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Three Questions You Must Answer Before You Die

July 12, 2011

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 their country clubs for 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. 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 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 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 like John Maxwell 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?

25 Comments leave one →
  1. July 12, 2011 6:22 am

    Brad, good to be back and have your posts in my inbox.

    While away, I read a book called ‘Screw Work, Let’s Play’. It asks these same questions but phrases them differently.

    Calvin and I read a chapter a day in different locations and then spent time working through the questions. We have created ‘play’ books for ourselves and we have chosen to make definite changes to what we are currently doing: spiritually, emotionally, physically, relationally and career wise.

    Something that kept coming back while I was reading was how important one’s inner circles are: who are the people that I am talking to and interacting with the most? Are we edifying each other? Lifting each other up? Or is it a competitive benchmark that happens in subtle tones? Or is it a degrading negative everyday conversation that simply repeats itself over and over with little growth?

    Also, whilst talking to my business partner in South Africa yesterday, we got onto the topic of excuses. It is so easy to make excuses, valid ones, that deter us from Life in its fullness.

    Perhaps a relook at our inner circles and the excuses we make is the starting point to getting closer to the answers we desire when asking the big questions.

    Lastly, I would add a fourth quetsion in there for myself. Do I know God? For me, that is the ultimate question that answers all others.

    • July 12, 2011 9:35 pm

      this is good stuff…. thank you Claire.
      ( and you too Brad of course. of course. )

    • July 13, 2011 4:53 am

      It’s good to have you back, too, Claire! GREAT comment here. Sounds like that vacation was extremely worthwhile. I love the idea of taking the book and working through a chapter a day in different locations. Primes the mind and the spirit both, while seeking to build your life out.

      Your point about watching who is part of our inner circle is so crucial. My wife calls it “toxic relationships.” She refuses to spend time on relationships with people who are sucking the life out of her in negative ways rather than building up and encouraging. I agree that we can find ourselves in situations with negative people without even realizing it.

      Thank you for such encouraging, uplifting and motivating words!

  2. July 12, 2011 6:58 am

    I love the Shrinking Camel post, thank you! I believe this is the best one yet for serving as an wake up call for me! I will save this, share this and review regularly.

    Do I have your permission to tell more people about this site and encourage followership?

  3. July 12, 2011 7:18 am

    This cuts to the core of our identity, how we define ourselves. With every dollar we spend, we “vote” on what’s important to us. With gobs of money, would we change?

    And if our days were cut short, how then would we live?
    Great questions that should help us define who we are.

    • July 13, 2011 5:02 am

      My wife and I had our list of things we would do with the money, of course. But once those are checked off, you are really back to your old life – what are you doing with it? I hesitated to say I’d quit my job, because there is something about the structure and routine of it, enjoying the work and the people, making an impact, having built up my reputation, etc. Although I did go down the writing fantasy track – what if I could do it full time? I didn’t think that would be enough, so I threw in consulting and speaking, too. But that also can be a grind. So it’s just as well that I not win the lottery!

  4. July 12, 2011 7:40 am

    I had to think about this for a little while before I circled back to my inner Calvinist. The answer to all three questions, for me, comes back to glorifying God and enjoying HIm. With so little time left, there would be no question about self-indulgent behavior that didn’t glorify God. So I think I would be all about emphasizing the enjoying Him piece–loving Him, loving others, giving to others, spreading the joy lavishly. My kids are (nearly) grown, the need to plan for their financial future is behind me, so I’ve actually been feeling the freedom to give more open-handedly. That’s what has been motivating me to work lately–the idea of having more money to give away. Winning the lottery would just be icing on the cake.

    But I was probably predestined to say all these things.

    • July 13, 2011 5:14 am

      You are so funny, with your “inner Calvinist.” But your answer here sounds so gloriously simple and liberating. Perhaps that is because this is the season where you are at in life?

      But what about your writing? That is something you seem to have taken on as a new path, something you did at this point in your life both because of the freedom of time, but also you had to get to it… Is that true?

      I think we’d all feel liberated if we could answer these questions in terms of what we give away to others.

      Thanks for your generous spirit, Nancy!

