Entrepreneur Journeys: When to Leave Your 9-5

Starting out as an entrepreneur is one of the most exciting times of your life. Being able to follow your dreams and pursue your professional passion invigorates and empowers you in ways you never dreamed of. 

By Jackie Kossoff 


One of the questions you inevitably face as you begin to create your dream business is when to leave your 9-5. Like many women, you probably landed an office job right out of college. That’s what everyone tells you is the right and safe choice. Now that you’ve realized the corporate life isn’t a panacea, the biggest, scariest decision you have to make is when to leave your 9-5, cubicle-centered life.

I wish I could tell you that this question has a one-size-fits-all answer.  I speak from experience when I say that it is different for every woman. In fact, the time you ultimately end up leaving may surprise you.

I was introduced to the online entrepreneur world back in June 2017. Though I  had never considered owning my own business, just three months later I signed up for a group business coaching program. It was the single best, most exciting decision I have ever made!

Throughout the process of building my business, I was cautious. My plan was to sign several high-paying clients, reach consistent $5k months, and then hand in my notice without having to worry that I would need to dip into my savings to support myself as I continued to grow my business.

Fast forward to November 2017, and my 9-5 threw me a curveball. While I had felt stagnant in my position for months, it had never become unbearable until this moment. The news that I received left me feeling professionally insulted and vastly underappreciated.

At this point, my group business coaching program was coming to a close. I had built a solid foundation for my business and signed one client from my existing network of friends and family. I had a significant amount of money in my savings account thanks to moving back in with my parents after graduation. I knew that my time would be better spent building my business instead of continuing to work in an office where I felt miserable and professionally stifled.

As with most of my major life decisions, I wanted a second (and third) opinion. I am extremely fortunate that my parents and friends were supportive of my decision to start a business. However, I knew that starting a business while I still had a regular paycheck was much different from making the leap to full-time business ownership. After speaking to one of my closest friends from college (she had freelanced for a year while living the nomad lifestyle), and my dad, I knew I wasn’t going to be homeless if the worst happened. Even my mother—and she  is much more financially cautious than my father—was supportive of my decision to leave sooner than expected.

The very next week I handed in my two-week notice.

The world did not end. No one was angry with me. Some of my coworkers were shocked, but they were all very excited for me. In fact, I am now an official vendor and still occasionally design advertisements for the company.

I left my 9-5 on the last day of November 2017. I was 24.  I didn’t feel nervous or afraid. I felt this was the decision I was supposed to make. It was the right time for me to live my entrepreneurial dreams, dreams I had discovered only five months before.

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Jackie Kossoff is an entrepreneur in Los Angeles. Learn more about her on her website, www.jackiekossoff.com, and her Facebook page, www.facebook.com/jackiekossoff. Her Instagram handle is @jackiekossoff_la.