Don’t complain about the game. Change the game you’re playing.

In the annals of self-help and fluffy business books, this idea is nothing new. But it seems to bear repeating, anyway:

So if you wanted to change this business model of orifices, as Jobs described it, would you play it safe, as the Nokias and Motorolas of this industry have been doing for many years, or rewrite some of the key rules, from pricing to UIs, as Apple has done with the iPhone?

Apple’s iPhone dilemma: Wall Street or customers?

As above, so below. As in business, so in life. Because business is life, too. And so is design. And product design. And business. These things are all the same thing.

A Bedtime Story for Pig-headed People

There was once a little girl who figured out something important about the world at a very young age.

The thing she learned was not without its costs.

When the girl was little, she was already too stubborn and willful to listen to the kids who told her “you can’t.” But she was too young and naive to notice the subtler approaches for what they were, and she usually listened to grown-ups.

Time passed, and the little girl grew up. Sometimes she failed, but mostly she succeeded. Above all, she learned things. She learned, for example, through several harrowing adventures, why the other kids really disliked her and why the other teachers made her take spelling tests even when she always got all of the words right on the “pre-test” before studying.

She learned that adults are almost always just as confused as kids, only bigger and with more destructive toys. She came to understand that the “real world” is basically a game filled with people playing along. Then she spent the next decade or so refusing to play by the rules, and remaking every “game” she played in.

Every step of the way, she had people telling her she couldn’t (or at least shouldn’t) do things the way she was doing them. Sometimes they were well-meaning at heart (or at least, that’s what they told themselves), other times they were just petty.

Two kinds of argyle

They said You can’t make jokes in your company brochure. Don’t say ‘may contain nuts.’ Nobody will hire you. Act like a professional.[1]

And You can’t not graduate high school. You’ll never go to college. You’ll never earn any money. You’ll end up doing sales or something. Plus you’ll always regret missing your prom.[2]

And There’s no room for another Mac web site. Seriously. You won’t get any readers.[3]

But while they shook their heads, wrung their hands and sighed (and tried to force their will on her), she just kept on doing what she was doing. And sometimes she failed, but mostly she succeeded. Above all, she learned things.

She’s not old enough to qualify for “happily ever after” yet, but she’s surprisingly happy and successful. And all the time, people wonder how she does it, assuming that she has some kind of magic that they don’t have.

She spends a lot of time trying to explain that she’s not magical at all, just pig-headed.

This is Not Actually a Bedtime Story

So the girl in the story was me. Duh. No, I never thought I’d fool you, I just wanted to run with the bedtime story concept. And then contradict myself in the next section. I never claimed to be predictable.

I’m not even predictable to myself. This article is not going the way I expected, by way of example. Heck, I can’t even entirely understand my past: I’m not entirely sure, looking back at my life, how I turned into the person I am. It’s a bit of a mystery to me in some ways, and an open book in others. Hindsight is not 20/20—that’s a lie. It’s more like 20/50. Maybe 20/40, at best.

But I can tell you one sure thing about all the naysayers you and I met and meet and will meet in life:

Those people are almost always wrong.

This is where my apparent navelgazing ties back into the beginning of this essay. The article I quoted was talking about changing the rules of the game, rather than playing the game everyone else is playing. And the article was also talking, indirectly, about these people.

The people who insist on telling you that you can’t are often actually saying I can’t. For whatever reason: fear, self-doubt, teachers, managers or parents who quash them (whom they let squash them), a complete lack of belief in their own power, a kind of sublimated jealousy and rage because you succeed where, of course, they “can’t.”

Castle window

It’s true that this stuff sometimes comes straight from the mouths of people who care (or purport to care) about you, your business, your product, your career, whatever. They may think they’re trying to do right by you, but I’ve found that the people who say such things are afraid of life… not just for themselves, but for you, too. They’re afraid you might fail because they’re so horribly afraid of failing. They’re afraid that you might succeed, too, because what kind of light would that cast on their failure to do exactly what you’re doing right?

