The Offshore Voyaging Reference Site

Second Level Thinking About Offshore Voyaging Boats

As I have mentioned before, I have, for nearly two decades, self-managed our investments. And as part of that process I do a bunch of reading, although, as the years go by and I learn to separate the fools and those talking their book from the truly wise, the list of authors gets smaller.

One of those I read is Howard Marks, one of the wisest of the wise. Marks often talks of second level thinking, and how, if more of us did more of it, the world would be a better place and fewer people would have shitty—I said that, not Marks—outcomes in both investing and life.

Here’s Marks on second level thinking as it applies to investing:

First-level thinking says “it’s a good company; let’s buy the stock.” Second-level thinking says, “It’s a good company, but everyone thinks it’s a great company, and it’s not. So the stock’s overrated and overpriced; let’s sell.”

First-level thinking says, “The outlook calls for low growth and rising inflation. Let’s dump our stocks.” Second-level thinking says, “The out-look stinks, but everyone else is selling in a panic. Buy!”

Of course, the classic recent example of a win for second level thinkers was the March low in stocks, followed by a massive snap back. First level thinking resulted in selling into the dip and second level in buying.

Second level thinking is hard, but also well worth it, because even if we only manage to do a little—I struggle all the time—we can still profit.

Anyway, enough with investing, let’s look at applying second level thinking to offshore voyaging:

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Marc Dacey

Fiirst level thiinking: Belt. Second level: Add suspenders. Many of our systems on board that are critiical are duplicated; main and spare halyards, doubled uppers, and a bypass valve on our hydraulic steering so we can steer, if needed, with a tiller (windvane optional). The windlass is both manual and electric and the three of us have even brought the all-chain rode 30 kilo SPADE anchor aboard by hand, although this made our son complain, just to see if we could tackle it, pun intended.

We have found what every liveaboard knows: cruising is boat repair in exotic places, so it’s best to opt for robust systems in the first place, preferably installed with ease of access and simplicity of operation. That means leaving the snug pilothouse or semi-sheltered outside helm to work at the mast and that means having installed jacklines and related hard points for the tethers in logical positions the whole way there and back. In that sense, “second level” iis very much like holiistic thiinking: delving into the process of how actions are connected on a sailing machine yields the best options, which will vary from boat to boat, but will be similar in spirit on every boat, because every boat can be understood.

Marc Dacey

Ideally, yes. But consider the selection of the manual-electric windlass…it was premised on the unexpected failure of electric power combined with the need to raise or lower an anchor. If the electricity completely fails on a modern boat, does the weight of a sextant and an almanac or a GPS and a Ziploc full of batteries seem like an added complication, or just prudent? That said, we regularly cull items from the manifest that can’t justify the freight.

Eric Klem

Hi Marc and John,

I have to agree with John about being hesitant about belt and suspenders solutions.  In my engineering work, I run into people’s desire to implement this sort of approach regularly and once you actually look at it, it is usually the wrong solution.  Some regulations actually encourage it and usually end up with worse products as a result.  A few things to keep in mind are:
– There are always trade-offs in adding something.  The obvious one is usually cost but weight, size, inertia, power draw, etc all become factors.  Think about if someone told you that you should have a redundant stay for every piece of standing rigging, the increase in weight aloft would be totally unacceptable and that assumes that you don’t also go to a heavier mast so that you can tension up both sets without having a compression failure.
– The transition to a redundant system is always tricky.  What will detect that you have a failure? Can you have a period of manual operation?  Will there be shock loading?  If we take the example of standing rigging again, you can’t leave it slack or the resulting movement and shock load will likely break it too.
– Redundant systems need to not be operational when the primary is in operation.  So if we tension up that second set of rigging and share the load, we can have a failure in 1 piece that then overloads the other failing it too.  We should have just used 1 slightly stronger piece.
– Redundancy takes time both in initial setup and in ongoing inspections and maintenance.  What is this time being taken away from?
– There is an irresistible urge to cut corners on the primary system if there is a backup even if the backup is crummy. I watch some engineers successfully ignore this urge but many fall into this trap.

