21 Lessons Learned from 16 Years of Hustling


Today I turned 27. For whatever reason, this feels like an important birthday. And it has been one helluva year, with huge changes (good and bad) that I’m still only now coming to terms with.

While reflecting (and all that touchy-feely jazz), I realized something: Just how long I’ve been at this, the project of my life, the Project of Me. I’ve been hustling since I was 11, when I got my first freelance gig and realized there was a whole other world outside of middle school.

At 12, I hustled and scrimped and wheedled and bought my very first computer that was all my own, a deal I found on Usenet. At 14, I dropped out of high school to homeschool myself. At 15, I moved out of my abusive mother’s house and never looked back.

At 20, after years of unremarkable, dilletante-y freelancing, a pathetic and anxiety-producing (lack of) social life, and desperate, mindless clinginess, I got:

  • dumped & kicked out by my long-term boyfriend
  • scammed out of 3 months’ work by a pathological con artist
  • ran up a bunch of credit card debt as I ran completely out of money
  • caught a bad case of mono
  • got so sick I couldn’t work
  • had my car stolen (by my ex-boyfriend, no less)
  • nearly got sued by a client whose work I was too ill to complete

Yep, all in the span of about 6 months. I hit rock bottom, and there was nothing for it. So I got real and rebuilt my life. I changed just about everything… except my name and my sense of humor.

In short: I went on a completely life-altering Crusade of Amy. Nobody who knows me today would recognize the me of 7 years ago, if they hadn’t watched it happen. I’m still a work in progress, but I have learned oh so very, very much. (All the hard way.)

So, for those of you who love list posts, and who love a take-no-prisoners kind of philosophy, and for those of you who are in the midst of great change yourselves, I present to you: A big old grab bag of the most important lessons I’ve learned in my entire, eventful, dramatic 27 years on earth and 16 years of intentional hustling (both personal and professional).

These are numbered for ease of use, but not arranged in any particular order.

21. Be yourself on your own terms

Don’t compare yourself to other people. No, really, I mean it. Don’t identify with any labels, or traits, or habits, or tools, or things you do — and take careful note when you find yourself doing so automatically, anyway.

It took me years to embrace being a woman. You know why? Because I believed in the label, despite hating it. I believed that “woman” actually meant something… and then I’d look around at all the girls and women I knew, and the way they behaved and what they valued, and I’d feel embarrassed to be “one of them”. Or, if not embarrassed, just terribly out of place, because I couldn’t identify with them or understand them at all.

But you know what? Turns out the label doesn’t mean a damn thing. There is no such thing as Women, The Group. It’s just a bunch of people who have the same anatomy (mostly) and some shared traits (sometimes). By buying into the label, I was not only alienating myself, but insulting & denigrating other women for not living up to my idea of what it should mean. What a total ego trip!

So now, every time I see some kind of “holy war” rage on the internet (whether it’s about gender, politics, industry acronyms, or programming styles), or a rift form in a real life community, I thank my lucky stars that I’ve given up the job of defining & judging the world.

(It also took me years to get over the idea that I ought to be Serious Business. That the right thing to do was to Think Serious Thoughts, Do Serious Work, and Look the Part. That, because I was so smart, it was embarrassing and wrong to love silly music, be loud and boisterous, to wear flamboyant colors and draw attention to myself… Needless to say, I’ve got green hair. And I’m wearing candy-striped socks and a neon yellow hoodie right now.)

20. Everyone can change, but almost no one ever does

Be an exception. Become a student of life and a student of change. Journal. Take notes. Analyze what you do that achieves what you want, and what you do that doesn’t, and figure out how to change the latter into the former.

You only get one life. Make it count.

19. Admit it: the problem is probably you

And if it isn’t, you should claim it anyway, cuz nobody makes progress by blaming others. The path of blame leaves you with no further action except to sit on your butt and share your woeful tidings. Taking responsibility (and blame) for yourself, on the other hand, gives you a path to becoming a more excellent individual.

Even if it really was somebody else’s fault, and there was absolutely nothing you could have done to change the outcome that time, you still win. Because you’ll be stronger, better, faster, smarter.

18. Be your own harshest critic… but only with love

It’s rare that anyone will pay enough attention to anything — a book, a poem, an album, a painting, a piece of software — to truly understand what went into it, and what didn’t. You, on the other hand, as a creator, know. You know when you’re phoning it in. You know when you cut corners. You know when you didn’t do enough prep work or spend enough time on it. You may be the only person who will ever know. So you have to call yourself on your own shit (but with love).