Of course you might fail.

Big deal.

This thing’s not over til the fat lady sings—and your corporeal vessel is rotting in a casket somewhere. Until then, it’s all up in the air and nothing is final. You can’t get through life without screwing up spectacularly, anyway, so you might as well choose opportunities to screw up awesomely. Awesome screw-ups make better stories than mediocre screw-ups. Awesome screw-ups are rich goldmines of good old-fashioned learned-my-lessons and opportunity.


Of course, you might succeed instead.

If you’ve taken the time and effort, in fact, it’s quite possible that your instincts are right. Things can be made to work. It takes sweat and blood and passion and the willingness to adjust your course and dedication and hope and repetition and self-honesty and all sorts of other touchy-feely things, but it can often be done, one way or another.

But don’t worry, success won’t shake off all the naysayers. (It might mean your employers, teachers, or parents back off, though. But then again, maybe not.) They’ll stick with you to the bloody (or champagney) end. If you succeed, they’ll write it off as luck. If you fail, they’ll take great glee in poking you with sticks and I told you so‘s. They’ll even invent failures according to some weird inverted logic, just so they can feel like they’re scoring points on you. The better your apparent success, the more self-congratulatory they become.

Think of them as remora fish: they’ll be with you forever, but totally forgettable. No, better yet—think of them as a barometer. If somebody, somewhere, isn’t screaming that you are going to fail, you must not be trying very hard.

The Pithiest Lesson

It all comes down to this: Some people make themselves into doers. The rest make themselves into what they probably call realists, cynics, or John C Dvorak—but often, in reality, they’re merely complainers.

That’s just the way life is.

But you get to choose which you are, which you become. And you can change, if you want.

The Burden of Proof (and Learning From Your Mistakes)

I’m all for going anti-establishment (but not for the word “anti-disestablishmentarianism,” because that’s just crazy). Don’t let the naysayers convince you that they know better than you… usually.

I don’t mean to say that you can literally do anything. Of course we’re all bound by reality. (Then again, it seems that every century discovers that reality is not what we thought it was.)

And I don’t mean that every idea that pops into your head is worth fighting for to the bitter end. Lots of ideas are bad. You have to learn to discriminate them for yourself… and that, in my opinion, comes only through playing full-contact life.

And for that matter, not all advice is bad. I also don’t mean you should ignore everybody who ever says anything negative about your plans. Sometimes they’re right. It depends on who they are and how they say it. It also depends on your idea and how much legwork you’ve done to satisfy yourself that it’s a good one.

There are things you can do to increase your odds.

Fortune cookie: If you can't be a sun, don't be a cloud

When you’re developing your thing, look for cues from “the real world” to see if it makes sense. Hit the stacks. Stretch your mind—and your research skills. Have people succeeded doing your kind of thing, in your field or in some other field? (Winning strategies to learn from often appear in weird places.) Where’s the precedence?

And if you’re getting advice, look at the person who’s giving it (which would obviously include me, paradoxically). What have they done in life? Are they high-achieving individuals, by their own measure? (This might mean an utterly relaxed, non-rich, non-lauded, non-traditional lifestyle… if that’s what they wanted.) Do they have any real reason to claim to know what they’re talking about? Are they—god forbid one dare to ask—happy?

If no, then they’re probably not the people you want to listen to. After all, who takes his car to the mechanic whose own car never runs?

Case in point: There may not be a direct precedence for the iPhone since nobody has done it with phones, but boy have other companies made a killing designing closed systems that sell through user delight rather than a long list of features. (Including Apple, a few years before. Big “duh” on that one. Analysts—complainers, not doers—will never learn when to stop pooping on others’ success, will they?)

Help Yourself Succeed

Balance is not only good, it’s the natural state of the universe. If the Seesaw of Gumption and Knowledge is vacant at one end, you will never get to go up and down. You can’t expect to succeed just because you’re doing your own thing. You have to work for it. You don’t win just by being contrary.

