Circumnavigation – Advice and Concerns

“To profit from good advice requires more wisdom than to give it.” – Wilson Mizner


So, I made a post the other day outlining a plan to operate as paid crew aboard someone else’s boat, in order to gain a bit of experience. Afterall, a circumnavigation certainly isn’t a small goal, and with very limited sailing experience – a circumnavigation has many ways of ending badly.

You can find the post here.  After writing it, I posted a link to that in a Google + sailing group, and I received a really thoughtful reply from someone who had circumnavigated before. The reply was something I was really glad to hear, but it also helped cement some of the thoughts I’ve had surrounding the mental aspects of circumnavigation.

Here’s the word-for-word advice I received.  I’ve bolded the things that I’ve been grappling with.

My points for you:

• You will change. 
• It is easy to go but hard to come back: It is easy for a slave to become free, but difficult for a sailor to be slave. 
• You cannot go home, as home will have changed.
• It will take longer than you planed.
• You will spend all you will.
• An automatic pilot is more reliable than crew, feed it well, and carry loads of parts.
• 99% of people who talk of going, never go; 99% of people who buy a boat, never leave harbour; 99% of people who leave harbour, never get past 100nm of home. Find a reason to put to sea and not a reason not to.
• Re skills needed: Patience, Acceptance of other ways of living, Accept you cannot control your environment. Learn how to navigate without electricity. Be self sufficient. Try and be as good seaman as your great grandfather was. Learn to: anchor in 25+ kts; anchor in 20 meters of water; to tow; drive the boat backwards in 25+kts.  Have a routine before you put to sea, to check the boat and compass. 
• My Books I studied and took with me: 
Nigel Calder: How to be a diesel mechanic; Refrigeration for boats; Boatowner’s Mechanical and Electrical Manual (buy him Heineken beer if you see him), Jimmy Cornel ; World Cruising Routes and Pilot; Complete Guide to Anchoring and Line Handling; The 12 Vot doctor; Cook books.
• Where there are no doctors.
• You will lose your last name and that will be replaced with your boat name, so name your boat wisely. John on a boat called Wild angel is John Wild Angel.
• Rough weather: Each boat and each situation is different, so there is no one way. I am a Jordan series fan, but it depends upon the boat and proximity to land. Buy a whitewater kayak helmet with a visor, so you can breathe in the foam that is blown in rough weather. Buy good quality waterproofs, as you will wear them for days. Avoid extreme weather, it is painful. Keep your bunk dry; take the waterproof off as soon as you come below decks. Learn to sleep in the cockpit. Wear a harness all the time on deck, as it does not wear the harness down. If you fall overboard in bad weather..say goodbye. Be careful cooking in bad weather (I wear my waterproof trousers when I cook). Buy a pressure cooker. Buy a stout and a canvas bucket, good for many things.
• Land is danger, when is doubt head out.
• Keep a formal log, along with a social log. The formal log is for any accidents, and should you lose your electronics, then you have a last position and bearing. The social log is so that you can be the old bore at the yacht club bar who has done everything.

I’m not going to attempt to write about those points quite yet, as they’re issues that really require some pondering.  I just wanted to point out, that while the idea of this trip sounds kind of dreamy (are you picturing a margarita in some remote spot, as the sun goes down?).  The bottom line is that there is a ton of personal, financial, and physical risk involved.  This isn’t a sailing trip around a couple of civilized, protected islands.  And I’m not going out with a full crew of experienced sailors.

English: French map of the first world circumn...

The first circumnavigation (Photo credit: Wikipedia)

Honestly though, those aren’t even remotely close to my biggest concerns.  Here’s what’s been in the back of my mind for the last couple of months:

  • A shift in mentality:  I’ve been through really life (and mentality) changing scenarios before (see: fighting in Iraq, losing family/friends, etc).  When these events happen, even if you are able to become acclimated to “society” again – it takes time and nobody can possibly see things the way you do (their issues revolve around children, jobs, mortgages, etc).  And it’s not their fault, it’s yours, you’re the outsider.
  • No chance of a career:  Anything I’ve gained in my “career” to date will be largely shot.  This really isn’t a huge loss, I don’t put much stock in “careers.” It seems too much like indentured servitude. But it will obviously pose problems when I get back and need to find some source of income.  More importantly, I believe this will shift my mindset (even more) away from consumerism and the objects others in society deem important.  Which isn’t a problem – except that shifts like this largely make you seem anti-social (promise, I’ve been there).
  • People move on, the world keeps spinning:  Honestly, after the novelty of the idea wears off – people return to their daily lives and (if you’re lucky) you’re an afterthought – “Remember that guy, who I used to work/drink/eat/dive with? Yeah, I think he took off sailing.”  Without a doubt, your family, friends, and others move on.
  • “Home” loses it’s meaning:  Another one of those things that I can live without, but it does have an effect on the lonely wanderer.
  • Budget?  What budget?  I can’t possibly, really budget for this. I know from others trips that they plan to be gone for 3 years and come back in 10, and only after they’ve sold all of their belongings (remember, possessions don’t mean anything anymore).  Then they borrow money to start their lives over (from scratch), all the while planning their next escape.  So if I’m planning 5, and the experience agrees with me – I suppose I may be starting from scratch at 40.

To be fair, these are incredibly “first-world problems.”  And none of them are even remotely insurmountable.  That said, I’d be a fool not to consider these points before I drop everything, sell everything – and really, fundamentally change my life.

English: sailing boat

(Photo credit: Wikipedia)

The bottom line is that I welcome a change – normal life is tedious and boring (on a good day), a life of debt and consumerism isn’t for me, a “career” feels like slow death,  and I find myself planning ways to escape daily.  More importantly – few people have the gumption to do this, and when (or maybe if) I pull this off – it’ll make for some damn good stories, pictures, and videos.



I hope you folks subscribe, so you’ll get to live this vicariously (or hell, even make a visit to see me).  You can also like my Facebook page (up, on the right) or follow me on Instagram (also up, on the right).


Cheers, until next time.


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Working On My Sailing Experience

“I wish to have no connection with any ship that does not sail fast; for I intend to go in harm’s way.” – John Paul Jones

While I really don’t plan on intentionally putting myself in harm’s way, I am planning to encounter rough patches and stormy seas.  And to that end, I need to work on my sailing experience.  What does a guy do if he really just wants the cliff notes though?  If you’re thinking:  “buy a book” – it’s a good start, but when you’re in a rough patch offshore – experience counts.

A sailor in strong winds off Nicaragua remains...

(Photo credit: Wikipedia)

Learning to sail won’t be a huge stretch for me, I’ve spent many hours on many types of boats over the years.  Everything from sportfishing boats to liveaboards, even sailboats.  But actually learning to be self-sufficient (and safe) while sailing the most remote (see: best) spots on the globe, isn’t something that happens overnight.  So the reasonable alternative is to gain some first-hand experience in bluewater sailing from an experienced sailor.

That’s not something that just comes across your plate when you’re working full-time (or more) at a growing software company in Austin, Texas.  I can’t just pop down to the local bar on Thurs/Fri/Sat and start spreading the word.

There may yet be hope, here’s my rough plan:

  • Get my finances in order to leave (updates soon)
  • Get my real estate in order (updates soon)
  • Wind down my professional life
  • Hitch a ride on someone else’s boat as paying crew (subject of this post)
  • Buy my boat
  • Take off with (a little bit of) experience under my belt

Finding a ride on someone else’s boat isn’t easy though.  The only real way to do that is via cruising forums.  If you’re new to this idea – sailors and full-time cruisers have forums too, and in those forums sometimes “Crew Wanted” and “Crew Available” posts are made.  Hopefully, via one of these posts I’ll find an easy-going sailor cruising an interesting area that’ll let me tag along for a couple of months.

Map (rough) of the Marquesa Islands, French Po...

(Photo credit: Wikipedia)

My first thought was to make the passage from Panama through the Marquesas, but I’m a little worried about the timing on that one.  After some research it looks like the best time to make that crossing is Feb-April, and I really don’t think I’ll be ready to drop everything and take off that quickly.  Even more importantly, I’m pretty sure that I don’t want to wait two years to begin learning to sail.  I can’t bear that much anticipation.

Another major crossing would be ideal.  There’s nothing like spending nights on watch and days without the sight of land to test your mettle.  I don’t think it’ll be a big deal for me, but I can’t be sure until I’ve done it.  So tonight I made a “Crew Available” post, here’s what I wrote:

Hi there,

I’m planning a circumnavigation, but before I take off on that I want to gain some experience crewing another boat, early/mid ’14. Thus this post.

