An Entrepreneur’s Story: When to Quit Your JOB

Written by on August 19, 2008 in your Business with 2 Comments


The following is my response to comment from a friend – who asked the question

It would prove an interesting story on your thought process over the years to finally waking up one day and deciding to quit. Obviously that’s overly dramatic as no one should quit a job without an idea or better yet much of their income replaced by their new venture. It would help those who may currently be racked with fear of the “what ifs” and at least determine if going solo is for them.

Video Expressions was my first entrepreneurial venture in 1991. It was through that experience that I learned that it is possible to eat without a 9 to 5. Most people from the time that they are 4 or 5 years old start thinking about what they want to be when they grow up. Initially, it is fireman or baseball player – later it becomes refined based on our aptitude. In 11th grade, since I was good in math, I was invited to participate in an after school program to encourage kids to pursue engineering. From that point on, I was determined to become an engineer – especially when I found out how much money they made.

I would go on to complete my bachelor and master degrees in Electrical Engineering and then move 1100 miles away from home in sunny Florida for my “dream job” in icy cold Massachusetts. About a month or so into the job – I knew that I couldn’t do this for the rest of my life. It was too restrictive. The best hours of each day were devoted to the 9 to 5 and I had to fit in life around the job.

I think that everyone has that epiphany – some sooner than others. The later one has it; the more committed one is to a 9 to 5. They really aren’t committed to the 9 to 5, but they in are debt up the wazoo. A 9 to 5 is simplest, most practical and most guaranteed way to pay the bills. It is amazing the freedoms that people will give up for security – the guarantee.

When I started Video Expressions, I had been out of school for 4 years. I wasn’t married. I didn’t own a house. I hadn’t run up any serious debt. So, from that perspective it was the ideal time to quit. Unfortunately, I didn’t know squat about running a business and about 11 months later – I was back punching a clock.

Although Video Expressions was a flop, I wouldn’t trade those 11 months for anything. When I went back to the 9 to 5 – I had a completely different perspective. My goal wasn’t to become the best design engineer I could be – it was to learn the skills necessary to be successful in my next venture. I quickly moved out of engineering into marketing and eventually into sales. I went to business school at night and received an MBA. Once I decided that trading stocks would be my next thing, I developed a game plan and most importantly saved as much money as possible. The death of any entrepreneur is lack of capital.

All of that preparation took many years. It would be 14 years from the time I shut down Video Expressions until I started The Time and Money Group. Sure I could have done it in less time, but the journey was fun. Matter of fact, my last 6 years wining and dining customers, as a salesperson, was a hard job to walk away from. So, at least for me – I didn’t wake up one day and say I quit. It was a long process with many twists and turns.

Every entrepreneur’s story is a little different, but speaking for myself – the journey has been fun, the destination is a blast and I wouldn’t trade it for anything. If you are considering flying solo – just do it. The worst that can happen is that your business fails. If that happens – welcome to a proud fraternity that includes just about everyone that has ever formed a business. The experience will be far greater than walking around thinking what if. Also, employers love people that are self-starters. As an ex-entrepreneur you will quickly find another 9 to 5. On the other hand, your venture could be successful and you will be living your dreams.

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  • Marcie

    I left my job in February of this year to pursue my passion of writing. While I have not started making “real” money, I am learning a lot. I didn’t know so much was involved in writing for magazines. It is great. AND, should I have to return to the workplace, it will definitely be part-time. I can pay my bills while working on making my dreams come true.

  • Amanda

    I would have to agree with you whole-heartedly that although no one wants to admit they failed, holding on to the lessons learned from a failed business gives you an entirely different perspective on your next venture, and an appreciation when you succeed. From my experience, most entrepreneurs are always entrepreneurs-it doesn’t stop after the first (or second) failure and many thrive on the lessons learned. Thanks for sharing your own experience.