Career Change & Personal BrandingBlog

I looked down at the page of notes I’d just written, and suddenly, hot tears started pouring down my face. In that moment, I knew. I knew I had no other choice but to quit my job and become an entrepreneur. The problem was, I was terrified.

I’m no stranger to job changes, or even career changes, for that matter, but this particular leap from employee to entrepreneur was a chasm I had never dared cross, and that day as I sat at my kitchen table, fully coming to terms with the fact that starting my own business would indeed be my next step, the full weight of my fear was all-consuming.

Climbing The Corporate Ladder

I didn’t know any entrepreneurs when I was growing up. Everyone around me worked a 9-to-5 job in exchange for stability and a paycheck, and I was brought up to do the same.

I started my professional career as a fourth grade teacher with Teach For America, doing my part to help close the opportunity gap and ensure that all students had access to a great education. After a couple of years in the classroom, I thirsted for an opportunity to have an impact on more than just the twenty-five students in my classroom, so I went back to school to study game design, in the hopes of creating educational games.

After a few years in the games industry, I then transitioned into the field of learning and development, creating gamified online training programs for companies like Google and LinkedIn. Over the years, I fell in love with design. I loved the challenge of coming up with new ideas, the sheer beauty of a well-designed product, and the impact that my designs had on others.

One thing I did not love, though, were the meetings. The farther up the corporate ladder I climbed, the more my daily calendar was crowded with meetings. Stakeholder meetings, planning meetings, client meetings, team meetings, review meetings. I had meetings coming out of my ears, and I barely had time to do the design work I loved. I was miserable.

The Side Project

It was around this time that I began searching for a side project, something outside of my 9-to-5 job that would reignite that passion in me again. As it so happened, I had an opportunity to put my design skills to good use by helping my husband (a real estate agent) redesign the website for his business. I jumped at the chance, and through this side project, I developed a love for real estate investing.

I realized that real estate investing could be my way out of the corporate world. Through investing in more real estate, I could create more passive income, thereby offsetting the income from my job and giving me the opportunity to work less or quit my job altogether and spend more time with my family.

As I talked to friends and family about my real estate investing ventures, I realized that there were many people out there who might be interested in leveraging my experience in real estate to invest alongside me. They were hungry for that passive income too.

So at this point, I had a W-2 job that was draining my energy, a side project that lit me up, and the tiniest voice in the back of my head prodding me to jump ship and consider starting my own business.

The problem was, I didn’t think I could go through with it. Back in my game design days, I had worked in multiple startups, and I saw firsthand how incredibly difficult it was to get a business off the ground. I didn’t want to put in all those long hours, especially now that I had two young kids at home.

But still, something was nagging me at the back of my mind, driving me forward, so I dove into personal and career development books, podcasts, blogs, and meetups in search of an answer.

The Moment I Knew

One day, lots of soul-searching exercises later, I found it – the exercise that changed everything.

It was a simple little exercise, really, and I almost didn’t do it because it seemed so simple.

I took a sheet of paper and divided it into 3 equal parts. Then, I labeled the sections Dangers, Opportunities, and Strengths.

Then, I listed all the potential dangers related to quitting my job. I wrote down things like “loss of income,” “halting my career progression,” and “isolation from peers.”

Then, without stopping, I moved on to the Opportunities, listing things like “work when and where I want,” “free myself from the negativity at my current job,” and “build wealth for my family.”

And finally, I moved on to my Strengths and wrote things like “I dream big,” “I’m a problem solver,” and “I don’t give up.”

When I was done with all three lists, I kept going. I created another Dangers / Opportunities / Strengths list for building my own real estate investing business and proceeded to think through the potential pitfalls and opportunities of that venture.

I wrote until my wrist was sore and I had no more to write. Only then did I put down my pen to look at what I had written. In that moment, I saw in plain black and white how the Opportunities and Strengths far outweighed the Dangers. And because of that, I knew. I knew that I had no choice but to face my fears and brave those potential dangers, or else I’d be relinquishing so many opportunities and wasting my strengths.

Prior to seeing it all written down, all those fears and opportunities were swimming around in my head, and the fears far overshadowed the opportunities. When I wrote them down, however, I was able to see them at face value.

I still cried though. Actually, I sobbed. I sobbed from the fear of knowing what I had to do, and from the relief of having finally made the decision to leave my job and reclaim my life.

The Transition

I won’t pretend that the following months were easy. There were certainly thrilling moments, but there were also really difficult, and sometimes awkward, moments. But in the end, I was free. After 10 years as an employee, I was out on my own as an entrepreneur for the first time.

A funny thing happened after I quit my job. As an employee, I’d always thought that the hardest part about being an entrepreneur would be figuring out how to make money. But as soon as I became an entrepreneur and opened my mind up to the possibilities out there, I realized that there are countless ways to make money; the difficult part was not in figuring out how to make money but in figuring out how I wanted to make money.

It’s a subtle difference, but one that made all the difference, because it led me to get crystal clear on the business I was building and the audience I was trying to serve. Rather than chasing 50 ways to make money, I honed in on just two. And then I gave those two everything I had, putting to use all my years of design experience, iteration, and problem solving to get my business off the ground.

Fast Forward

Since I’ve become an entrepreneur, many people have asked me if I could see myself going back to a corporate job. The honest answer? Absolutely not.

When I was working as an employee, I didn’t allow myself to consider the other path, so I tried everything I could to make the employee mold fit me. But once I tried on entrepreneurship for size, I realized that, perhaps I was never cut out to be an employee, that perhaps I was always meant to forge my own path.

These days, I am a proud business owner. Together with my business partner, we continue to grow our business and serve new clients every day. The only meetings on my calendar these days are meetings I purposefully put there myself.

And as for those seemingly huge Dangers I’d listed in my notebook before I made the leap to entrepreneurship, those have become mere blips in my journey. In their place, the Opportunities and Strengths continue to fill my days with energy, passion, humility, and gratitude.

About Guest Contributor Annie Dickerson

Annie Dickerson is the co-founder and managing partner of Goodegg Investments, a company that helps people learn about and invest in real estate syndications (group investments). To date, Goodegg Investments has co-syndicated over $400 million in real estate assets around the country.