Why You Need to Re-evaluate Doing What You Love

doing what you love

“Do what you love and the money will follow,” is perhaps the most popular piece of career advice. You can find Maya Angelou on Pinterest saying, “Don't make money your goal. Instead, pursue the things you love doing and then do them so well that people can’t take their eyes off of you.” Or Oprah Winfrey: “If you do work that you love, and the work fulfills you, the rest will come.”

The problem is, no one tells you exactly how much money actually will follow. Will doing what you love earn you enough to cover rent, health insurance and retirement contributions? Or will you have to work two other jobs to scrape by?

No one wants to be a dream crusher, but economic realities have a way of putting aspirations into perspective — even those that don’t seem far-fetched.

Take me, for example: I’ve been pursuing my dream of a career in journalism since my days on the high school yearbook staff, and now I’m a professional writer and editor. I love what I do, but I hate the uncertainty of the industry. Since 2009, I’ve lost my job five times through three magazine folds and two rounds of mass corporate layoffs. I’m an optimistic person, but when I’m entrenched in yet another seemingly endless job search, it’s hard not to wonder if I pursued the right career path.

Emily Westerman, career coach and founder of Whole Life Fit Coaching, doesn’t want to stomp on your dreams either, but she has a caveat: “Anything is possible, but you don’t know if they will be possible in your circumstances.” So, whether you want to open up a bakery or become an investment broker, follow these steps before you make a drastic career change.


Test drive the reality of the market. “First you want to test the practicalities of [what you want to do]. Are you living in a place where there’s a market for it? Are you filling a need that hasn’t already been met?” Westerman says. If you can, she suggests doing market research and finding people who have taken the plunge with a similar career choice.

What were the pitfalls they found along the way?” Other questions to ask yourself: What are the practical steps to getting this position? Do you need a license or a different degree? What’s the job market like? Are you in the right city?

Evaluate how much of a financial risk can you take. If you decide to go for it, you need a contingency plan in case things don’t work out. Is there a certain amount of money that will sustain you? “For some people, the money isn’t as significant depending on their situation,” Westerman says. But for most of us, it is, so be prepared. “It’s important for people to give themselves a time frame. It’s good to have plans A, B and C,” Westerman says. “Never dip into your retirement. If that’s the only way you can make your dream come true, don’t do it. You don’t know if the money will follow.”

Don’t forget that it can take longer than you think. If you do the research and run the numbers and realize that pursuing your passion isn’t possible right now, don’t feel like you’re condemned to a life of drudgery and monotony at an unfulfilling (to put it nicely) job. “People shouldn’t feel like they have to give up the dream, but instead work towards it more slowly,” Westerman says. “It doesn’t have to be now or never.”

Consider similar work in a different field. In work, as in life, things don’t always end up looking the way you imagined. “Sometimes it’s not going to be the exact dream, but there’s a variation of the dream that’s more practical,” Westerman says. “Is there something closer to this dream that will make you happier than what you did before?”

For me, that means instead of my ideal situation (a full-time staff position as an editor where I can focus on one publication), I’m freelancing for several different websites. It’s not where I’d pictured myself at this point in my career, but I’m making valuable contacts, learning new content management systems, strengthening my resume and otherwise trying to be practical about my situation while I pursue new opportunities.

“People need to let go of the idea that if it doesn’t work now, it will never work,” Westerman says. “Circumstances could be more favorable later — that’s where the research is helpful. Maybe revisit it in two or five years. Or, do little steps so when you’re ready to delve into it again you’ve prepared, like getting needed credentials or do the market research,” she says. “It’s important for people to have passions and have dreams, but you need a reality check at the same time.”

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