Have you ever bought into the idea that entrepreneurs have a flash of genius, a business idea engine built in their DNA, and talent to launch a successful business the day after they walked out of school or Corporate America?

I imagined that story, however, my journey unraveled in a very different manner. In fact, I told myself I would never leave Corporate America because I wasn’t entrepreneurial enough. I thought that I wasn’t creative enough, have good ideas or the genetic makeup (whatever that means!) to start my own business. I struggled to spot any special, sellable skills I had, and if I thought about life beyond Corporate America, I had many doubts about what I would ever do.

Reflecting now on my career journey, an underlying desire to creatively run my own business may have been trying to manifest. Because of this, my transition from corporate office to entrepreneur happened gradually by choosing to work for smaller, more entrepreneurial companies over time.

From Big to Small

I got my first job at age 15, flipping french fries at McDonald’s. I worked there because my friends worked there – we had a lot of fun.  In college, I spent time as a waitress, and worked as an assistant manager at a major retail chain. My last year of college, I started in banking because my roommate told me about the great working hours and tuition reimbursement. That was good enough for me as a money-strapped college student!

From the year 2000, banking is where I stayed.  The people, the opportunities to work across many divisions and the unbeatable benefits kept me there for 14 years. However, I began to realize a big disconnect. I was easily bored which left me constantly looking for what’s next. While the company was great, I didn’t feel great caught in the red tape.

I thought that climbing a career ladder at a big company would bring happiness and a feeling of success, but each promotion fell short of that.

Kelli Thompson

I mustered courage to leave banking in 2012, itching to do something a little bit more creative, with fewer compliance rules and structure. So, I went to work for a technology company that was still in start-up, test-and-learn mode. I got the first taste of what it was like to be creative and innovative, it was started by a woman who left her corporate job to test a big new idea.   

Two years into this enjoyable career venture, I was traveling to see a client when I got a fate-filled plane seat. I sat next to Cy Wakeman, an entrepreneur and mentor whose philosophy I’d followed since 2006.  We’d kept in touch over the years, and I was certified to teach her Reality-Based Leadership philosophy. I taught leaders how to create a drama-free life and how to live happy even when life is messy.

She offered me an opportunity to come work for her, I was ecstatic and scared at the same time because my old thoughts kept me wondering: What ladder are you going to climb if company isn’t big? What if there’s not going to be opportunities to keep you challenged? What if I get bored?

Oh, I was wrong and far from bored. Rather, I was constantly challenged with creative ways to speak, write, and to engage with clients.  Soon, many clients began to request one-to-one leadership coaching, to which Cy volunteered me. I was again, excited and scared, so I enrolled in Martha Beck’s Wayfinder coaching program to improve my skills.

As I’m in this coaching program, I have some pretty big epiphanies. In fact, my entire world was rocked because I realized that I was the one that needed coaching. Over the years I had said yes to many things that went against my natural talents in favor of what seemed like career success in worldly terms. I strived for the title and salary, instead of surrendering to what truly brought me joy. Coaching helped me rediscover what made me tick – the freedom to be creative and working 1-1 with people in difficult times to inspire an a-ha! moment.  I enjoyed watching others find more freedom and creativity, while dropping many of the imprisoning thoughts holding them back.

Three Lessons That Helped Me Leap to Entrepreneurship

What I learned from my journey from big company to small and into my own leap is:

First, entrepreneurs are comfortable with not knowing if an idea will succeed or not. Entrepreneurs are special, not because they have an ideal “personality profile,” but because they are not afraid to throw up an idea and test it.

Second, you are rewarded to be different. Every act of entrepreneurship is an expression of creativity. Whether you choose it full time or as a side hustle, it provides freedom to use your special, creative talents in unique ways.

Finally, there is the freedom to simply play, which is naturally motivating and challenging. When you can constantly be creative, you suddenly don’t need this ladder to climb anymore because its creative pursuits are endless.

Entrepreneurship is an expression of creativity.

Kelli Thompson

This slow journey didn’t prevent fearful thinking about taking the big leap. Despite the allure of doing exactly what I loved and working from home in my slippers, all of those old fears came to haunt me. The common “What If?!” tunes from my inner liar were: What if I fail? What if I’m not creative enough? What if this isn’t in my DNA? What if I can’t keep this thing going? What if nobody wants to buy what I’m selling? What if everybody thinks is a stupid?

People won’t often talk about them, but I have no problem sharing that these doubtful beliefs probably won’t ever go away. I’ve come to welcome them as normal but instead, I choose not to believe these thoughts like I used to.

Have you ever dreamed of running your own show, starting a business on the side or even staying home with your child(ren)? Maybe you were like me and believe you could never take the entrepreneurship leap. Here are three questions to reflect or journal on:

  1. What is it that you really want?
  2. Why can’t you have it?
    1. List all those stories down of why you think you can’t have it. You’re not ready. You’re not qualified, you’re not creative enough.
    2. Now, ask yourself, are these reasons really true or is that just the inner liar in our head that spins lies to keep us from what we’re truly called to do?
  3. Finally, if you acted like you didn’t believe these thoughts about why you can’t have it, what’s one little step you’d take tomorrow? What’s one new thing you’d try?

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  • Kelli Thompson

    Leadership Coach | Writer | Speaker

    Kelli spent years climbing ladders and leading teams in Corporate America before taking the leap into entrepreneurship, starting her own business as a leadership coach, writer, and speaker. She helps women unlock their potential and lead more confidently to achieve their career goals and ideal lifestyle (hustle free). She is the founder of the Rise Confidently Leadership Masterclass series for women leaders. Her two favorite roles are wife and mom.