By Cliff Ennico

Sometimes in my entrepreneurship classes and coaching sessions, I run across someone who genuinely has no idea what to do with the rest of his or her life.

Usually, but not always, they are corporate executives who have been downsized after 20 or more years of loyal service to their employers. All they have ever known is the job which they have just left, and in many cases those jobs are no longer in demand – either because of overseas outsourcing, technological advances, or just plain obsolescence. They have no choice – they have to “begin again” from scratch and retrain themselves for a job that will keep them solvent into their retirement years.

Very often, with such people, I ask the question “what did you want to do, or dream about doing, when you were 18 to 21 years old – your high school and college years?”

The question is not frivolous. You can tell a lot about a person by the way in which he or she answers it.

There are two things you can say about any 18 year old person: (1) they are physically (although perhaps not in other ways) mature, adult human beings; and (2) the doors to the world are entirely open to them. They can move in any one of 100 or more different career directions. They have not made any of the life commitments (marriage, a mortgage, student loan debt) that can keep you locked into a certain track. The choices made during the high school and college years – even minor ones – can set a young person on a trajectory that will continue for decades afterwards.

I’ve learned over the years that every person on Earth needs to get something – often just one thing – out of their career in order to be happy. And very often you have identified that “thing” by the time you are 18-21 years old. What you should do at that stage of life is look for careers that offer you that “thing”, and ignore career paths that don’t. Sadly, most of us don’t – we “sell out,” go for the money, status, or whatever, and have to make the best of careers that deny us that “thing,” hopefully leaving us enough leisure time to look for that “thing” in our nonwork lives.

Show me what someone wanted to be during those critical formative years, and I will tell you a lot about that person. If that person wanted to be an artist or ballet dancer, I know that person values creativity. If that person wanted to be a forest ranger, I know that person values the outdoors. If that person wanted to be a professional football or basketball player, I know that person values physicality and competitiveness. If that person wanted to be a media celebrity or actor/actress, I know that person needs to have an audience. If that person wanted to be a politician, I know that person values power and influence. If that person wanted to be an engineer, I know that person likes tinkering with things. You get the idea.

It was therefore with great interest that I picked up my friend Doug Campbell’s latest book “The 16-28 Solution: Unleash the Passions of Your Youth” (Success Coach Publishing, $16.95, available at He looks at a slightly longer time period than I do — the years from age 16 to 28 – and argues that “events, emotions, experiences and aptitudes from that critical formative period in our lives are what cause the alarm bells to go off for us whenever our careers reach important points of transition.”

The book offers five case studies of entrepreneurs who learned to manage difficult career transitions through an in-depth study of the key decisions they made and lessons they learned during that 12-year period. The author’s own example provides perhaps the most illuminating parallel between the “things” we did then and the “things” we do now:

  • In college Doug majored in Spanish and international relations – today he is involved in a microlending program to poor peasant farmers in Latin America;
  • He also tutored Native American children in college – for the past 30 years he has been co-owner of a Sylvan Learning Centers after-school tutoring franchise in Connecticut;
  • He also coached golf during his college years – today he coaches golf at a high school in Connecticut;
  • While studying at the University of Virginia’s Darden School of Business, he started an Entrepreneurs’ Club – for the past 18 years he has coached entrepreneurs and business owners in his own consulting practice.

Buy Doug’s book, and take his practice exercises. You will be amazed what you will learn, not only about your former self but how the ghost of that former self is still with you. You may no longer be able to play bass in a heavy metal band, but you almost certainly can find a career outlet that will fulfill your need for creativity well into old age.

Cliff Ennico (, a leading expert on small business law and taxes, is the author of “Small Business Survival Guide,” “The eBay Seller’s Tax and Legal Answer Book” and 15 other books.