If your idea is, say, to drop out of high school because it’s killing you slowly with its embrace, teach yourself, start a business and make yourself semi-famous in your field through teaching people stuff—and, say, you researched it, and have books and reasoning to back you up—well, more power to you. It worked for me.

If your thing is to do business with personality, sustainability, or really great customer service, go for it. If you want to be multidisciplinarian in a weird way, please don’t hesitate. If you want to opt out of the part of our society that says you have to have a 9-to-5 job, house, car, spouse and 2.54 kids to be happy, we’ll be delighted to welcome you. If you want to live your life differently, define everything you do with a given purpose, invent something new, build something radical… I have two words for you: rock on.

Do the work. Then do your thing.


Other people will tell you different, but screw ’em. People like that don’t invent the iPhone. People like that don’t change other people’s lives for the better. People like that often don’t do much, period. And they’re very often not happy.

Instead, go and play in a touring band while being a consultant. Teach programming with comics. Form an entire business around helping companies understand something nobody even cared about a few years ago in a country that’s not even your homeland. Make art out of math. Revive the tradition of musical vagabondery. Turn a squatted building into a grassroots center for culture and art. Go from knowing nothing about photography to being truly kickass in 6 months. Run for president. Change graffiti from vandalism to art form. Keep building and loving something that everyone claimed was a failure before it even started.

Approach serious topics with humor. Enter a crowded market. Do things you’re uncomfortable with. Zig where your competitors zag. Write everything with personal pronouns, stories, and metaphors. Take things away instead of adding. Use funny colors. Redesign. Move. Do business by your principles first, always. Do what you feel in your gut is right.



Remember, Lest Ye Morph into a Fox “News” Show Host…

Just remember to back up your pigheadedness with research and hard work. Ignorance and laziness combined with pigheadedness turn you into… well… one of those other people.

Talk to me.

I want to hear your voices. Tell me your stories.


[1] For a while I was a hyper-‘professional’, obnoxious little businessperson—when I started doing consulting as a young teenager. Then I realized I hated it, and that the people who kept pushing me in that direction weren’t exactly paragons of success and happiness. Then I named my company “infocookie,” met clients in t-shirts and jeans, made jokes in the brochure and brought them cookies baked with my favorite recipe. And then I grew up even more and designed this. Yeah.

[2] Yes, for those who haven’t gotten the memo: I don’t have a high school diploma. Not even a GED. Oh, my life has been one long disappointment since then! If only I had listened to the guidance counselor! (Mr. Johnson, for the record: I was right about everything I said to you.)

[3] I’ve lived a strange life. I ran a very successful Mac-oriented “news and opinion” site from 1999 to 2003 or so (as a kid). My original idea was to write with personality, and explain tech for lay audiences. The income from the ads helped me move out of my mother’s house at a young age and shore up the dry times in my consulting biz.

No Comments

  1. Greg says:

    Hey, that’s Powell’s!

    In regards to your point, the other half of conventional failure not being as scary as it seems is that conventional success is not nealry as transforming as it seems.

    The older I get and the more experience I have the more I learn this: on the other side of each success, it’s always just somebody’s normal life. As I meet people who’ve succeeded in ways I’ve fantasized about (and make a few bits of progress that way myself), I’m always amazed at how much they just spend their days confronting a new set of mundane problems, and how much their happiness (or not) is determined by their own mindset and therefore unchanged by their change in circumstances. As someone smarter than me once said, our reward for solving our problems is not paradise, flowers, fame and fortune, or the singularity, but, hopefully, if we’re lucky, a better, more interesting set of problems.

  2. Neil Wilson says:

    It’s nice to know there are others out there who feel the need, nay compulsion, to paddle their canoe upstream.

    Thanks for sharing that with us.

  3. Manik says:

    Energetic Article!