About me: caucasian, male, 29, recovering professional in the software industry (see: not as athletic as I used to be). Strongly prefer the ocean to the office, have spend multiple days in sailboats without seeing land (but much, much more time on powerboats).

I’m a freediver, spearfisherman, avid traveler, ceviche fanatic, and enjoy the occasional glass of red wine. I prefer to not see land for extended periods, and thoroughly enjoy (almost?) everything on the water. Read/write as much as possible.

Easy going, have more than a couple of stories and have traveled extensively. Born in Dubai, lived in Europe, dove off of the coast of almost every Central American country. Prefer dives to resorts and local culture to expensive trips.

Don’t mind splitting food/bev/entertainment expenses as long as they’re moderate. Can have a very flexible schedule starting early/mid 2014, let me know what you have in mind.

Because I want to buy a catamaran for my own circumnavigation (after crewing), I’d prefer to crew on a cat. That said, I’m not going to turn down anything that sounds fun on a mono. Cheers!



If that sounds like something you’d see on a dating site, consider that this person will be:  sharing very cramped quarters, meals, drinks, conversation, and tons of quiet time with me.  To that end, I think they deserve to know the stuff that makes me tick.

I’ll letcha know how this does, I’m as curious as you are.


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first wahoo death sharks

My First Wahoo Spearfishing (and a Brush with Death)

“Can you make it down here tonight?”


In reality – I could, but I’d have to drop everything, pack all my gear and blow off the next few days of plans, work, and school.  Never mind the 3 and 1/2 hour drive, the fact that I wouldn’t get any sleep, and would be a wreck Monday.  Last time I tried something like this I came down with Bronchitis and was useless because I couldn’t dive.Spearfishing Gear


So, naturally, I said yes.

Pack.  Leave. Quickly.

I’m Out

I was on the road – it was about 11PM and that put me at my buddy’s close to 3AM.  We were leaving at 5AM and I’d had about two hours of sleep the night before.  Energy drinks kept me in some limbo between sleep and being awake, but soon enough I was there. Trying to sleep.  Shit, this isn’t working.  Finally the alarm went off and I stumbled around the dark house getting all my crap together and loading the truck.

My host (and the captain) is a good dude, but he definitely isn’t a morning person and I was short on patience (nothing new here).  I wake him up a third time and even raise my voice a little.  He’s up, let’s get this party started.  On the way to the marina real exhaustion starts to set in, the only thing keeping me from dropping into a really crappy mood is that I can probably sleep on the ride out.

 Load the boat.  Gas fumes fill my nose and don’t help the oncoming sense of nausea.  This was a charter – the clients seemed alright, a huge relief.  They were all tuned up and ready to go.  Check the weather.  Shit.  It’s going to be a rough ride out – they’re calling 3-5’s all the way out.  Too late now.

Rough Seas

English: Rough seas at Brighton Marina The wes...

Rough seas on the jetty (Photo credit: Wikipedia)

No dice on sleeping on the way out – the boat (a stable 36′ Contender with twin Yamaha 350’s) is pitching heavily.  When I tried to sleep in the bow I was being thrown a couple of feet into the air every couple of seconds.  Good thing I don’t get seasick.  Back on deck the wind chills me (it’s just a bit over freezing) and the saltwater stings, but I’m loving every minute of it.  This is where I’m supposed to be.


We talk about tactics and sharks – nothing new, but this would be my first time supervising clients in the water and hunting wahoo at the same time.  My main purpose was making sure the clients understood what they needed to do, that they didn’t have a blackout underwater, and to keep the sharks off their backs.  I got this. 

It takes more courage than I’ve ever had to display in combat – to justify stripping and putting on my wetsuit in the wind, salt spray, and near-freezing temperatures.  Wetsuit on, almost there.  Lack of sleep, and the stress of leaving and rushing had taken its toll – I was starting to wonder what I was doing out in the middle of the Gulf of Mexico, during the middle of winter, during the middle of a storm.  Am I f*cking nuts? 

The Joy of Wintertime Wahoo

Jesus Christ the water is cold.  It immediately snaps me out of my funk.  I’m back, it’s on. Fish are all around me, then sharks.  I lead the way and take a couple of shallow dives to get warmed up.  The clients are floating, probably still shocked by the cold water and a little worried about the (very curious) bull sharks that are making passes at us. My breath hold sucks – I’m lucky to have 30 seconds underwater before the contractions start.  My mental state isn’t letting me pass the initial “get to the surface” feeling and my dive-reflex isn’t kicking in.

Ocean Triggerfish

Ocean Triggerfish (Photo credit: Thespis377)

The first Ocean Triggerfish start coming up from the deep – we’re drifting over the spot.  Amberjack are next and the clients start easing down, but they stop short of 30 foot.  That kind of dive isn’t going to work at this spot, the wahoo are sitting at 50 foot – if they’re home.  But this isn’t my trip – I’m just here for backup.  One client gets back in the boat – the sharks make him nervous and he’d rather line-fish. Fine with me, one less diver to worry about. No wahoo are home.

Run and Gun

Back on the boat the engines go from silent to a dull roar and we’re doing 35 knots over the whitecaps to the next spot. This is run and gun diving, if the fish aren’t home, we’re not hanging around.  The next spot is a little better.  We do 3 drifts and see a couple of lone wahoo.  These aren’t the monsters I chase around now, but it didn’t matter – these were the first wahoo I’d seen underwater.  Adrenaline fills my veins, I have tunnel vision and the only thing I can hear is the thumping of my heart in my ears.


Wahoo (Photo credit: Wikipedia)

“Right behind you!!”

I’ve been yelling at the top of my lungs for 10 minutes.  For all the prep, all the risk, all the money, all the time – the wahoo keep going right behind the client when he’s underwater.  He doesn’t even see them.  When he surfaces we exchange six words “keep your head on a swivel” and go back to the diving.

The sharks are thicker at this spot and are nipping playfully (or not) at our fins. They aren’t huge – it would more likely be a nasty scar than a mortal wound.   Another wahoo passes behind the client.  I wait until it’s far out of his range, take a breath and being an Olympic-style swim towards the fish.  It eyes me but doesn’t pick up speed.  I’m closing, but it’s still 50 feet away and my contractions have started – I’m going to need air soon. Just two more kicks.  It’s a hail-mary and I know if I miss I’m going to be in a pile of shit with the client and with our captain.  Everything slows down, I aim and put pressure on the trigger.
Bull sharks

Bull sharks (Photo credit: Mercury dog)

The shot was so long the spear actually arched, but it was a lucky shot and it landed right in front  of the tail – it might just hold.  The wahoo takes off and I kick desperately for the surface – I pushed it on that dive.  On the surface I watch my line take off and let out a bellow – I just pulled the trigger on my first wahoo!  I won’t forget this. Now I’m in shark-defense mode.  The sharks have picked up speed and are starting to swim erratically and they seem to jerk through the water – they smell blood.  I can’t lose this fish to sharks.

The wahoo wasn’t a monster – it might have been 35 pounds.  It only made a single, fast run and then some kicks towards the surface as he started to give up.  I was there to meet him.  With my first wahoo on the boat, and with my adrenaline pumping I yelled a little about a photo and dove back into the water hoping someone would follow with my camera.  


first wahoo freedive spearfishing
Over the next few drifts I spent some time in overwatch mode; keeping an eye on the sharks, playing with the marine life, and just relaxing while the client dove and worked to get into some wahoo.  I was completely relaxed, finally.  I made several dives to 50 foot to see if the wahoo were deep, they weren’t.  We saw sporadic loner wahoo a couple of times, but no schools and no monsters.
On one of these dives I was coming up and my speargun fired – completely on it’s own, my finger wasn’t even near the trigger.  The recoil of the gun smashed it into my side and made me involuntarily lose my remaining air – thank Poseidon I was near the surface.  I jumped onto the boat and caught my breath – that friggin hurt.   A little examination and it looked like I would only have a bruise.  That wasn’t cool.  Upon inspection of my speargun, we all concluded the spear hadn’t been set correctly against the mechanism – something that would have been the diver’s (my) error.  I dismissed it, but I shouldn’t havesecond freedive spearfishing wahoo

Round Two

Here we go again – the client had another wahoo pass within a few feet of the back of his head. I waited until I was sure the wahoo was out of range, and then I made an underwater sprint to close the distance and land a hailmary shot in the wahoo’s tail.  With fish number two in the boat I was a bit in the doghouse – the client had paid for the trip and I’m the only one landing fish.  In my defense, the client had more experience than me and every advantage – he just wasn’t seeing the fish.  I was banned from pulling the trigger again, unless it was an over-zealous shark.  No problem, I’d run the boat with a huge smile on my face.
We slept tied to a rig, about 70 miles offshore that night.  It was rough, cold, and wet.  I didn’t get much sleep for the third night in a row, and I was feeling it.  Our client didn’t do very well on the drifts that day and was on his way to getting skunked.  So we did what any self-respecting crew would do in this situation, stop at a rig and do a deep SCUBA dive to try to pull up an amberjack or big grouper.  I was completely satisfied sitting on the deck, but I could tell the captain wanted to shoot something – which means I needed to be on overwatch, in case something went wrong.


