Stepping Out: Unexpected Thoughts on Being an Entrepreneur

When I resigned from my job in April, I assumed that I would find another job within an organization. I immediately began exploring possibilities where I could use my years of organizational experience and a newly minted certificate in nonprofit management in an executive management position.

I was excited about the changes, and nervous about how to translate my church-based experience into other fields of leadership, but I was confident that my work background, skill set, personal profile, education and references would open opportunities for me. And although job searches in today's work environment are arduous and largely impersonal, there has been some progress. No job, but what feels like progress.

One day along the journey I had a person suggest to me that I start my own business. My laughter could be heard down the hallway! But that laughter turned into consideration, and the consideration led to imagination, and imagination led to consultation, and consultation led to articulation, and articulation is being converted into action. I am starting my own business. Are you laughing now?!?

Since some of you might also be in transition, I thought I'd offer some of my thought process. Maybe it will help you. If you'd like, I'd be glad to talk with you more directly. Drop me a line.

Here are some of the thoughts that I've wrestled with along the way. I'm pretty sure my wrestling is not done.

Point: I don't have much to offer. Even though I have rich and varied leadership experience, there is a nagging sense that such experience is not really experience. I've had great staff members to cover my backside. It's hard to point to the specific skill sets that distinguish me.

Counterpoint: My experience and education are unique and profound. I am frequently surprised when practices and concepts about leadership and organizations that for me are intuitive are heard as new (and helpful) ideas by others.

Point: I am not an entrepreneur. I've always worked in organizations with a set job description and lots of bosses. I don't know anything about starting something from scratch.

Counterpoint: My whole life has been entrepreneurial. Within the context of my jobs, I have always been a creator, initiator and developer. Each of my jobs required major changes, and it was an entrepreneurial spirit which helped me thrive in those situations.

Point: I am at the wrong point in my life to risk self-employment. While my wife and I share the income burden, I have always been the primary wage-earner. Insurance, retirement savings, paid vacation and the like are all part of the work culture that we count on.

Counterpoint: There will never be a better or right time to take the risk. This is my mid-life. Well designed and astutely managed self-employment will be different, but it is not impossible. We will learn to adapt to a different financial flow to our lives.

Point: I am a team player and this is an individual sport. It will depend wholly on me, and I work better in teams and as a leader of groups.

Counterpoint: Already I see that I will not be alone. There are several wise advisers walking with me. There are potential partnerships emerging. I will able to use my passion for working collaboratively to bring people together.

Point: I don't have my act together. I am a flawed and limited human. I have weaknesses and vulnerabilities. I am unsure at times. My brain doesn't always work the way I want it to when I want it to.

Counterpoint: I don't have my act together. I, like the people and organizations I work with, am a flawed and limited human. I, like those I serve, have weaknesses and vulnerabilities. I, like those I would encourage, am unsure at times. Amazingly, my brain still works, and in mysterious, unique and wonderful ways.

There are, of course, other points of concern. Where will the business come from, especially that first contract or two? How will I respond when things don't go as planned? Will I be able to focus? Will the work become too consuming?

But the possibilities are too great to ignore, the calling too strong to shrug off. I love helping others perform at their best. I have a passion for healthy organizations and a deep understanding of how leadership fosters that health. I like questions, big, hard, complex questions alongside simple obvious ones. I have a unique view of how artistry impacts leadership, a perspective cultivated as a musician and bureaucrat.

So here I am at a crossroads in life I never anticipated. How I got here is still a bit of a blur, and where it ends up is definitely hidden around the corner. The current vantage point, however, holds a clear vision. It is a vision for how artistry leads and how blessed I'll be to help others find that synergy.