People often quote Beckett's well known phrase from Worstward Ho -
"Ever tried. Ever failed. No matter. Try Again. Fail again. Fail better."
It's quoted (out of context of course) and interpreted all over the place as meaning something like this: "try again when you have failed, and even if you fail again try again, and eventually you will succeed." It's tempting to think of it that way - especially as my writing leave has begun with a series of less-than-satisfying days and several outright useless ones. But I think that interpretation does Beckett an injustice, and doesn't really help us either.
There's something about our self-help culture, with its myth of success, that somehow promises us that if we keep trying and don't give up, eventually we will succeed. But I think Beckett was talking about something else entirely. It's not that it's impossible to succeed, but that "success", by its common definition, is too small an ambition. "Being a success" is shorthand for being a winner in the eyes of the world, but that kind of success often comes at a moral, personal or ethical cost. If you become rich, or well known in your field, but have no good friendships or have lied or cheated to get there, then success is a thin reward. On the other hand, to be a success in the true sense of the word - to be good, and have integrity, and be loved for it by the few who know - is often not what gets us noticed, applauded or highly paid.
And more: if you are doing anything worthwhile there is no precise standard of perfection that, once achieved, means you have arrived. Write the perfect essay or the brilliant novel (aged 18 or 27 or 45) and allow yourself a little self-critique, and you will quickly notice that it could have been so much better, that the next essay, novel, poem, invites you to greater depths. Play a piece of music beautifully, and you find that there are yet more nuances to explore. Run your personal best and within a week or two you find yourself wanting to improve on it. The goalposts always move. There is no such thing as perfect, and success always stops short of depth. Others may decide that your second novel is a "success" but if you are really good at what you do, you won't believe them. And, if we are to take the sense of Beckett's phrase in its context, there is also the suggestion that the speaker is also lamenting his limits: he has never tried anything else but this one thing, in which he feels he has failed (bearing in mind that the person who feels a failure may already have a PhD or a Booker Prize). Other avenues remain as yet untried. Try again, then, could mean try something else, just as much as it means try again.
So try again, or try elsewhere, and fail again, and accept that there is really no such thing as success per se. Accept, even, that ultimately you can't "succeed" because while novels and movies and other nicely constructed stories have an ending, life never does. For most of us, all of us probably, life is a series of starts and middles, none of which come to a nicely conclusive moment filled with meaning. Everything, really, tails off somewhere and it is left to obituary writers and autobiographers to create the meaning and the closure.
You could see all of this as rather dark. Why would we want to embrace the idea that you will fail, or at least fail at success? Beckett's words in Worstward Ho were rather dark, certainly. But Beckett was full of humour too, and there is a sense in which claiming always to fail is comedy not tragedy. It releases us from the lie of success, frees us from the obligation to adopt its thin veneer, and allows us to do whatever it is we do for its own sake.
You could say this about redefining success: refusing to let it mean simply a course of action that ticks the boxes and gets attention, but is ultimately hollow, and reclaiming the word for the road less travelled, or for attempting your deeper dreams and ambitions. Or you could say that success, and fulfilment of one's true humanity, are different things, and choose between them. Whatever terminology you arrive at, I think the thing is to let go of the prevailing myth of success. Try, and fail, and don't give up, and try something else. Let life take its course, but believe it is about more than short term rewards and applause, or how the world views "success". And whatever you do, don't reduce Beckett to some lame self-help motto.