Entrepreneurship

Re-Entering the Entrepreneur World after a Comfortable 9 to 5

What did I need to change to transition successfully?

Ours is a life of constant reruns. We’re always circling back to where we’d started, then starting all over again. Even if we don’t run extra laps that day, we surely will come back for more of the same another day soon. -Joe Henderson

I took a five-year hiatus from corporate America to start my own company in the middle of my career. Work had become a toxic place. My husband and I started a video production company.

Video production was my third company, having started my second company as a free-lance insurance agent while working as an engineer. Opening a sole proprietor insurance company required passing the state insurance tests (life, annuity) to become a registered agent. I took classes and passed the tests. I continued my full-time job as an engineer. When we left the state, I did not renew the insurance licenses; my corporate career was booming. Selling insurance required a commitment of time I could no longer allocate to it.

My first company was born when I was just a teenager. As a 16-year-old mother in Chicago, I could have taught the small business master class. I hustled everything out of the back of my beat-up car. Hair products, bean pies, cassette tapes, watches, penny candy, sandwiches, and snow cones. I could “hook you up”, 24/7. I never shut down. If you had a dollar, I needed it. Running this small one-person business taught me my first lessons in customer service, urgency, negotiation, finance, and manufacturing.

Unexpected Disruptions

I did not think I would miss was getting ready for work early each morning. It turned out the daily routine of getting up, exercising, showering, dressing, and applying make-up was a touchstone of my everyday life. My spirit liked the pattern and the predictability of knowing the start of my day.

When I tried sleeping until I woke up organically, there was an interesting problem. My eyes opened at the same hour every day, no matter what time I went to bed. My mind woke up. I didn’t need the alarm. My day started with or without me out of bed.

Another daunting thing about returning to entrepreneurship is realizing there are no other people or resources than the owners (us). We were the entire company. My spouse was still working full time. Our savings purchased the sound and video equipment needed to work with film companies. When we started this new business, Florida had a tax incentive to attract filmmakers to the state.

An example of a significant difference in my role in corporate and our small business occurred when we brought our equipment. Instead of calling the IT (Information Technology) department for recommendations, I spent hours online identifying the candidate equipment for purchase. Once I had the options, I compared the best choices, including the cost of financing or paying cash. My husband reviewed the technical specifications and determined he liked none of my options, sending me into research mode again. It disappointed me he did not like my choices. The transition to an entrepreneur required humility.

Reality versus Perception

While working, since I was an executive, I seldom experienced rejection. My team members would come to my office to provide me with input when they thought I proposed policies that wandered off in the wrong direction.

Most who disagreed with me did not say, “No, you are wrong.” Instead, they took time introducing me to the concept — that they disagreed with me. I convinced myself I was easy to talk with; therefore, I was getting the truth (and nothing but the truth) from my team. Nope, I was not. My perception of my communications with my team was not their reality.

I received another ego hit because I recognized I had worked hard to establish an approachable demeanor. My reaction to unfiltered truth meant I had not. My team coddled me without my noticing. I wondered how much ground we lost because they slow-walked lousy information.

After those two incidents, I reviewed what it took to be a successful small business owner. My ego would not survive multiple random hits as I adjusted to my new role. I needed to be proactive by figuring out how to reengage to my hustler roots. I asked myself a few questions. What traits did I have that I needed now? What did I have to change to re-enter the world of the entrepreneur?

What to Change?

The corporate traits that would help me transition were, I was hard-working, used to long hours, honest, driven, project orientated, full of integrity, finance-oriented, and ruthless. My ability to work undeterred with unrelenting day-to-day problems was desirable because there is always a parade of issues to deal with in a small business.

The corporate traits I needed to adjust were: the seemly bottomless pit of money to resolve a problem no longer existed, the need to be right, having access to multiple experts on-demand, having a personal assistant, and a moderate sense of urgency.

Once I accessed my skills, technical adjustments were much more straightforward than ego-related ones. For example, there was no problem switching from the leader with specialized expertise (manufacturing) to the jack of all trades. One day, I vacuumed the rugs, accepted shipments, met with a potential client, reviewed contracts, took the mail to the post office, and paid the suppliers.

The mentality of having unlimited people and financial resources were tough to adjust to. There were no wads if cash to throw at problems. There were no department heads to accomplish tasks. I examined problems in excruciating detail to shorten timelines. If the sound guy we subcontracted did not show, guess what, we covered. If the boom person was ill, you were the boom person until they arrived. (PS do not be the boom person because they spend the entire day with their arms raised above their head!).

The corporate traits I needed to adjust were: the seemly bottomless pit of money to resolve a problem no longer existed, the need to be right, having access to multiple experts on-demand, having a personal assistant, and a moderate sense of urgency.

A Form Change

Once, we were the sound recordists for an indie titty vampire movie scene where the actors were attacked in the shower naked. They removed all men from the set. Only the female actors, the camera operator, and the sound people were allowed. They pressed me into service because I am a woman. My job that day expanded to set-dresser, best boy, and grip. The set-dresser makes sure the set is right before the cameras roll. The best boy helps with electrical equipment, and the grip works with the camera operator. None of those activities were in our contract, but on a small film set, they press all contractors into service.

Another time, a female dancer did not show up for a brief twenty-second dance scene; who did it? You know. Me. Flexibility was part of the job as the business owner. Could you imagine me dancing around in my corporate office because contracted dancers did not show up?

Be Like Water

It took three months before I fully reclaimed the skill set to be the business hustler/owner I was before. The return to the world of an entrepreneur was difficult. Years later, when I returned to corporate America because of an urgent need for premium health insurance, the transition back to a 9 to 5 was easier because I knew how to analyze my behavior and adjust.

Re-entry to different work environments is not like being re-born; instead, it is more like water’s transitions. Water is still water, no matter if it is liquid, ice, or steam. The essence remains the same. It is water and can assume all its forms as needed, just as I was me. The hustler, the business owner, or the corporate executive were all me as I entered, exited, then re-entered distinct phases of my work life.

Toni Crowe retired as the Vice President of Operations to pursue her dream of being a writer. Toni has written six books, two of which won the 2019 Reader’s Choice Gold Awards. Her bestselling business book, “Bullets and Bosses Don’t Have Friends: How Do You Manage A Man Sitting With His Dick in His Hand?” was one of the winners. Her first book, “Never a $7 Whore” was the other.

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