It’s windy on the bay, and the current could carry a sloop eighty miles south to the mouth in less than half the time then when under normal sail. It’s choppy, with three feet waves and whitecaps, and even here at the shore waves pound the riprap in regular intervals and the spray is salty and piercing.

A bank of clouds hangs seemingly on top of the Eastern Shore twenty miles east; dark clouds, stretching from the horizon up and high enough to block the sun even now at nearly ten a.m.

It’s not normal out there.

At the convenience store a waterman said he wasn’t going out and another said he just got back. The first asked what made him chance such conditions when the oysters and rockfish will be there tomorrow and the second said, “I’m a waterman. And I know what I’m doing.” He wasn’t taking a shot at the first; he quickly commented on it would have been more prudent to wait.

But he didn’t wait.

It’s a tough call, sometimes, isn’t it? When do you wait? When do you step up and watch a bit, see how the tide rolls? Half of it is confidence, half of it is experience, half instinct, half willingness to fail and embarrass yourself. But maybe sometimes success only comes when you’re willing to put in four halves instead of the standard two.

This is true in all things. Anyone can go the distance; just keep your head down and don’t die. Or, as John Denver noted, “Growing isn’t hard to do; just stand against the wall.” So what is the next part that drives watermen into rough seas when even the oysters are quite literally bedded down?

Van Gogh said, “Those of us who live; why don’t we live more?” Took me a long time and a lot of leaning on others to understand this. Partly because when I was young—twenties mostly—I was the second waterman. I headed to places somewhere beyond reason, driven by something other than rational thought. But after a while you get tired, as if you saved up all the failures and missteps to use all at once at sixty-years old.

Or maybe I just slipped into some more comfortable clothes a la waterman number one, which, really, is only a half-step from going back to bed, though he certainly is the more practical one. We find out just how ordinary we are when ration takes over, we recognize our lack of good judgement, our extreme ways when you either have to hit it right or you end up begging for mercy for needing help yet again. There is no middle ground for the second waterman. Yeah, it may be safer tomorrow, he might think; but I might die tonight.

How do you know when the odds are against you?

Something shifted in me this past month. Something significant.

For five years I’ve been Waterman One. This after a lifetime of not only not leaning on others or contemplating consequences but moving forward with innate confidence. But we all learn at different times. We all grow up eventually and recognize our mortality, our faith or lack thereof, our true passions, our fears; when the completed file is piled higher than the “to do” stack.

It is the question which haunts all artists, all of us, who work in a field where hesitancy and self-questioning mean obscurity. How do I know I’m not just wasting my time?

Van Gogh didn’t hold a paying job for the last ten years of his life. He ate paint. He drank turpentine. He had syphilis, was bi-polar, manic depressant, had epilepsy before there was medicine for it, cut off the lower half of his left ear in a fit of rage and nearly died, was hated by painters and dealers, lived with a prostitute and frequented others, drank steadily, and even his own brother– a leading dealer of the time–couldn’t sell his work and suggested he do something else. Today his works sell for between 80-100 Million dollars each and he is considered one of the most influential artists in history.

“One must work and dare if one really wants to live.”

I have no idea how much time is left for me. Almost no one does.

Almost.

Life certainly does not have to be in the extremes, but it should also not be a constant state of hesitancy simply because nothing has gone right.

It’s the “get back on the horse” thing.

It’s the “like riding a bike” thing.

Yesterday a friend of mine said she has some very specific regrets in her life. Then she quickly noted what we all say when we say that; how, no, no regrets; “it is what it is” and “I made the right choices at the time” and “everything happens how it does for a reason.”

I waited just long enough for her to believe I agreed, then said, “No. That’s bullshit.”

Laughter followed by a quiet, almost a whisper, “I know.”

Because regrets help us recognize where we didn’t trust ourselves and maybe should have; they help us see some semblance of truth in our life instead of some veneer to justify our actions. I have no problems with regrets; they teach us not to live out the definition of insanity. They help us to step up to the plate because last time we didn’t bother and now we’re sorry. It is, plainly, how we learn from mistakes.

Did Waterman Two regret going out? Did Waterman One regret staying ashore? Maybe both, maybe neither. But I bet most of us wish we were Waterman Two.

Thoreau wrote that, “To regret deeply is to live afresh.”

I don’t have enough space even on this infinite space of pages to list my regrets just in the past five years, let alone my life. I should have gone to Austria; I should have gone to Monterrey, I should have stayed in New England, I should have driven right by, I should have stopped.

Whatever. But knowing some of those truths has made it easier to stand up next time for what I should have done last time. Of course. Or to keep silent longer. Or to say something.

You know what? It’s always windy out there, and calm days these days are few and far between. Hoist the mainsail and ride it out.