What If?

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

About the Author

  • I’d like to throw in the question “What if I forgave myself for X,Y and Z?” I think this question is important because as we start to forgive ourselves for past “mistakes” or alleged “failures”, we can let go of the negativity and self punishment that comes with dwelling on our past choices. Then, we can start to have a present mindset and focus more on what could and can be done NOW. That is very exciting and powerful – to think about what can be done right now.

    I love this list of questions and I ask myself many of these each day. If I don’t like my answers, I try to think of a way to incorporate changes, no matter how small.

    I’m only 28 years old, but the thought that haunts me most is “What if I waste my time and my life?” I am of the mindset that we’re all here on this earth for a reason and that is why we each have varying talents, strengths and experiences. If we don’t put these natural gifts to use every day – I do think we are wasting our time. Nothing good can come from that and really, we’re not guaranteed a tomorrow – we just hope for it.

    • “What if I waste my time and my life?” – This question is pure gold.

      I’m always surprised at how quickly life moves and I never want to feel like I wasted any of it. It’s really the question behind this entire list of questions. Are we wasting our time and our lives and taking them for granted, or are we making the most of the time we do have?

      Like you, I believe we are all here for a purpose and to not fulfill that purpose is the greatest tragedy of life.

  • I knew those words sounded familiar! I just watched that movie and that part got to me. And this post really got to me. Thanks!

    • I find it funny that a chick-flick made us both ponder life’s deeper meanings. Either it’s really good writing or we need to read more. 😉

  • I’d love to get to the end of my life and not have to ask “what if.” Right now, those two words are worse than a 500 lb. chain wrapped around my neck.

    Great post, man. Cuts right to the heart in a necessary way.

    • Thanks, Jason. We’re all grappling with these questions. You’re not alone and I’m glad you found this post helpful.

      We all have those weights. It’s our choice whether we continue to carry them or if we choose to let them go and live differently. My hope is that everyone who reads this post will choose to let go of the past and live the life God’s given them. What we do with the time we still have can have great impact on our lives and the lives of others.

      We all have a choice. It’s what we do with it that matters.

  • Kaarib

    A little late here, but I had an epiphany a few years back when I realized I would much rather regret the things I did than the things I failed to do, or didn’t have the courage to do. And right now I’m in Juneau, Alaska, a town I’ve wanted to come back to for nearly 30 years, working on building a business of my own where I can be anywhere.

    Thanks for the excellent list, I want to print that out and make sure I focus on what matters instead of what doesn’t.

    • Never too late! That’s awesome, Kaarib! I love hearing stories like yours. I want to make it up to Alaska for a visit sometime. I hear it’s incredibly beautiful. When I do, we’ll need to hook up and grab a local beer (something I also hear is quite tasty).

      Thanks for your kind words and for taking the time to read this. I just posted another article called “Warning: 6 Signs Your Legacy Will End Up In A Trash Can” that you might like. You can read it here: http://travisrobertson.com/legacy/warning-6-signs-legacy-trash/

      What kind of business are you creating? Keep me posted on how it goes and let me know if I can help you in any way.

  • Great post. Everyone’s “what ifs” could (should?) be different just like everyone’s talents and strengths are different.

    I also believe that while we have been given a choice, to choose or not to choose worthy goals, ultimately we must attempt to reach our potential. This is how we develop as people.

    The only tricky part is picking too many goals at once and not putting the focus on them to actually achieve them.

    I’ve stopped watching TV because it was not on my what if list and a lot of stuff that needed time was. No regrets either. Choices.

    Love your message “Don’t Settle”.

    • Thanks, Doug! You’re absolutely right that focus is huge if you want to accomplish anything in life. It’s great to have big goals but they don’t necessarily need to all be done at once. In fact, they often shouldn’t be.

      Love to hear that others have given up TV! Only the occasional movie makes it into our house. 🙂