Don’t rip on your work or yourself, just tell yourself, “C’mon now. That may be pretty good, but you know you could do better. Here’s how.”

17. Make no room for whiners, users, or vampires

Imagine that you only have so much energy for life, and that there are two types of people: 1. people who add energy to your life, and 2. people who suck it up or waste it. Do your very best to only associate with people in the first category. Haters, nonconstructive critics, attention whores, apathetic losers, chronically needy people, sycophants, and toadies are all drains on your energy bank. Get rid of them.

16. Don’t make excuses for people

Make it a goal to not become an obstacle to growth in the lives of others. If people you love (or even just like) fuck up, don’t make excuses for them. Treat them like an adult, and act as if you assume, at all times, that they are responsible for their own choices and their own behavior.

Hold yourself to a higher standard (see Lesson #19) and model productive, growth-oriented thinking for everyone else.

15. Laugh at yourself first

You can’t be blackmailed by something you admit publicly — and neither will laughter hurt you if you start it. Bullies and haters rely on cringing fear, and secrecy. So abolish those things. Laugh at yourself first, and the bullies will have to sniff elsewhere for their kicks.

Plus, life’s just more fun this way.

14. Be what you want to have, and do it first

To have friends, be a friend. To gain love, be loving. To gain others’ trust, be trustworthy and trusting. To connect with people who will create energy in your life, learn how to create energy in others’ lives. To laugh, learn to make others laugh. To hear others’ experiences, share yours.

Don’t get caught waiting for somebody else to make the first move, because that moment may never come.

13. Get real about what love means

Deep down, we all wanted to be adored and cherished for exactly who we are, right now. And fuck anyone who tries to tell us otherwise. But that is the thinking of a child — and we are adults, so we know, however deep down, that to have the love we want, we must earn it.

True love (platonic and romantic) is about opening, and growing, and thinking of others. And it is the best reason to strive to be a better person.

12. Be honest about what you really want in life.

Don’t steal others’ goals (money, beach bum lifestyle, dreamy hobbies) out of laziness. You not only won’t get what you really want, you’ll never even have the drive you’d need to achieve the stolen goal, either. And that means you’ll get nothing but half-assed effort and full-assed disappointment. So get real about what you truly want in life. Take the time to figure it out. When you figure it out… don’t deny what you truly crave, no matter how much you think you shouldn’t want it. The heart wants what the heart wants, and chances are, your heart knows better than your brain.

11. Always admit when you’re not giving your best effort…

And when your best effort doesn’t work, redouble your efforts, and quadruple if necessary. (Not just working harder and longer, but trying all the different ways and angles you can.)

10. …but know when to quit, without regrets and without looking back

When you’re doing your absolute best, but you’re making no headway for a good long while, cut your losses without regrets & don’t look back (except to learn from it).

Some problems can’t be solved by working harder. A few can’t even be solved by working smarter. (Especially the type of problems where you have to convince someone else to change — when in doubt, see Lesson #20.) There’s something to be said for knowing when to quit.

(These two lessons have been especially meaningful for me over the past 12 months, when I closed a partnership that wasn’t ever going to work (despite trying many different approaches), decided to move back to the US for my own happiness (despite trying all sorts of ways to make a happy life here in Austria, for nearly 3 years), and decided to have surgery to help me correct a health problem I “could” but knew I never would be able to fix on my own.)

9. Expect the best of everyone, but always believe the evidence

Be trusting by default (except when it comes to contracts and negotiations). But take note when a person shows or tells you what they’re really like. I don’t mean when a person makes a mistake. Everybody slips up once in a while, does something that they regret (and that makes others cringe).

But when a person tells you up front what they’re like (“I’m kind of a jerk,” “I’m not interested in anything serious”) — or when they show meanspiritedness, hatefulness, cowardice, dishonesty, apathy, or a tendency to control or use others more than a couple times — take note. Take their behavior at face value and believe it (and especially don’t make excuses for them — Lesson #16 in action).

Corollary: the more a person talks about how great, honest, giving, etc., he or she is, the greater the chance they’re anything but.

8. Stop waiting for an invitation

Cuz it’s never gonna come. You’re never going to receive an invitation to greatness, or even pleasant mediocrity.