All that being said, there are times when a belt and a piece of string in the pocket or a belt and a spare belt in the pocket or even 2 belts at once make a lot of sense.  In my view, these are usually things that don’t fail from loading but fail from random software bugs, undetectable corrosion of electronics, etc.  After all, there is a reason why reliability calcuations are done very differently for electronics and mechanical items.  An autopilot is a great example on a shorthanded boat, the failure modes are hard to detect ahead of time and seemingly random when they happen.  But if one does fail, you still should troubleshoot it while operating on the second one as if it was indeed corrosion or something, the second identical unit may well have issues as well.  The only time that I can think of where a true belt and suspenders solution is called for is in a critical application where you don’t control a likely failure point of the system so you need a completely separate solution.  A great example would be celestial navigation for the navy as a foreign power likely has the ability to take out a key element of GPS.  But for us average sailors in most areas we could actually be okay with good dead reckoning skills and we should be carrying the stuff to do that anyways so this is more akin to the belt and a spare piece of string.


Marc Dacey

Perhaps surprisingly, I agree. Of course, from a certain point of view, a sailboat’s auxiliary motor is suspenders to the belt of the sailing rig, but cruisers like the Pardeys are very rare indeed, if inspirational to many.

Marc Dacey

We have the same, and I recall from Tony Gooch, the longer the passage, the better the vane does compared to the AP. I also did a delivery during which both AP and vane failed. That’s passage making!

Michael Lambert

Third level: when we are stuck with a given situation, our brains create “synthetic happiness” by tricking ourselves that that situation is in fact desirable. So one trick to be happier is to eliminate as much sense of choice as possible. I did this when boat shopping, I wanted a boat that could be sailed in the cold and shallow draft. Long story short: I “HAD” to buy a Boréal. And so I can feel defensiveness when hearing ill of my future boat, since my brain is trying to convince me the road I’ve taken is the best road. Of course when fitting out I have tons of choices to make, and they will be informed by John among others, for example concerning mast reefing pending report from Colin after shakedown. But in the end, it’s helpful to know that we all do it.

Michael Lambert

That’s a great example of the effect. Inside helm plus shallow draft led me to think about Chris white cats for a bit, but I didn’t fancy dodging two hulls through the noodle soup, and I wanted to fit into places like damariscove and seal trap at isle au haut, so I wrote off cats AND their speed. Now that the decision is made, I’m quite fine with it, and I’m well on my way, I hope, to considering Samara II to be the perfect boat for me! And yes, there will be a code 0 and asymmetric.

Michael Clarke

But how do you self-manage your investments when you’re off on months-long voyages with limited contact with the rest of the world?

Matthieu Chauvel

“It never was my thinking that made the big money for me. It always was my sitting. Got that? My sitting tight! It is no trick at all to be right on the market. You always find lots of early bulls in bull markets and early bears in bear markets. I’ve known many men who were right at exactly the right time, and began buying or selling when prices were at the very level which should show the greatest profit. And their experience invariably matched mine–that is, they made no real money out of it. Men who can both be right and sit tight are uncommon.” — Jesse Livermore.
…Never thought this kind of reference might find its place in the Morganscloud space, apologies to all for the drift away from sailing technicalities if perceived as such, but it seemed appropriate just this once (wish boat ownership and cruising lifestyles could be entirely dissociated from profitable or at least reasonable investing, but I doubt that very much for most of us, even for those who might not realise it yet). Back to my cave, won’t do it again.

Jo Blach

But does it stop at the second level?

Couldn’t it go on like this?

I‘m lazy. If the control-lines are all available in the cockpit, I’ll adjust them much earlier and more often than if I have to prepare to go to the mast in a safe matter. Or I decide “I‘ll just quickly …” and not bother with how things are done properly this one time.

On the other hand, at the mast I can raise the main mostly manually without much winching. This alone has saved me more times I care to admit from damage. Bad things happen when I happily keep cranking the winch when I shouldn’t.

