Bruce Sterling nails it: "This syndrome seem common among older-and-wiser famous over-achievers."
I am more guilty of screwing this up than most: if there is one single thing I could fix about myself, it would be to be better at systematizing when I say yes and when I say no. It's something I've been aware of since the 1990s, when I read Neal Stephenson's infamous, brilliant open letter/FAQ explaining why he's not answering your email.
And of course, I'm as guilty as anyone else of putting demands on other people's time, because the world is a collective effort, and the way we make stuff happen is by enlisting other people in our causes and projects. Every time I do it, I twitch with guilt at the idea that I'm adding to the burden borne by the people I admire, to their pile of deathbed regrets about not saying no better.
Then there's Austin Kleon's excellent discussion of saying no, and privilege, and how to figure all this stuff out.
I think I have figured out two of the root causes of regrets, for what it's worth:
1. Favors asked do not arrive in orderly, time-bound ways. Someone asks you to give a speech in two years, or advise them on a project that will start next year. You can apply the time-honored heuristic ("if I was asked to do this right now, would I still say yes?") and have it pass that test. But two years roll by and life happens, and when your obligation comes due, you're behind schedule on something urgent, or your family needs you to help with something traumatic or just difficult, and you are honor-bound to do whatever you acceded to back in your dim pre-history.
2. You can apply a reasonable standard to your yesses, but the standard lags behind what's reasonable. You might say, "I will only take freelance work at $x/word" or "I will only travel to events where the audience is likely to be so-big or bigger." But if you are doing well -- if your work and profile are gaining in prominence and demand -- then by the time your yes comes due (see 1., above), you may realize that, all things being equal, you should be applying a higher standard to your yesses. You're doing work for $x/word (or $x/hour) that is coming at the expense of work you could do at $(3*x)/word. You're turning down 1000 people to speak to ten people -- or you say yes to everything, and then find yourself with Goethe on his deathbed, wishing you'd been "able to abstain from public business" to "live in solitude."
If you're conscientious, you won't take this out on your askers. The person paying you $x/word is paying all they can afford, and they asked and you agreed of your own free will. So you turn in your best work on time, but the only reservoir you can plunder to do the $x work and the $(3*x) work is your personal time, or time you really owe to your loved ones, or both. So yeah, as Bruce Sterling says, by the time you're an "older-and-wiser famous over-achiever," you will be regretting this.
Worst part? It's not like you can't see it coming from a long way off.
“I have ever been esteemed one of Fortune’s chiefest favorites; nor will I complain or find fault with the course my life has taken. Yet, truly, there has been nothing but toil and care; and I may say that, in all my seventy-five years, I have never had a month of genuine comfort. It has been the perpetual rolling of a stone, which I have always had to raise anew. My annals will render clear what I now say. The claims upon my activity, both from within and without, were too numerous.
“My real happiness was my poetic meditation and production. But how was this disturbed, limited, and hindered by my external position! Had I been able to abstain more from public business, and to live more in solitude, I should have been happier, and should have accomplished much more as a poet. But, soon after my ‘Goetz’ and ‘Werther,’ that saying of a sage was verified for me–‘If you do anything for the sake of the world, it will take good care that you shall not do it a second time.’
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