After backpacking about 240 miles through the green mountains of Vermont and the hot fields of Massachusetts, I came up with five questions you can ask yourself to help figure out what is your passion.

#1: The “Billion Dollar” Question

One of the best ways to determine your passion is to find out what you would do if you had tons of money.

Write down what you would do with the majority of your waking hours if you had a billion dollars in the bank.

Obviously, with a billion dollars you wouldn’t have to work, although some lunatics might. Don’t worry about how you will spend the money. Yes, I’m sure that you’d donate 99 percent of your wealth to the poor and needy. Great. That’s nice, but the goal here is to find out what you would do with most of your time. Clearly, there are many things you might do with your hours, but what would consume the bulk of your time? Would you travel? Teach? Write books? Help the sick? Build homes? Trade stocks? Collect meat cleavers?

Your answer is extremely telling. Look at what you would be doing; most likely, that is your passion! It’s hard to believe that it’s that easy to uncover your passion, but the Billion Dollar Question is extremely effective at revealing your hidden passion. Some people feel that their passion must be something that is deeply locked away in their subconscious and nothing short of hypnosis will reveal what it is.

It’s not that complicated. In fact, once you realize what your passion is, you may not be surprised. This is normal. After all, you have probably been dimly aware of your passion for some time. It’s just that we all have a tendency to deny our passions and not chase our dreams for a variety of reasons, and usually it’s related to economics. The Billion Dollar Question removes that barrier and lets us think freely. Indeed, most people believe that they can’t afford to chase after their passions because they think it’s too hard to make money chasing their passion. After all, we have bills to pay like the mortgage, credit cards, car payments, children’s education, groceries, and the NBA Sports Package on the satellite network.

These expenses are so overwhelming that it gives us no time to contemplate what life is all about. It reminds me of a funny exchange in Voltaire’s hilarious 1759 publication, Candide:

“Do you believe that the Pope is the Antichrist, my friend?” said the minister.
“I have never heard anyone say so,” replied Candide; “but whether he is or he isn’t, I want some food.” — Voltaire

Candide can’t entertain philosophical questions because he’s hungry. Similarly, we can’t contemplate fundamental questions on life because we’re too busy just trying to make money to put food on the table.

That’s why the Second Principle about financial management is so important. It’s hard to hike with passion until you learn to beware of summit fever. It’s important not to raise your standard of living to a level that doesn’t let you pursue your passion. Otherwise, you’ll be so besieged with your day-to-day obligations that you won’t have a chance to do what you really love doing. You may need to make a few sacrifices to bring your standard of living in line with your earnings to give you the freedom to do what you love.

"I cannot make my days longer so I strive to make them better." -Henry David Thoreau

#2: The “What Catches Your Eye?” Question

If the Billion Dollar Question doesn’t help you figure out what your passion is, then consider another exercise, called the “What Catches Your Eye?” Question. This exercise may help narrow down the list if you have many passions, or may help bring out the one passion that is deeply hidden in your mind.

When you flip through magazines or newspapers, what catches your eye? What are the words or the themes that make your eye stop and want to read more about that subject? Write down all the words and subjects that come to mind.

The possibilities are limitless, but some examples are: movies; basketball; stocks & bonds; gardening; interior design; philanthropy; opera; sports cars; antiques; anthropology; pottery; tango; diabetes; Africa; hot springs; skunk wrestling.

Of course, you may have many interests, so just write down your top five, although it’s best if you can narrow it down to your favorite one or two. If you’re struggling for ideas consider looking at what pages you bookmarked on the Internet, or go to your bookshelf and pull out your favorite books to see if you can detect a pattern.

For example, in the 1990s my eye would naturally get attracted to the words “robotics” or “robots” or “artificial intelligence.” (I know, I’m a geek.) I realized that the subject naturally fascinated me. Therefore, in 1995 I co-founded a robotic vision system company in Silicon Valley to pursue this passion of mine.

Only passions, great passions, can elevate the soul to great things. — Denis Diderot, Pensées Philosophiques, 1746

If you have several subjects that interest you, pick your favorite one. This is an area that you enjoy learning about, and may even be an expert in, and yet you’re currently doing it for free! Imagine if someone were to pay you to research or be an expert in this subject! That’s the beauty of hiking with passion! Above all, don’t limit yourself to subjects that you think could pay money. Even if you can’t imagine making money, don’t worry about that now—we’ll deal with that later. For now, just think without restraint and write down topics that grab your attention.

Perhaps you still can’t focus on anything in particular because (a) you haven’t found any one subject that stands out, (b) you’ve found many and can’t decide, or (c) your neighbors are screeching their fingernails across their blackboard again.

If you have many interests, compare the answer of the What Catches Your Eye? Question with the Billion Dollar Question. Is there some common ground? Is something overlapping in both questions? If you’re still stuck, then try the next question.

#3: The “Leisure Time” Question

Some people might not have gotten too many ideas from the last question because they don’t read much! Then again, if you’re reading this book, you’re probably not part of the “My TV Is My Sole Source of Information” crowd. Brainstorm on this:

Analyze what you do with your free time. Write down everything you enjoy doing with your leisure time.

It rarely hurts to brainstorm some more, so use this question to increase your list of passions. This question helps identify what you enjoy doing. For example, some people enjoy remodeling; others see it as a chore. Some enjoy stargazing; others would rather be in a nightclub. Some people enjoy long backpacking trips; others think we’re nuts.