The dive down the legs of an offshore oil rig is always an amazing sight.  Life teams around the rigs – huge schools of jacks and snapper swirl around me as I make my descent.  I limited myself to a quick 150 foot bounce dive, with an appropriate amount of air for a deco stop.  Everything was going fine, I was watching the guys as they broke off and started kicking around the structure.  At 135 I saw a cubera snapper that I knew I was taking home.  He descended, so did I.  At this point we were well into a very risky depth – but I did a quick check around and the guys were alright.  Deeper.  There.  The cubera made a run around the rig leg, and I was waiting for him to come out of the other side…. But he didn’t.  Sometimes the fish are just smarter than us, and this is their playground – I’m just a visitor.  I lowered my gun removed my finger from the trigger area and checked my depth gauge.  I saw 163 feet.  Then everything went fuzzy.


I saw 163 feet.  Then everything went fuzzy.


Night Rig

Night Rig (Photo credit: arbyreed)

When I opened my eyes, saltwater was stinging them and I realized I had a mouthful of water.  My mask was off my face and my regulator wasn’t in my mouth.  I could feel pieces of my teeth in my mouth and tasted iron.  Not good.  I shook my head and immediately, instinctually kicked toward the surface.  When I looked up I realized I would never make it. So  I played the “your-regulator-is-behind-your-back-at-163-feet” game – which is no fun.  I found my regulator and managed to get a breath of air – but even after purging the regulator, it was spewing air out of it at an unsustainable rate.  I was in trouble.  Mask on.  My mask was half-full (or half-empty?) of water, my eyes were stinging and I was becoming aware of some serious pain in my mouth and nose.  But I had much, much bigger problems – my air continued to spew out of my regulator, I was at 150 feet underwater, and I had about 750 pounds of air (decreasing rapidly).

Air bubble

SCUBA bubbles (Photo credit: riandreu)

As I kicked toward the surface I looked around – I signaled trouble and it was pretty clear I needed help.  The captain kicked toward me as I ascended.  On the ascent I noticed the spear from my speargun dangling beneath me, and realized for the first time what had happened.  My speargun had again misfired, the recoil slamming the but of the speargun back into my face – knocking off my mask and punching the regulator out of my mouth. I remained cool and calm, but in my head there was definitely a bit of panic rising.

At 35 feet I grabbed a rig leg, and the bubbles streaming from my regulator had slowed – but only because I was almost completely out of air.  I purged the valve again, and for some reason – this time the bubbles stopped  entirely, leaving me less than 400 pounds of air in my tank.  I was sucking for air, but well within range of the surface.  At this point, running out of air only meant I would end up bent – but I could solve that with another “drop and hang” at 35 feet, on another tank. Our captain showed up next to me and we buddy-breathed.  I could tell there was a bit of “what-the-hell-happened” in his eyes, but I was much more worried about my teeth at this point – I could tell the front two were broken.

The rest really is history – I made it on the boat, wasn’t bent, and even took a picture before I explained the situation to everyone.  After getting on the boat we all did a bit of the “I’m glad you’re alright” stuff and headed home.  I took some Aspirin for my tooth/face ache, smiled, and drank a beer (which really hurt when it hit the broken teeth).  Nothing a dentist couldn’t fix and certainly not the first teeth I’ve broken.  freedive spearfishing wahoo and grouper
At the end of the day – we all made it back, we were all (kinda) smiling, and we all left the dock with wahoo for the dinner table.  But it almost didn’t end up that way.  This was my first, but certainly not my last brush with death while spearfishing.  I can honestly say it didn’t shake me, and that it didn’t keep me out of the water very long.  While we’re on the subject though – spearfishing (freedive or SCUBA) is dangerous – there are just a ton of variables.  Everybody I know that does it, has either seen or experienced someone dying or having a close call.  If you panic easily, don’t ease into it, don’t take the proper safety precautions (training) – you may very well end up being a statistic.  I almost did, and this certainly wasn’t my first rodeo.
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leave it all mentality healthy

7 Steps To a Healthier “Leave It All” Mentality

The mind is everything. What you think you become. 

– Budda

I don’t think words exist that are any more true, in any text.

I’ve begun to really try to prepare myself for the circumnavigation, mentally.  And what I’m finding is resistance – not just from others – but from myself.  Rather than beginning to live more frugally, I’m having a hard time giving up delivery when I’m at home.  Rather than beginning to sell things I don’t need or use, I find myself continuing to acquire things I know don’t matter. This is not what I expected.

Change is something I work hard to incorporate in my life.  If things get stale, I change.  If things are going badly, I change. If things are going well, I change (ideally continuing to improve). But I’m finding it hard to change now, and I can’t put my finger on it.  I had some time to think about it on my motorcycle the other day (between warp-speed, hairpin turns) and I really think it has to do with my job and being too comfortable.

Which means I need to get out and take a little risk.  And this is my accountability – and hopefully some inspiration for you to do the same.  Here are my steps, with goals – hopefully some of them will resonate with you.

Step 1 – Drain the Bank Account

This isn’t what it sounds like – I’m not giving everything away or buying everything I’ve ever wanted.  But I want to be riding closer to the edge – I want to worry, just a little, about money.  So, the vast majority of my “disposable income” is going somewhere I can’t touch it.  I need the stimulation, I need the uncertainty, I need the push – to keep me on my toes.

Goal – December 2013.

Step 2 – Quit the Shenanigans 

The new rule is I get one Friday and one Saturday night (per month) to cut loose.  The rest of the evenings are spent at home, watching movies, or doing something productive.  I love to have a couple of beers with friends, so this is a big deal for me.

Goal – Yesterday.


Step 3 – Focus on Independent Work

I could fill up 5 people’s calendars with the projects I have going on (but I’m scaling that back too) – so there is NO excuse for not being insanely productive.  And I have NO excuse for pissing off a day or an evening or a weekend.  Unless I’m taking a break – but that’s not an excuse, that’s a necessary part of maintaining a healthy balance.

Goal – Yesterday.

Free weights

Photo credit: Wikipedia


Step 4 – Focus on Health

I have two gym memberships, and for some reason I’ve been making excuses for not using either.  It’s bullshit. I do have a legitimate reason for not visiting the gym twice a week (I spend two hours commuting Monday and Wednesday), but that leaves 5 days per week I can workout.  More working out = more energy, and I know that’s going to lead me to a better place mentally.

Goal – lose 10 pounds and regain strength, December 2013.


Step 5 – Take Any and All Measures Necessary to Quit the 9-5

Yep.  You read that right.  Before I go on this circumnavigation, I’m quitting my 8-6 (ish), well-paying job.  I find myself rushing everywhere, unable to take time for the things that matter (health, food, basic life maintenance) and so I’m quitting.  I want to work for myself, on my schedule, without all the bullshit that comes with a typical 9-5.  I’m over it.  Some of this is under my control – some of it (really) isn’t.

Goal – January 2014 I’m self-employed.


English: For Sale by Owner Sign svg

Photo credit: Wikipedia

Step 6 – Start Selling the Accumulation of Soul-Sucking Crap

I admit it – when I buy something I expect it to be with me forever.  There has been only a single time in my life when I bought something with the intention of selling it (ever), and that was recently (two days ago).  But I’m done with it.  I’m over the materialism, I’m over the borderline hoarder mentality, and I’m over the stress of having too much stuff.

What the hell do you tell your family though?  Something like: I don’t want any more presents for my birthday, I don’t want trinkets that you picked up at the gift shop, I don’t want gifts from your travel. Please spare me – I’m going to have to sell it, and then I’m going to feel guilty for selling it.  In effect, you’ll be paying money to make me feel guilty.  

