Three Questions You Must Answer Before You Die

Every now and then it's good to take an enormous step back and evaluate where you are in life.

My friend Rob did this for me over breakfast the other day.

You’d like Rob. He is a smart, successful, energetic, forty-something investment banker. The whole package, you might say. Or, what I once assumed was the whole package, but now I know better. Anyway, I’ve gotten to know him through some business and professional dealings over the past few years, and we’ve forged a budding friendship.

Rob and I met up at an upscale diner near his home in a tony suburb of the city. I’ve often wondered what the appropriate use of the word “tony” should be when describing affluent settings. Friends, this was it.

The place was packed. This particular establishment somehow seemed to collect many of the area’s most prominent movers and shakers en route to the country clubs for their morning rounds of golf. How else to explain why on earth so many casually well-dressed middle-aged men were eating breakfast at a diner at 8 am on a Thursday morning instead of working?

Rob ordered a massive breakfast. “I eat breakfast like a king, lunch like a prince, and dinner like a pauper,” he announced, all fit and trim and enthusiastic as the waitress arrived with the third course of an egg white omellete. Then he told me about his super awesome exercise routine.

After a while we got talking about more serious matters: our jobs, priorities in life, how satisfied and fulfilled we were at this point in our careers. He’s thinking about a major job transition.

Rob said that whenever he considers significant life decisions, there are three reflective questions he thinks about as a checkpoint.

1. If you won the lottery (pick a number. A very big number), what would you do?

This question gets to the essence of what you really, really, really want to do with your life. The source of your dreams. This scenario blows up all the excuse-making and resource constraints and limitations and just says, “dude, what do you really want to do?” It's a good litmus test to determine if you are moving towards that path in some form or fashion - even if it is only a gravelly, dusty side-track path for now - or if you are missing it altogether.

2. If you knew that you only had five years left to live—yet you would miraculously be in perfect health until the last breath—what would you do?

This gets at your priorities. In this scenario you don’t have the luxury of decades to build something, so you must concentrate on a more urgent time frame. You might as well get some level of fulfillment and joy from whatever it is that you are doing. It starts narrowing down the field.

3. If you had only 24 hours left to live, what would you regret not doing?

This is the most impactful question of all, getting to your core spiritual values. What didn’t you do with your life that you felt that you were meant to do? Maybe you should have mended a relationship. Maybe you’ve neglected your kids while pursuing your career. Or, maybe you spent too much time focusing on everyone else's agenda, and never developed your own sense of self. You could have done more for others. Given more. Been more.

I spent yesterday afternoon talking these things over with my wife.

I don't know. Some people think these schlocky self-help exercises only serve to keep generic motivational speakers employed. But it does get right to the heart of things, doesn't it? And look, Rob is doing this, so it must be effective, right?

Post by J.B. Wood.

Image by Darlene. Used with permission. Sourced via Flickr.