Why the Ambitious Are the Least Likely to be Successful

by Alexander Heyne · 29 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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{ 26 comments… read them below or add one }

Praveen April 6, 2013 at 4:15 pm

That is cool a webpage with rank 1:). Although I disagree with you. Ambition has what made all the technology you are enjoying at the moment possible. Nikola Tesla, Edison, even Einstein was ambitious in his own way. Ambition (thinking big), and hard work is a powerful tool. Most people don’t need ambition to be moderately happy and pay their bills. Ambition should be used with simplicity to get things done, to extend yourselves and break through your self limiting beliefs and barriers. We all have barriers to get our desires accomplished and ambition can break through them. It will make you try things you have never done before and will make you the best in your career through sheer determination and one pointed meditative mind. It clearly shows you have a scatter mind, but still ambitious. Be one pointed and firm in your goals. And lastly Good Luck :)


Jamie April 29, 2013 at 3:37 pm

I couldn’t disagree with this article more. This sentence sent me into a rage:

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

How on earth did you come to this conclusion? You may have deluded yourself into believing that you’re ambitious. Ambition gives people passion and drive which makes all the difference versus someone who isn’t ambitious. This alone makes ambitious people more likely to succeed.


Alexander Heyne April 29, 2013 at 4:52 pm

Hi Jamie —

I came to that conclusion based on my experience with being an ambitious over-achiever my entire life, and continuing to be ambitious once I was starting a business. It didn’t help me much.

You don’t need ambition to show up everyday and do the work. You don’t need ambition to learn the skills necessary to succeed. You don’t need ambition to become a success or a millionaire or do incredible things.

I don’t think ambition gives people passion and drive. I think you’ve got it a bit backwards infact. Passion and drive give you ambition. In fact, I don’t see any way for ambition to give you drive and passion – seeing as ambition is entirely focused on ego – achievement. Passion and drive come from within. You can’t force yourself to be passionate. You can’t force yourself to be driven.

I think maybe you’re believing that ambition is going to guarantee you of your success — you might want to reconsider though, because it won’t necessarily. And there are many many other qualities much more inherent in “being successful” or an outward achiever than just being “ambitious.”

Hope that clarifies my point —


Jason August 14, 2013 at 12:13 pm

I disagree entirely. Thus far, everyone disagrees with you. You’re even disillusioned in your rebuttal to Jamie. You wrote a notable editorial and did a good job in a certain sense, but that is all it is, an ill-intelligent opinion.

Please give us your concise definition of success.


Alexander Heyne August 18, 2013 at 10:17 am

Hi Jason,

I really believe that ambition is a mental illness. You don’t need ambition to succeed. Ambition only works great when you’re forcing yourself to do shit you hate, because you value external goals you have set for yourself.

Practice – habits – is what leads to success. Sometimes ambition is present, sometimes it’s not.

What is my definition of success?

Doing what I want, when I want to, with whomever I want. Success varies highly from one person to the next – and I think it’s important to realize that rather than just accept some packaged definition of success that society gives.

… Otherwise you may realize you worked your entire life for stuff you didn’t care about. Then you get lost. Then you end up emailing me :D

– Alex


Billy October 6, 2013 at 6:12 pm

I think a critical point is that, you can start with ambition, and end up with a healthy regular schedule of work that satisfies not only external rewards we originally, and continue, to seek, but, to also find joy in work we find internal resistance to, from time to time. I’d argue that we all, at some point, find resistance to just about anything and everything we encounter. I think Stephen Pressfield’s, Do The Work (http://amzn.to/1hv841z), illustrates this nicely. I also feel we shouldn’t discount mindset, and from what perspective we move forward in going about our daily lives. I totally see your point, if you are stuck looking for external rewards over a long period of time, month after month, year after year, it is not sustainable. It’s the same reason why I don’t stay at my high paying corporate job only because of the benefits and great salary, that’s only a starting point. If it weren’t for the intrinsic rewards of not only developing software engineering skills, but also learning how larger organizations work, and improving my learning how to learn (e.g. SQ3R, mind mapping, visualization, etc), I don’t think I would have made it as far as I have in my 12 year professional coding career. I think a lot of the commenters haven’t taken a step back to see the bigger picture here — ambition can be very bad in the long term, if that is the sole fuel moving someone forward. He never said it served no purpose, only that, hopefully, over time, that initial ambition will be replaced with other, more sustainable experiences, such as: enjoyment, passion, resolve, genuine interest, learning, sense of meaning, personal development, reflection, etc.

Thank you for this post, if nothing else, I feel it has succeeded in compelling some to reflect more on their work and their approach in life, which is the point of this kind of article anyway, right?


Alexander Heyne October 24, 2013 at 4:21 pm

Billy – you get me 100%. Exactly what I was going after. And Steven Pressfield’s book is fantastic.