I’ll take support, I’ll take a little bit of genuine (organic) promotion for my cause. Of course, I’m sure there will be a point where I need something on the trip – and at that point maybe my family/friends will send me something that I really need (I’ll have some brownie points by then, surely).

Goal – Big ticket items sold by February 2014.


Step 7 – Start Telling Everyone “No”

I’m completely fed up with saying “yes.” I can’t accomplish anything I want when I’m busy pleasing everybody else. To be clear – anybody that knows me understands that I’m not known for being overly generous with my time.  I simply don’t have much to give.  But I’m clamping down even more.  Even tonight there was the inevitable distraction that I could have avoided had I said “no.”  And guess what?  I should have.

I can feel the clock ticking, and I when I’m busy pleasing others – I feel them sucking the energy from me.  Energy that could be spent working towards one of my (huge) goals. Energy that could be spent working on one of my many projects.  Starting yesterday, I’m doing what I want, when I want, and if people don’t like it – I’ll understand completely.  But I won’t feel guilty anymore.

Goal – Yesterday.



When I got the panicked call that my Dad was dying, I was terrified.  My whole life changed, I knew he wasn’t going to make it and I wasn’t going to get there in time.  It was one of the most heartbreaking things that’s happened to me.  But I’ve come to understand – it was a liberating thing as well.  My father instilled in all of us, early, the value of money – having a “good job”, and working hard.  And if that was what I really wanted, that would have been just fine.

But when I think about work, material possessions, and what we (in America) have come to accept as “life” – I really only see it as a form of mental, financial, and societal slavery.  It’s everything I don’t want, but it’s been pushed so hard that I almost lost sight of what matters to me – my freedom.

Things became even more clear this year, when I got the same type of call about my Mother.  Thankfully – she did survive and she’s now back to 100%.  But here’s what those moments have taught me:  Your life is full of bullshit.  That bullshit is a drain on what you should be.  That bullshit isn’t necessary.  That bullshit can be cut out.  That bullshit, if you let it, will completely blind you from what is important.  Until that moment when it all becomes clear.  And then it’s usually too late.  

Death may be the greatest of all human blessings.

– Socrates

The phone call I answered, late that night was a gift not many get to experience this early – it stripped away everything that didn’t matter and reminded me exactly how fragile life is.  I remember being deployed in Iraq and coming to this conclusion – but somehow, coming back into American society started to corrupt me again.  It took a brush with the death of a loved one to remind me.  Funny how death works – how it closes important doors, but it brings us together and forces us to confront things in our own life that might otherwise go unexamined.

Remembering that I’ll be dead soon is the most important tool I’ve ever encountered to help me make the big choices in life. Because almost everything – all external expectations, all pride, all fear of embarrassment or failure – these things just fall away in the face of death, leaving only what is truly important.  

– Jobs

But this wouldn’t be a fair post without a couple of caveats:

  1. I just bought a second (used) motorcycle – and I’m not giving it up until I’m leaving.  Everything else will go.
  2. I’m going to take time off when I need to.  I’m not going to sacrifice quality of life.
  3. I’m going to continue to eat delivery occasionally.  I’m not giving it up completely, but I’m cutting back.
  4. I’m going to have the occasional drink socially with friends – catching up doesn’t count as Shenanigans.

My last non-essential purchase

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Convention and Tradition are a Trap

First – a quick apology about the tardiness of this particular post, I’ve been fighting with my Mac and my external hard drive for a couple of weeks and things still aren’t back on track.  You may also find it a bit philosophical/introspective, but I’ll let you be the judge. So, with that said – here’s my post.

“Status quo, you know, is Latin for ‘the mess we’re in’.”  – Ronald Reagan


Fighting Convention and Tradition

The last couple of weeks have felt like I was fighting both Tradition and Convention, two things I don’t put much stock in.  Not that I don’t appreciate the value of them, I’m fighting the notion that they’re a reasonable explanation for someone’s actions or belief system.  Marriage, children, organized religion, and a traditional American middle-class life have been at the heart of this particular debate.  I’ll be the first to admit it – speaking out against convention and tradition make people very uncomfortable.  And that’s not really my goal.

But, the unconventional and the non-traditional don’t have a support system – by definition.  They need a voice, and I have the sneaking suspicion that I’m not the only one who feels that way.  That suspicion was confirmed recently by a guy I’m privileged to call my friend and that’s a couple of decades my senior.

Photo of Wisdom Path

(Photo credit: Wikipedia)

Here’s our Skype conversation:

Friend:  “[Time is] all any of us have dodo, it’s all about how we use/waste it.”

Me:  “Maybe, but most people don’t have 5 years to just f*ck off (speaking about my trip).  Or maybe they just can’t figure out how to finance 5 years of f*cking off.” 

Friend:  “Not so sure. We sort of decide what we are going to do. Go into the Army, go to college, get a job in a factory.  It’s not that they don’t have the time, it’s the lack of courage to take risks.”

Me:  “That’s probably true too.  And there’s this idea that your life is supposed to be kinda cookie-cutter… Get a job, find a lady, have some kids, get a house, give up and relegate yourself to a mediocre existence.”

Friend: “That’s the f*cked up American template, for sure.”

Me:  “I have to admit – it sounds good because it would be so much easier and there’s so much pressure to just do that… but then I’d be dragging my knee around every corner on the motorcycle just for the tiniest bit of adrenaline.”

Friend:  “It’s not easier. It’s harder. And it’s a f*cking trap.”

Now, if this was some college-age punk or another friend of mine who was an adrenaline junkie – I’d probably dismiss this conversation as ego-polishing.  But this friend is over 60, has a child, a wife, a house, and a nice BMW motorcycle that I’m happy he chooses to ride with me and my motorcycle.


Old News - canon rebel t2i

(Photo credit: @Doug88888)

“It’s Tradition” or “It’s Conventional” Aren’t Answers

That  subtitle says it all.  If approached at the end of my life, when someone asks why I did something or lived a certain way – the only answers I don’t want to give are the unexamined answers:  “It is tradition” or “I gave into societal pressure” or “It was conventional.”   Specifically in the realm of marriage, children, religion and the mundane life of most middle-class Americans.   They say our American Middle Class is disappearing – maybe, but I’m not convinced there is much we should save.

wedding rings

Photo credit: Wikipedia

On marriage:

I don’t believe marriage is for most of us, certainly not me (yet). It’s an archaic institution that has long outgrown it’s purpose, and if you simply look around – you’ll see that we’re not as inclined (as a species) to follow through with it as we once were.  First time marriage has less than a 50% success rate, second time marriages are successful about 33% of the time, and third marriages have a remarkably shitty success rate of 27%.  And for what benefit would one take this risk?  I don’t see much logic in it, until much later in life.  People’s goals, ambition, and focus change – often very quickly and in this day in age “forever” is much longer than it was.  There simply isn’t a compelling reason for it anymore besides Convention and Tradition – and you know how I feel about that.

On children:

I think overpopulation is a real concern and having more than a couple of children at this day in age is either:  a) irresponsible (as in:  I didn’t take the proper precautions and now I have 5 kids) or b) selfish (as in: I love kids and I want them, they make me happy) or c) stupid (as in:  I didn’t think about it)

That get your fur up a little bit?  Well, let me explain.  First – exponential growth is crazy stuff, do some reading or just look at this graph of human population growth:

Graph of Human Population Growth

The graph above can be found here. And the argument that it’s not first-world population growth is bullshit too – a child in the US consumes 66 times the resources that a child in India does.  We may not be growing as rapidly, but our waste and overconsumption is serious stuff. Where are we going to be by 2083?  About 10 BILLION people.  If you’re in the US and reading this, you may not care – but do a bit of traveling and you’ll see the horrible impact we’re having on the environment as humans.  Ever been to a landfill, seen a trash city, or heard about the island of plastic in the Pacific?   Again – forgo the tradition and convention, having more kids isn’t helping anything.


English: World Religions by percentage accordi...

Photo credit: Wikipedia

On organized religion:

I believe it’s a nothing short of a form of mental slavery.  If you really believe in your organized religion, I’d encourage you to think about why.  We all know it’s not logic or scientific discovery that led you there, so what was it? My hypothesis is it’s society/tradition/convention that encourages it.  It’s fairly common knowledge that children are most often persuaded in religious preference by their parents.  And childhood indoctrination is something that people are becoming more and more aware of and against – prominent authors that are critical of it include:  Nicolas Humphrey, Daniel Dennett, Christopher Hitchens, and Richard Dawkins – who argues childhood indoctrination is actually child abuse.

