Is It Time To Leave?

I have observed that most prepared entrepreneurs are in their mid to late 30’s. I have financed many of them. Something happens when the corporate citizen feels the draw to  become an entrepreneur. I know because it happened to me. Here is my story.

At 30 years old,  I was asked by a potential acquirer of the company I was leading at the time, “Where are you headed?” I said, “I want to be running a $1billion software company by the time I am 40.” I never really thought about that question until I was asked. When I answered it, I was as sure about the answer as I was about anything in my life at the time. I had ambition.

I was making progress on this goal when I came to realize I lost interest. I was 37 years old and I was president of a US division of a UK based public IT services company with $60mm in sales. The money, the prestige, the perquisites, and life in general were all great. The problem was I was miserable.

Suddenly what was once good, even excellent no longer held my attention. I thought, “this could not possibly be my problem” so I blamed others.

My boss is too detailed. He is driving me crazy. Selling to F500 CIO’s was predictable and boring. The industry I was a part of were not smart enough or good enough for me. The employee base was disloyal and self-centered. There was a lack of variety in the work. It was same old, same old, day in and day out. I was traveling to much, drinking too much, thinking too much, working too much, playing too much, making too much and none of it was enough.

But the real problem, I was not being the man I knew I was supposed to be. I finally had the guts to admit it. But did I have the guts to change?

Here’s my path from corporate life to entrepreneur and investor

1. Analyze Your Dreams

I came to realize, and then had to admit, I did not want my bosses job. I did not care about what he cared about. He valued working hard, playing hard and spending hard. I tried it for the last 15 years and it did not bring me fulfillment.

My values and the values of the people I worked with were different. I was at a crossroads. I had to either abandon my values for the company’s values and continue my career or I had to leave.

Here is what happened. In the midst of this personal confusion, my boss and I had breakfast. Our business was highly dependent on the economy and things were not well. A week earlier, he asked me to join the executive management team in taking a 10% cut in pay to show the shareholders we were in this downturn together. The money did not matter to me but I acted completely irrationally toward his request.

At the breakfast, my boss got to the bottom of it (for me). He said “If you are not happy here then you should leave.” I said, maybe I should leave. We parted that morning. (To this day I am not sure if I quit or he fired me.)

Now I was free to pursue who I was supposed to be, but who was that?

2. Go Back To Your Last Good Memory

I romanced how great it was to run a startup. So I joined a startup. They raised money around a great team and product but needed a CEO to grow it. Who better than me and what better situation than this?

It was wrong for me and wrong for the startup. About six months into the startup I felt like I was revisiting management issues from earlier in my career. They were important issues but not interesting issues to me. To stay was not fair to the shareholders or the management team and employees. I moved on.

I continued to pursue my original ambition of running tech companies but it was not to be. I got close on running another one but was not hired. I helped start a professional services firm and my cofounder quit.

Finally, I came to realize I was not supposed to be running tech companies. The change included a change in occupation. This was scary.

3. Cut Loose (From What’s Holding You Back)

During my time of unemployment, my son asked me, “Doctor Phil (our next door neighbor) is a doctor. What are you?” I was devastated by this question from a four year old. I thought about it and said “I guess I am just your dad.” He answered “That’s great.” This was the beginning of the rebuilding process.

I was put on a shelf. This was the first time in my life I had time to think. I had no mission, no direct reports, no work to get done and no idea what to do next. I prayed for the first time in a long time. All I had was God to turn to. I was so desperate I made all kinds of ridiculous deals with God if he would get me employed and provide for my family.

I was becoming a man God could work with.  Within three months, I came to realize I was an alcoholic and accepted an invitation from a friend to an AA meeting. This began a one year journey which ended in me giving my addiction to a higher power, getting sober, working the 12 Steps, seeking God and ultimately seeking forgiveness and surrendering my life to Jesus as my Lord and Savior.

To think, all this started with me being unhappy at work. I guess God gets our attention by eliminating what is the focus of our attention at the time.

4. Get Ready For Your Next Assignment

Remember the company where my cofounder walked out? I realized I was not the right person to run the company. Immediately after this, I received a call from a friend and former coworker who was looking for a sales management opportunity.

I remember the lunch like it was yesterday. I told him he appeared to be like many software sales people, looking for the next fast train just about to leave the station. He was 36 years old and he needed to start a company. He knew who he was and could create a great company based on his values. He asked: “What kind of company would I start?” I told him I just happen to have one.

Bob, as the CEO/Founder and me as the founding investor built two great companies in 20 years. We just successfully exited from the second one in January 2014.

Thanks to Bob and his decision to become a startup CEO in 1993, this was the beginning of my second career as a professional angel investor. God uses my experience, network and resources to help entrepreneurs achieve their dream of starting and running their own company.

Making this kind of change in your life is difficult. Not making it leads to a life of regrets. When the dissatisfaction in your occupation hits, no matter what your age, you need to trust the process. Step out and see what God does to bring you to your destiny.

What’s your startup entrepreneurial challenge? Your tweets help me decide what to write about next. @cpaparelli

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