Originally written in December of 2011, the following quote from famous author and person-who-is-suddenly-quoted-about-everything Neil Gaiman is once again making the rounds online for the New Year:

I hope that in this year to come, you make mistakes.

Because if you are making mistakes, then you are making new things, trying new things, learning, living, pushing yourself, changing yourself, changing your world. You're doing things you've never done before, and more importantly, you're Doing Something.

So that's my wish for you, and all of us, and my wish for myself. Make New Mistakes. Make glorious, amazing mistakes. Make mistakes nobody's ever made before. Don't freeze, don't stop, don't worry that it isn't good enough, or it isn't perfect, whatever it is: art, or love, or work or family or life.

Whatever it is you're scared of doing, Do it. Make your mistakes, next year and forever.

This kind of thing has always struck me as dubious advice when applied to the Big Things in life, and it's always coming from people who are in a position – professional and financial – to weather quite easily the consequences of their mistakes. Sure, it's great advice if you've always wanted to learn how to paint but have been afraid to try. But the "Go for it! Follow your dreams!" line of argument is, for all but the people who live life suspended over a giant financial cushion, almost universally a terrible one.

We all have something we'd love to be doing with our lives that we are not. The reason we are not is because our societies demand that we make some money. That's why we all work at jobs we almost inevitably hate – because if it was fun they wouldn't have to pay people to do it (note the preponderance of unpaid internships in fields like media, fashion, and entertainment). To the extent that we like or enjoy our jobs, 99% of us would still quit tomorrow and do something more enjoyable if we suddenly found ourselves with millions of dollars.

There's nothing wrong with any of this. It's just life. We work because we have to, and we accept that we can't all be living our dreams. Why not? Because many of us have very silly and impractical dreams, hence the name. Your dream to open a little used book store in an adorable, hip neighborhood (with astronomical rents) might run contrary to the fact that you could not actually make money and support yourself with such a venture. Or maybe you just aren't the kind of person who has any talent for running a business. How much tolerance for poverty do you have? I mean, you can move to Hawaii and surf all day if that's what you've always wanted to do with your life and you don't mind being homeless. I don't suspect many of us are ready for those kinds of privations, though.

Earlier this year The Guardian (UK) ran a much-discussed story about the top five regrets given by the dying in hospice care. Number one was "I wish I'd had the courage to live a life true to myself, not the life others expected of me." This sentiment makes perfect sense from the perspective of an older, dying person reflecting on life, but it does precious little to provide the rest of us with guidance. What people mean when they engage in this sort of hindsight is, I wish I had made different choices and they had all worked out. In other words, I would have chosen differently assuming it would have led to XYZ ideal outcome. And how often do the choices we make in life really lead to the ideal outcome? Maybe Grandpa is regretful that he spent 50 years as an accountant (the kind of responsible career "others expect of us") when he had always wanted to open a restaurant. He certainly would have been happier had he opened that restaurant…provided it succeeded to his satisfaction. Had he opened the restaurant and it went bankrupt (as most do), ruined him financially, and his marriage failed under the strain, would he really have been happier as a result? Or would he be 80 years old in a state-run nursing home for the poor (instead of in hospice) thinking, "I wish I had listened to Mom and stuck with accounting"?

Often we are afraid of making certain choices for the very sound and excellent reason that the odds of failure are exceptionally high and its consequences severe. You know you could quit your job, cash in the 401(k), and do whatever zany thing it is that you'd like to do with your life. You also know that you're likely to end up dead broke and facing a bleak future for you and your family if you do that. Yes, you might succeed and you'll be thrilled that you took the risk. What might happen rarely balances out what is likely to happen, though, and the classic Survivor's Bias ensures that we only hear about the Neil Gaimans who quit their job to write novels, not the thousands of others who did as he did and failed spectacularly.