The Hard Truth About Going From Employee to Entrepreneur

I landed in commercial nuclear power operations at the tender age of 18, and it did not take long to discover that I had an aptitude for the work. By 22, I was a licensed Reactor Operator — nearly unheard of at the time. By 25, I had earned my Senior Reactor Operator license and continued climbing through shift operations, supervision and management.

By 38, however, I had the uneasy sense that I had mastered the profession and done about all there was for me to do.

Then I was introduced to the idea of “unlimited income potential.” Sales and business ownership seemed to offer something my utility career could not: a direct connection between effort, skill and financial reward. So I did what, in retrospect, looks almost reckless. I left a secure utility career after 19 years, moved from Michigan to Washington, D.C. and discovered very quickly that reality is where you land when the bottom falls out of your world.

It became clear that competence as an employee inside a large organization does not guarantee success in an entrepreneurial setting.

From the outside, sales and entrepreneurship can look like freedom. Plenty of books, seminars and programs will show you how simple the transition can be. I know because I read many of those books and went through several of those programs.

Over the years, however, I learned that moving from employee to entrepreneur requires passing three very different tests — tests that do not get nearly as much attention.

1. Can you survive the transition?

Before making the leap, I would ask four questions:

1. What is your “why?” A sufficiently powerful reason can sustain you when the early excitement wears off. For me, I wanted to resolve a concern that had bothered me for years: If I lost everything, could I build it back again? Not everyone thinks this way, but more than a few nuclear operators do.

2. What are your income sources? My wife worked full-time and had benefits, which helped smooth some of the many income troughs I would experience.

3. What condition are your household finances in? We maintained varying levels of liquid reserves and had utility pensions waiting in the distance. We also sold our Michigan home and rented for several years, both to reduce expenses and free up cash.

4. Is your spouse ready for the concessions and uncertainty ahead? Entrepreneurship rarely affects only the entrepreneur. Income volatility, delayed gratification and changing priorities become household issues very quickly.

2. Do you have the skills required to engage the market?

The next test is whether you have the skills required to engage the market. There are many, but four deserve special attention.

1. Can you persuade people? I thought I was very good at this. Inside a large organization, I had developed a reputation for being competent, direct and strong-willed. I could tell people what needed to be done, and most of the time they did it. When they did not, there was always a supervisory chain available to compel action. Try that in the marketplace. Customers do not report to you. Prospects do not care about your title or the initials after your last name. You must earn their attention, their trust and ultimately their willingness to act.

2. Can you sell something — anything? The ability to sell a product or service is the lifeblood of any venture. Mark Twain is often credited with the observation that a person who has carried a cat by the tail learns something that cannot be learned any other way. Sales works in much the same way. You can read books, study techniques and attend seminars, but eventually you have to convince someone to buy.

3. What is your valuable skill? My early answers were nebulous: high standards, strong leadership, problem-solving ability. Those qualities look good on a résumé, but they are not particularly useful in a marketplace crowded with choices. A customer needs to understand what you can actually do for them.

4. What market need can your valuable skill satisfy? I am a serious math guy. In nuclear power operations, that ability had an obvious home. Outside that world, I had to discover where those same skills created economic value. Eventually, I realized I could use them to solve financial and tax problems. Put another way: Where is the starving crowd, and what can you offer that it already wants?

3. Can you endure the uncertainty long enough to succeed?

This is a reality that few gurus spend much time discussing. I had to grind for roughly 10 years before I really mastered what I needed to understand. These questions matter because they test emotional makeup more than academic or intellectual ability.

1. Can you persevere until you finish? This applies in both small and large ways. You need the perseverance to get to “done,” not merely stay busy and try hard. That was one of the biggest lessons in moving from employee to entrepreneur. The market does not pay for effort. It pays for completed work, solved problems and delivered value. You finish one job, then another, then another, until eventually there is a business where there was once only an idea.

2. Can you handle rejection? Rejection can sting badly enough to make you question your decisions, your offer and sometimes yourself. I had to learn that rejection is also information. The market may be telling you that the offer is wrong, the audience is wrong, the timing is wrong or the message is unclear. The challenge is learning from rejection without allowing it to define you.

3. How do you cope with ambiguity? My unofficial motto was, “Hold on, let me overthink this.” I had to learn that entrepreneurs rarely get complete, verified information before making important decisions. At some point, you gather what you can, weigh the risks and move.

4. Can you come back from setbacks? To paraphrase Rocky Balboa, life is not about how hard you can hit, but how hard you can get hit and still keep moving forward. I have replayed that idea in my head more than a little. Every entrepreneur eventually takes some hard hits. I know I have. The question is whether you can absorb them, learn from them and keep moving.

Before you make the leap from employee to entrepreneur, understand that being good at a job and being prepared for entrepreneurship are two very different things.

It is easy to watch Shark Tank, read a success story or attend a seminar and imagine yourself on the other side. What you usually do not see are the years of uncertainty, rejected offers, financial compromises, wrong turns and lessons that came before the success.

That does not mean you should not make the leap. It means you should take inventory before you do. Can your household survive the transition? Do you have the skills to engage a market and persuade people to pay for what you offer? And do you have the temperament to keep going when the answers are unclear and the results are slow to arrive?

The encouraging part is that you can prepare for much of this. You can strengthen your finances. You can learn to sell. You can sharpen a valuable skill and find the market that needs it. You can practice making decisions with imperfect information. And you can begin testing yourself before your paycheck disappears.

Entrepreneurship has ultimately given me much of the freedom and opportunity I hoped it would. It has been nothing short of life-changing. But it took far longer, and required far more of me and my wife, than I imagined when I walked away from that secure utility job.

Before you ask whether you are ready to become an entrepreneur, ask a better question: Who do I need to become to build the business I imagine?

I landed in commercial nuclear power operations at the tender age of 18, and it did not take long to discover that I had an aptitude for the work. By 22, I was a licensed Reactor Operator — nearly unheard of at the time. By 25, I had earned my Senior Reactor Operator license and continued climbing through shift operations, supervision and management.

By 38, however, I had the uneasy sense that I had mastered the profession and done about all there was for me to do.

Then I was introduced to the idea of “unlimited income potential.” Sales and business ownership seemed to offer something my utility career could not: a direct connection between effort, skill and financial reward. So I did what, in retrospect, looks almost reckless. I left a secure utility career after 19 years, moved from Michigan to Washington, D.C. and discovered very quickly that reality is where you land when the bottom falls out of your world.