I was fortunate enough to create my dream job.  Following my passion, I worked for many years as a residential real estate developer until it was taken away from me by the 2008 housing crisis.  At the time I had two speculative projects under development, which I eventually lost to the bank.  Rather than the $1 million profit I expected, I posted a $999,980 loss.

Several years later, as part of my recovery, I wrote The $500 Cup of Coffee, a financial guide to financial independence, to inform and inspire young adults to build and hold onto their wealth.  (Now I’m building the Pay or Save app to help them achieve their goals.)  I also joined SCORE as a volunteer small business mentor.

Since COVID struck in March 2020, I’ve met (via phone and zoom) more than a hundred small business clients.  In the early days of COVID, many of them were trying to replace loss income by adapting existing businesses or starting new ones.  More recently, they want to establish secondary streams of income by following their interests.

Do you follow your passion or the money?

When I was young, they said, “follow your passion and the money will follow.”  I’m not sure what they say today, but undoubtedly times have changed.  Scott Adams, the creator of Dilbert, the syndicated cartoon strip that lampoons corporate culture, says follow success and passion is likely to follow.  Citing his own experience, he once invested in a restaurant and was very excited when crowds lined up around the block.  But a few years later, when the restaurant was failing, his passion turned to frustration and annoyance.

So, which is it?  Does passion lead to money?  Or does success and money lead to passion?  The answer obviously depends on lots of factors both inside and outside of your control.  In addition to your personal talent, interests, drive and values, the state of the economy plays a strong hand.  I certainly didn’t choose for the economy to collapse in 2008.

The Nature of Work

Work is both a blessing and a curse.  No matter how much we may love our jobs, we often experience work as a burden or intrusion.  And no matter how much we may hate our jobs, we are also thankful to be able to work to support ourselves and families.

As work is both a curse and blessing, how do we make the most of our working lives while remaining true to our personal goals and values?  How do we balance the desire to work our dream job and the need to earn a living, especially when passion and career do not easily align?  Do we take a high-paying job even when it doesn’t feel like the right fit?  Or do we do take the better fitting job even when it pays considerably less? 

Pros and Cons of Choosing a Career You Love

Most of us spend more waking hours at work than any other activity, so it only makes sense to work at something we like.  When we like what we do, we find more pleasure in our work.  We experience a greater sense of purpose and satisfaction by devoting our time to something that’s personally meaningful to us.  We are also more motivated to achieve, which often leads to personal growth as well as career advancement.

There can be a downside, however, when you convert your passion into a job.  When you rely on the thing you love to produce your bread and better, your relationship with it changes, especially, when it translates into work that’s not easy to obtain or doesn’t pay well.  The thing which once animated you with joy could now feel like a weight that’s holding you back.

Pros and Cons of Choosing a High Salary Career

One of the most obvious benefits to a high-paying job is money.  With money comes status and safety.  When you have enough money to pay for the stuff that you want and need, then your place in the world feels a lot more secure.  But most (corporate) jobs that pay well are draining.  They demand long hours in high-pressure environments where opportunities for personal recognition and advancement are often limited.  If you’re stuck in a position that doesn’t fit you well, a flush bank account isn’t enough to fill the emptiness you may feel inside.

For most of us, following passion or money is not a binary choice.  A few of us have the good fortune to work at jobs we love that pay well.  Those of us with limited training and skills can be lucky to find a job, any job at all.  The same can be true for college students graduating into a restrictive job market. The choice between a passion job and high paying job often does not exist for them.  Then there are those who make a (healthy) choice to keep their work and passion separate.  They work to live, and live to pursue their passion on weekends and evenings.

Finding Your Passion

What happens when we don’t know what we’re passionate about?  Which begs the question, do we need passion in our lives to be successful?

Passion clearly gives our life meaning and provides the motivation to act and achieve.  But I’m not sure that it’s needed to excel at work and earn a decent living.  I know several people who have done very well at jobs that they claimed to hate.

