When Do You Get to Live Your Dream?

Few of us are blessed with a career we love, can't get enough of, will joyfully and tirelessly work at until we drop. The rest of us have hopes and dreams of someday taking a chance on something different.

Sooner or later you're going to have to confront one of the toughest dilemmas in life and answer this question: How long do I have to keep doing this and when do I get to live my dream?

Conventional wisdom says you should milk what you've got while you can, stick with what you're good at, and never let go of a good thing.

That doesn't stop a lot of us from quitting while we're ahead, going out on top, and rolling the dice on something new and exciting.

It's a tough call and tougher now than it used to be. Used to be that if you worked hard for a few decades and saved a little nest egg, you could safely call it a day and turn in your suit for whatever pleases you - retirement or some Zen gig you've always dreamed about like a winery or an island bar or something.

These days, you can throw all that right out the window. The economy's a moving target. Nobody knows what qualifies as a nest egg anymore. Today's safety net can be full of big gaping holes when you actually need to fall on it. Yup, it's a tougher call than ever.

Nevertheless, I'm a big fan of taking risks in life, and not necessarily for all the usual reasons. No, I'm not saying you should throw caution to the wind and do something really stupid that might end up with you and your family on the street.That said, you can create a nice little hell for yourself, right here on earth, by playing it safe and spending your entire life kicking yourself over what could have been. So you don't end up there, here are five factors to consider when deciding whether you should play it safe or roll the dice:

Trust your head or your heart? There are all sorts of ways to look at this. Listen to your analytical left brain or your inspirational right brain? Trust your logical thoughts or your deep feelings? Don't complicate things. Just trust whatever has worked consistently for you in the past. If you tend to use logic to overrule your fearful instincts and that's been good to you, stick with it. Get it?

You can drive yourself nuts looking back and wondering what if? Long ago, a very wise person said that to me and he turned out to be right. Here's a thought experiment you should try. Picture yourself on your deathbed looking back at this point in time. How do you feel, first assuming you stuck to your present course and then assuming you rolled the dice on something new and risky? That should tell you a lot. Basically, regret is a bitter pill to swallow and it gets more and more bitter the older you get.

The safe bet doesn't always turn out that way. One of the things people never think of is that sticking with what you know and what's comfortable, even if you're an executive making big bucks, may not turn out to be as safe a bet as it seems right now. The reverse is also true: the risky venture may turn out to be a hot ticket. Sure, there are probabilities involved, but nothing's cast in concrete. Nothing.

Who do you listen to? When it comes to gut-wrenching decisions, most of us will ask our friends and loved ones and maybe a trusted mentor what they think. Just keep one thing in mind. People close to you are also stakeholders in your decision and, as much as you'd like to believe otherwise, they won't be thinking entirely of you when they give their opinion. Also, even objective advisors will tend to reinforce their own personal decisions. At the end of the day, none of them will have to deal with the consequences of your actions the way you will have to.

Sometimes you have to say, "What the F___." Not only is that a great line from Risky Business, it's also one of the tenets I've used to live my life. Granted, there were times when it didn't look like such a good idea, but over the long haul, everything turned out fine, just like in the movie. All things being equal, I say go for it.