It doesn't come easily to me. Sloppy dress--easy. Sloppy appearance--haven't shaved in a week. Sloppy topsides--easy. I've learned to like substantial rub rails and dock rash, and can ignore seagull poop, at least in moderation. Sloppy marinas-- my favorite ones, since properness for appearance sake rubs me all wrong. But sloppiness in functional things also rubs at me, even on my laziest day. Perhaps even in this, I need to learn to change gears.
Being an engineer works against me. I like things to work correctly and efficiently. There's also my active nature; my wife thinks I just can't sit still. She says I should relax more when cruising, not understanding that tinkering and adjusting and generally fooling with things is at the heart of messing about in boats. Just sitting--if for too long--is torture. Give something to fix--not something unpleasant, preferably something rewarding--and I'm much happier.
Sloppy sail trim. I just can't do it. I've owned too many performance boats, where speed was everything. Why would I buy a high performance boat, suffer all of the compromises that accompany that choice, only to sail slowly and poorly? As a cruiser I still see poorly trimmed sales as just plain ugly. I don't grind and trim all day long, but I spend a few minutes getting very close to right and then leave the autopilot to stay close. But I hate the look of a wrinkled sail, over trim, or an uncontrolled twist that would better suit an Annette Funicello movie.
Sloppy anchoring. I loath doing something twice that I could have done once, had I paid more attention. I enjoy doing something efficiently, easily, and with the minimum number of steps. I can't just drop a pile of chain on top of the anchor and hope for the best. I can't just drop a second anchor, some place or other, because I'm too lazy to set the first one properly and I worry. If a second is needed, it will be placed rationally and the rodes connected rationally. I'll spend a few moments gauging what the tide will do and how I will swing. I'll pay attention to the feel of the ground when the anchor takes hold, estimating what the bottom must be like and how the anchor will like it. I like to spend the afternoon securely parked and the night sleeping peacefully. Sloppy anchoring would give me more exercise. Mid-night excitement too.
Sloppy navigation. Well, perhaps I am guilty of this. I've spent too much time with shallow draft boats. I tend to glance at the chart in the morning, memorize what I think I need to (where I'm going and places the bottom might be shallow and rocky), and then just sail. I watch the GPS in a general way, but not the details. I've sniffed the bottom a few more times than was strictly necessary, entering an unmarked creek while distracted by daydreams of what the afternoon at anchor might bring. But I don't think I'm sloppy when it counts. Grounding on a coastal sandbar to be deadly. If the Chesapeake had rocks I'd be more attentive. I've piloted many miles of hazardous coastline; I'm only sloppy when it's safe to be.
I'm too cheap to be sloppy with sail covers or window covers. But I don't mind a kayak lashed to the side decks and a jerry can lashed to the stern quarter rail, if they serve a good purpose. I don't mind fishing from the dock or leaving some cut bait on a board, so long as we are still fishing.
Sloppy planning. I've made progress. When I first started distance planning, I made a list. Now I leave more on the boat and sometimes untie the lines without any firm notion of where I'm going, the destination determined by the wind forecast. A float plan? Pretty funny.
Unfortunately, the reality is the opposite. Somewhere in my subconscious, as I motor out the channel, I'm considering the forecast I read, considering the waves I see on the horizon, factoring my mood, and making a very informed decision. Sloppy and rash planning is just plain difficult for us old farts; we've made or seen a lot of mistakes and just can't aim ourselves toward a grand epic without real effort. Descending from a grand snow and ice climb in the Tetons with a long-time partner, we questioned why, in all the years of climbing together we had never experienced a real epic, not in thousands of climbs. Although we had cut it a bit thin a few of times, we knew the line between epic and dead is thin, and we maintained a safety margin. We had stayed just within our abilities.
Sloppy maintenance. I'm not sloppy when it comes to quality of work. I keep my boats a long time, really try to make every fix or modification and honest improvement, and then sell them for more than I paid. I keep my work area neat when on the hard; basic courtesy to the yard and my neighbors. But if we're talking winterizing and spring clean-up... well, I've covered that before. I'm not above used parts, dumpster diving, and re-purposing, but only if I can match or improve upon original quality.
Maybe there is hope for me. I have a few sloppy traits--the megayacht group in Cape May pointed them out--a foundation I can build upon. I could learn to like the curve of a stalled sail. I can try catching fish with the spinnaker. I suppose, so long as I am becoming old and physically decrepit, I need to encourage decay of my mental faculties without further delay.