Jean-François Eeman

Dear John,
Can I reassure you ?
The philopshy of our new 47.2 is NOT coming “instead of” the old philosphy;
The new Boréal 44.2 will still have the halyards and reefing lines at the mast.
And we kept the fundamentals of Boréal : single rudder, doghouse, centerboard and keel embryo…
We launch the first 47.2 “Chiara”on the 22th of September (weather permitting)…
Begin of October we will take her to La Rochelle. The show is cancelled but the 47.2 is nominated “Voilier de L’Année 2021” (Sailing boat of the year 2021 in France ) and “European Yacht of the Year 2021” in the category “Blue Water Cruiser”. Selection and testsails are in La Rochelle.
After that we’ll sail her side by side with Milonga, our 47, to compare sailing performance.
We’ll let you know the comparatives…

Mark Ellis

Re you point about rig automation: I have always been weak of arm, sore of back and now, bugger it, old of age. And I have always wondered why you couldn’t get a large sheet winch that was also single speed. Single speed allow you to swing the handle back to a comfortable pulling position- thumbs up all round. Is there such a thing as a large single, but low ratio, speed winch? I’ve never seen one. Or maybe it’s time to add lame of brain to that list? Value your thoughts.

Mark Ellis

Thanks John, much appreciated. The ratchet winch handle looks ideal. Interesting that it is no longer made. I look forward to your eWincher review.

Marc Dacey

What just occurred to me was this: why not weld a winch socket onto a racheting breaker bar? The leverage would be significant, and the “sweep” could be as wide or narrow as is comfortable.

Dick Stevenson

Hi Marc and all,
With regards to a ratcheting winch handle, they were available in Sweden 15-20 years ago. Despite research, there was no indication that they existed in the US, until a friend happened to be in Sweden and knew I wanted one and got it for me. If anyone has a sailing friend in Sweden, he/she might look around.
And Marc, agreed. I have always thought that a good quality ratcheting wrench with an insert to go into the winch (as is used by the right-angle drill power assist devices for winches) could be cobbled together (perhaps with a welded on upright handle). Often the winches that are restricted from full rotation of the handle are mostly brought in by hand and only need the last few feet or inches brought in by handle so the handle might not need an upright component. I know that is the case for my staysail winches.
My best, Dick Stevenson, s/v Alchemy

Marc Dacey

Since Quebec City, I have been religiously rinsing my ratchets and other hand tools exposed to salt water in fresh water and dosing them with WD-40 and light oil. So far, so good, but I expect attrition.

Eric Klem

Hi John,

After one of your comments in another post, I picked up a ratcheting winch handle this winter and I have to say that it is great when used right.  Early on, we keep it in non-ratcheting mode and get the sail most of the way in.  Once we are almost there, we drop it into ratcheting mode for the slower speed on the winch.  Yes, it is slower than going all the way around but there are points where the ergonomics are so bad that it is really a struggle to go all the way around and we find that about a 120 degree swing in the easy push direction is just perfect.  When it is really blowing, my wife no longer ever asks me to grind in the last bit.  Now if we had a bigger boat with more ergonomic winch placement, it would probably be pointless but for a boat where your leverage stinks in certain positions, it is great at the very end and makes a fine normal winch handle the rest of the time.  

Having also tried it on winches where you are prevented from going around, it works great provided that it is a line that doesn’t need much adjustment such as one that is mainly hauled in by hand.  I hate these arrangements but they are amazingly common, it seems that designers ignore the inevitable later addition of a dodger.

The big downside is that it is heavy.  If you drop it, you could break a toe easily so you do need to be careful.

David Zaharik

Hi John,

I have a Boréal 47.1 and love her. As you may recall we sailed the coat of France, Spain, and Portugal to Gibraltar last summer, took a break to get out of the Schengen area for 90 days then returned to sail to the Canaries, Antigua, up the chain to the Bahamas, and due to Covid to Florida to get home to Canada before the boarders shut. So we had about 6500 nm of off-shore sailing.

We shipped Beyond the Blue home from Florida and for the past two months have been coastal cruising. As you know a completely different animal. Much more close hauling, reaching and light airs… well I can report that the 47.1 is not only a balanced incredible machine off-shore, she is magnificent in light airs as well. In a narrow channel we tacked with the main and solent in 5 knots of wind doing 3 knots… crossing the Salish Sea (Georgia Strait) we had 17 knots on a close reach and were doing 8 – 9 knots full main, full genoa. I have both a Code 0 and a gennaker but have not used them yet here… continuing on the same day, we ghosted through the islands in 5 knots doing 3.5 easily on a close reach… very well balanced boat.

