Bringing Light to a Shadow Career

The Artist’s Way by Julia Cameron describes “Shadow Artists,” or people who had the desire to be an artist, but were either discouraged from or just gave up on their dreams, falling into a world of could-have-beens and regrets. What often happened is that these people then worked on the “outskirts” of an artist’s career. Someone who wanted to be a singer, for instance, wrote songs instead, or someone who wanted to be an actor became a writer.

In reading Cameron’s book, I realized that I was really a “Shadow Entrepreneur,” in that I had always wanted to be an entrepreneur but lived on the outskirts, working in the world of finance and in the role of CFO instead of founder or CEO.

Many people reflect upon their career choices as they grow older and realize that their circumstances or fears kept them from pursuing what they really wanted to do. But not many people have the luxury or the circumstances needed to give everything up and start over. So how can C-Suite leaders who can’t or won’t give up their “Shadow Careers” bring their passions to light?

First, it’s important to understand why you’ve opted for a shadow career, as the answer is usually more complex than “it just worked out that way.” Many people suffer from some form of hidden guilt or negative experience from the past. Some of us suffer with this throughout our lives, allowing it to sabotage or hold us back from achieving our true dreams and capabilities. There is a fascinating book called Imaginary Crimes: Why We Punish Ourselves and How To Stop by Lewis Engel, PhD and Tom Ferguson, M.D. that examines these types of issues in depth.

The most obvious issue many of us face is some form of inferiority complex where we seek to overcompensate for perceived weaknesses, resulting in either tremendous success or extremely antisocial behavior. Over-compensating can result in a superiority complex that offends people around us. Those who do not address the complex at all can suffer from low self-esteem and weak confidence levels.

My personal guilt or inferiority complex has been the feeling that I could have achieved more and a lack of fulfillment from what I have actually accomplished. In many ways, I have accomplished a lot and have much to be grateful for, with a happy, healthy family, a fun, challenging job, working with great people and making a good living, but there has been something missing.

My father was a successful entrepreneur and came from a long-line of businessmen. His great-grandfather, John Hornby Maw, was an amateur artist, painting alongside JMW Turner, a leading British artist from the 18th Century. He and his sons also founded a tile company, Maw & Co, which became one of the largest decorative tile manufacturers in the world. My father followed in that line and was a key figure and role model in my life. I was always fascinated and excited by the world of business. I met many other successful businessmen during my formative years and always wanted to be an entrepreneur—I yearned for the risk, reward, excitement, satisfaction, and control over my own destiny.

In my case, I got talked into taking a less risky route in life by my father and pursued a relatively safe profession in the accounting and finance world. This shadow life has treated me well but failed to satisfy my true burning desire, leaving me with an empty feeling of success.

What am I doing about this? Well, I am now investing in startups, advising and mentoring entrepreneurs, and making an effort to become financially independent. I also learn and contribute as much as I can in my role as CFO and advisor to a CEO. I am expanding my network and focusing on self-improvement, all of which I know will be key to my future success. One day, I hope to pursue an entrepreneurial venture of my own.

Most people can’t drop everything and start over right away—and moreover, the very idea of starting over entirely can bring its own form of paralysis. So try thinking smaller as you make your plan to transition to the place you really want to be. Ask yourself questions such as:

What skills do I need to gain in order to do what I really want to do? How can I parlay the skills and experience I already have to get started? What kind of financial cushion will I need in order to pursue my dreams?

As a leader you know that it’s critical to couple drive with follow-through. The greatest recommendation I can make for CEOs and leaders who want to bring light to their shadow careers: find the support system that will keep you advancing toward the career you want and works for you. As a leader you’ve probably already engaged with a coach for presentation or speaking support. For me, working with a coach who understands my long-term goal of becoming an entrepreneur and holds me accountable to the myriad steps I need to take to get there is invaluable.