Why Making Money Scared Me As A Business Owner

Confronting imposter syndrome has been a significant turning point for me, fundamentally altering my perspective on money and enriching my understanding of the multi-faceted value our businesses bring, both financially and in terms of community impact.
Why Making Money Scared Me As A Business Owner

Imposter Syndrome.

I encountered this term much later in my entrepreneurial journey and had I only known about it sooner, it could have eased much of my early self doubt.

For those unfamiliar, Imposter Syndrome is a psychological pattern in which an we doubt our abilities and internalize a deep-seated fear of being considered a ‘fraud’.

It manifests in various forms, but in my first several business ventures, it presented itself as severe guilt over having customers pay us money.

Yes, I quite literally had a fear of accepting the one commonality all businesses need to survive.

Back in my club ownership days, I felt guilty when collecting a room rental check from a promoter booking a show.

I was plagued with anxiety while working the door and having to charge customers money to come see their favorite band. Even though most of this money was immediately used to pay bands, staff, and go back into the business for repairs, my unease persisted.

Equally, several years later, I felt both excitement and guilt when customers wanted to book a desk at our coworking space, a maker needed a place to sell at one of our pop-up markets, or when a band wanted us to screen-print t-shirts for their upcoming tour.

I think back to all the times we undercharged customers, gave things away and failed to recognize the value of what we were doing.

I’m not really sure why I felt this, but I tend to chalk it up to an insecurity around money. I had a middle class upbringing and, while we didn’t struggle like some of my friends, it also wasn’t abundant.

Through punk rock and the people I surrounded myself with, I developed a very anti-establishment, anti capitalistic mindset.

Yes, I realize that this belief is antithetical to being an entrepreneur.

All businesses share the common need to make money and, deep down, I believed making money was wrong.

I failed to realize that I was actually solving somebody’s pain points, providing a service deemed valuable, and in most cases, helping others make a lot more money.

On most nights at the club, the promoter renting the venue left with 3 times more money in his pocket than we saw.

When I printed merch, the bands buying wholesale t-shirts from us were able to sell them for 3-4 times what we charged. This helped support their touring efforts and, quite literally, allowed them to keep gas in the van.

Startups and entrepreneurs renting space from Cowerks could keep costs down. We provided not only an affordable and turnkey office solution, but also a network of other entrepreneurs for them to plug into.

Our network of local artists, makers and food purveyors who sell each week with us at FRESH markets are equally plugged in. We provide not only a community of shoppers but fellow entrepreneurs to share, learn and grow with.

In each of these situations I struggled with this guilt.

I failed to see the value we were creating, both economically and socially.

I’m not quite sure what changed - perhaps it was experience, education or even just recognizing when people were selling much less for way more, but there was a shift.

Today, I am much more comfortable exchanging value for money, but my imposter syndrome has learned to manifest in different ways.

For example, the boutique experience we offer at The Surf Village is a luxury my family could never have afforded growing up. It’s worlds away from the budget-friendly campgrounds and state parks that were my vacation spots as a child.

It’s also quite a far experience from the surf camps and backpacker hostels I would spend weeks and months in through my 20’s and 30’s and I still very much gravitate towards when traveling today.

This led to a realization, I don’t have to be my own customer. While it’s nice to create products or services that you would use yourself, it’s not a requirement for their success.

Our high occupancy rates this past summer validated that there were plenty of individuals and families who found immense value in what we’ve built.

The number of repeat bookings we are seeing for next summer further confirms this value.

Confronting imposter syndrome is an ongoing process.

It’s important to remember that it will rear its ugly head in ever-changing and increasingly subtle ways.

When it does, I find solace in the fact that I am greater than any of my businesses, and my businesses are greater than me.

Remembering this helps me to stay humble during the highs and resilient during the lows.

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