A Small Business Owner On Imposter Syndrome, Self-Doubt, & What She Had To Overcome To Start Making Money

By | Tuesday, November 09, 2021

This article is created in partnership with Squarespace.

“Am I ready to start a business?”

It’s the question that plagues so many aspiring entrepreneurs and keeps some of the best ideas stuck in planning-purgatory. It’s even worse if you’re a perfectionist because your mind is constantly changing, which only leads to never-ending procrastination 

So instead, ask yourself these two questions:

When is the wrong time to start my business? 


When is the right time to start my business?


Now that we’ve got that out the way, it’s just a matter of locating our starting point. What do you need and how do you start? 

Recently, we had a chance to chat with wedding planner extraordinaire Jamie Wolfer. As CEO of JW Coordination, Jamie reveals that one of her more challenging tasks as a new entrepreneur was convincing herself to finally start.

As for how she got over the fear of finally starting a business, she admits she didn’t. But in the end, a leap of faith paid off.

“I don’t know if I ever truly felt ready to take the leap, necessarily. It wasn’t like a big turning point or a big light switch moment. It was a slow build of confidence for me until I reached the point where I thought, ‘You know what? Enough excuses. Let’s just go for it! Because there’s not going to be a big light bulb. You’ve built up enough. You’ve done enough work. It’s time to launch. It’s time to go!’

“So the advice I would give [to anyone] is to bet on yourself sooner. So many times I just stopped or held out. I didn’t make that leap or take that jump because I was so scared of failure that I didn’t even try.”

When asked how she managed with little-to-no start-up resources, she admits it wasn’t easy.

“In the beginning, it was by the skin of my teeth. Whatever I could afford, I would do. Then when money started rolling in, I really needed to allocate my finances properly, otherwise, I would be spending too much on advertising and not have enough left over for other things. So it was trial and error.”

While Jamie encountered her share of business setbacks, she also shared some of her better business choices that later set her up for success.

“The best investment I’ve made in my business has been using the right software. I am a huge fan of working smarter and not harder. And if there’s any sort of technology that can streamline things for me, sign me up,” Jamie says.

She continues, “Since the beginning of my business, I’ve used Squarespace. I have been a Squarespace user for five years. Like I said earlier, having good tech is unparalleled. I need something to just handle that situation for me. I know what my gifts are and I know what they’re not, and I am not a web developer.”

Jamie goes on to explain exactly how Squarespace has been good for her company, as well as her peace of mind.

“My experience with Squarespace has been absolutely phenomenal because I could make all the pretty things in my head come out on the page. I simply love the user-friendly interface of it because if there was any sort of coding or weird letters squished together, I wouldn’t understand what to do with that. So using Squarespace has been a way for me to save time and still present the professional brand that I want to show potential clients. I can still look professional as heck without spending hours upon hours working on a website that completely confuses me.”

While Jamie is happy to have landed on the right technology to help make her work more efficient, she admits that her confidence is still a work in progress.  One way she overcomes this is by measuring her success by her talent and not time.

“Self-doubt and imposter syndrome can be so hard. ‘Who am I to be running a business and asking people for money? I’ve only been doing this for 12 months. Like, are you crazy? There are people who’ve been doing this for 10 years.’ So that’s been the hardest part — overcoming that. And it’s still something that five, six years into this that I’m struggling with, but I’m better at it now.

“The biggest personal journey for me is recognizing that I may not have been doing this for 10 years, but that doesn’t mean I’m not darn good at it.”

If you’re ready to get started building your own website, head to Squarespace for a free trial. With our offer code “FINANCIALDIET,” you can also save 10% off your first purchase of any website or domain.

Image via Unsplash

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