I was at first reticent about the main and reefing lines at the mast but I installed good Antal blocks on the main luff and on the reefing points. Further I installed an inside jackline system, using your suggestions for home made harnesses tailored to the size needed and situated around the boat. I found going forward to be a comfortable experience and the ease of using the mast situated lines as rigged comforting.

I found the engineering reasoning of the Boréal team to be extremely well thought out and functionally efficient. Frankly the only thing I wish was different was that they had a manual reversion for the windlass, which they don’t. They have never had a failure, but to me, that is tempting fate…. I hope our windless never fails as well. A seasoned sailor gave me some sage advice to carry a 4:1 block and tackle from the mast to the bow as a back up (plus some sort of protection for the deck should I ever have to use it.)

I think Boréal used second level thinking throughout their design and I am glad they didn’t let me override any of their decisions. My thinking had to be adjusted but I have the better boat for it.

Drew Frye

The first thing to come to mind, with the first author quote, was the exerciser in x-order thinking about a glass of poison in the movie, “The Princess Bride.” You need some manner of proof in both the first and second order thinking, or it’s just babbling. Of course, it was a funny movie and I’m just teasing.

It’s an exercise in critical thinking. You have to watch out for straw men, group think, dated conventional wisdom, and early adopter enthusiasm at every stage. Think like a scientist, striving to separate what you know from what you hypothesize, and to spot the variables you have failed to control. An example would be dragging at anchor; the peanut gallery will critique the ground tackle until trumpets sound, but 7 times out of 10 it was just the bottom conditions, perhaps something only where the anchor landed.

And this is why when someone with a new boat ask what they should upgrade, I nearly always say “sail the boat for a season first.” You’ll collect a lot of second level information.

Drew Frye

We don’t disagree much. Proper setting would have detected the problem bottom and moving usually solves that. Or perhaps just re-setting, if it was just a bad patch or you landed on a stick.

If the spade drags in ordinary conditions, I’m guessing you anchored on a rock slab or something similarly uncooperative. The solution is not more chain, bigger chain, or even a bigger anchor. The solution is moving.

I often make the mistake of assuming all sailors understand the basics, which of course, is a basic failure in critical thinking on my part!

Marc Dacey

Speaking as a sailor who didn’t grow up sailing and didn’t buy a boat until age 38, learning “the basics” is highly situational. One can ‘get by’ as a fair-weather sailor in a temperate zone and simply never have a casual set of informal skills seriously challenged by unexpected conditions of weather, ground or even maintenance. That is why my wife and I, once we decided to attempt long-term cruising, did deliveries and took RYA courses, diesel and electronics and rigging and navigation instructions, and taking the boat out in snotty weather just to get used to when enduring it would not be optional.

There are more sailors like that today than people who started as kids in Sunfish and 420s, I would wager, which goes a long way to driving boat design and attitudes toward going to the mast to handle halyards. Someone who sailed as a kid, like my wife did, doesn’t think twice about it. To get to second-level thinking, one has to have a nearly complete grasp of first-level thinking, i.e. ‘the basics’. That’s a huge variable. Also why I learn so much here!

Roger Neiley

After many years as a member and learning a ton from your articles I finally have to disagree with you on one point – halyards and other control lines terminated at the mast. I’m now in year 20 of enjoying our Saga 43 with all control lines available on the aft end of the cabintop under the protection of the dodger. On previous boats with the need to work at the mast I often deferred reefing, did not adjust halyard tension to optimize sail shape and still ended up spending way more time up on deck which is clearly less safe than being tethered in the cockpit.
The value of being able to fully control the rig without testing my balance skills on deck is especially clear when short handed, at night and even more compelling when singlehanding. With a winch on the mast and lines exposed before they turn to lead back to the cockpit I do have the option to work “up there” but have never felt the need over the past 2 decades.
Here’s just one of many scenarios: 0 Dark 30, breeze builds as your lone crewmate is trying to get some sleep below. Totally imprudent to go on deck to reef without waking him or her to keep an eye from the cockpit. Contrast this with my 2 minute reefing procedure from the relatively secure cockpit. Crew comes up an hour later to begin their watch and is happily surprised they never woke during the sail shortening.
Like you say, we all have our preferences but I’ve found the cockpit control center is where I prefer to be when fatigue, fear and increasing age factor into decisionmaking.

