos are stuck in your camera roll, head over to @calhounedits for quick editing tutorials, or book a free 30-minute consult here:[link]

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