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When Is It Worth Chasing the Dream?

Pros and cons of pursuing the dream career, relationship, home, and vacation.

 Gerald Wildmoser, Noun Project, CC
Source: Gerald Wildmoser, Noun Project, CC

If life feels mundane, it’s understandable that we dream, grasping for something to make life more exciting: the dream job, the dream relationship, the dream home, the dream vacation.

We may be especially likely to aspire to a dream amid the grayness that the COVID restrictions or disease have foisted on us.

But as a long-time career and personal coach, I’ve seen some people achieve their dream at least partially but too many who haven't.

For each of the aforementioned common dreams, here are pros and cons of shooting for it and how to optimize your chances.

Chasing the dream job

Pro: You spend most of the best hours of your life at work. No one should accept a mundane work life, at least without having tried for the dream job. As the saying goes, “Shoot for the moon. Even if you don’t make it, you’ll land among the stars.” Just find something you care enough about and are talented enough to motivate you to work hard at it. Even if you fail, you’ll feel good about having tried.

You can reduce your risk by assessing your chance of success against the opportunity cost. For example, if you’re seeing more and more interest, including financial, in your artistic work, great. If not, weigh that career against what you’d otherwise do with the time and money you've invested and likely will continue to invest in that career.

Con: What usually ends up contributing most to career contentment are ethical work, stable employment and pay, a decent boss, opportunities to learn, and good coworkers. And those are more easily found away from the common dream careers: sports, arts, entertainment, etc. Some of my happiest clients have decidedly unsexy work: Social Security administrator, customer service manager for a utility, scrap metal importer.

Chasing the dream relationship

Pro: The great relationship suffuses contentment across your life, even when you're apart from your partner. Conversely, think of all the misery that accrues from a bad relationship.

So make the effort to find and maintain a relationship with an attractive, kind, solvent person who doesn’t have a fatal flaw: Have high standards in reaching out to candidates online, when taking classes, and in set-ups. Prioritize such sources over those in which physical attractiveness is the first screen: in the supermarket, in a bar, at a loud party, or walking down the street. (Alas, we're all aware that many of the aforementioned may be limited amid COVID restrictions.)

Con: Most people themselves aren’t dream partners. Hold out for that and you may be waiting for Godot. Go not for a dream but for your match.

Also, recognize that increasing numbers of people are growing to prefer the freedoms of solohood.

Chasing the dream home (This also applies to part of a home, for example, as I saw on a recent ad, ‘Your dream kitchen in three weeks.”)

Pro: For many people, home is indeed where the heart is and unless the home feels right, life feels too incomplete. And home is where you and perhaps family will spend so much of life.

People who care deeply about home are far more likely to derive enduring pleasure from home, and even just from “the kitchen of your dreams” than from, for example, 5-star vacations, diamonds, Rolex watches, upscale cars, etc.

Con: The cost of a dream home or even a demi-dream home is inordinate, often forcing the owner to endure a lucrative but unrewarding job. Many high-paying jobs pay so well because they’re not particularly pleasurable: insurance sales, comptroller, fundraiser, and bond trader come to mind. Or that dream career requires many years of expensive, also not particularly pleasurable training: physician and professor come to mind.

And that assumes you’ll keep such a job for the life of your mortgage. Alas, that’s far from certain with jobs ever less secure whether because of COVID, automation, or offshoring.

Better to find less expensive sources of contentment. No, you needn’t live in a leaky basement apartment in a war zone, but the single decision to live in modest digs can help you choose the job you'd prefer and free you from the worry that comes with owning a dream home. And you avoid the nightmare that has occurred to countless owners of dream homes who, because of just one unanticipated event like a health crisis or losing their job, end up struggling with the payments, the taxes, the insurance, and eventually lose their home, to the family’s sadness and the embarrassment of having to tell everyone they're “downsizing."

Chasing the dream vacation

Pro: When asked, “What would you do if you had only six months to live?” many people say travel. They love experiencing different cultures, seeing and photographing vistas and exotica, buying local goods, plus the overall adventure and growth experience of it all.

Some such people say that travel built their confidence—they saw that they could negotiate strange environments.

More broadly, many travel lovers speak of treasured memories that last a lifetime.

Con: In a triumph of confirmation bias over reality, many travel buffs tend to forget the negatives. If fair-minded, they'd conclude that the benefits have been outweighed by the cost, the hassle, the sicknesses, the bad weather, the ripoffs, etc., plus the opportunity cost: what they could otherwise do with the time and money.

Think of all the time and money you’ve already spent on vacations. Now imagine you have all that time and money back. Would you spend it on travel or on something else?

Or perhaps an answer lies in a different sort of travel: Might seven day-trips likely yield more pleasure with less hassle than that eight-day/seven-night airplane trip to a far-flung place?

The takeaway

Of course, some dreams are worth chasing, but dreaming implies irrationality. What will yield you more pleasure is a clear-eyed assessment of the probability of achieving the dream and the benefits and liabilities likely to be derived compared with the financial and human costs, including the opportunity cost. Sometimes, it is wise to be coldly rational.

I read this aloud on YouTube.

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