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How to Choose a Career You Will Love


I often get asked by high school and college kids for career advice. Over the years, I’ve distilled it down to two steps. This is what I tell them:

There are two steps to choosing a career. If you do the work on each, you will exponentially increase your chances of having a career you will love.

First, identify people who do what you think you want to do and follow them around. Don’t stalk them, volunteer to help them for a month or two. Give them free labor in return for learning about their work.

I know what you’re thinking, duh, of course. But this obvious first step is often skipped.

How may college graduates jump to law school, business school or other graduate school and invest countless hours and money into their studies only to realize two or three years later that they hate being a lawyer, teacher, accountant or financial advisor? But now they’re in big debt and have lost two to three years of earning capacity.

Make a serious effort to shatter your misconceptions. Bring a big hammer. Find out what the work is really like by shadowing someone who does it. You will discover what she actually does, how she does the work, whom she works with and where she works.

  • Does she work in a big company with lots of coworkers? Does she work by herself?
  • Does she have to drive a long way to get to work?
  • How does she have to interact with bosses, clients or customers?
  • Does she control how she works or do others tell her what, where and how to do the work?
  • Who dictates her hours?
  • How does she get paid and how can she get paid more? Does she have to be picked by her boss for a promotion or does she have a direct path like achieving measurable results?
  • Does she have to socialize with people she won’t want to socialize with?
  • What is the emotional output of her work? Is it paper pushing or does she make art or make people’s life better?
  • Does she work in a cubicle in a big city skyscraper, at a desk in a small town or in her home office?
  • How does she have to dress? Does she have to wear suits and heels or can she wear jeans and Toms.

You will find the real work is not like pop culture portrays it. The everyday life of an attorney is not like a John Grisham novel. Working in a restaurant is not like Food Network Star. Being a worship leader at a church is not like American Idol. Working in retail is not like Pawn Stars.

You may find you thought you would like the work, but now you don’t.

But be careful. Your decision should not turn on a discovery the work is hard. Rewarding careers are hard. Don’t be afraid of hard work.

Second, after you’ve done your research, and you think you’ve narrowed it down, ask yourself whether that career will give you the life you want?

This goes beyond how much money you will make. It’s about what your life will be like in that career both now and ten years from now.

  • Do you want to be home with your spouse and kids for dinner every night? Then don’t be a chef at a dinner restaurant.
  • Do you want to work in the entertainment industry? You may need to move to Los Angeles or New York.
  • Are you strong and like to do physical work? What happens when you get older and throw out your back?

No question you will change your work many times in a lifetime, but if your work is a foundation you can build on, you will be in a good place.

What if you learned you really like the work, but not the way it’s done? Good news. Technology has made it possible to bend many jobs into your lifestyle. The way a job has been done is not necessarily how it has to be done.

If you really want to be an attorney, but you don’t want to work in a downtown office with high stress people with egos, maybe its ok. Maybe you can bend the work toward your lifestyle. More and more attorneys have robust practices working from home.

Andrew Malcolm at Investor’s Business Daily reports in his column on the poor economy that while the number of employees at start-ups has plunged, there is a greater share of new firms with no employees — one-man shops.

One-man shops are growing for several reasons. First, unemployed professionals have given up finding a job with a firm and have hung out their own shingle. Second, technology makes it easier than ever before to hang out your shingle. Cloud computing and apps have significantly lowered the cost of doing business while making it easier to do business. Work that five years ago took three people to do can now be done by one person.

The future will be full of “unemployed” entrepreneurs of one-woman shops. It’s what Daniel Pink described ten years ago in his wonderful and still very relevant book, Free Agent Nation.

To summarize – do the work to find a career you will love. Volunteer for someone who does the work you think you want to do and learn all you can. Then discover if you can do the work and have the life you want. And just because the work is done a certain way now, doesn’t mean you can’t bend the work to your lifestyle.

Notice I have used the terms “career” and “work” interchangeably, and I have not used the term “job.” This article is not about finding a job. A job is what you do to pay the bills, and in this economy you need to do what you need to do to survive.

What I’ve described here is how to find work and a career you will love.

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