    Reminded me of Mark Twain’s quote: Not all horses were born equal; some were born to win!

  4. Jeff says:

    The real secret is that Amy makes kick ass cookies.

  5. Justin says:

    You’ve managed to put how I’ve been looking at my own life into a very pretty set of words! I made all the "mistakes" I should normally avoid:

    • Married right out of High School.
    • Quit my manual-labor job with benefits to "do websites".
    • Dropped out of college because it was keeping me from getting real work done.
    • Left my cubicle in a big company to do it on my own.

    I’m now making a decent living doing what I love, from home, still married to my wonderful wife, enjoying our brand new baby boy. I’ve never been happier.

  6. Bira says:

    My life went perfectly according to "The Plan" until about three years after I graduated college. I was in a medium-sized software development firm with Big Enterprisey plans in its head. They said every employee was highly valued, but of course they would say that. It didn’t take Sherlock Holmes’ deductive prowess to see that, when it came right down to it, programmers were seen as cogs in the machine, trained monkeys. You weren’t really in a valued position until you got to the point where you told programmers what to do instead of doing it yourself.

    After three years of this, during the second Big Enterprisey J2EE project for the same Big Enterprisey client, I complained I was getting a little unmotivated, you know? And since I work harder on stuff that I like, wasn’t there anything cooler I could do? It would make everyone happier.

    They say they’d think about it, and after a while I was told very forcefully that yes, the work was boring, and yes, it would be boring for a long time to come, and several other times after that. And I had to put up with it, because they were one of the better companies to work for, and out there was worse. So grow up already, will ya, little monkey?

    So I jumped ship, and turned my hobby of doing little programming projects for foreign customers into a full-time occupation. I now work the same 40 hours a week I did before, but with tools I like more (Ruby and Rails rather than 8-year old Java stacks), in a cooler project, and for people who respect me more (and whom I in turn respect more). All this without leaving the confort of my home :).

  7. Liana says:

    Hi Amy,

    I love your blog. Forwarded this one everywhere. And couldn’t resist commenting this time.

    In college, I was a computer science and theatre major. Everyone thought I was crazy. As an application consultant in my 20s, I was able to fund my professional acting career in New York City for many years. People thought I was just lucky.

    Now in my mid 30s I’m married and pregnant while working as a senior software engineer and taking classes at Harvard Univ in the evenings. People thought I’d fail. My husband is a hunky dream, my baby is healthy, my bosses love me and I think I’ve got a B average right now.

    Now people expect me to quit my job after the baby is born. Instead, I’m working with others to restructure how development is done at the Berkman Center where I work so when I get back from maternity leave I can help lead technical innovation in our organization.

    I’m six months pregnant now and on Saturday I have a gig with the Victorian Carolers to sing at the Natick Mall.

    "You can’t". Ha! It ain’t even worth it unless someone says, "you can’t"!

  8. Erik Kastner says:

    I can’t say how lucky I am to have you in my life as a friend and some-time co-conspirator in web junk.

    😀 ::hug::

    p.s. I spelled "conspirator" right the first time!

  9. bq. "Yes, for those who haven’t gotten the memo: I don’t have a high school diploma. Not even a GED."

    Same here… I left high school the week I turned 17, which is 11 years ago next week.

    I always chuckle to myself when people ask me where I got my degree. No school debt… just a passion to teach myself things and try my best to not fail at new things.

  10. Frédéric says:

    Hello Amy,

    This kind of post is one of the reasons I love your blog. Always refreshing.

    I’m going to print this post and display it (translated) in my office… If you allow me.

    See you

  11. Peter says:

    Go Amy !!

  12. I have found that after one or two big successes (the first CD-ROM technical manual pub sys) and present challenges (moving my analyst business to the Silly clone valley), that the following is true:

    The more emphatically someone says in response to your inventive idea, "That is the dumbest, stupidest idea I have ever heard", and if they really punctuate by bending forward as they say, "stupid", I have found that you may have actually found a great idea.