Everyone on this planet is self-absorbed. Too wrapped up in their own lives to have any energy to devote to worrying about yours. Nobody will care more about your life and your achievements than you will. Nobody knows more about what you can really accomplish. Nobody is going to invite you to do your best work, do something really awesome, or to change the world. Nobody but you.

So get on it.

7. When it comes to business, always know your power ratio

You need to know when “they” need you more than you need them. Figure it out and then make your decisions accordingly. (And “business” includes regular old employment.) If you’re in a business arrangement with somebody, and you’re getting a crappy deal, you have only yourself to blame.

6. Everything is negotiable, so negotiate.

Haggling and negotiating can’t physically hurt you, so why let the fear stop you from doing it? Bonus: (if you’re any good) chances are that your boss or your clients need you more than you need them. Again, nobody will advocate for you more than you will, so get on it. And if you’re scared of negotiating, pick up a couple books and then create a practice program for yourself.

That’s how I managed to negotiate a 4-day work week (of 8-hour days) at the age of 22 at my second, staid, semi-corporate job… and many other lucrative deals since.

5. Ask

Every job I’ve ever had, I got by asking for it. Yep, that’s right, I didn’t apply for a job listing — I asked someone in the company, specifically, if they had (or would create) a place for me. And I told them why they ought to.

Again, everyone is self-absorbed — they don’t look at you and think, “Gee, I wonder if she could help us out?” No. You gotta take initiative and plant that idea yourself.

Asking works, and rejection won’t kill you. Try it.

4. Unless you’re a humongous ego, you can always charge more

True fact. The smarter and more thoughtful people just about always undercharge. This is out of an absurd, misplaced sense of guilt. It helps no one, and hurts you (and sometimes even your customer/employer), so quit it.

Educate yourself on value and price accordingly.

3. Everything is a skill

Can you learn to be funny? Can you learn to be outgoing? Can you learn to give inspiring talks? Can you learn how to sell? Can you learn to be a great kisser, or to be one of those magnetic people who draws interest? Can you learn to be a person other people love to be around? Most people don’t think so. But I can tell you for a fact, the answer is “YES!” You can learn all of these things and more. How do I know?

Well, until I got totally fed up with my tiny, sad, insular life at the age of 19, I was a wallflower with social anxiety who always managed to interrupt at the wrong time and who made loopy jokes that nobody ever got, who talked way too much (to the point of awkwardness) to compensate. I spent all my time with people trying to decide what to say, and so I was a terrible listener. I butted in. I forgot people’s names. I didn’t realize when I was making one horrible faux pas after another, because my working understanding of people was so poor. I was terrified of rejection, of every type. I literally hyperventilated my way through my first serious public talk.

Now, everyone thinks I’m a natural, and naturally hilarious, extrovert and gifted speaker. That’s all because they have no way of knowing how hard I sweated it out to get there. Thanks to years of applied effort, I now understand people (perhaps too well), am no longer held captive by my fear of rejection. And I have it on good authority that many consider me to be an excellent listener, too. (I even got to be great at names — but sadly, that’s something that my chronic illness wiped out. Sigh.)

You, too, can create an “exercise” program and “obstacle” course for any “natural” skill you want. There are books on everything (even kissing). If you remain bad at something you want, get real and admit it’s cuz you don’t want to put in the effort.

2. It’s never about you

Read something on the internet and get all offended cuz the author dissed your favorite life choice/programming language/company/90s band/vampire novel? It’s not about you. Somebody thought you weren’t worth their time, attention, kindness, or money? Not about you. Somebody slammed you or you work? It definitely wasn’t about you. Somebody made a sexist, racist, ageist, weightist, whateverist comment to you? No way it was about you.

Somebody tried to screw you over, to manipulate you, lie to you, hurt you? It’s not about you.

Remember how I said everybody is self-absorbed pretty much all of the time? It’s the god’s honest truth. We’re all trapped in our own little darkness behind the eyes, and so just about everything we do is about us. Some need we have, some problem or desire or bias of ours. We so rarely even imagine the other people as being fully functional beings like us… we tend to look at them as paper cutouts that walk and talk. And who pays attention to paper cutouts?

So when somebody does something that pisses you off or hurts you, remember: it’s not about you. They’re probably barely even thinking of you. Don’t wonder, “What does this say about meeee?” Because the answer will almost always be, “Nothing at all.” Ask, instead, what it says about them. (And then analyze your own actions the same way. Fight the animated-cut-out syndrome. Remember: there are real people in there.)

