"How did you know you were ready?"


My Great-Uncle Buck was a successful, self-made businessman. He grew up on a farm in Arkansas and later moved to Seattle with his wife, Lou. He started out dirt poor working in construction. Later, he began investing in storage units, then office rental properties, and eventually became a self-made millionaire. You would never know it. He wore the same pair of Levi’s jeans and denim shirt every single day of his life. He knew what was important in life, and it wasn’t flashy, material things.

In 2010, I received the opportunity to work at a rental business with the intention of purchasing it at the end of the year. Owning my own business was something I have always known in my heart I wanted to do. The date had been set; on January 1, 2011, I would take over ownership of this business, but as the date grew closer, the more the fear crept in.

That summer (August 2010) I flew to Seattle to visit Uncle Buck. (Yes, that really was his name.) He’s the only other member of our family, other than myself, who really had an entrepreneurial dream and had gone for it. He was the perfect person to talk to about my trepidations and fears. 

So there I was, sitting in his gorgeous home looking over the Puget Sound in Washington, sipping on a glass of wine, and I will remember the following conversation for as long as I live. I told him about my fears. I said, “I’m scared to do this. I really want to do this, but what if I fail? What if I get in over my head? What if I’m no good at this? What if I lose everything?”  

And then I asked the question, “How did you know you were ready?”

He looked at me and said, “I remember just looking at Lou and saying, ‘We’re happy right now just the way we are. We live in a small home that we like, we drive a very modest car, we have good friends. The worst that can happen, if we completely fall on our faces and this whole business dream fails, is we go back to living exactly the way we are living right now and right now we’re happy, so I don’t really see much risk.”

Then he asked me, “Are you happy right now?”

I said, “Yes.”

He asked, “If you don’t do this, will you wonder every day if you could have?”

I said, “Yes.”

He replied, “Well, then you just answered your own question. You don’t have a crystal ball. There’s no way to know if your business will succeed or not, but if the worst thing that happens is you go back to living the way you’re living right now, then there’s your answer. You go for it.”

I know how scary it is to take the leap. I remember the pit in my stomach when I signed what felt like an unending stack of papers when I purchased my rental business (that I later transformed into what it is today, a floral design business). The one thing we have to remember about fear is that it’s only temporary, but the regret of not doing something because we allow fear to hold us back can last a lifetime.


Welcome to the blog

Hi! I'm Jessica Zimmerman, top wedding planner and floral designer.

Born and raised in Arkansas, I’m a proud wife and mama to a 5-year-old daughter and 3-year-old twin boys. A true believer in freedom, flexibility (and of course, incredible flowers), I’m wholly devoted to creating a life I love to live every single day–not just on the weekends. From travel to business to weddings, this blog is full of features designed to inspire other busy mamas (and businesswomen) to make a living from their passion without giving up their lives.

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AUG 8, 2019

Entrepreneurs Looking for More

Meet host of the Zimmerman Podcast, Jessica Zimmerman, as she shares what it takes to grow your business while living the life you love. To make sure you never miss an episode, hit subscribe now!


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