    I have been shopping a business plan for a business that I am an expert in, but need liquidity to get the software done, even prototypes. I have been wasting time pitching this blue collar mobile dispatch plan to VC’s who are NOT interested.

    So, ideas and execution are everything. Amy, you are the greatest, I have been following you for years – keep up great work.

  13. Raymond Law says:

    Amy, you speak my mind!

    People often say things like "You can’t", "You shouldn’t", "You should", … are so scared of you succeeding. That will make them look like a loser. These people need to build their confidence on other people’s perception because they are not self confident. They try to destroy your self confidence as well. However, they may be of good or bad intention, consciously or subconsciously.

    The only thing matters is we recognize this and be able to filter out these naysayers and only allow genuine suggestions to our brain.

  14. Alex Hillman says:

    I read on the freshbooks blog recently that the thing that sets entrepreneurs apart is that we are too naive to see the obstacles in their way.

    I thought it was a great definition and aligned incredibly well with your thoughts in this post.

    Which, by the way, totally freaking rocked. And I’ll second Erik’s notion that we’re lucky to have someone as sharp and open as you in our circle of friends.

  15. Nice Post.. I’m getting a feeling that you are filling up the void left by Kathy Sierra 🙂

  16. Edin M says:

    Brilliant post!

    Your path resembles mine very closely. It is nice to see people out there who are brave enough to express their beliefs and follow their dreams…

    Your post made my day… thank you. 🙂

  17. Amy says:

    Nice to hear from all of you… (Erik and Alex: hugs 🙂

    I love hearing stories about people who beat the odds.

    @Greg, that’s also true, excellent point. No matter how big the success, you’re still you (and the others are still themselves). Every time I’ve gotten into some "exclusive club", it’s never turned out to be as exclusive or mystical as it seemed from the outside. In fact, I always kinda come away with the feeling: if people only saw how the sausage was made…

    @Jeff, heh. Thanks 🙂

    @Muthu, oh, I don’t think my feet are quite big enough to fill those shoes… but thank you, I’m definitely flattered.

    @Liana, @Justin, @Bira, thanks for sharing your stories. I think people in this world could always use some more inspiration to do things their own way.

  18. stephanie says:

    I love this. I am now signing "Wind Beneath My Wings" quite loudly (in my head, at least) in your honor.

  19. stephanie says:

    uh, make that "singing." ah hell, i’m both singing and signing.

  20. Dwayne Sudduth says:’re quite an inspiration (and I hope you sent your old guidance counselor your blog..).

    The education ‘system’ is a monumental failure–it’s at least 2 decades behind, and you (and many others) are living proof of that. While I’m not a developer (yet–working on that) I am a network geek–mostly self-taught, though I did take a couple of courses when I was downsized, mostly just to pass the time. I had a couple of years in college, mostly just having a good time, I certainly didn’t learn anything useful to my post-college life.

    Mucho Success to you, m’lady.

  21. Jose Espinal says:

    Excellent post really, it got to me to the point where it woke up all the dreams I had of being independent and innovative.

    Thanks Amy! U rock!

  22. Marcio says:

    Nice post. I guess I live far away from you, but we have almost the same problems. It´s kinda funny..

  23. Alain says:

    Today is my birthday, in four days a new year, in five I quit my job.

    Time for me to start clean and what a better time then the begining of a new year?

    I always wanted to have my own business, I am 31 now, if I dont start it now it is soon going to be much harder to do so.

    The problem is that I have very few people to cheer me toward that route. Job security and good salary seem to be an acceptable offset to boring and non chalenging job according to them.

    Your text isnt the thing that pushes me to leave my job, it is just a confirmation that I am not the only person to think that way.

    Time to upgrade my life.

  24. Eddie says:

    Great Post amy! Thats so long and so insightful..

    Thanks, Eddie

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