Creating Confidence with Heather Monahan
Aug 5, 2026 · 34 min · 19 segments
Have you ever felt like you're trying too hard to make things happen? I've learned that the biggest opportunities in my life showed up when I stopped trying to be someone else, trusted myself, and…
We have a lot of new listeners lately I'm finding because I've been getting a lot of DMs, and I wanted to just reintroduce myself in case we haven't formally met.
So my background is I came up through corporate America and made it to the C-suite.
And after 14 years at one company and being promoted three times and being named one of the most influential women in radio, I was suddenly fired.
And it was a crazy, unexpected turn [laughs] of events which in the moment sucked.
I don't know if you've ever been fired, but it is a major punch in the gut in the moment.
But like anything, you know, in time, you know, I have this perspective now that I can look back and say greatest gift I was ever given.
We have to step into the uncomfortable, and in fact, maybe that's where the actual magic happens.
I had an 18-month non-compete, non-solicit which meant I could not go to a competitor, I couldn't work in the media business for 18 months, and I couldn't hire any of my former employees for 18 months.
And somewhere along that way I figured out if I'm gonna start over as a beginner, why don't I just double down and roll the dice on me? And it wasn't like an epiphany I had by the way.
That process actually took a while too because I was toggling back and forth between do I go back to a corporate environment in a new industry and try that or do I keep trying to go to work for myself? You know, I w- I was so uncertain and unclear.
We have a lot of new listeners lately I'm finding because I've been getting a lot of DMs, and I wanted to just reintroduce myself in case we haven't formally met.
So my background is I came up through corporate America and made it to the C-suite.
And after 14 years at one company and being promoted three times and being named one of the most influential women in radio, I was suddenly fired.
And it was a crazy, unexpected turn [laughs] of events which in the moment sucked.
I don't know if you've ever been fired, but it is a major punch in the gut in the moment.
But like anything, you know, in time, you know, I have this perspective now that I can look back and say greatest gift I was ever given.
We have to step into the uncomfortable, and in fact, maybe that's where the actual magic happens.
I had an 18-month non-compete, non-solicit which meant I could not go to a competitor, I couldn't work in the media business for 18 months, and I couldn't hire any of my former employees for 18 months.
And somewhere along that way I figured out if I'm gonna start over as a beginner, why don't I just double down and roll the dice on me? And it wasn't like an epiphany I had by the way.
That process actually took a while too because I was toggling back and forth between do I go back to a corporate environment in a new industry and try that or do I keep trying to go to work for myself? You know, I w- I was so uncertain and unclear.
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