  5. July 12, 2011 8:05 am

    SUCH a great post, Brad! Though I don’t {think} I’d change anything if I had 24 hours to live, except escape work and just play … I DO think there are some valid questions to ask when it comes to work. At the same time, though, I try to keep my pulse on whether I am working to my strengths (giftings) and if God placed me where I am, or if He thinks it’s time for me to tackle something different. I spend a lot of time thinking about what I *should* do, and as a result I sometimes forget to look at the purpose in what I’m doing now, and how it might prepare me for something else later on, even if the Right Now isn’t quite exactly what I want to be doing. All of this makes me so dependent on God’s leading and guidance, that’s for sure!

    • July 14, 2011 5:20 am

      Thanks, Amy. I don’t think I would change much either. When I was younger, I had this constant worry that I was missing something – that I may have made some mistake and was missing my bigger purpose in life. But as I have gotten older, I see that my whole life has been on purpose. I am fairly satisfied, and no longer have these unrealistic, wild expectations. And I feel pretty good about how things have turned out, too.

  6. July 12, 2011 8:55 am

    I like these questions. They’re different ways of asking the same old questions, but they’re phrased practically enough to really get you thinking. The last question reminded me of a quote I once heard: “Take care of your body like you’ll live forever. Take care of your soul like you’ll die tomorrow.”

    • July 14, 2011 5:17 am

      It’s not like I go around thinking about what if I die tomorrow. But stepping back and asking the question sure does put things in perspective.

      • July 14, 2011 5:24 am

        I like the phrase, “Work like it all depends on you, Pray like it all depends on God.” When we do that, the pieces do seem to fall together. I like Loren’s quote there – “Take care of your body like you’ll live forever. Take care of your soul like you’ll die tomorrow.” When faced with eternity, if we have lived for God here on earth, we won’t have regrets.

  7. July 12, 2011 9:42 am

    This is a fantastic post, Brad! Will surely be spending some time thinking about what my own answers to those questions are. And evaluating what may need to be adjusted based on those answers.



    Virtually Yours,

    • July 14, 2011 5:22 am

      Thanks Anne-Marie. You should do like I did: sit by the pool for an afternoon contemplating these things with your significant other. It’s good to have someone else to bounce it off of, once you’ve thought about it for a while.

  8. July 12, 2011 1:16 pm

    I had to check the comments to see what others were answering. Since not many have thus far I thought I’d share my knee-jerk reaction to these questions.

    1. Win the lottery: Noticed my answers all boiled down to one thing – freedom. I’d eliminate all my debt, splurge on a few luxuries, leave my job, and travel. When my adventurous spirit is exhausted, I’d return home to pursue entrepreneurial ambitions. All on my own time.

    2. Five years to live: Motivation feels more about stopping things than starting things… Stop building and banking on long-term investments (in people, ventures, finances, etc). Stop wasting time on things like TV. Stop waiting for things to happen and instead start taking risks and actionable steps toward something… anything really.

    3. Regret not doing: Give more? Not really sure. To be honest nothing is really striking me in this matter. Maybe that’s a sign of youth. Haven’t lived long enough for major regrets yet.

    • July 14, 2011 5:34 am

      Mike – I love the way you came right out and answered these questions. I thought of writing my own answers in the blog post, but it would have gotten too wordy.

      Good thing about not having major regrets. I hope that is sticks for a long time.

  9. July 12, 2011 6:20 pm

    that big cloud looks like the head of a troll doll… or an elephant.

  10. July 12, 2011 8:26 pm

    I’ve asked myself these kinds of questions before, and after nearly living these questions, my answers changed. I’ve always wondered how to live these way when the stakes aren’t so high, though. What if I’m going to make $50,000 a year for 30 more years. What’s a reasonable expectation in those circumstances?

    I loved this post. Loved the way it just cut through everything else to say who am I, who do I serve, and what is it I should be doing?

  11. July 13, 2011 6:15 pm

    1) I’d move to Colorado or Wyoming
    2) I won’t do that because if I only had five years, I’d focus on getting my kids ready to live without me.
    3) I’d have a big party and invite all my family, friends, and online peeps.

  12. July 14, 2011 10:40 pm

    This is powerful Brad… And beautiful too. It really helps to boil things down and give us the clarity we all need in life.
    Thanks again for a wonderful work-life lesson.

  13. Susan DiMickele permalink
    July 19, 2011 7:08 pm

    You’re right, I would like Rob. I love people who think like this. Would love to see what he does next.

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