Hi, there! I’m Kathy, a former C-Suite exec turned executive coach and artist. I share honest takes weekly about what it takes to lead and how to shape a meaningful career. I don’t pretend to have it all figured out, and I don’t expect you to have either. But that doesn’t mean you can’t achieve more and feel more at peace while you do so. So glad you’re here.
“We can hear you!” one of my friends wrote in the chat last Friday.
I was so relieved to see it after the prior week’s Substack Live snafu, where I didn’t set up my mic properly and no one heard anything for 25 minutes.
I went on to say what I’d been afraid to say for months: I’m an executive coach, and I don’t love leadership content. I don’t seek it out. I don’t read it for fun. Coaching the person in front of me is what makes me feel most alive. But the articles, the frameworks, the posts? They drain me.
The result, at least on the call, was … drumroll, please … crickets.
Almost. One listener wrote in the chat that she’d spent 15 years as a travel producer and never read travel content.
That’s the thing about putting out a message that has tremendous weight for you. It might not elicit anywhere near the response you imagined.
To be fair, two friends messaged afterward with warm support. I had voiced something they had felt themselves. They wanted to talk more, to work through their questions and maybe to join me live.
And even without their messages, which were very welcome, I found value in simply expressing what was true for me.
It reminded me of something I see every week with the leaders I coach: even successful, senior professionals at the top of their game can trap themselves.
Sometimes you need a shake-up to wake up.
Early in my career, before I left the highly coveted finance career I had launched myself into, I spent years battling with what I knew to be true: it wasn’t a fit.
I didn’t enjoy reducing a business into logo-ridden charts and spreadsheets of 0s and 1s. The culture of investment banking was dog-eat-dog and ruthless competition. I didn’t trust my colleagues, my bosses, and ultimately, even my friends. Most importantly, I never felt a surge of energy from helping businesses access capital. That period of my life felt like an out-of-body experience, as if I were watching myself go through the motions but not actually experiencing it. Perhaps it was a way to protect myself from a life that didn’t feel like mine.
Only when I got really sick, with multiple blood draws a week and prescriptions that spilled out of a pill box, did I finally re-enter my body. Only then did I admit I wasn’t happy. That maybe I had chosen wrong. That maybe it was time to make a change.
Up until then, I had pretended to love the job, relish the opportunity, and go all in. Friends and family from the outside could see that physically I was ill (bloated, pale, 20 lbs heavier in 6 months). But I could fake it well, especially to myself.
The medical results shook me up enough to realize I needed to face my self-created, gilded cage. No amount of money, prestige, or external validation was worth my health.
That’s when I finally admitted to myself, and then to family and friends, that I needed a change. Saying out loud that I was going to leave a world I had worked years to enter wasn’t as scary as I thought, once I had freed myself from the assumptions that had trapped me.
There was more than one way to be successful, to make money, to be valuable, to matter.
But until I said it out loud, the cage was still locked.
When you silence yourself, you silence your potential.
After I left investment banking, I had a series of wonderful career experiences, helping to grow technology companies, launching multiple businesses, including Hulu, and transforming businesses like the NBC local TV stations and the Knot.
I loved the climb in every one of those roles. Learning a new industry, getting acclimated fast. But once I got over the hill, I’d ask myself: Do I really want to read more about weddings? About streaming? About selling things online? The answer was usually no. I forced myself anyway, and it drained me.
Every time I made a switch, the first step was saying out loud what I wanted, what was missing, what didn’t feel right.
It was always scary to say so. When I left NBC, I was one month shy of receiving a pension. It still boggles my mind that I even had the option. Pensions are like fairies and goblins, the stuff of stories. But I had the chance to have one, and I left it, and I have never regretted it. I didn’t even enjoy the next job I took, and it was still the right decision to go when I did.
Every career change is a risk. But it’s also an opportunity to expand your network, learn about a new organization, and test your skills. Transitions also keep you nimble, learning new systems, cultural dynamics, and norms.
