Is it better to be a modest success than a grand failure?

Dear Literary Ladies,
I’m plugging away at a modest but steady writing career, but sometimes I think about aiming higher. I admit that I’m afraid to fail— and then look foolish to myself and others. What about you? Do you think it’s better to stick with what you do best, rather than stick your neck out and possibly fail?

Is it better to be extremely ambitious, or rather modest? Probably the latter is safer; but I hate safety, and would rather fail gloriously than dingily succeed.

—Vita Sackville-West, from a letter to Virginia Woolf, Aug. 1928