The Messy Middle and 4 Ways I'm Moving Through This Period of Life

Embracing second acts and worst-case scenarios.

 “I’m in the messy middle of embarking on what feels like a “second act” of my career. In some ways, this shift feels like a colossal failure. I have worried that I’ve ruined all I’ve built in the process. But does sunsetting one thing so you can explore what will follow it mean you’ve failed?”

If I have a terrible encounter with a stranger, it stays with me. There is one encounter in particular I’m thinking about a lot these days. 

I was sitting in my studio when a man walked in and asked to speak with me. It was 2014, my breakthrough year. I was consistently booking jobs, had my first collection in Target stores, and had a lot of national press. It was the golden age of social media and it was the year I left salaried positions for good to put all my eggs in my own proverbial basket. 

I was living my dream—the dream I had worked tirelessly for. Timing and hard work aligned—and now it was time to seize it. As incredible as it all was, I felt awful. The opportunities seemed endless, and all I could think about was how I would choke. 

It is not uncommon for people to have a hard time adjusting to the pressure that comes after we get what we work for. I couldn’t figure out why it felt impossible to do simple tasks like answer emails. I retreated, avoided, and worried. When it came time to work, I felt exhausted. I judged myself to avoid those who judged me and so my disordered relationship with social media was born. 

Yet that is a story for another post, so to be brief: I was not in a great place when this man entered my studio. 

He began pitching me about life insurance (or something like that) and how my audience could make “us” a lot of money. Within a few moments of speaking with him, I realized he had emailed me a few times about “collaborating,” and I hadn’t responded. He decided that no response from me meant he should find me in person. I didn’t know how to react. I was caught off guard, and I was scared that he had figured out where I worked and then showed up, feeling entitled to my time. 

He became increasingly aware that I was rattled by this unexpected visit. When I asked him to leave, he became angry. “Why have an office if people are not allowed to drop by your space?” he taunted. He said several other demoralizing and sexist things, but this is what I remember most clearly:

“Someday, you’ll be irrelevant. And then you’ll be wishing someone like me was knocking on your door.”

Those words took the wind out of my chest. Because in my gut, I knew there was a tiny bit of truth in his statement. What happened with Wit & Delight that year wasn’t going to last forever, and I was going to have to face that.