Before any Career Decision, Ask Yourself 5 Questions You spend most of your waking life with the person you love and at work ... shouldn't you love both?

By Steve Tobak

Opinions expressed by Entrepreneur contributors are their own.


Career decisions are matters of the heart. Think about it. You spend practically every waking hour either working or with your spouse. Shouldn't you love them both? Besides, the only thing worse than slaving away at work you can't stand is being married to someone you don't love.

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? They were determined 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.

So, before making any career-related decision, I've always asked myself five questions, and that's served me well. Today, after 30+ years, 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?

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.

That's always been my litmus test and it's worked out quite well.

Related: What You Need to Do to Make a Midlife Career Change

What are the odds of a big payoff?

My parents were not risk takers so I've always gone the other way. I never thought much about salary. After all, your salary just ends up paying the bills. Rather, I've always thought in terms of equity: the motherlode, the haymaker, the windfall.

Equity is the big bucks that will take you to financial security and freedom. There are exceptions, but for most careers, that's a pretty good rule of thumb. Everyone in high-tech made their money via equity.

And while you have to roll the dice, you don't want to make dumb bets either. You want the best odds of a big payoff. That's why I think climbing the corporate is important. Top executives get all the stock.

Related: Why Quitting a Great Job Was the Best Decision

What do I have to lose?

The downside risk is important. Some people overanalyze it. Others don't consider it at all. But 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.

Related: Bravely Facing the Epic Decision of a Career Pivot

What does my gut say?

The other four questions are all logic-based, even the fun one. But after I've answered them all, I still ask myself what my gut tells me. If there are red flags, I listen to them. Understand that I haven't always done that. The times I haven't, I've paid the price. Now I always listen. Trust the red flags of your intuition; they're usually right.

That's the bottom line. Pay attention to reason but in the end, trust your gut. You know, the same way you fall in love.

Wavy Line
Steve Tobak

Author of Real Leaders Don't Follow

Steve Tobak is a management consultant, columnist, former senior executive, and author of Real Leaders Don’t Follow: Being Extraordinary in the Age of the Entrepreneur (Entrepreneur Press, October 2015). Tobak runs Silicon Valley-based Invisor Consulting and blogs at, where you can contact him and learn more.

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