And lastly, but not leastly…

1. Memento Mori

Finally, my grim but beautiful secret, one so important that I plan to make it the theme of my very first tattoo:

Memento Mori. Remember EVERY DAY that you’re going to die.

Look at your life as it is currently, and ask yourself, “How would I feel about myself on my deathbed if I lived out another 40, 50, 60 years exactly like this?”. Do an Ivan Ilyich on yourself. Then, if the vision horrifies you, figure out what you need to change, and do it.

When you think about your eventual death, everything changes. The things that seem “little” on a weekly or monthly basis can suddenly become critical — and things that seem catastrophic right now can look trivial.

Maybe today you’re spending too much time on work that doesn’t feel worthwhile to you. Maybe you are working with people you don’t hate, but you don’t really like either. Maybe you’re living in a place that doesn’t feed your soul, and telling yourself you’re doing it “just for now, for the money/family/convenience/whatever.” Maybe you don’t spend enough time with people who lift you up, people you love. Maybe you’re in denial, imagining that if you just tough it out a little longer, your real life will begin.

Today those may not seem so important, but if you stretch that out over the rest of your life? Compounded by the fact that nobody’s gonna do a course correct for you? Whoa nelly.

On the flip side: Bummed today cuz you quarreled with someone you love over something trivial? Or because you can’t afford something fancy you want? Or because you owe taxes or student loans? Or you think somebody on the internet is wrong (or angry at you)? Well. These things shall pass, you know they will.

And if these little nagging problems truly dominate your life, use your deathbed fantasy to realize how little you will care about them in the future.

Take the teeth out of death. Use it as a lens to improve your life.


The list goes on, but I’m tapped out (and you probably are too). So, tell me: what lessons have I missed that you’ve learned the hard way?

Get my next bootstrappy gettin-shit-done essay delivered straight to your inbox. (And be first in line for tickets & discounts.) Drop your name in the box!


  1. Rainer Blessing

    Wow, I didn’t know there were that many books about kissing :D

  2. Jamie Lawrence

    Embrace the pain — use it to motivate you, make it something you can push against, fight with. For me, this was physical pain which is definitely the easier. I’m still trying to make it work for emotional pain. But turn that negative pain into a positive force.

    How you conduct yourself the only constant that matters — There are things which happen in our lives which are totally beyond our control. Accept that, accept that we can’t change them but don’t let it change you. Viktor Frankl’s “Man’s Search for Meaning” was a hugely influential book for me.

    Thanks for introducing me tothe phrase “Memento Mori” because that’s my top lesson: when you leave the house in the morning, you might not come back; when you fall asleep, you might not wake up.

    • Amy

      Thanks, Jamie! I like your addition. Same goes for fear, shame, embarrassment, too. They’re only useful if it’s teaching you something (or actually saving you), which is so rarely the truth…

  3. Dave Churchville

    Excellent post – very nicely done Amy.

    As my former mentor Christine Comaford likes to say, it’s all an illusion anyway, so you may as well pick one that’s empowering.

    Took me much longer than 27 years to figure out that’s it’s never about you, and that truly taking responsibility is the only way to get out of the paralyzing blame and frustration with others game. Still working on that one.

    • Amy

      Christine sounds like a wise woman, Dave!

      As for deeply knowing it’s not about you… that is one of the hardest ones. Even I still forget it sometimes.

    • Amy

      Thanks, Nils! And really, I’m not 27 inside. The whole “quitting high school and moving out at 15” thing means I feel more like I’m 40.

  4. Rishi

    This list was really nice. Each one is helpful on living a happier life. Thanks for writing it up and Happy Birthday!

  5. Andrew Frustburger

    Happy Birthday !

    I’m twice your age and with less than half your wisdom. Thank you for sharing you’ve shone a light into a dark corner from which I was plotting my next move. Godspeed!

  6. Liz

    Bravo, as always!!

    I am so happy I found your blog several years ago, Amy. It has definitely been one of the gems on the net that has been consistently awesome, from code to biz knowledge to general life advice and everything in between. Thanks so much for offering your words of wisdom :)

  7. Elia Freedman

    I will add one: do the right thing whether others are or not. This could be a big thing like being honest when something unexpected falls in your lap like a company giving you a refund you didn’t deserve. Or this could be a small thing like smiling or saying hi even when others don’t.