T.P. November 16, 2013 at 3:12 am

I agree entirely, but your thinking runs straight against mainstream culture. Selling this idea would be like raking water uphill. It’s one of those things that if it works for you it is your advantage, but anyone who doesn’t already know it wouldn’t want to believe it. Sadly, as we’ve seen, they’ll attack you for it. That’s what happens when you openly oppose the dominant culture.


Alexander Heyne December 2, 2013 at 7:15 pm

T.P. that’s why I’m happier and live a life 10x more exciting than people in the “mainstream culture.” Doing what everyone does just gives you what everyone else has. If you want the lifestyle you see your parents living… then just do what they did. If you don’t want that, don’t follow them.


Kiki Gard December 19, 2013 at 11:18 pm

It is much more fun reading arguments, I mean comments, based in semantics than being in one. I liked the article though. I love a self fulfilling prophecy, that’s probably why I agree. Call me a bit of a nihilist if this makes sense to you, but I agree with both side & I disagree. I don’t think ambition is inherently bad (as mentioned above, it depends on your definition), but I don’t see the point in having it. I does seem like a nice fairy tale though. Good on you Alexander Heyne.


Dwayne Lindsey March 16, 2014 at 11:47 am

To an extent you’re right, but I think you’re confusing ambition for obsession.

Being ambitious doesn’t necessitate that you lock yourself in a dungeon and forsake everything you love to get ahead. That’s maniacal.

Ambition just means that you’re able to get ‘in your zone’ when it counts, effectively balancing when it’s time to work hard and when it’s time to play.

Ambition is being able to moderate your work ethic, dedicate 100%, 50% of the time. You can be just as ‘in the moment’ when you work as when you are spending time off.

It’s not really fair to younger people, who may have grand aspirations, that all ambition is bad just because you burned yourself out. They should still dream big and work hard, but never forget to set a TIME for it instead of making it ALL of their waking hours.


Ems May 17, 2014 at 8:26 am

“Ambition is a mental illness”? This is the most ridiculous thing I’ve heard. Sounds to me like your terrified and deeply threatened by this very word.
Of course ambition leads to success it’s a key motivator in getting the best out of what we strive for in life, be it work, family etc. If you’re not the ambitious type or may have been disappointed with your efforts or how situations have gone for you in the past, that’s fine, but writing articles on the subject does not mean your views are correct. Chill out, not everyone in life needs to be highly ambitious but those who are I guarantee you AMBITION is the driving factor behind their determination, motivation and success! So to all you negative souls out there keep in mind, your life is what you make of it! Trust me with positivity and ambition in your life, contrast to what this article claims, you will in fact live a longer and more fruitful life.


ash May 28, 2014 at 8:14 pm

I am way too ambitious and obsessed about making good music. It’s gotten so bad that I just can’t make anything anymore. I can’t make myself even start on a new project. Lately I am slowly realizing that it’s because I am not enjoying the process anymore, I want to get to this high level but the things I have to do to get there don’t really interest me. The key to getting there is to enjoy making not so perfect music, and to learn to play not so great music. It’s a struggle.. Can’t believe I have to re-learn how to have fun making music. It’s such a great feeling once I do get in the zone tho


Alexander Heyne May 29, 2014 at 10:12 am

Totally Ash – noticed myself falling into this trap too. Why not take a week (or month) to just make music without any goals?


Billy Fisher June 1, 2014 at 6:47 pm

This reminds me of what an old college instructor once told me for writer’s block, which seems as applicable to any creative endeavor, and has served me very well in software development: do your worst work.

What I’ve noticed is that, when your do your worst work, you can actually achieve a sense of flow almost immediately; then the rest just falls into place, any edits to the final piece simply become a part of flow. I’ve also noticed this seems to help eliminate unnecessary expectations that only serve to slow down the creative process.

DK July 11, 2014 at 12:14 am

Funny since I both agree and disagree with you at the same time which makes me think your partly onto something :).
I totally agree you need to find things that feel like “play”..
I pretty much hate working for anyone else and that is my nature. I work really hard even when working for other people but no amount of hard work will make me like it or be happy.

Therefor i’m driven (ambitous) to be independent and work for myself -but that is only one part of the puzzle. You also need to find something that you can do and enjoy, so your work can flow.

So anyways I think it’s ok to be ambitious – but you need balance and you need to find something that makes you flow, which is what I think your saying here.


Stefan October 23, 2014 at 7:52 am

This article describes my life perfectly. I work fulltime, have a business on the side and trying to get another one going. I’m making money but I am constantly miserable. I feel that I cannot pull away from any of it because I have a wife and kids to support, so I just keep on sacrificing my own happiness to try and keep my family happy. I always have more to do and have less and less time to spend with my family which is totally messed up since I am doing all of this for them.


David October 25, 2014 at 3:43 am

Ambition gets people to where they want to be. I believe you may be thinking of obsessive rumination. Athletes envision winning their games. I am ambitious myself and although I’m not where I want to be, I’d be in a worse place if I wasnt. Stressing about success doesn’t help, but ambitiously envisioning it is how we got the light bulb today.


