“What do you want to be when you grow up?”

When your business is your passion, finanicial concerns aren’t the only retirement-related fears. (John Amis/AP)

The retirement question feels very similar — and I’m no more prepared to answer that than I was to say what I wanted to be when I grew up. It is much easier to plan for retirement when you work for someone else than when you work for yourself. And I think the question on when to retire is as emotionally driven as it is financially driven.

The concept of retirement is a source of mental competition and peer pressure when you are gainfully employed by someone other than yourself. Your employer encourages you to put money aside, makes the process relatively easy and often even matches some of your contribution. You almost feel guilty if you aren’t trying to be fiscally responsible about your future. As an entrepreneur, though, sometimes it’s hard enough to make payroll for your employees, let alone to have enough to set aside for your own retirement three decades away.

Those working for someone else in the world of Corporate America can’t wait to think about retirement, talk about retirement and plan for retirement. Now I think I understand why. Because as much as someone may enjoy his or her job, it is still on someone else’s terms. And who wants to do that forever? The countdown to retirement is, in reality, a countdown to escape. When you are an entrepreneur, what are you trying to escape? Your dream? Your passion? Your true calling? It seems strange when you look at it that way.

So what’s left when we stop living our dream? Many entrepreneurs are afraid to find out. In fact, I know entrepreneurs in their 70s who aren’t even thinking of slowing down.

When I was a part of Corporate America, I took basic steps to prepare myself financially. But admittedly I have not focused on it at all since going out on my own. It is like the difference between working in your business instead of on your business.  

I’m just not there yet. Payroll is immediate and retirement is theoretical. I know the steps to take to be financially ready, but who will help me to be emotionally ready? Sounds like it could be a great business for some entrepreneur to start!

Michelle Thompson-Dolberry is president and “chief fire starter” at  EMDO Enterprises, a Los Angeles-based firm that provides consulting and event management services to small businesses and nonprofits.