A Couple Big Questions To Ask Yourself Right Now

I’ve proclaimed my love for Tim Ferriss’ podcast around here, yes? I just love it. Podcasts are having a moment, and I latched onto that bandwagon like it was headed for the promised land. Listening to them during my commute makes me feel motivated and accomplished, rather than irritable and angry which, let’s all agree, are far easier emotions to exert when stuffed into a subway car.

Tim chats with all sorts of interesting folks, from entrepreneurs to CEOs to authors to scientists. Last night I listened to an interview with Co-Founder and President of Pixar, Ed Catmull, and this morning I got into a talk with Kevin Kelly, the Co-Founder of WIRED. I think what I love about podcasts is that they give us access to these amazing people in a way that’s unlike any other medium. The host essentially just picks their brains in casual conversation. In one of my favorite episodes, three guys sit around shooting the shit just talking about life while drinking wine, and it was great.

The reason I bring this all up is because Kevin Kelly said something that I CAN’T stop thinking about.

He asked, and I’m paraphrasing here, what would you do if you had six months to live? And what would you do if you had a billion dollars? Chances are, whatever you answered to the first question is something you would do regardless of having a billion dollars. That being said, what would you do right now, even if you don’t have a billion dollars?

Let that sink in for a minute.

Still with me? Okay. So I really, really want to agree with this, but I have a few qualms.

First off, things I would do if I had six months left to live are things I probably wouldn’t do if I knew that I’d live longer than that. And yet, most of the things I would do if I had a billion dollars are in fact the same as if I had six months to live. That’s a mind twister, I know. I’m going to show you my lists in order to explain.


If I had six months to live

1. Stop working full time

2. Spend time with loved ones

3. Travel (that includes hitting all the best restaurants in the world)

4. Live on the beach

5. Donate all my money to an animal shelter

If I had a billion dollars

1. Stop working full time

2. Travel (that includes all hitting the best restaurants in the world)

3. Buy a house (probably on the beach)

4. Invest in and go full throttle with CTK

5. Take classes to learn something awesome like how to speak French, or play the piano, or become a Sommelier.

Allllrighty. I highly recommend jotting down your own lists. It’s a cool experience to actually write these things down and see what comes out. It’s also interesting to see the common threads. I think if you asked people either of these questions, many would answer “Quit my job” to both. I get pretty deep about that topic here, explaining why I left my job in advertising last year. Let me clarify that I 100 percent do not believe we should put up with jobs that make us overly stressed, sad, angry, unhealthy or bored. It’s a sure-fire way to ruin our lives. I do however run into a wall when it comes to taking the paycheck away altogether. I’ll be the first to admit it: I am terrified of not working full time. Quitting a secure position would be easier if we knew what the future looked like (whether that’s death – yikes, sorry to get weird here – or a billion dollar payout). Okay, so that’s qualm number one.

Qualm number two: I wouldn’t do some of the things on my billion dollar list (like buying a house) if I had six months left, because what’s the point? Same philosophy applies to four and five.

Then I ran out of qualms.

I thought there was a lot more to it than that, but turns out not really. According to the first list yes, theoretically I would be “living as if I were dying.” Which is something we’re always told to do, but then again it’s not very practical. The second list seems like a fantasy.

And yet, many of the items are similar if not the same.

So what’s the point? Kevin Kelly’s point, is that you don’t need to wait for either the prospect of death or a billion dollars to live the life you truly want. Like I said, I really want to adhere to this, but find some of it impossible to be completely honest. A lot of it has to do with limiting beliefs. But this exercise really did make me think about what I want. What would I do if I wasn’t afraid, if I knew I couldn’t fail? If I died in six months, would I be happy with the life I’m leading? And what’s preventing me from doing the things I truly want to do, regardless of how much money I have? I’ve made a lot of strides in the past year around this thinking, but I have a long way to go and I suppose that’s the point; to be constantly evolving and pursuing a life we desire. Not to look forward to the time when we can finally retire, or to chasing a billion dollars. To chase feeling good.

Deep stuff, you guys, deep stuff. But worth thinking about for sure, right?

I’m really curious: what tops your list for each question? Tell me in the comments below. Maybe we can all quit our jobs together and move to the beach.

One Comment

  1. VERY interesting article. While I was reading it, it made me questions a lot of things- and gave me the confidence to go for more….. THX for writing!

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