SLF November 6, 2014 at 12:01 am

I totally agree with EMS.
I think Alexander Heyne couldn’t achieve success in life or in business, that is why he claims ambition didn’t work for him. A piece of advice : try harder next time or better luck next year because being ambitious my friend makes you better in every single way


Alexander Heyne November 7, 2014 at 5:02 pm

Haha, it’s an awfully easy scapegoat isn’t it? To just say I’m some obese cosmic loser in my parent’s basement. Here’s the question (since I obviously found a chink in your armor): is it true?

– Alex


Norelief November 29, 2014 at 11:08 pm

How old are you? Because I am old enough to know that you are 100% correct. From bottom 1% to top 1%, from caring so deeply about changing the world for the better to feeling deeply bitter and cynical…I can attest that you are spot on.
Ambition is a crime against yourself and your family.
You are lucky to learn this lesson before it is too late, assuming you are 20 to 30 years younger than me!
Success has its perks, don’t get me wrong. And there is nothing wrong with hard work. It is the attitude itself, the seeking after lofty goals, that will kill your life. This is true even after you achieve those goals. My advice is 1-don’t try to change the world. You can’t. You will experience only pain. 2-work for your SELF and your FAMILY not some “ambition.” Screw ambition. Ambition sucks. Get money, then kick back and enjoy it. 3-shut out the voice of that person in your head that tells you you have a duty to use your super high IQ, super talent, or whatever. Screw it. See advice number 2.
Good luck.


Alexander Heyne January 13, 2015 at 2:09 pm

Hi Norelief –

I’m 27, but unfortunately ambitious enough that I’ve noticed it’s toxic to happiness. It’s a paradox: ambition will make you successful, but it’ll make you miserable – almost 100% of the time if you let it.

Great advice on ignoring the people saying you should do XYZ- there’s that old saying that the ultimate way to unhappiness is trying to be what everyone else says you should be – even if it’s your parents.


Kirk Michael Gravatt December 25, 2014 at 6:15 pm

I stopped having fun a long time ago. Always focused on money, and now I don’t know what I want to do.

It’s hard to rewire yourself.


Alexander Heyne December 31, 2014 at 12:42 pm

Kirk – I am 100% like you. It can be very difficult to remind yourself how to have fun again, it’s a constant struggle for the ambitious to re-program that.


P. March 16, 2015 at 6:05 pm

This article spoke directly to me. I am 27 myself, and have spent the greater portion of my life sitting in university libraries researching and studying my a** off. Like many others, I was told that education was my first priority, and that if I worked hard enough I would end up on top of the world. I have even been described as “intellectually ambitious” (which offended me slightly, as I wondered why I hadn’t been described as simply “intelligent” :/ ).

I did end up on top of the world, it was just in a way that I did not expect. Truth be told, I ended up sitting in the most beautiful libraries in some of the most affluent places in the world. That, I can say, was a wonderful experience. Towards the later part of my academic career I felt a sense of fulfillment and happiness. Yes, I had forced myself to research, write, and give presentations on subjects I had no interest in all along the way, but I had mastered the art of being an academic through long term dedication. I enjoyed the opportunities it offered, but, even after years of practice, the process itself was stressful, forced, and down right miserable for me.

And then, it was time to graduate.

I remember talking to my academic advisor about going further and getting a PhD. He asked “do you REALLY want to?”, I thought for a second and responded “being a student is all I know.” That, of course, was not the right answer. I was uprooted and thrown into the “real world” and have been in it now for two years.

I am not sure, but I think the current economic situation has much to do with how the past two years have played out. Getting degrees and good grades from impressive schools will get you a job interview, but not necessarily anything else. The number of years in a particular field is what is rewarded with titles and high salaries these days, not hard work. On top of that, still believing that hard work would lead to success, many employers have taken advantage of me. I have gone far beyond my call of duty (practically running businesses, writing the meat of media publications, making complex websites, etc) while being an unpaid intern, a $7.25 hourly paid employee, and a worker salaried below a living wage. All without the consideration of pay increase, even when I asked.

I have even been fired because of my ambition for a company’s success. I was told that I “did not fit in” and that I wanted the company to grow and achieve more than what the other employees could digest.

So, what now? What do I do? What do I ENJOY doing? Hell if I know. I just know that I need to be happy right now, live in the present, stop forcing things, listen to my heart rather than my head, and relax (which is difficult, with gigantic student loan payments coming due soon).

I also have to tell myself not to hate the universe for not paying up the success I gave up everything and worked hard to “win” for so long. It isn’t real, it is a cultural misconception, an empty promise, and I am trying every day to let it go.

Forget the semantic arguments of the other comments. I completely understand the gist of what you’re saying and agree with you whole-heartedly.


Alexander Heyne March 17, 2015 at 10:43 pm

Hey P – Great point, and I appreciate the raw honesty here.

Now the million dollar question – What next? What’s the next step for you then?



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