A few years ago, I hit what I now call my early midlife awakening. Even when I was working, I felt a pull toward building something different, something of my own. I had always dreamed of owning a company, and I started to think that I could be pretty good at it. I should mention that this was toward the tail end of the Girlboss era, where Instagram made entrepreneurship look cool and easy. Little did I know that Instagram doesn't show you the hard parts of running a company, just the highlights.
Anyway, I took a big step and took on running a makeup company. I raised money and officially could call myself a CEO, chasing the dream I'd held for years! I worked incredibly hard at turning it into a success, and… I failed. That’s the sort of thing that knocks you down where you find yourself crying and thinking now what?
The truth is, most people hit that “now what?” wall at some point. They just don’t talk about it. A lot of us are pretending that we have a plan, while inside we’re terrified we missed our chance. The world is overflowing with podcasts, brands, new voices, cool people. It’s easy to look around and think, Why even bother? There’s nothing left for me to add. But if you listen to that voice, you won't be able to move forward.
When I was paying back investors from my makeup business, I couldn’t see where I’d end up. I didn’t have a crystal ball to show me that I'd wind up where I am today (and I'm really happy with how things have turned out). What I know now is that it’s less about having a perfect plan, and more about building practices that help you move forward—even when you’re unsure of what’s next. It sounds cliche but it truly is all about the journey!