If you do spend quite a bit of your leisure time watching TV, then analyze what you look at. Do you notice a pattern? Are you watching a lot of sitcoms? If so, write down that you might consider a career in comedy. Don’t worry, that doesn’t necessarily mean getting up on stage and cracking jokes. Somebody is writing all the scripts for those sitcoms. Maybe that could be you? Is there a local theater company that could use you? What about trying to become the next Dave Barry? If you want to be a real comedian consider a career in politics.

Do you spend most of your time watching the news on TV? If so, what stories attract you? Write down that a career in media might interest you. Do you enjoy watching the political debates on TV? There are plenty of think tanks out there who need hard workers. Do you enjoy the local news? Consider becoming an activist for a cause that you’re passionate about. Do you love following sports? The sporting industry is a multi-billion dollar industry with plenty of avenues to get involved.

It’s fascinating to see what people do with their leisure time. It’s those few hours where you’re doing something because you enjoy it. Nobody is urging you to do it. You’re doing it because it’s fun. If you can transform that passion into a job or a career, then you’re optimizing your life.

#4: The “You’ll Succeed No Matter What” Question

Here’s another effective exercise to uncover your hidden passion. Let’s assume you drink a potion that gives you the power to succeed in absolutely anything. No matter what you decide to do, you’re guaranteed to succeed.

For example, let’s say your dream is to become a famous pop star, but you can’t sing. Thanks to this potion, you’ll become famous anyway despite your voice, just like Jessica Simpson. If you can’t act, you’ll somehow become a superstar despite having zero talent, just like Keanu Reeves. And if being a writer is your dream even though you can barely write your name, then after drinking this potion you’ll soon be writing personal development books based on the Appalachian Trail. (And yours will actually be good.)

If you were guaranteed that you would become successful in whatever you pursued, what would you do?

Would you become a poet? A stockbroker? A fashion designer? A media tycoon? A sports star? A great mother?

Nothing great in the world has been accomplished without passion. — Hegel, Philosophy of History, 1832

We frequently don’t do what we love because we lack confidence. We fear the unknown. We tell ourselves, “I’m not good enough,” or “I’ve just had a lot of bad luck.” But now with the genie out of the bottle, you can have as much luck, skill, and talent you need to succeed. Analyze your answers and see how they compare to your answers in the previous questions. Are you starting to see a common thread? If not, try the last question.

#5: The “Who Would You Switch Places With?” Question

This question is somewhat tricky because you have to forget about the money issue.

If you could switch places with anyone, who would it be?

Although you might pick someone famous, it’s perfectly acceptable to pick someone you know personally, like Bob at the corner store.

Two rules: first, you can’t pick someone who is dead; second, don’t take into account how much money the person makes—instead, look at the daily responsibilities of the job. The idea is to find the person you would like to switch places with today. Who do you look at and think, “Man, I would love to have her job!” In other words, whose job would you take and not even consider it a “job”? Be sure to think about everything that comes with the job too, not just the glamorous side.

For instance, you may fantasize about switching jobs with Julia Roberts so that you could live the lavish life, but would you be willing to put up with the stresses of fame and the process of making and promoting a movie if you didn’t get paid $20 million per film? Would you do her job if you were only making $25,000 a year? Pick the person’s job, not the person’s pay. Look at what they do day-to-day, and figure out if you would enjoy doing that—even at a modest pay.

Once again the possibilities are unlimited. You might want to switch places with CNN’s Anderson Cooper, Donna Karan, your Senator, the coach of the Nebraska Cornhuskers, the CEO of Ford, the local librarian, the editor of Car and Driver, the local building contractor, or Britney Spears.

I get to go to lots of overseas places, like Canada. — Britney Spears, when asked what she enjoyed about touring.

Although I’ve named many famous people, you should consider people in your community. After you imagine their day-to-day life, the good and the bad, ask yourself if you would do their job even if it paid you 20 to 50 percent less than what you make now. When I worked at Microsoft, some employees wondered why billionaires like Bill Gates keep working. The answer is simple: they’re pursuing their passion. They don’t view their job as “work.” These working billionaires would be doing their jobs even if they were paid a pittance. In fact, Bill Gates basically did just that when he started Microsoft. That’s what hiking with passion is about.

Now that you’ve picked someone you’d like to switch places with, start scrutinizing her life. Search the Internet to learn as much as possible about her daily life, or if the person is local and not super famous, ask if you can have an informational interview. Find out how her life really is, not just the exterior image. Try to confirm that her job and life are what you imagine them to be. What are the downsides? Is the person away from her family all the time? Does the person work on weekends? Is the person in fact on America’s Most Wanted List? If after all your investigations you still admire the person’s way of life and wish you could follow it, then start learning how the person got where he or she is today (we’ll discuss this more in Chapter Four).

For example, while I was walking through Massachusetts I thought I had discovered my dream job: Research and Product Development Executive at Ben and Jerry’s. Why? You get paid to eat a lot of ice cream.

So later I investigated and discovered that it’s not that glamorous. Arnold Carbone (who held that position) said that when experimenting with coffee flavors he might create 15 batches per day. By the end of the day, his head feels like it’s going to explode. Moreover, some ice cream concepts are just stupid. Somebody in B&J’s research department had the bright idea of creating chocolate-covered-potato-chips-and-sour-cream-and-onion-flavored ice cream. Yuck. That would even gross out a hungry thru-hiker.

So that’s why today I’m a writer and not the Research and Product Development Executive at Ben and Jerry’s.

This is a modified excerpt from Chapter 3 of Hike Your Own Hike: 7 Life Lessons from Backpacking Across America. You can read the whole first chapter for free. Or you can buy the book at my shop, Amazon, Apple’s iBookstore, Barnes and Noble, and Google Books. (The best deal is at my shop). It’s also available as an audiobook.

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