Why the Ambitious Are the Least Likely to be Successful

by Alexander Heyne · 19 comments

Ambition is a mental illness.

It will not make you any more successful than anyone else.

And it definitely will not make you any happier.

For many years, I was that typical “ambitious” type. You know, I started stuff. I got good grades. I didn’t waste my time. I wanted to “change the world.”

I hustled my way through high school and college, got pretty good grades, and then entered the real world to realize that ambition is poison. 

And the sad truth is that being ambitious makes you no more likely to be successful than anyone else.

After college I started working on more and more projects on my own. I was going for the whole self employment thing, I was busting my ass, I was sacrificing friends and playtime like ambitious people were supposed to do right?

Except that after a year I was totally miserable, and unfortunately for my ambitious self, didn’t really achieve too much.

And that’s when I stumbled upon a couple important revelations.

The more you focus on success the harder it is to be successful

A major focus of this blog, Milk the Pigeon, is success and how to get “there.” That’s inevitable. It’s an obsession of mine and not really a choice – I couldn’t remove this quality from myself if I wanted.

The problem I’ve realized, after reading just about every success book out there, is that success is just like happiness – you can’t read books on success and expect to get closer.

Yes.. re-read that.. focusing on success will not get you ANY closer. And in fact, it’ll probably make you miserable because you’re focusing on the wrong thing.

Do the athletes that make it to the olympics focus on winning their olympic matches every time they train? Do they focus on winning? You want me to be honest? I doubt it.

Pro athletes focus on improving themselves over and over and over, on getting better and better. They focus on breaking personal goals over and over again — they focus on pushing and improving day after day. They focus on turning that 4:30 mile into a 4:27 mile.

Side effect? They get better. Side effect? Beating the opponent in a race. Side effect? Winning the olympics.

Success is a side effect.  It’s a side effect of many things invested in, over time.

The deceptive 4 qualities that will get you further than most, while making you more successful and much happier:

#1 If you like stripping, drop out of school and become a stripper (intrinsic interests) 

I don’t know how western society got this one wrong. But most of us have this idea that success or high achievement takes more work, it takes effort, it takes struggle, it takes discomfort.

But a lot of the people I talk to that are really good at their craft don’t talk about struggle, or pain, or agony. Work, yes. But not struggle. There’s not really much of an internal feeling that they want to avoid the work. It’s not easy, and it can get frustrating and tedious, but again there’s no intuitive pulling away feeling.

When I was young, I used to take Judo with a lot of my friends. One of my buddies really really loved the class. I loved it too, but part of my love was the love of “getting good at stuff.” I would train every day because I wanted to get good and I liked seeing improvement; I also liked the attention I got from the instructor who noticed how quickly I improved.

After less than a year I was better than 95% of the students in the entire gym. I thought it was pretty pathetic that guys who had been training for 6 years weren’t as good as I was, since I had been there for maybe 8 or 9 months. I  kind of frowned down on them, thinking that they were lazy or not committed since they weren’t interested in training every day.

As it turns out, at about the year, year and six month mark, I ended up losing interest. It was boring and I was onto better things. I wasn’t enjoying the process anymore and I wasn’t enjoying the daily training on my own.

And as for my buddy – despite many on/off periods, 10 years later he is still training and is a pretty damn good fighter.  His fire was never quite as strong as mine because his emphasis wasn’t on “getting good.” He just did it because he enjoyed it. If he didn’t want to train for a week, he wouldn’t.

As it turns out, I later learned that people that have fun and enjoy the process of what they’re doing outperform externally motivated people in the long-run, by far.

“Intrinsically motivated people usually achieve more than their reward-seeking counterparts. Alas, that’s not always true in the short term. An intense focus on extrinsic rewards can indeed deliver fast results. The trouble is, this approach is difficult to sustain. And it doesn’t assist in mastery — which is the source of achievement over the long haul. The most successful people, the evidence shows,often aren’t directly pursuing conventional notions of success. They’re working hard and persisting through difficulties because their internal desire to control their lives, learn about their world, and accomplish something that endures.”

-Daniel Pink in Drive


#2 Play on playa playa (the emphasis on play and flow)

One of the next biggest problems with focusing on ambition and success is that most of us forget to play.

When the deadline gets closer, we lock ourselves in the dungeon and work harder. When the stress increases we isolate ourselves further. Because the solution is always work more or work harder.

The problem is that both of those are total bullshit. They’re lies we’ve been fed because we think there’s some insane kind of direct correlation like this:  more work + harder worker = more success.

Except it’s not true.

