Late last week, my wife Lisa came down with some cold/flu thing so we swung by our nearest Redbox to pick up a movie. What we ended up with is the ultra chick-flick “Letters to Juliet.” Other than being your typical, predictable film, it was cute.

Then something unexpected happened. Toward the end of the movie, one of the characters said something that knocked me upside the head:

“What” and “if” are two words as non-threatening as words can be. But, put them together side-by-side and they have the power to haunt you for the rest of your life.

If you want to create a life you’re proud of, build a legacy, and live a life with few regrets, you need to wrestle with the “What if” questions right now. Here’s a tip: read them as if you’re at the end of your life looking back. Then ask yourself what you can change in your life today. I’ve broken them into categories to make it easier to think about the different areas of your life.

Warning: You will ask these questions eventually. Better now than when it’s too late to do anything about them.

Career
What if you started that business you dreamed about for years?
What if you made your living doing something that made you feel alive?
What if money were no object? What would you do?
What if you could answer that question with, “I’m already doing it”?
What if your unemployment was really just an opportunity to try something new?
What if you didn’t accept that “this is how life works”?
What if you didn’t spend 2 weeks each year escaping from the work you do the other 50?
What if you found a job that combined your strengths and passions?
What if you spent less time in front of the TV?

Risk/Fear
What if you didn’t care what other people thought of you?
What if you acted in spite of your fear?
What if you said “Yes” when fear told you to say “No”?
What if you said “No” when fear told you to say “Yes”?
What if you didn’t quit?
What if you did quit?
What if you failed knowing that at least you tried?
What if you didn’t fail?
What if you didn’t learn from your failures?
What if they laughed at you?
What if they gave you a standing ovation?
What if you tried out for that team or applied for that position?
What if they say no?
What if they say yes?

Relationships/Family
What if you worked as hard on your marriage as you do in your job?
What if you spent more time with your kids and less time with your work?
What if you made the phrase “I love you” part of your daily life?
What if you called your parents more often?
What if you said, “I’m sorry”?
What if you said, “I forgive you”?
What if you said, “Thank you”?
What if you did something unexpected for someone you love, just because?
What if you did something for someone who couldn’t give you anything in return?
What if your memories were filled with more laughter than tears?
What if you cared as much about others as you do about yourself?

Health
What if you exercised just 20 minutes each day?
What if you quit smoking?
What if you lost weight?
What if you ate better?

Finances
What if you had no debt?
What if you spent less money?
What if you saved more money?
What if you gave more of your money?
What if you cut up your credit cards and consumed less?
What if you paid for things with only cash?
What if you didn’t measure your success by how much money you made or stuff you had?

Spirituality
What if you prayed more and worried less?
What if there is a God?
What if that God loves you?

Live Without Regrets

What if you could do it all over again?
What if these questions weren’t filled with regrets?

What if you got to the end of your life and never wondered, “What if?”

It’s better to ask, answer, and act on the “What if” questions now rather than wait until you’re older or until you’re told you have just a short time to live. We can’t go back and change what’s been done. But we can learn from the past and change how we move forward.

Don’t settle. Don’t accept status quo. Don’t wonder, “What if…?” It takes courage. But your family, your friends, the world, and your legacy are waiting on you to live with courage.

Photo courtesy of fadedmilkyway

Every day, I get the privilege to hear from and work with both aspiring and actual entrepreneurs. It’s an honor and I love every minute of it. As a result, I’ve begun to see a pattern in the questions I receive via email or in conversations and I’ve realized something:

There’s a large and often frightening gap between where most people are and where they want to be, but they’re not sure how to close it.

This gap is caused by a breakdown in three distinct areas of your life: heart, mind and will. In this three-part series, I’m going to address each of those three areas to help you close that gap.

Heart – Get Passionate!

Let me just start by saying this: Most of you reading this HATE your job. In my head that sentence had a curse word I’ve edited out. Be honest: you also put one (or two) in when you read it.

Back in January, a study was released stating that only 45% of Americans are “satisfied” with their job. I don’t know about you, but I’m not happy just being “satisfied” with my job. Here’s what satisfied really means: “I don’t really like what I’m doing, but I’m paid too well to put much thought into leaving.”

If you’re content with “satisfied,” you should stop reading my blog.