I’m not sure I’m qualified to tell anyone how to raise children or what to believe – but I find freedom, numbers, science, and logic compelling – and it seems like every organized religion I know of has worked very hard to remove those things from their organization.  Even worse – studies show that the more educated and intelligent you are, the less likely you are to believe in organized religion – a foreboding statistic if you also realize the sheer numbers of religious folks.

English: Suburban tract house in California

Photo credit: Wikipedia

On the traditional American middle-class:

It sounds horrible to me.  I’m supposed to relegate myself to some type of indentured servitude, where my masters are children, the economy, a flawed society, some corporation, and some customers.  Have we made all of this technology and all of this progress for this? What’s funny is that we, as Americans, have these “epidemics” that involve things like obesity and prescription drug addiction.  And in true American form, we sue and blame everyone else without taking a hard look inside.  What’s missing from our lives that leaves us with holes that we fill with prescription drugs and fast food? Everything.  Our connection with nature (and the perspective that brings) has suffered noticeably.  Our connection between food and nature and activity has suffered as well – to the point that we, as a culture, criticize people who continue to work to hunt and bring (natural, high-quality) food to the table.  And as hunters we’ve done a shitty job of only hunting for things that we bring home and only shooting what we can/will eat.


But back to the subject:  the traditional, American, middle-class life holds nothing for me.  I not only am uninterested in it, I’m uninterested in the value system it relies on, the consumerism it breeds, and the lack of freedom we end up with by following that route.  Is the dream really to have a mortgage, multiple car payments, two weeks (if you’re lucky) of vacation, no time to pursue hobbies and interests, no time and energy to workout and enjoy nature, and the stress and pressure all of that brings?  If that’s the American Dream, I beg you – let me wake up, it sounds nightmarish.


Like a Bad Dream

Photo credit: Keoni Cabral


Alright Nate – we get it, what’s your point? 


My point is this:  if you’re leading an unexamined life, just going with the flow – I believe you’re cheating yourself.  Examine your life, your belief systems, and your goals – and if that examination leads you away from Tradition or Convention, GOOD.  Convention and Tradition are a trap – break the chains!

Showing the strain

Photo credit: Brian Smithson

“The reasonable man adapts himself to the world; the unreasonable one persists in trying to adapt the world to himself. Therefore all progress depends on the unreasonable man.” – George Bernard Shaw

Convention and Tradition are dead people’s baggage – you don’t need it and you can give it back.  It’s perfectly legitimate, and even noble, to lead a non-traditional, non-conventional life.  In the next two years I’ll be getting off my soapbox and practicing what I preach (with The Nomad Trip) – it won’t be easy, but it will be worth it. Follow me on Twitter, Instagram, Facebook, Google Plus, or subscribe to the blog by clicking here.

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How to Finance Travel

As you may or may not know, I’ve decided to circumnavigate in 2017 and decided to keep a travel blog to document the process.  This post is about how I hope to finance travel (for 5 years).  It’s definitely not going to be easy and it’s definitely going to take some planning and hard work.  But – in the spirit of transparency, I wanted to share what I’ve learned and the avenues that I’m considering.  So, on to how to finance travel:  let’s start with the requirements.

finance travel

(Photo credit: @Doug88888)

Financial Requirements

Here are my financial requirements:

  • Toward the end of 2016 I need $150,000 cash (for the boat)
  • From 2017 on:  I’ll need about $2,000 per month (to be comfortable)
  • If I want internet connectivity (and I do) it’s an additional $1,000 per month
  • Safety net of $5,000 at all times, starting 2017

I plan on sailing about 5 years – the minimum total cash I’ll need is $215,000 for the trip.  Of that I expect to (conservatively) recoup about $90,000 from the sale of the boat when I return.   If I want Internet connectivity the cost increases – it’s $275,000 and the same amount recouped when I return.  Bummer, that’s a boatload of money and a big goal.

To increase the complexity of this – I want to have some appreciating assets to offset the massive expenditure I’m about to have. Once again – a big goal… But I refuse to give up, this is a very first-world problem and can be solved.  So, the question remains – how to finance circumnavigation?


How to Finance Travel – Brainstorming Some Ideas

So I’ve been thinking, and here are my revenue options (that I know of):

  • Start a website that makes money (travel blog, membership, or ?)
  • Record the trip and monetize it somehow (movie, book, podcast, or ?)
  • Allow friends/family to donate (not something I’m fond of)
  • Sell spots to come spearfish with me while I’m traveling (very limited market)
  • Sell partial ownership of the boat to offset the boat expense (iffy on this – partners complicate things)
  • Offer freediving training while I travel (have to become a better diver and it requires planning/coordinating)
  • Use Kickstarter as a means to finance a film series that I promote (I’m going to write about this, I’m open to ideas here)
  • Get trip sponsors from lifestyle companies (Costa Glasses, Riffe Spearguns, or ?)
  • Invest in Real Estate (but that requires a manager, and doesn’t have huge cashflow unless you invest huge $)
  • Start a company and sell it for a bunch of $ within two years (or be able to operate it virtually part-time)

finance travel

(Photo credit: jakeandlindsay)

I’ve started some things….

So far, I’ve taken a couple of steps toward some of the above.  Here’s what I’ve done to date:

  • Started 3 blogs (including this travel blog, and it’s a TON of work) – I’ll link to them soon, I’m switching domains now
  • Started a software company with a co-founder (AutoProjex – don’t judge too harshly, it’s in beta)
  • Been looking hard for a four-plex (the market is really hot here in Austin)
  • Kept my full-time job (but the sheer amount of work is taking its toll)
  • Let one person commit to buy-in on the boat (I’m not sure if I’m going to let anyone else do it)

On those blogs…

  • I have one that I’m centering around business growth (I know enough about this to make a solid start) – I expect to put AdWords on this one and generate a small amount of money from this.  Hopefully a little from affiliates too.
  • I have one that I’m centering around freediving training (I know enough to train any new or mid-level diver) – I expect to gain a following, rank up in SEO and then deliver actual online training via video for a fee (membership).
  • I have this travel blog that I’m centering around my trip, the prep, etc and I hope to be able to document my thoughts and journey well-enough that it’s valuable to a certain audience, some sponsors, or ???

On the software company…

  • We’re creating a way to automate construction management for SMB construction companies (and eventually all contractor-based companies)
  • I expect to work a minimum of 50-70 hours a week on it, and I’ve begun outsourcing some of the work that is time consuming
  • We’re developing it based upon the Lean Methodology, but we have an Ace in the Hole – we have access to some pre-developed project-management software
  • I don’t know what I’m going to do when I leave for the trip – if we survive that long I’ll worry about it then.  Ideally I’ll have my portion of the work down to 10-15 hours/week (when I’m traveling) and when I get back I can work the way I like to work – 70(ish) hour/week sprints.
  • If I can’t do that, I’ll work out someone to replace me in the day-to-day and I can work in the SkunkWorks department when I want to come home and work hard.

On finding sponsorship or creating a series of videos/podcasts…

This is going to be challenging, especially considering my work schedule right now.  But, my thought is that if I can video a big chunk of the trip – including underwater, remote villages, epic spearing/diving – I should have some pretty damned unique content.  I don’t know of a single other person (in the world) that’s doing anything similar – and certainly no travel blog that could compete.  Hopefully the volume of original content will be worthy of some sort of viewership or monetizaton.

A tactic I plan on using here is to invite top-notch freedivers, sailors, adventure travelers, travel bloggers, or spearos out from time-to-time to do interviews and to guest-star.  I work best in a collaborative environment, and I think some of the people I contact will be pretty hard-pressed to say no.

Do I expect this to finance travel?

Short answer:  I have no idea.

Long answer:

  • I expect the software company to be generating a fair amount of revenue by 2017, but it’ll be really dicey the first two years.
  • I expect the combination of all blogs to (hopefully!) generate $1k/month or so – so I can justify having an Internet connection on the boat.
  • I hope to get a couple of sponsors to provide a monthly stipend (how much?) if I include them in my content
  • I hope to use Kickstarter to finance pieces of the trip (by offering as rewards – co-hosting the content, name mentions in content, or even a week on-board in a certain area).  I have no idea if this will work, but it’s a thought.

In case you haven’t noticed, I’m still very much in the “ideation phase” so please – share any ideas you have.  And subscribe to the blog if you want to stay in touch!

