Career choices are among the most important decisions you will ever make. And you should make them with your head and your heart.

Think about it. What’s more important than your career? Not much. You spend nearly all your waking hours working or with your spouse. The only thing worse than slaving away at work you can’t stand is being married to someone you don’t love.

We all want our work to mean something, but it’s easy to forget that career decisions are also business decisions. After all, there are bills to pay and money problems are the worst. I mean, who doesn’t want to be financially independent?

I grew up watching my parents work 9 to 5 making peanuts at jobs they hated. They were miserable. Why did they do it? To give me a chance for a better life. And I was not about to let them down by squandering the opportunity they worked so hard to provide.

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So, before making any career-related decision, I’ve always asked myself five questions; they’ve served me well as a litmus test for any career move. Now I advise others to do the same.

Is it practical?

There are always practical aspects to any job or career change. Does the location work? Will the hours work? Does it require you to do something unnatural that’s not really your thing? Does it fit with your overall goals? Is it a step in the right direction?

Don’t get me wrong. I’ve always been pretty darned flexible. I’ve commuted across the country weekly for over a year, but it was for a great job I loved that made my career. In any case, you and your family should know what you’re getting into upfront.

Does it sound like fun?

Everyone talks about loving what you do, but how do you know you love it until you do it? That’s right, you don’t. But if it sounds like fun and the people you’d be working with seem pretty cool, then, barring any red flags, it’s probably worth a shot.

Of course, things are never quite what they seem. It always takes a few months immersed in a new job before you figure out what you’ve gotten yourself into. But if it doesn’t seem like it would be fun upfront, trust me, it’s not likely to get any better.

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What are the odds of a big payoff?

My parents were not risk takers and they were miserable, so I sort of went the other way. A good salary is great, but if you believe in yourself and the company, you might want to put more weight on pay-for-performance. Salary will pay the bills but bonus and equity windfalls can be the ticket to financial security. They were in my case.

If you do roll the dice, make sure you don’t make any really dumb bets. You want the best odds of a big payoff. That’s why I think climbing the corporate ladder is important. You don’t really get stratospheric bonus and equity incentives until you reach the executive ranks.

What do you have to lose?

The downside risk is important. Some people overanalyze it. Others don’t consider it at all. You should. I don’t care what it is, every job or career has a downside, a risk, a dark underbelly that nobody likes to talk about. Try to find out what that is.

Most don’t even realize that going with one decision has an inherent opportunity cost – the cost of all the opportunities you don’t get to do because you’re otherwise committed to the one you’ve chosen. You have to consider that.

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What does your gut say?

The other four questions are all logic-based, even the fun one. After you’ve answered them all, ask yourself what your gut tells you. If there are red flags, listen to them. The times I’ve ignored my them, I’ve always paid a price. Trust your intuition; it’s usually right.

That’s the bottom line. Pay attention to reason but in the end, trust your gut. You know how to do that: It’s the same way you fall in love.

A version of this originally appeared on

Image credit Roy Blumenthal via Flickr