Scott Adams offers an interesting perspective on this subject.  When he worked as a commercial banker, he learned from his boss that the best customer is the one who has no passion, just a desire to work hard at something that looks good on a spreadsheet.  He placed his bets on the loan customer who wanted to open a dry-cleaners or a fast-food franchise – boring stuff – rather than the sports enthusiast who was opening a sports store to pursue his interest in all things sporty. Like some guys who say they love their wives, passion-driven customers often disappeared when things turned bad.

With the notable exception of Adam’s old boss, most every article I’ve read says that passion creates happiness and fuels productivity at work.  Some people, like my friend and artist, Ann Lorraine, were born with tons of it, while other’s struggle to find it.  For those who may wonder, “how do I find my passion?” here are some good questions to start with:

• What makes you smile? (people, places, activities, projects, etc.)

• What activities make you lose track of time?

• What makes you feel good about yourself?

• What do others typically ask you for help with?

• If you had to teach something, what would it be?

• Imagine yourself at the end of a long life. What would you most regret not doing?

• What do you want to be remembered for? (Most people, who knew you personally, will remember the kind of person you were rather than what you did for a living or how much money you had.)

• What kind of work/life balance do you want?

• How do you want to spend your days and what kind of people do you want to spend them with?

How to Measure Success

By now you know that when you chase someone else’s expectations, you end up resenting them and feeling unsure about yourself.  When older people reflect back over their lives, some of their biggest regrets result from deviating too far from their inner compass.  These include:

• Education/Career. Following their parents’ expectations rather than their own
• Work/Family. Spending too much time at work and not enough time at home with loved ones
• Worrying too much about money, which prevented them from taking more chances.

The happiest people define success on their own terms starting with an understanding of what drives them and how to optimize their personal abilities.  While self-awareness is key, it’s equally important to understand how others receive your efforts.  If you consistently misread or ignore the directions of your employer, the demands of your customers, or the needs of your loved ones, there’s a good chance your actions will not produce the desired results.

Are Goals for Losers?

Instead of focusing on fixed goals like a dream job or six figure salary, it may be a better idea to follow Scott Adam’s advice to forget about goals and focus on systems.

• A goal is a job. A system is to continuously look for new opportunity.
• A goal is a big salary. A system is to continue to improve and use your skills.
• A goal is marriage. A system is to develop satisfying personal relationship.

Adams says goals are for losers. Here’s why.  Let’s say you set a goal to lose 20 pounds.

• When you don’t succeed, you feel like a failure and are constantly disappointed with yourself.

• When you do succeed, after you celebrate, the thing that kept you motivated for so long is now gone. Your options are to feel empty and useless or to set new goals and start the cycle all over again.

When taking a systems approach to weight loss, you stand a better chance of success.  You avoid the latest crash diets, which can have a contrary effect, especially when feelings of privation lead to binging.  Instead, you start to eat healthier – maybe start by cutting down on soda – and exercise more.  Nothing crazy, maybe just a walk around the block or taking the stairs instead of the elevator to the second or third floor.  As you start to feel better (and look better), you’ll be motivated to continue.  And once your reach your target weight, you’ll maintain rather than putting your lost weight back on.

Without realizing it, I have followed Scott’s system approach most of my life.  I’ve always felt that the journey is the destination, or to use Scott’s vocabulary, the system is the goal.

For many years, I had the good fortune to follow my passion, which is real estate, before I left it, due to circumstances beyond my control, but I don’t miss it.  The reason I don’t miss it is the same reason I loved it.  I loved it because it engaged all my talents, challenged me creativity, and stretched my in ways I had never been stretched before.

Post real estate, it took some time to regain my footing, but I eventually discovered other opportunities – like writing a book, developing an app, and mentoring small business clients– that also engage my talents, call on my creativity and challenge me in new ways.

I’ve learned that as long as I remain engaged and active and have a chance to exercise my creative muscles, I’m just as happy as when I was pursing my passion.