Are you sure you want to quit your job?

Posted on October 01, 2014 by Tom Rubens, One of Thousands of Business Coaches on Noomii.

Confession: I have never had a real job. Oh, sure, I had a paper route as a kid…until I set all the papers on fire one Sunday….long story. My friend Larry hired me to help him cut the grass at a few homes in the neighborhood….not really much of a resume builder. In high school, I was a bus boy/waiter at the local deli….until I had a “difference of opinion” with one of the owners. Then came a series of debacles at drug stores, fast food chains, and travel agencies. It was clear that I just wasn’t “good employee material.”

My first real break came driving a taxi in Honolulu during my freshman year in college. This was the ideal situation for me. The taxi company charged $16 per day for the drivers to rent the cab, and we got to keep all the money we earned….Plus, the cabs at that time were simply regular cars with a taxi light on the roof, which we could take off when we were not working. This solved two problems: I now had a car to get to and from school, and I had a job that allowed me to set my own hours….and it didn’t hurt that it turned out to be a great way to meet tourist girls looking for fun on the island.

In taxi driving, I found a way to make money that didn’t involve a boss. This was very cool for a 20 year old with a big mouth and authority issues. I learned valuable lessons about time management, and got my first taste of entrepreneurship. I would probably still be driving that cab, or perhaps I’d own the cab company, but I missed Chicago and moved back to be near my friends.

I have spent the next 40 years of my life working for myself in some way or another. I traded options and commodities on exchanges in Chicago, bought and sold minor league sports teams, invested in real estate, started a real estate brokerage, and now I inspire and instruct business owners and entrepreneurs on how to transform their businesses and their lives, by giving them the tools they need to succeed.

While I still love working for myself, this life is not for everyone. I learned this lesson over 20 years ago, and it has stuck with me ever since.

At the time, I was the General Partner and General Manager of The Grand Rapids HOOPS, a team in the Continental Basketball Association that I had purchased with a group of investors. We had a strong following of loyal fans, and the games were all about family entertainment. As a life-long Cubs fan, I knew that the most important thing we could do was deliver a good time to our fans. Wins and losses can be tough to control with a tight budget and a league wide salary cap, but I made sure that smiles were abundant every night. Our half-time entertainment was far more important to most of our fans than the opposing team or our back-up point guard.

We were in the middle of our third season, and although our fan base was very supportive, the local newspaper was on my back about everything from press box seating to coaching changes to our cheerleader’s uniforms. From the beginning, they had been less than enthusiastic about my presence in their town. They saw me as a big city carpetbagger who had brought a team to their town without going through the proper channels.

Wins were hard to come by, and I felt that we needed a few to get the paper’s focus off of me and back to the team. One night, after listening to a particularly tough road loss on the radio in my office, I went home and couldn’t sleep. I was worried that the paper might just win the battle and break me and the team in the process. I loved what I was doing, and knew that our fans respected us and the work we put into every single aspect of the games and the culture of our franchise, but I was beginning to fear that the constant bombardment of negative energy from the newspaper just might be too much for us to bear.

I had 30 investors who trusted me to run the franchise and return a profit; 10 players, two coaches, and a trainer who expected major league perks on a minor league budget; a sales, marketing, and PR staff that needed state of the art tools to bring in the revenue we needed to keep this party going; and Joannie….our office manager. The stress of keeping everybody satisfied, while doing my best to act like the pressure wasn’t getting to me, was taking it’s toll.

After that sleepless night, I drove to the office the next morning thinking that it might be time to throw in the towel. My mind wandered….Maybe it was time to sell the team to a local guy…someone the paper could bless as the savior…while ridding the town of the Chicago menace. Or even worse yet, what if I couldn’t find a buyer? How could I go back to my investors and tell them that I had failed? I felt the shame of telling my staff that they would have to find new jobs after they had placed so much faith in me. The agony was overwhelming. I was in full-on victim mode. Woe is me….I don’t know what to do….boo hoo. That was my mind-set when I pulled into our office parking lot at 8am, ready for surrender.

To my surprise, parked at our front door, was a shiny new Pontiac Grand Am. What was that car doing here? I knew that no one on our staff was in a position to buy a new car–after all, I signed their paychecks! No way could they afford such extravagance, and it was too early for a salesman to be calling. The only way to answer this pressing question, was to walk in and find out….which is exactly what I did….and in the process I learned why some people would rather have a job than a business.

It had never occurred to me, in over 40 years on the planet, that anyone, given the choice, would ever choose to just have a job, rather than own their own business. Why work for someone else, when you could be running the show? Why take orders when you can give them? Why let someone else control your destiny? Why work for a paycheck when you can work to build a legacy?

When I walked in the door of my office that morning, I learned the answers to these questions….and my life is far richer for that lesson.

“Did you see my new car?!!!!!!” Joannie was beaming from behind her desk. “Isn’t it beautiful?!!!! I was so excited that I couldn’t wait to get in to show it to you!”

In her excitement, I don’t think Joannie saw the disoriented response that I felt throughout my system. It was as though one of the fundamental principles of the universe had just been proven false. I had no idea what to do with this new information. After the requisite pleasantries, I retreated to my office and closed the door.

I sat down at my desk, buried my head in my hands, and took in what I had just learned. I spent a sleepless night worried about the future of my business, and all the lives that would be touched by my failure….while Joannie went out and bought a new car.

She left work and went to a dealership…test drove a few cars…inhaled the intoxicating new car smell…spoke with the finance manager….got a loan and drove off the lot with her new car! I went home, wallowed in self-pity, and rolled around in my bed in fear. Who do you think had a better night?

She wouldn’t have traded places with me for a million dollars….and why should she? She had an entry level job that was easily replaceable. Her needs were modest, and they would be met just as well at her next job. She lived for her son, and her friends and family. If the HOOPS never won another game, her life would remain blissfully secure.

Starting your own business is not always an easy road. It can be immensely rewarding, and personally gratifying….but there is a potential downside. It can take you away from your friends and family for long stretches of time. There will be sleepless nights….I promise you that. Failure is always an option….it has happened to the best, and it can happen to you. It is a lifestyle choice that you must consider before you go off and fire your boss.

Sometimes, entrepreneurship can be best appreciated as a spectator sport. If you are thinking of taking the plunge, but need some guidance with the process, give me a call or drop me a line. I’d love to hear about your plans and join you on the journey.