Ben Pearre

“First Level Thinking: I’m getting older so I’m going to automate everything on my boat, electric winches, electric roller furling, the whole schmear.”

THIS. As a slight public-health nerd, this is exactly (half of) what goes through my head every time the beautiful stillness of the morning is torn by someone going 500 metres in a motor tender. What happened to the health-enhancing, seaworthy, capable, versatile, non-destructive, beautiful rowing tenders that used to be a dime a dozen? I know it’s boat-specific since rowing craft need to be more carefully shaped than motorboats due to the limited power , but any thoughts?

Dick Stevenson

Hi Ben,
Think, perhaps, a nesting dinghy. I have a Danny Greene’s Chameleon nesting dinghy which has served me well since 2013 or so. It rows very well and is just over 10 feet in length. It is not a Bahamas/Caribbean tender as I would not wish to go long distances for snorkeling or diving with gear and inflatables will be lots easier to get in and out of from the water. That said it moves very nicely with a Torqeedo electric outboard and goes quite a ways on a charge as it slips through the water so easily. Rowing is more satisfying, however.
Nestaway has a number of nesting dinghies/boats in various lengths in the UK. Nesting dinghy manufacturers in the US seem to come and go, so I am not sure now what there is out there.
My best, Dick Stevenson, s/v Alchemy

Luis Salcedo

Oh well, I am late to comment as I just read this very interesting article, lived on board our 33, french built vessel for 20 years, it was custom built to go around the world and other than using the mold for the hull, the rest was modified, including the deck that was way too much rounded from side to side…, just in case. On a solo stint from FL to the northern coast of Brasil, I had to reef with my left, while hanging on for dear life with my right arm around the mast. First thing I did once back in civilization was to have built two SS balconies, one per side, high and with three legs, what a relief…not only I could rest my lower back but also carry two 50 lt jugs, one per side. Had nothing but the main sheet at the cockpit. Personal story.

Chuck Batson

Yes! LOVE this article. Thank you John. 🙂

John Maturo

I sail a 1978 Baltic 39 in New England. Powerful, fast, stiff with 44% of wt in a deep fin keel, huge spade rudder,(she tracks like she is on rails) cockpit to companionway via bridge deck, semi flush deck, all halyards at mast, slab reefed main, roller Genoa, detachable Dyneema cutter stay with runners and with hanked on storm jib, retractable sprit with dyneema bobstay, manual self tailing winches. I race her occasionally (Block Island Race week) and sail offshore. She is the boat among all of my boat owning friends that everyone wants to sail on in light air or a blow. I fit our couples life style to a boat that is robust, simple, secure, seakindly, and fast. I am 66 and my offshore and racing companions range from 60 to 70. I bought her and set her up based on my experience and great advice from men like you and John Kretschmer. Your article is spot on. In port we are not the most accommodating below, but then we have huge flush decks for lobster and wine bashes my wife throws for our sailing companions. Your philosophy is exactly why we did not trade up to a Baltic 43 which would need powered winches to handle the sail trimming and hoisting. We will be in NS and PEI next summer if Covid subsides and we have a new president that will actually manage the pandemic.

Alex Fricke

Great article!

Nick Willis


Great reference to Marks on investing. I’m not sure though that the pandemic lows of March are a good example of correct second level thinking on buying. As it stands now, the market has recovered, but that does not mean a second level thinker buying in March was right (perhaps lucky to-date, which I would argue is not the same thing as being right).

If you read Marks’ letters during this period, he discusses positioning more defensive (not a net buyer at that time). I recommend a read of his memo dated May 28 (titled “Uncertainty II”) where he discusses low probability high consequence events.

Thank you for an absolutely brilliant and informative site.