Why I, An Amateur, Spend Time Parsing Politics

When I stepped back from running my company nearly two years ago, I had three good business reasons: risk management, talent retention, and strategic renewal. I also made one huge mistake: I had no real plan for myself.

I didn’t consider myself retired. I’m an “un-exited business owner,” which means that my money is still largely tied up in the company. Intellectually, I knew that money was mine, and that I could take a modest draw to cover my bills without impacting Steyer’s ability to grow. Nevertheless, my first instinct was to seek an income elsewhere.

For a few months at the start of 2024, I returned to the “exec comms” work I’d done earlier in my career—helping business leaders with their messaging. But this time around, I found no joy in that work. It didn’t pay what it once had but was as taxing as ever, and I missed my team. I hated working alone.

It was a singularly strange stretch in my 30-year business career. By stepping aside I had done the right thing for my company. I was sure of that…and I was so unhappy. Worst of all, my visions of finally becoming the perfect caregiver (patient! cheerful!) disintegrated daily on contact with reality. “First, do no harm,” I’d think to myself as I took to the woods, ostensibly to walk, but really to muffle the detonations.

Fortunately for me, it was an election year. Once I realized why I felt terrible—I neededfulfilling work, I needed a new team—I carefully unwound the ill-fitting exec comm commitments I’d made and went all in on several political campaigns instead. I wasn’t a leader; I did what I was told. It was all grunt work—knocking doors, registering voters—but I didn’t mind one bit. Saving America from Donald Trump seemed so urgent; I was happy to pay myself to pitch in. 

And then we lost. 

Losing the election was a gut punch—but it didn’t make me want to back away from politics. It did make me want to think more deeply about who I work for and what I spend my time doing. By the end of last year, I felt like I’d found the right pool to swim in—but not yet the right lane. This year, by zeroing in on the work of dispute resolution and coalition building, I feel like I’m getting closer—but it’s still a process. 

In response to my post last week, I got this email: “Does it matter whether the Democrats caved or were strategic?” Here’s why it matters to me: I don’t know how long I’ll have the luxury of paying myself to do unpaid work I view as important. Trying to discern—as best I can anyway—who’s got a spine, who’s got a brain, and who’s using them in careful combination helps me decide where to put my time and energy. 

But that’s me—and my situation is, I’ll grant, a little unusual. If such questions matter to you, why? I’d love to know. One reason I share my stories is with the hope of hearing more of yours. 

Thanks for reading,
Kate

Some notes:

• Speaking of exchanging stories, the last What Now Zoom of this year will be on Monday, December 1st at 5:30pm PT/8:30pm ET. Here’s the link. For my part, I’ll share more about my D.C. trip, including my thoughts on Braver Angels (gah! I still hate the name!), citizen-led initiatives, and more. I’ll also roll out my plan for next year’s discussions, which I’m shifting to a 1:1 format due to facilitator fatigue on my part—the downside of committing to full-time dispute resolution.
• My company’s name Steyer (pronounced sty-er) comes from founder Marty Steyer, who is not related to the billionaire political candidate Tom Steyer. As I tell political organizations I’m considering supporting: “I’m in a position to give time not money. We are not those Steyers, not those Waltons.”
• Writing about money is inherently awkward, so I use “my” versus “our” to leave my (Montana-level private) husband out of it. But the fact is: what’s mine is his and vice versa, and not just by Washington State law. I couldn’t have rolled the dice on buying a company without his emotional and practical support, and part of what sustains our current situation is that he continues to work around the clock (::raised hands emoji::) at the task of building his business.