Time to Quit Your Day Job? 5 Ways to Know

We do a lot of talking these days about becoming an entrepreneur, following your passion, and doing great things. Well, that's easier said than done. There are practical aspects of that equation that can be enormously challenging to overcome.

For one thing, most of us are gainfully employed. It isn't easy to just pick up and leave a career we've invested in, whether it's the right move or not. Then there's the risk factor. We have responsibilities, a mortgage to pay, kids to raise and put through college. It's hard to risk a sure thing for an unknown, especially later in life.

Nevertheless, there's a lot to be said for following your dream. You may not get rich, but you will enrich your life. And at least one school of thought says that you'll be more successful doing what you love doing than anything else. I couldn't agree more.

I took a hard left turn 23 years into my career and, although it's been quite a challenge, it's also been incredibly satisfying and invigorating. There's nothing like jumping headfirst off a high cliff to get the adrenaline flowing and make you feel young again. But before you jump, do these five things; they will help you make the right call.

Take a long, hard look in the mirror.

What do you see? If it's someone who took the path of least resistance early in life and has been locked on to that trajectory ever since, who would suffer deep regrets if she didn't at least try to find her true path, that's some pretty good motivation, right there.

If, on the other hand, you see someone with a romantic notion of doing his own thing instead of working for the Man, that's probably not going to work out so well. You've really got to figure out what your motivation is. What are your objectives, your priorities? What are you trying to prove and to whom?

Understanding what your true motives and goals are will help you and your family--an important part of the equation, by the way--to assess the risk and make the right decision. It'll also help you avoid waking up down the road and realizing you made a change for all the wrong reasons, like "the grass is always greener."

Don't try to be what you're not.

You're not really trying to change as much as you're trying to find the real you, the path you were meant for. I know that sounds amorphous, but that's just the way it is. You'll know it when you find it. If you're not sure, then keep looking.

I started out as an engineer, but that really wasn't for me. So I got into sales, then marketing. Lo and behold, that was the real me. Everything got easy. And I climbed the corporate ladder like a monkey.

You see, people can change under very specific conditions, but if changing your DNA, so to speak, is a prerequisite for your career shift, I wouldn't do it unless you've got a considerable financial safety net.

Look for problems, not solutions.

Most entrepreneurs are people looking to do something new and different; they search for ideas, for solutions. That's usually the wrong place to start. What you need to find first is a problem that you feel passionate about solving. With any luck, it's one that you're uniquely qualified to solve.

One of the most important questions venture capitalists ask when evaluating an enterprise is: Does it solve a big problem? Does it eliminate a customer pain point? Does it help customers either do something they really want to do but never could, or do something far better, easier, or less expensively than ever before?

Another way to think of it: Don't try to do something great. Not initially. Just try to find a problem you think needs to be solved and do that. Mark Zuckerberg wasn't trying to create a company or do something big when he started Facebook. He just thought it would be cool to be able to rate women's looks online. That was it.

Go where the money is.

I don't care what anyone says: tossing out years of experience in one career to jump to a new one, perhaps even an entrepreneurial endeavor, is extremely risky. Best case, you will take a financial hit. And you have to be prepared for various not-so-best-case scenarios, as well, especially if you've got a family to support.

I'm not saying don't do it, but consider this. Giving up a solid paycheck to start something new on a shoestring budget in a commodity business where you might end up slugging it out with entrenched competitors for single-digit profit margins is for the birds.

Of course, money shouldn't be your primary motivation, but you shouldn't throw caution to the wind, either. Look at fields and industries that have more than a snowball's chance in hell of you making it and making ends meet. Go for growth markets in which venture capital firms are investing, for example.

Find a great team.

There is tremendous power in groups--at least the right groups. The same goes for complementary partnerships. Find a wingman, or be somebody else's wingman. Find a great team to be a part of or create one. Most successful startups have more than one founder. Bill Gates had Paul Allen. Google's Larry Page had Sergey Brin. It's true in any field. It took four extraordinary people who seemed anything but extraordinary at the time to make the Beatles.

Warren Bennis co-wrote an amazing book about great groups called Organizing Genius: The Secrets of Creative Collaboration. Check it out. Even if your group isn't magical, at least you will have others to share the work and the misery with. Remember: When you're doing something new or making a change, support is key. No kidding.

This column originally appeared on Inc.com.