    Happy birthday! Elia

  8. Satya J

    Dear Amy,

    I really like the post.

    I felt all the points which you have mentioned are some where hidden in my heart. Your categorization of points ..is too good.

    Happpy B’Day.

    • Amy

      Thanks, Satya! I’ve been thinking & writing about these lessons (in my private journals) for so long… wasn’t sure anyone would like this post but now I’m glad I made it public :)

    • Amy

      That’s certainly the one that’s most important to me right now, since Thomas & I have been attacked by a bunch of haters lately… it’s so hard to not get involved, so I need a reminder myself! :)

      • Amy

        Haha, Linda, I was wondering if you were having a “Boy Named Sue” situation :) (BTW, the picture is from your email address on gravatar.com — using the same email addy as your man? That’ll do it… you can set up another email address for yourself and your own pic :)

  9. Nash

    Find your secret to life. My secret to life is to: have a good time. Find yours.

  10. Peter Jennings

    Hi Amy, a really great post, thanks! There’s a lot to digest – I’m sure I’ll be coming back to it a lot in the next few days/weeks.

  11. Claire Tompkins

    Wow, Amy, there’s so much greatness in here I can’t even pick out a favorite to quote. I’m inspired. Especially inspired to get out there and ASK. Thank you. And happy birthday!

  12. Ryan

    I would add to #4: Don’t undervalue your self-worth, even in your own mind. It’ll never profit you.

  13. Belinda

    Love this post! Shared it on FB. Your list is made of awesome and wisdom, 2 two bestest things. Ok, thats a lie, Awesome and Cake are the two bestest things, but fr the purpose of this comment, we’ll replace cake with wisdom.

  14. Dayo ajayi

    You inspire me, Amy Hoy. This was an awesome post. Happy birthday!

  15. Nick Silva

    Happy birthday Amy, and thanks for this great post.This is a pretty comprehensive list, and I strive to do so many of these things, the only useful tool I’ve adopted lately is a little meditation practice.

    Imagine yourself; When you are wrapped up in yourself and struggling over small disappointing BS, it’s amazingly powerful to imagine watching yourself. Not judging, not participating in the BS. Just a little distance from the whirlwind in your head. I’ve caught myself doing this a lot lately, and I find it really helpful to calm my hyperactive imagination.

    All the best, and here’s to many more happy birthdays!

  16. Anthony


    I stumbled upon your site during a Google search. Fantastic blog. And Happy belated birthday.

  17. John Gallagher

    Such a brilliant post. I’m going through a difficult time work-wise right now and so many things on here are helpful. It’s tough to realise that I’m not good enough for the challenges that the work I’ve taken on present to me. So numbers 19 and 11 are really helpful – I need to focus on getting much, much better.

    Number 21 is also something I really struggle with. Comparing yourself to the classic heros of the Web 2.0 world is so unhelpful when you’re building your first, inevitably flawed, product. And, especially coming from you, it’s really helpful to hear.

    I really needed this post right now. Thankyou.

  18. Derek Jensen

    Amy, I’m in the process of rebuilding my life as well. Thankfully I have the support of college life and atmosphere to help me.

    I truly took this article to heart and it’s been copied and saved for future reference. Thank you!

  19. Dan

    Loved this. I’ll add one that I’ve just recently come to realize after beating myself up for several months, and one which should be remembered by all entrepreneurs- all people are different, and unless you are selling a commodity, no product can be all things to all of them. This is the very reason why entrepreneurship and capitalism work so well, and it is very much to your advantage.

    Launching a product is scary and exciting. But I can guarantee that no matter what you are selling, there will be a healthy contingent that says something like “eh, that’s kinda cool, but [insert large, established company] is already doing that.” Don’t believe it. At least not until you have thought long and hard about your value proposition and the customers to whom you are selling and explored it with them.

  20. Ben

    Your list changed my life. Its was everything that used to be a cloud in my head until you sorted it all out and put it into words. I’ve never related so much to a stranger in my life.

    The world needs people like you.

  21. Grace

    Dear Amy,

    I found this article through Stella Feyman’s newsletter. I loved it. I turned 27 this year too, and had the similar feelings with you. I’d like to translate this article into Chinese to share those lessons with more people, if you feel comfortable with it. Let me know.


  22. VL

    Amy, this article is amazing and all these lessons are just what I was looking for. I’m your newest fan. God bless!


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