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The Bahamas Sailing Adventure (my beta)

bahamas sailing adventure

I call this “my beta” because I wasn’t really sure that I could handle being stuck on a sailboat for more than a week, with the same crew, and be comfortable without being connected to the world.  Good news is “my beta” was an awesome experience, one that I’d like to duplicate for much, much longer -my next adventure is another sailing adventure.

The Plan

Pretty simple – we wanted to get away from the Christmas rush, go somewhere remote, and have a sailing (bareboat) adventure.  Problem was we needed someone much more qualified than I to skipper the boat. I had just the guy; now I needed to convince him to come with us.

deserted island

A typical Bahamas island

This started a long, and relatively stressful period where I told everyone I knew about it and hoped that someone would jump at the chance.  It was like herding cats.  Schedules, budgets, and desires had to be evaluated, then aligned.  Our goal was to keep the entire trip under $2K per person, including airfare (which was pricey).  We managed, but it wasn’t by much.

The Boat

our boat

Ended up being a pretty small Beneteau (“bendy toy” as our captain called it) in order to account for a constantly changing number of crew, everyone’s budgets, and everyone’s comfort.  We rented from a French operation down there – Navtours. I’m happy to report that the boat was in good shape and the Navtours crew were pretty easy to work with.  No complaints here.

The Crew

As with any sailing adventure – our crew grew, then shrunk – got as big as 9, but eventually settled at a modest number:  5.  This was perfect – the captain had plenty of room, and each couple (there were two) shared a berth.  We ended up at 2 girls and 3 guys, an excellent mix.

a room aboard

A room on the boat

After we got firm commitments, I fronted the boat deposit and wrangled everyone into a set timeline.  Then I spent the rest of my time gathering funds (which I hate doing). Then everything was set and we were all scrambling to get the right gear – freediving gear, spices we wanted to cook with, and general boatwear so that everyone was happy during our little sailing adventure.

The spearing gear was a PITA to secure; seems like everyone wanted long, lightweight polespears – but nobody wanted to pay for the Riffe Carbon Pole-Spear (which I really like, but it’s pricey).  So I bought the spears that everyone wanted, and as it turns out, the one thing everyone would complain about.

No worries though – we got it done.

Finally together

It seemed like our sailing adventure got here too quickly, but not nearly fast enough.  I’m convinced that planning a vacation is almost as much fun as the vacation itself (the anticipation!). After a grueling couple of weeks at work for everyone (getting ready to leave for 9 days without communication sucks) – we were off.

Myself, my girlfriend and another couple met at the airport and went through the typical delays and confrontation with TSA as we tried to explain what all the gear was, without using the word “spear” or “spearfishing”.  Our captain is the definition of a “lone-wolf” and we were left to hope that he’d make it there and find the boat.

view from plane

View from plane

We took a small plane from Miami to Nassau and then begin navigating the city to find our harbor and port – without getting shafted by a local taxi driver.  We negotiated a (semi) fair rate, and before we new it we were headed to a marina – the wrong marina.

Finally, there we were – looking at our tiny floating home (for the next 9 days).  I was in a hurry to get under way but our captain (in true form) decided to walk.  So, we waited.  I had my first beer, got the gear on the boat, and we ate our most expensive meal of the trip at the marina.

Big buger

That’s a big burger…

Shopping:  Wow, never shopped like this before.  We bought so much of everything – but it turned out damn near perfect.  After loading up the stuff I wanted, I rolled to my favorite spot – the liquor store.  Beer is expensive, rum is cheap!  Normally this wouldn’t be a problem – but the occasional beer after diving is really, really nice. I bought a little bit of beer and a bunch of red wine and rum.

Since our modus operandi for our sailing adventure was to complicate everything – we decided to stock up on groceries and alcohol without planning our ride back to the marina.  Luckily the locals are forgiving of us, dumb, not-so-great-at-being-self-sufficient tourists.  Other than that, we did keep the tourist thing kinda low-key; nobody wore a fanny pack.

First Days

We were relieved that our captain found our boat and went through the necessary familiarity training and inspection.  That night was a restless one, we spent it at the dock and I was more than ready to be diving and sailing.

under motor

The next morning came and we were off fairly early.  We sailed a little, but mostly we just wanted to get somewhere we could dive.  So we headed to the nearest island, took the dingy out, and found some decent reef. It was surprising to me how hard it was to find a decent spot to dive – but that day I found a couple of holes with fish and snagged my first lobster, snapper and grouper.

snapper, grouper, lobster

Bowl of snapper, grouper, and lobster

The next day was pretty neat – we dove the same spot and we managed to take home lobster, grouper, snapper, and even a decent amberjack.  Note to self: shooting and landing an amberjack with a polespear is noticeably different than landing one with a speargun…

ben with a nassau grouper

Ben with a Nassau Grouper (they match)…

We feasted that night and spend the rest of the night drinking rum and wine and listening to our captain tell stories about his circumnavigation.  We all knew this was a really lame “sailing adventure” compared to an 8-year circumnavigation, and his stories only reinforced that we needed to make this leap… The next stop was a little marina. We explored an island there and found some cool reef to dive on the other side.  That piece of the reef wasn’t very fruitful, but we managed.


Grafitti – island style


big lobster

Big lobster

Over the next few days, the reef ended up being productive for us – we harvested what we needed to eat and did some pretty amazing diving. Dan was the star of the trip, landing a 25 pound black grouper with a tri-tip polespear.  To be clear – this is a hell of a feat.  The tri-tip polespear he was diving with is meant for lionfish shooting (an invasive species), and hadn’t killed anything more than a small snapper. But, that day he managed to sneak up on a grouper (that I couldn’t get close to) and stun him with the tri-tip polespear.  Then he smacked the grouper again, and quickly pulled him to the boat.  In fact, when I caught up with Dan next – his grouper had just regained his senses and Dan was trying to get him into the boat…

big black grouperbig black grouper

A respectable Black Grouper

During this time the highlights included playing with some nurse sharks, seeing (and being a little afraid of) sea turtles with heads bigger than ours, and catching more lobster than I could eat (but everyone else made up for my lacking in this department).

swimming with nurse sharks
Playing with the sharks

Final days

Things never did “wind down”, but we spent some time just hanging out in what are some of the most beautiful parts of the Earth.  In hindsight – if it would have wound down, it wouldn’t have been a sailing adventure. Clear water, cool breezes, and great friends made it a truly amazing experience.

just hagning out

Just hanging…

There was an interesting point; where we had eaten so much lobster (at least twice a day, every day) that we would find them and leave them.  Great problem to have, right? Hell, we were going to go back to port with 1/2 a grouper – it seemed like food was everywhere.  Everything said and done, when we got back to port we had only one fillet left and some snacks – almost perfect planning.  Naturally, our stash of alcohol ran out a little too early – but we were probably better for it.

another big lobster


The only thing I pulled out of the ocean that no one would cook/eat was an octopus.  Only one other crew member was interested in helping me prepare the octopus so I ended up returning it to the ocean – bummer, I really like calamari.

I catch an octupus

It was time to head back to port, and a good portion of the last day we spent running around Nassau.  We even mingled with the brash, annoying cruise-ship travelers for a bit before finding our way back through the more genuine parts of the city.  Speaking of genuine – Nassau, like many other tropical destinations – is littered with fancy storefronts on a single, main drag.  But in the interior – it’s quite poor (maybe even desperate).

cruise lines

Never did we feel threatened, but when we were walking through parts of the town we had police officers slow down and ask us if we were lost… Which is never a great sign.  It may not have meant much, our light skin made us stick out like sore thumbs.

Going home (whatever that means)

Actually getting ready for the flight was less painful than it usually is, but no less sobering.  Our sailing adventure was over.  While we were all fine with returning (the trip had been awesome!), none of us were quite ready to give up the experience.

Bahamas sunset

Special thanks to Ben, Dan, Kristen and Tess – couldn’t have made this happen without an awesome crew.  And thanks for agreeing to come with me, on what is (I hope) our very first sailing adventure in a long string of sailing adventures – stretching all over the world.

I’d like to connect with you – and the easiest way to stay tuned is to subscribe by clicking here.

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big wahoo

Sharks and Big Wahoo – A Spearfishing Trip

Big Wahoo

A typical catch for Jeremy.

Spearfishing big wahoo is still one of the most challenging things I do.  They’re the fastest fish in the ocean, have soft flesh, are beloved by sharks, and make blinding runs after shot.  Landing a monster takes the right gear, a bunch of patience, and some tactics you can only learn with experience.  I’ve made several multi-day trips into some of the best big wahoo hunting area on earth, but every time I’m humbled.