There are a couple key qualities about play that will make you way more successful (not to mention happier) than those who over-emphasize work (especially when it’s forced):

A. Play means you’re probably doing something you enjoy, and chances are you’ll stick with it if you enjoy it.

If you are enjoying it, chances are you’ll outlast people who do not enjoy it, no matter how much fame, money, or recognition is at the end of the rainbow. = Longevity

B. Play takes care of your mental health. 

I can’t even tell you how many things I have gotten into and have gotten extremely good at in a short time (comparatively speaking), but have felt anxious and stressed 24/7. Most of the hobbies or activities I take up that I get good at I quit because the overwhelming pressure I put on myself to get good outweighs the enjoyment.

When you play you ensure that sanity comes first. You’d be surprised, sanity is pretty important. It always surprises and disappoints me when I see what a high percentage of successful people are divorced, unhappy, and overweight. They obviously aren’t doing it right – they’ve just decided to work more.

Play = Long-term sanity and health

C. Play gets you into flow easier. 

Tell me how many things you have truly not enjoyed that you’ve stuck with 1,3,5 years down the line.

Tell me, are you mind-blowingly good at the job you can’t stand? Are you insanely motivated to show up every day to work and get better?

What about your hobbies and the stuff you do in your free time?

For those of you who love training in some sport, going to the gym, blogging, reading, etc. Does anyone have to twist your arm to get you to go? No, right? And that’s the essence behind play - it’s easy to do forever as long as it feels like play. The exact opposite is true when you are overly focused on “getting stuff done.”

“There is no reason to believe any longer that only irrelevant ‘play’ can be enjoyed, while the serious business of life must be borne as a burdensome cross. Once we realize that the boundaries between work and play are artificial, we can take matters in hand and begin the difficult task of making life more livable.”

- Csikszentmihalyi  

#3 Intuition (it ain’t just for women)

 The ambitious are also much less likely to follow their gut and go with their intuition. 

I think that is for a number of reasons: we’re told to force things and work hard, we’re too focused on getting shit done than on being patient , receptive, and observant, and that we’re way too concerned with efficiency and maximal use of time.

We’re too myopic in our view of reality and much too focused on success now, as soon as possible, and less likely to quiet down and see what our gut says.

The problem with this insane emphasis on efficiency and productivity is that it just doesn’t benefit you.

Really, read 53 books in a year? If they really are extremely useful books with a lot to digest, how the hell can you honestly apply even a small percentage of that book, let alone in a week? If you’re a business person the answer should be obvious: there’s no way in hell!

Really? Put your iPod on 2x speed so you can listen to twice as many podcasts?

Really? Skip the gym so you can get more work done?

Wake up people.. none of this shit benefits you in the long-term. And it doesn’t even make you any more successful!

Your gut will tell you which people to trust, which ones to work with, which businesses to pursue and commit to, what you enjoy, what you hate, where to live, and what work not to commit to.

But when you invest all your time into stuffing in massive amounts of information in your head and trying to maximize your use of every 36 seconds, you don’t have a moment to sit down and say: Hold up, which one of these projects deep down do I want to pursue?

Many ambitious people are inherently distrusting of themselves and often other people, thinking “They can do it all themselves” and that by sheer work and willpower it all can be achieved. Wake up kids.. that’s not at all how it works.

Your gut will get you further than your intellect – but you have to stop the over emphasis on more books, more work, more stuff, more experience.

When you’re tired, sleep, when you’re frustrated, stop and play, when you’re inspired, write longer than the 40 minute period you have allotted for yourself as maximally efficient.

The curse of the ambitious

I call this the chronically ambitious and chronically unhappy” syndrome.

We’ve been told before to enjoy the process, or to go with our gut, or to find something we enjoy.

I know you have heard this before.

But if there’s just one personal that listens to me, one ambitious person who is making themselves fucking miserable trying to be “successful”, listen to these last few words:

“Work more” needs to be replaced with “do something that doesn’t bore you.” Interest gets you infinitely farther than any forced work.

“Work harder” should be “go with your gut.” Shortcuts exist.

“Struggle, hustle, and persevere” need to be exchanged with “play more at work.”

Ambition is a mental illness that saps excitement and happiness from life, and leaves a person wondering where the time went.

Ambition is poison that shifts your mind from thinking about “having fun right now” to having fun “some day over the rainbow once I get shit done.”

Well guess what? Once you put yourself in the hamster wheel of “I’ll relax once I get shit done” you’re like a crackfiend  who is gonna quit once they take one more hit.

Kill ambition. You’ll live longer, be happier, and will ultimately be successful.

And one day, someone will ask, “So what’s the secret to your success?” And you’ll respond, “I didn’t know there was one.” 

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