Being in a job that you hate for an extended period of time will crush your spirit. Often, it will make spotting your passion difficult since “hope” was a word you stopped using many years ago. Heck, you’re just happy to make it to Friday. Trust me. I was there.

You need to dig down into your heart – into the core of your being – and really determine what you’re passionate about. Avoid questions like “If you had a million dollars what you start doing tomorrow?” since they’re complete fantasy. You probably don’t have a million dollars and it’s loaded with the idea that you need a million dollars to even think about changing your career. You don’t.

Try this instead:

“I [place curse word here] HATE my [possible word here] job. I don’t have a million dollars so that question is bull[crap]. Therefore, quitting my current job tomorrow would likely be foolish and irresponsible. However, I’m going to spend about 1/3 of my life working and I really, really, really don’t want to do this any longer than I absolutely have to. I know that I can start making decisions now that will pave the way for me to do something that I will truly LOVE by figuring out what I’m passionate about and doing that in every free moment I have. Over time, I will figure out how to monetize this passion.”

The Fantasy of Passion

Most people believe that if they were doing something they’re passionate about, life would be all roses-and-unicorns-and-cuddly-creatures. It’s not. But we’ll tackle that in the next post.

I would really love to hear your thoughts on passion and career below. Are you doing something you hate as a career? Are you “satisfied” with it? Are you passionate about it? If not, are you making plans to change your career?”

In 1519, Captain Hernán Cortés landed in Veracruz to begin his great conquest. Upon arriving, he gave the order to his men to burn the ships. As I imagine it, someone then laughed and Cortés promptly thrust his sword into the man’s chest. After which, the rest proceeded to get hammered on rum by the glow of the blaze. Almost like a bloodier version of The Pirates of the Caribbean with Cortés played by Johnny Depp.

Here’s the lesson: Retreat is easy when you have the option.

Let that ruminate in your brain for a moment. I had to.

We all cling to something that acts as our escape hatch or our exit strategy (in the negative connotation). It’s our safety net “just in case…” What we fail to do is honestly complete that sentence. We lie to ourselves. If we were honest, we would say, “This is my safety net just in case I get scared.”

We postpone action until we no longer feel fear. Either that, or our actions are shallow attempts never designed to succeed. In reality, we must learn to act decisively in spite of our fear.

Burning Things that “Make Sense”

“That doesn’t makes sense.” We love that phrase. We love to hide behind it. We tell ourselves that certain things don’t make sense. It would have “made sense” for Cortés to keep a ship or two if not his entire fleet. But Cortés was on a mission and he knew that the only way to keep himself or his men from quitting on the mission was to take that option off the table.

What Cortés did was force himself and his men to either succeed or die. Retreat was not an option. I believe that to truly achieve the level of success we each desire, there are times when we need to “burn the ships.”

The question we have to ask ourselves is this: What are my ships? What am I afraid to let go of?

I can’t answer that question for you, but I can give you some areas to consider as you ponder the question, “What ships do I need to burn in my life?” Take a look at them, then feel free to add your own in the comments below.

As you consider each one, if it jumps out at you, ask yourself why. What is it that makes it hard to burn? Is it a false sense of obligation to it? Is it fear of the unknown? Is it fear of being perceived as a failure? What is it?

• Your Current Job – Are you afraid of trying something new? Are you comfortable? Are you convinced that this is as good as it gets?
• Your Field of Employment – Have you been dreaming of a career change? Does every ounce of your work drain you? Are you a people person stuck behind a computer screen? This is one I had to wrestle with.
• A Bad Business Deal – Why is it a bad deal? Why can’t you let it go? Do you feel obligated to the relationship?
• An Unrealistic Dream – Sometimes this is the toughest one to spot. I enjoy watching TV shows like American Idol because you get a chance to see people who are willing to put it all on the line in front of a national audience for their dreams. During the tryout rounds, you’ll witness as people who are ill-prepared give what they believe to be a stellar performance. Unfortunately, they don’t recognize the lack of skill in themselves. It’s sad because they are neither willing to put the work into accomplishing their dreams nor willing to modify them accordingly. Instead of dreams they have fantasies and that is a sad state for anyone to live in.

What are other “ships” that often need to be burned? What “ships” have you burned? How did it feel at the time? How does it feel now?