It was a good trip – solid divers, an epic spot, and (finally) a weather window we could head out (over 100 miles) into the Gulf.  Sharks and big wahoo are the norm here and we love it.

Almost everyone had been to the spot, and we had a captain who could regularly put us on big wahoo (check him out here).  There was a new guy, but he seemed solid enough for a run out there – as long as he didn’t freak out when he saw the sharks.  None of us would blame him if he did, we saw hundreds of sharks and big wahoo and usually had a couple of close calls on every run.  It’s not an exaggeration either – hell, a good friend of ours can’t land a wahoo without it being at least partially consumed by sharks (that’s him in both pics).  But I’m getting ahead of myself…

big wahoo

Jeremy feeding the sharks again.

Getting it Together

The plan started about a month in advance with plane tickets purchased from Hawaii and California to Houston.  Everyone arrived at IAH at the same time and we loaded up enough gear to outfit a small spearing army.  I’ve always wondered what other people at the airport thought as they heard us explaining to airline employees what was in our 7ft long, 100lb bag.  Even worse – if you accidentally let slip it’s a “speargun” or that it’s “spearfishing gear.”

Back to the story – we were going spearfishing and our target was big wahoo.  Our friends were here and we were stoked.  Excited talking, catching up, and rough jokes took all of 3 seconds to erupt – we knew we were going to have a crazy trip.  Nobody ever sleeps the night before (except for our captain) and everyone’s up early (again – except for our captain).   So we’re up, everyone get’s their fishing licenses and we head to the marina – cold, tired, but buzzed with excitement.

Big Wahoo
Prepping the boat.

We load a ton of extra fuel, some tanks (in case a fish gets tied up deep), too much processed food, some beer to trade for shrimp – and we’re off.  The trip runs about 6 or 7 hours one way, if we have a good sea and no mechanical issues.  I try to sleep but smashing through the waves and the constant smell of gasoline (from the fuel on the deck) keeps me awake.  We usually arrive sometime in the afternoon and start getting ready to enter the frigid water.  After a couple of passes we find the fish on radar and the first group makes the jump.

The air is so damn cold that none of us want to wet down our wetsuits to get them on, or take off the 3 layers of outer clothing necessary to don said wetsuits.  It’s in the 40’s (not all that cold to some), but there’s wind and we have to get wet to get in the wetsuit.  Without fail, out come the jokes about cold weather and naked dudes, not original – but consistent.  Then we untangle our gear – floatlines, spears, and giant spearguns are strewn all over the deck like some giant’s sewing kit.
Big Wahoo Gear

Too much gear.

Somewhere in the Gulf…

It’s hard to get the currents right – it usually takes a couple of runs to put us on the fish, but we get there. Somebody sees both sharks and big wahoo immediately.  A diver misses a big wahoo pretty quickly, not judging distance correctly and taking a shot that’s out of range.   The new guy is yelling about giant amberjack and we all secretly hope he doesn’t shoot one – it’ll take a few of us to help him get the fish in. Not that we have anything against amberjack (or new guys), but we’re here for wahoo.  And if you’re looking for a recipe for disaster, you don’t have to look much further than a green spearfisherman, a 100lb amberjack, and a bunch of deep-water sharks.

Then it happens;  someone finally sneaks up on a big wahoo and lands a shot.  And when someone has a fish on, you know it right away.  Everyone yells and at least two divers take off after the float skidding across the water (one diver for the wahoo, another to keep the sharks at bay).  There’s a noticeable tension too – it only takes a moment for the sharks to congregate on the fish.  Now it’s a fight to see who lands the fish – the sharks or us.
Big Wahoo Spearfishing

A float skidding across the water – a good sign.

This trip we landed about 2/3 of the wahoo we shot, only giving away 1/3 of our catch to the tax-man (sharks). No problem, we’ve had way worse odds.  Hell, trip before last we were landing only about 1/3 of the wahoo we shot – the tax man was especially unforgiving.  That’s when things get a little dicey too, after the sharks get the first fish they learn quickly.  And after the finish the fish, they’re in a frenzy and you’re the only thing left in the water.

We finish up the day with a couple of big wahoo, all of our limbs, and an amberjack – the new guy couldn’t resist.

Big Amberjack

Damien with the Amberjack we hoped he wouldn’t shoot.

Nights Aboard

That night we head toward the nearest rig, tie up, and put the fuel on deck into the boat.  God it sucks.  It’s cold, we’re exhausted, and we’re hungry – the last thing we want to do before settling in for the night is get covered in fuel.  But it gets done.  Sleep sometimes comes easy – not always though.

There’s the constant tension of being thrown into the rig and waking up stranded in the middle of the Gulf among the wreckage that was your boat. Sometimes it rains, sometimes the smell of fuel lingers, and sometimes the seas pick up and you spend the majority of the night levitating ~ 2 feet off the deck. We sleep (kinda) and then it’s light outside.

offshore sunrise

The sun is a blessing and a curse. It means it’s time to get up and go get underwater (sweet!), but it means we have to leave the (relative) comfort of our beds and put on our wet, freezing wetsuits (major bummer). We finally get moving and stuff our faces with processed, sugar covered, “breakfast food” on the way back to the spot.  There’s no coffee so some of the guys are chugging energy drinks – I’m tempted but I’m also pretty sure that stuff is toxic.

Getting Wet for Big Wahoo

We’re on the spot and now we’re trying to convince ourselves that we should get in the water.  Finally the lure of big wahoo makes someone take the plunge.

Big Wahoo Spearfishing

Putting off getting in.

Freezing.  The water makes it into my wetsuit and I taste salt, I’m awake now and I’m excited about this again. The blue is calming, exciting, and I really feel at home there.  Damn I miss this, I’d do anything to be able to do this more often.  Sharks pass but there’s only mild curiosity.  A couple of small ones make a pass but a quick poke with the speargun changes their mind.  Funny how chickenshit they end up being after the first aggressive pass.

Getting in the Swing

The flashers are dropped and we’re into full hunting mode.

This is the part I love; for the next few hours nothing else matters – not my job, my bills, my dog… Nothing.

My head’s on a constant swivel, and remind myself to turn around completely every now and then.  I’m watching the other divers.  I breath in quickly, but I exhale and make it last until I count to ten.  My heart rate begins to slow and I can see that we’re drifting over the spot, rainbow runners and ocean triggerfish come to meet me at the surface.

Three purge breaths and I’m down – of course we should be alternating divers but there’s only so many dives as we drift over the spot, and our dives are typically 30-40 feet – too easy.

Fish On!

Suddenly they’re here – we have 100ft of visibility but they sneak up on us.  Like a grey ghost, they materialize out of the blue – torpedo shaped and curiously eying us.  Somehow they always surprise me when they do that. 50ft away and there’s a wall of them – all big wahoo, some in the 90-100lb range.  The closest ones glide past and I angle toward them; kicking slowly, reminding myself not point until I’m ready to shoot, and keep closing the gap.  40ft, then 35ft – and my target starts to turn and increases the gap.  I’m almost a minute into the dive and I know contractions are right around the corner.  I see the other divers angling toward the wall of big wahoo and I have a choice:  leave the fish for them or forget my rule (don’t chase fish) and chase them in hopes of closing the gap. I chose the latter and, to my surprise, he let’s me close the gap.  30ft is my max range, and I’m there.

My lungs are screaming and the contractions have started.  I need to close the gap – just a couple more feet.  One more kick… aim… the recoil disrupts my line of sight.  I manage to see steel sticking out of the fish as he screams out of sight.  And on my way up my float line tightens and my float starts moving through the water. Hit.  Damn that was awesome.

big hammerhead shark

The taxman.

The sharks and the school of big wahoo follow myself and a friend as we chase the float; I’m hoping  he can land a shot on another big wahoo while I’m chasing mine.  The chase was short, the shot held, and now my friend takes a dive to check the shot and fend off sharks while I pull the fish to the surface.  In my experience, wahoo make one blistering run and give up – this one was no exception. At the surface we’re greeted by a hungry (big) hammerhead and another of the divers.  The divers circle me, spearguns facing out while the boat hauls ass to get the fish out of the water.


boating a big wahoo

Loading a small wahoo.

With a fish this size and with this amount of chop, getting the fish into the boat can be a challenge – of course, it’s a challenge I’m happy to face any day of the week.  With the big wahoo onboard, it’s time to take over for the guys on the boat and give them a shot at a world record.

