21 Lessons in 27 Years pink candles graphic

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’s 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.

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