I left my next company 6 months pregnant with my first child. By normal standards, a bad idea.
But I knew the company and the role weren’t right. After I pushed back one too many times on our CEO’s regular half-baked, 5 pm whiteboard brainstorms, I was no longer invited into the room. I didn’t treat it as an indictment of me. I treated it as a sign it was time to speak my truth again.
I started to reach out to friends to ask about opportunities. When a former boss was named CEO, I reached out. Within weeks, I was on the next adventure that led to me becoming CEO at 32. This wasn’t by design. It was all because I was willing to say out loud what was true, including what was messy.
Say what you know, and be OK with what you don’t.
Every time I was ready to make a change, I didn’t wait until I had all the answers. I started to get out the word long before I knew exactly where I needed to go. I trusted my network to help me.
I did the same at work. When I wasn’t sure about whether we needed to expand into a new vertical, I said so. I’m sure it was difficult for some team members to hear that. But I think the most entrepreneurial ones valued my honesty. They knew I was asking for their help to find the right answer; I wasn’t going to provide false certainty.
Few leaders feel safe to say what is actually true. The ramifications of getting it wrong always feel larger than the implications of not saying anything at all. I think it’s the other way around.
Silence only breeds uncertainty. And uncertainty is what the mind is most fearful of. When we don’t know, we only imagine the worst. The reality is usually much less scary.
That’s what I realized this past Friday.
If you watch the recording above, you’ll notice: It’s unscripted. It wanders. That was the point.
And yet, I got out of it exactly what I needed. I found a voice that I’ve been holding back. One that is more unfiltered, raw, and willing to show my full self, the parts that feel unpolished and not credible. The parts that make me the coach that I am and the leader I was. I can talk EBITDA and growth multiples. I also love talking about mixing paint colors and the right way to wash your brushes. Both are me.
I’m not yet sure what this chapter of my career will bring. It’s still unwritten. That uncertainty frightened me before Friday. But now that I spoke what I’ve been thinking out loud (and people heard), I sense different parts of me starting to shift.
Halfway through the Live, I felt my shoulders drop. My breath came easier. It’s the kind of relief I’ve felt every time I acknowledged that it was time to make a change.
The power I feel when I coach or paint is starting to show up when I think about writing. It’s happening right now as I type. It’s only happened once or twice before in the last 2 years since I started this Substack.
The story I told myself—that I don’t write well and that writing stresses me out—was just another cage, like the one I built for myself in finance. And just as it was then, actually saying out loud what is true for me has helped me break free.
Take Action
Perhaps part of your work as a leader, or your career chapter, no longer fits. Maybe you’re only seeing this today, or perhaps, like me, you felt it for months but were afraid to acknowledge it.
What if you gave yourself permission to play with the idea that the structures and designs you held true might no longer be so?
If saying it out loud to someone else feels too risky, take a more measured approach:
Start with writing. If a statement feels too much like a commitment, start with a question. Use this as a chance to wonder about what might no longer be true. Offer yourself room to write what you wish could happen.
Talk to yourself. In a quiet place, on a walk, in front of a mirror. If you can’t yet say it to someone else, say it to yourself. You’re trying the words on for size. Notice how they feel when you hear them, not only when you think or read them.
Tell something that can’t judge you. I couldn’t even admit this to the AI tool I write with. When I finally typed it, the relief was physical. A journal app, a voice memo, a chatbot: the listener doesn’t matter. Hearing yourself say it does.
The goal isn’t to be right. It might not even be to figure out what you exactly need to say or do. It’s about facing the part of you that has kept you safe, but also kept you from where you’re meant to go next.
Only when we acknowledge that part can we free ourselves from the stories that trap us.
If you want to share your thoughts with me, please reply by email, share them in the comments, or, if you’re a paid subscriber, write them in the Substack Chat. I’ll respond to every one.
And to the people who joined me these last two Fridays, thank you. I cannot express how much your support (and curiosity) means to me.
May you lead without limits,
Kathy
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