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One of the most popular (listened or downloaded) episodes of my #SaturdayMorningHustle podcast from March of 2020 involves Imposter Syndrome but not the "textbook definition" you might be familiar with. Everyone has had a moment (or more) of Imposter Syndrome when they internally doubt themselves. I have too, but in a different way than most people. Let's talk about it.

Imposter Syndrome, but not the typical imposter syndrome. A very different subset of imposter syndrome. For those of you who don't know, imposter syndrome is when people feel like when they're having success, they're put in charge or a leadership role, etc. but feel like they haven't earned it or they're not capable of pulling off what people are expecting from them. Thus, they feel like an imposter. That's imposter syndrome. It's self-inflicted. It's not necessarily something the world says: "you're not ready" or "you're not good enough" but you're doing it to yourself. For me, I've never actually had imposter syndrome in that way.

I've probably been the exact opposite. I've probably been too overconfident and willing to take on leadership roles and responsibilities before I was ready. So I've never had imposter syndrome when it comes to gaining leadership or being put in charge of something and then not feeling like I wasn't ready. It was probably the exact opposite. But I have imposter syndrome when I must get completely dressed up in a suit and tie, which is something I never really grew up around. It still makes me feel a little bit like I'm playing dress-up. So there's a little bit of imposter syndrome happening there for me. 

Here's the background. I was (late 2020 - early 2021) the Chairman of the Oklahoma Venture Forum, a professional group of entrepreneurs, service providers and investors. We have a monthly meeting with professional speakers, networking, etc. working to create bigger and better business opportunities in Oklahoma.

As the Chairman, I led this meeting of top business professionals every month. So I wear a full suit and tie, my nice glasses, pull my hair back, nice shoes, the whole nine yards. When I come into the building where I work with our office and co-working space, it's a lot more of an entrepreneurial space that's definitely a lot more of jeans and t-shirt type of place. Many times when I'm just in the office, if I'm not meeting with clients and I'm just working internally, I'm dressed in jeans and a t-shirt too. I'm a "dressed down when I can" kind of person. I have long hair. I have visible tattoos. All stuff that's more of the creative aspect of what I do, but I have my professional moments when I'm in meetings, presentations, etc.

Even when I have meetings with clients and prospective clients or networking, jeans and a sports coat are my entrepreneur uniform. I understand getting dressed up, but I don't necessarily feel super comfortable in a full suit and tie and the whole ensemble. However, I do it on occasion because my responsibilities call for it. But when I do, I have a little bit of imposter syndrome. I feel like I'm playing dress-up because I didn't grow up around suit and tie people. Both my parents were very working class. They never wore a suit to work.  
My grandparents on my mother's side were very religious and very much into attending church every week. We went with them a lot as kids and when I was a teenager. My father and my grandfather are my greatest role models in life. My grandfather would wear a suit to church. I didn't realize it as a kid, but now as an adult, I do. He had one, maybe two suits. I think he alternated between the two. He still never wore a tie. My grandfather preferred to be a little bit more on the silly side than on the serious side, even though he was a serious man. He ran many businesses, had much success. He had had an amazing professional life and personal life, but he only wore suits to church. My grandparents always dressed up for church. They took church very seriously, but it wasn't a suit and tie. It definitely wasn't a business suit and tie. He almost looked out of place in a suit because I was so used to seeing him in boots, jeans and a work shirt. He worked on his farm, had oil rigs and all kinds of things like that — a blue-collar approach.

I didn't grow up seeing someone put a suit and tie on, take the briefcase, and go to work like Wally and the Beaver did back in the day of Leave It To Beaver. That wasn't my experience growing up. My dad had one black sports coat. I think he wore it to every wedding and every funeral he ever attended. He never owned a full suit. I don't think he owned a tie. So when we would go to more formal things, like a wedding or something like that, he didn't wear a tie.

I grew up understanding that people in the world who dressed in suits and tie. I knew that. I saw that on TV. I saw that in other people around, but it wasn't something that was my experience. You have prom when you're in high school, and you rent a tux. It feels all goofy and silly. Even though you wear it, it doesn't feel natural or normal. Now, I go to formal events. Putting a tuxedo on for a black-tie event still feels very dress-up. 

Part of the fun for most people going to black-tie-type events is the level of dress-up.

When you go to a non-profit gala or something like that, you're wearing black-tie attire, but it's very structured even then. At my wedding, my suit was a white jacket with black pants that wasn't a sports coat, but it was a little bit of that casual combination. I've never been one who's formally dressed. So now, on occasion, when I'm formally dressed, I have a little bit of imposter syndrome. It just doesn't feel natural to me, even though I do feel I've earned the respect of the position and the authority to do so. 

Being the Chairman of the Oklahoma Venture Forum, I have no problem doing that. Playing that role and filling that responsibility, I have no problem at all doing it. But putting on the suit and tie to walk into a meeting dress that way feels like I'm an imposter.

In the grand scheme of things, you might have imposter syndrome when it comes to your role at work, your career, responsibilities, the way you present yourself, and how you're trying to get your boss to be impressed with you so you can get a promotion. 

If you're an entrepreneur, you're wearing a hundred different hats. You're the webmaster, and you're the accountant and the bookkeeper. You're the salesperson, and you're answering the phone. If you're an entrepreneur or run a small business or a startup, you're all these things. At some point, it could still feel like you're playing a role. That's perfectly fine. It happens to many people in a lot of different ways. So don't let imposter syndrome discourage you. Remember, it's all in your head. Many people go through it. Maybe not exactly the way you're going through it, or precisely the textbook definition of it. 

Whatever is in the back of your head telling you that you're not good enough, you're not capable or you're not ready - You don't have to listen to those things. You can go forward anyway. So when I put on the suit and tie and feel like I'm playing dress-up, I still do it. I still go through my thought process, and I come out of it okay. No one has looked at me and said, "what the hell is going on?" and no one has called me out as an imposter because I'm dealing with my own imposter syndrome. It's all in my head. So I can't use it as an excuse. 

Here's the key to all this rambling about imposter syndrome, do not let imposter syndrome be the excuse for you not to do something.

If you want to do something, if you need something, if you're building (a career, business, side hustle) something, if you need to put yourself out there, for people to accept you in a role... that's still not a reason to not do it. It's not very likely someone calls you out as an imposter, but the imposter syndrome is likely all in your head.