The Most Interesting Question You Can Ask Someone (Especially Yourself)

I’ve been thinking a lot about the concept of success recently. Specifically, what does it mean to be “successful?”

If you ask someone off the street for a 30-second answer to what success looks like, you might get answers like:

  • Be a millionaire.
  • Get famous.
  • Have six pack abs.
  • Get married, have 2.5 kids, a house with a white picket fence, etc.

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These are generic answers. If you really press someone about what success means to them personally, you’ll get a different answer from everyone.

Yet as a society, we are fascinated by all the rags to riches and success stories. We’re enamored by their back story, dissect everything they do and imitate their tactics in the hopes that by doing the same thing they did we can be as successful as they are.

X Instagram celebrity only eats raw fruits and vegetables. So, we do the same.

They swear by waking up at 5am. Better set the alarm a little earlier.

You get the drill.

There’s so many problems with this approach.

Instead, you can learn so much more by what they aren’t focusing on and the price – or in many cases prices- they had to pay to be “successful.” Sometimes, you have to look a little harder, but there are always tradeoffs.

That’s the most interesting question you can ask someone who has “made it.”

What was the price that you had to pay?

When you understand the price someone had to pay, that’s where you can get to the root of success, which lies in what motivates them.

Motivation is a complex and messy topic.

As Derek Sivers shared in this talk, there’s really only five true motivators.

  • Money
  • Prestige
  • Fame
  • Legacy
  • Freedom

After reading this article from Taylor Pearson, I’d add one more thing you can optimize for – interesting.

Motivation and success are tied together.

This all sounds deceptively simple. But, it isn’t. It can take years – even decades – to get this right. The vast majority of us get it so dead wrong.

Think about it. As Brene Brown shared in her now famous TED Talk, American adults today are the most overweight, medicated, sleep deprived, stressed and depressed cohort in US history.

Or, as Tim Ferriss wrote in The Four Hour Work Week.

“This is how most people work until death: “I’ll just work until I have X dollars and then do what I want.” If you don’t define the “what I want” alternate activities, the X figure will increase indefinitely to avoid the fear-inducing uncertainty of this void. This is when both employees and entrepreneurs become fat men in red BMWs.”

Coincidence? I don’t think so.

Most of us either don’t have the faintest idea why they are doing what they are doing, what they should be optimizing for or what they are willing to sacrifice.

Many defer to the one thing that they think we’ll make us happy. That’s more money. It is what we are bombarded with on TV, social media, music videos and ads.

You just have to look to this famous rapper to see what more money leads to.

Yet from my own experience, this is what I initially optimized for because that I was taught and learned growing up from my teachers, friends and family. You optimize to make more and more money, thinking that’s what will make you happy.

Money might not buy happiness, but it does buys some comfort (and better problems). That offers some peace of mind and some perceived certainty.

I get it – for some money may be your biggest driving motivator. But for me, while money is important, I hit a point of diminishing returns way faster than I would have thought.

For example, my first, grown-up job seven years ago, which I took simply because it paid well and was right after the recession and no one was hiring, would teach me that. I would quickly discover that the reason this entry-level job paid so well was because it was in a glorified retirement community. When you are 22 and live in a community where the average age is 70, all of the restaurants close by 9pm on the weekends and the nearest two cities are both an hour away (cough cough – Savannah and Jacksonville), your social life kind of sucks.

So once I became a little more self aware, I did what many of us do. I tried to optimize for like 4 of the things. I wanted a little bit of money, some prestige, to leave a legacy and lots of freedom.

That’s downright impossible. Trying to pursue them all at once is a recipe for unmet expectations, regret, endless frustration and depression.

You need to know which of these things is your primary thing that matters you the most.

As Jon Morrow said in this podcast with James Altucher, “You can do anything you want but there will always be a price / sacrifice in some other area. (it could be money, it could be years of your life, health, relationships, your marriage)”

You can be certain that not everyone is going to agree with your choice and some may flat-out tell you that you are wrong or selfish or call you a fool. It hurts especially if it someone you are close to.

This is downright scary, and why many people don’t lean into this discomfort. So, most people just imitate what they see those around them doing or if they are a little more ambitious chase what seems cool at time. And, then lash out when they see people around them “become successful.”

They numb themselves by grabbing that second dessert, have that third beer, binge watch that entire new Netflix show in the same night, lease the bright red corvette, buy the new shiny iGadget the minute it comes out and upgrade to bigger and bigger houses. Then, chase it all down with a cocktail of antidepressants and Ambien so that they can sleep at night.

We do all of these things to find comfort, happiness and try to selectively numb deep seated regret and unhappiness.

You see this pattern emerge in a particularly insidious form with the ever-growing self help industry. That’s supposed to be well “helpful,” but I think can actually be very destructive.

Let me preface this: self help can be an amazing resource when you use it as “a self help tourist.” It can help you see the forest from the trees. This is especially productive when you are trying to cope with crappy things that life throws our way.

The problem with self-help resources is the line for using it in helpful manners and in more self-destructive ways is very blurry and easy to cross. Too many get overly dependent on it. These “self-help junkies” feed on it to get their next high or some sort of validation they aren’t getting elsewhere.

The more they consume this content, the more they need it to feel good about themselves and their choices. They are looking to anyone else to tell them what to do because it is easier, more certain and far less painful than looking within.

It is not unlike how drug addicts feel when they score their next high. But instead of spending money on dope, they spend hours and hours every year reciting mantras and affirmations, hundreds of dollars on books and courses, thousands on seminars and workshops, etc.. Some may also seek “self-help gurus.” Some of these gurus appear almost “cult-like.” (Cough, cough The Cult of Tony Robbins) That’s for another post.

The kicker is many of these self help junkies are throwing themselves at coaches and gurus who have never done the things that they are trying to accomplish. The most “successful thing” the self-help guru has done has been to write a book or give a TEDx talk about you guessed it – “self help.” .

If that’s not terrifying enough taken to the most extreme, these people willing go to following an actual “guru” and joining a cult.

No sane person is going to shave their head, wear a robe, dance in the street, cut off all ties with the outside world and give all their money to some deranged cult leader without getting something in return. What they are “promised in return” is some direction and perceived certainty.

This is of course an extreme example.

While most self junkies won’t join a full fledged cult, they will continue to turn to these courses, books and “gurus” for the quick highs to feel good about themselves, look for certainty or to outsource all the answers they are too afraid to look within themselves and find out.

Often times, the only way to figure out what success really means to you is to figure all the things you don’t want and what you are not willing to sacrifice. Probably not the answer any of you want to hear. You definitely won’t find it at the end of the $99 self-help course.

It is also 100% guaranteed that if you find what your definition of success is, many, many people will tell you that you are wrong to strive for that. Sometimes even the people that you are closest to.

This also isn’t going to be a magic pill or a cure all for all disappointments or things that don’t go exactly your way. You’ll still have all of that. That’s just how life is. You have to take the good as well as all the shit.

When you know what motivates you and more importantly what you are and aren’t willing to sacrifice, it makes everything a wee bit easier. You are more able to endure the highs and lows without reaching for that extra large bag of potato chips, that 6 pack of beer, or your trusty bottle of Ambien.

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