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Imposter syndrome is an issue most of us have dealt with at some point. We read books and listen to podcasts about it. I know I have sat through more seminars than I can count trying to rid myself of the feeling that I am, in fact, an incompetent fraud.
I wish I could give you the silver bullet to fix it, but there isn’t one. The truth I have come to understand is simply this: You have to outgrow it.
For many of us, imposter syndrome is woven into our identity. For me, she showed up at every single phase of my life. And because she lived in my head all day, every day, I gave her a name — Leslie (apologies to all the Leslies).
She is incredibly cruel and excels at finding that one crack, that one button, and pushing it so hard.
“Why would anyone ever pay you to plan their weddings? You have no idea what you are doing.”
“Why on earth is this hospital letting you take this baby home? Surely they know you have never done this before.”
“Why would anyone ever want to work for you? You have no idea how to be a boss.”
Whenever I heard Leslie, it was for two reasons. The first was that I was scared. Terrified, actually. The second reason was because I cared about what I was doing.
But the interesting thing about outgrowing something is that you don’t realize it is happening until you are already on the other side of it. I outgrew Leslie in almost every step of my life. She told me no one would pay me to plan weddings, and then they did, for years, until I didn’t need that version of myself anymore. She told me I had no business taking a baby home, and I raised two humans who are, against all odds, turning out pretty great. (The parenting doubt, I’ll be honest, never fully goes away.)
Each time, I outgrew her. Each time, the version of me she was afraid of became the version of me that showed up anyway.
So naturally, as I began expanding my business, Leslie was ever present. She became one of the primary feeders of my depression, working overtime sowing doubt, fear and doing everything she could to shut down any belief that I was capable of something great.
I had gotten pretty good at shutting her out. But as I started acting boldly and taking steps to build my own future, she got so loud. And I have to be honest — she almost won.
What a lot of people don’t know is that buying and selling multiple venues requires a lot of precise steps and very specific timelines. For over seven months, I have been perpetually closing on a business or a real estate deal. I call it my waterfall closings. One had to close, then another, then another. I am walking into my fifth closing in just a few weeks.
This last one was the hardest, probably because it was the final piece. I have worked with an incredible bank for over 14 years, and they have been with me every step of the way. But there are some things that are simply out of anyone’s hands. I was going in for final approval, and everyone involved, me and the entire bank team, knew it was dicey. There was one last conversation with someone I had never met. He was the deciding vote. The person who scrutinized every penny and every projection to determine whether I was approved.
I walked into that meeting looking calm on the outside, but Leslie was there, whispering that there was no way I would be approved. I pushed her out as much as I could. I went through the meeting honestly, acknowledging my own concerns while making it clear that I knew I could get this off the ground. I was smiling, present and confident in what I was building.
More than a week later, I was leaving work on a Friday afternoon when my banker called. I wasn’t supposed to have their decision until Monday.
She started with: “I didn’t want you to have to wait until Monday…”
My heart sank.
“…but they are still going to approve this loan.”
I sat there in complete disbelief. I think I said something like, “Are you sure?” She told me she honestly didn’t know what I had said in that meeting because on paper, this was not a slam dunk. But whatever I said prompted this person — someone I had met exactly one time — to tell the bank they needed to keep me at all costs. That I was bound to be incredibly successful.
I managed to say thank you and hang up before the tears came in big, ugly sobs.
It wasn’t the first time someone had believed in me. But it was the first time a complete stranger saw what I had only quietly known deep down — that I could actually do this. On my own.
And just like that, Leslie went quiet.
What I could see clearly, maybe for the first time, was the army standing behind me. The texts, the emails, the calls, the hugs, the conversations happening in rooms I am not even in. There are so many people cheering me on, believing in something I was still learning to believe in myself.
No one cheers more loudly than my husband Sam.
I posted on Instagram about a call Sam joined with me and our financial advisor. We were walking through an investment account, and I had all the details — down payments, projections, the latest updates on the businesses. Normal enough. We hopped on, made small talk, and then I dove in.
Halfway through, I glanced over at Sam.
The look on his face completely stopped me. It was pride — pure, quiet, completely unguarded pride. My heart actually fluttered.
After the call, I sat with that look for a long time. He was proud of me, yes. But I think what I saw in his face was something deeper than pride. It was the look of someone who had always known what I was capable of, finally watching me realize it too.
And that is the thing about the people who truly believe in you — they are not surprised when you succeed. They have been waiting for you to catch up to what they already knew.
Leslie still shows up sometimes. She probably always will. But I have outgrown every version of her that has ever tried to stop me. The planner she said no one would pay. The mother she said wasn’t ready. The founder she said couldn’t do it alone.
I outgrew every single one.
And I am just getting started.
Dana Kadwell is a hospitality entrepreneur, multi-venue owner and founder of Hustle + Gather. She currently serves as the national president-elect for NACE, where she is helping shape the future of the events industry through leadership, education and community. Find her online at hustleandgather.com.