We hunted for the rest of the day and then the until noon the following day.  When we finally started the 6 hour ride back in, we’d boated multiple big wahoo (each), tuna, amberjack, and rainbow runner (which we ate on the boat in ceviche). Everyone is tired and happy.  We’re finally bundled back up for the ride home and we all have something to bring home for sushi, ceviche, or the grill.  More than that, we all have an experience we’ll never forget and stories we’ll tell for the rest of our lives.

When I get back I send some pictures of our catch and let people know that I’ll be bringing them fish.  That’s one of the things I enjoy about these trips – I get to provide family and friends with the best fish, fresher than they could ever buy it.

I hope you enjoyed this, it’s one of many, many spearfishing and freediving stories I have.  I’ll occasionally post these, in addition to notes and progress on my trip preparation.

Nathan's big wahoo


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8 Reasons I Want a Catamaran

I’m pretty sure I want a catamaran for my circumnavigation.

The truth is this depends mostly upon budget. Once you have your budget, you then look at your needs, then your wants.

I’m a strong believer that you can circumnavigate in a huge range of vessels.  And that’s not based on my opinion, it’s based on sailors actually circumnavigating on a wide range of vessels.  From this guy who sailed around on a 12 footer to people who have circumnavigated on massive trimarans with full crews (they did it in 48 days, see here).  So what is the minimum size one should consider?  I don’t know.



A friend of mine (pictured above in a local paper) has made a circumnavigation and he sailed on a 46 footer (I think).  I remember him saying that he thought 33ft is a minimum – but not any 33ft:  construction matters.  Some sailboats are made for coastal cruising and some are proven bluewater performers.  Personally, I’m most comfortable on something in the 40ft range (for monohulls).

But I’m actually looking to spend a bunch of time on the boat and I’ve been strongly persuaded by more than one cruiser that a catamaran is the way to go.  I’m pretty sold on it – except that that cost is about 1.75-2X the cost of a regular monohull. So what makes it worth the money to me?

Well, here’s my list:

1.  Catamaran’s are more stable

You spend a bunch of time at anchor (the majority of it) and it really, really makes a difference to be stable at anchor.  Sleeping, eating, entertaining, making coffee, cooking – are all much easier to do when you’re not rolling.  Any good sailor knows this and monohull advocates will tell you that you’re a crappy captain if you anchoring in spot where your rolling.  That may be true, but what’s also true is that there are sometimes limited mooring spots and that waves and weather change.

Equally importantly, while under way catamarans stay upright so walking, making food, keeping beverages upright, and fighting fish (if you’re lucky) are all made significantly easier.

2.  Catamaran’s have a larger salon

I want space to hang out, not in a hull.

Ideally I’d like the galley in that area, as well as some seating, and a bunch of windows.  Something like this (but with more windows – for ventilation in the tropics):


 3.  Catamarans are (often) faster

You’ll certainly hear a spirited debate about this subject if you bring it up among sailors.  Monohull advocates will also remind you about how a catamaran really isn’t a sailor’s vessel.  Cool, I have no problem with that.  I’m choosing sailing because it’s cheap, it’s natural, it’s quiet, and it’s not reliant on fuel.  I couldn’t give a shit what is considered “real sailing” and what isn’t.  From what I’ve read and heard – cats are generally faster, and that’s really important on those long passages.

4.  Catamarans have shallow drafts

This one can be hard to grasp, but it’s really important.  If you have a boat with a 7-8′ draft, you’re in a very different mooring situation than one that has, say – a 4′ draft.  The draft is the distance between the waterline and the bottom of the keel (the lowest spot beneath the waterline) and reflects the shallowest water that a boat can safely navigate in.

A catamaran typically has a very small keel because it doesn’t need the stabilization of a deeper keel necessary in a monohull. Instead, for stabilization under sail it has two hulls.  The types of cats that I’m interested in (38-40ft cruising cats), typically have a 4′ draft – while a comparable monohull would typically have a 6-8′ draft.

Why does this matter?  Because a shallow draft allows catamarans to get to anchoring spots that a comparable monohull wouldn’t be able to – say a really protected, but shallow cove.  And if you’re not interested in protected spots to anchor, a shallow draft still allows you to cruise into much shallower waters (like a really beautiful patch of reef).  Or provide you with a bit of wiggle room if you’re cruising through patchy reef.

5.  Catamarans have more deck space

This gives you many, many advantages including: more room for solar panels, more room for relaxing, more room for moving around your boat, etc.  Think of it this way: if you’re going to live in an apartment for the next 3-4 years, would you prefer a 400 sq ft apartment or a 600 sq ft apartment?  Easy choice, but it costs.

6.  Catamarans have more room for a dingy

Correctly outfitted, you’ll be able to store a larger dingy, and (maybe) more importantly you don’t have to stow the dingy everytime you pick up and move.  Instead, you simply pull it up on a couple of pulleys and you’re off.  This makes a big difference – our last trip on a monohull we spent an inordinate amount of time stowing the outboard and the dingy.

7.  Catamarans have more privacy

Catamarans have a ton more privacy.  Instead of all bunking in the same hull, you can have cabins in entirely seperate hulls. Obviously for short-term trips this isn’t a big deal, but for longer trips small things can really start to grind on you when you’re sleeping just feet (or inches) from everybody else aboard.

8.  Catamarans have two engines

Last, but certainly not least -If shit breaks, and it will – you really want to have two.  Engines are pretty important, even when sailing, and being stuck without an engine is way worse than ending up with a single engine (because you have two on a cat). Pretty straightforward but really important.


With all that considered, here’s what I’m considering – a 38-40ft Lagoon, Leopard, Jaguar, Catana, or Fountaine Pajot.  I’m sure there are more, and if anyone has any suggestions I’m open.  Here’s an example of what I’m looking for:


Disclaimer:  these are my opinions, not based upon personal experience.  My opinions are based instead on advice from others and a ton of reading. I’m probably wrong in part of this, please feel free to correct me.

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life of adventure

Getting Here – A Life of Adventure


First of all, this is a summary of my life to this point.  It’s not exceptional and probably mirrors many other people’s lives – there’s been both tragedy and triumph, adventure and boredom.  I don’t write this because I think I’m special, I’m writing it so those interested souls understand where I’m coming from.
So if you want to know my story, read on.


The Path

I’m a lucky guy.  There’s absolutely no denying it.  As a matter of fact, I’m so lucky that I’ve suffered serious guilt about how lucky I am.

I’ve survived things that other people didn’t, I have a family that’s set me up for success, and people have given me chances in my professional life.  I’ve experienced adventure that I would never be able to describe in words – from freedive spearfishing over a hundred miles offshore, to engaging in firefights outside of Baghdad, Iraq.  From learning to really ride my motorcycle, to sharing some epic diving trips in remote spots with amazing friends.

There’s been no shortage of adrenaline or adventure.  But it wasn’t always like this.

I bore you with an endless list of issues I’ve had, but in summary:  I’ve lost brothers in battle, had romantic interests violently killed, lost family members (most painfully – my father), and endured a variety of failures both personal and professional.

Honestly I don’t do well with failure and throughout the process there have been periods of serious self-doubt that border on depression.  The earth-shattering, soul-crushing kind of self doubt that makes you question every decision you’ve ever made.

Abandoning “my future.”

Early in college a friend died in a Jeep rollover and I stopped caring about college.  They ended up kicking me out on academic probation – apparently final exams are meant to be attended (who knew?).  That failure lead to a shitty manual labor job, living out of a shitty trailer, in a shitty town in Texas.  The level of people I worked with were illegal immigrants (good people) and drug addicts (sometimes good people).

I wasn’t making any money, couldn’t afford my cell phone payments and my student loan payments were beginning to pile up.

Risking my life for a different future.

Eventually I decided to join the military, not really seeing any way out (and it meant I got that adrenaline/adventure fix). I did alright in the military and really enjoyed the camaraderie and the no-bullshit attitude.  What I didn’t enjoy was the lack of real leadership (commanding isn’t leading), insistence on rules, and lack of genuinely motivated and ambitious people (nothing against any of my friends – you were the exception).  Admittedly, I also have a little bit of a problem with authority.

My career essentially ended when I was offered a promotion, and they resorted to telling me I wouldn’t last “in the real world” (meaning being a private citizen). I declined the promotion. The truth is – I was starting to realize that the war my friends and I were fighting was bullshit.  It was ruining our country, drastically increasing our national deficit, and ruining our credibility worldwide. And we weren’t doing any fighting that was satisfying, we essentially drove around waiting to get blown up. Not cool.

I couldn’t bear that level of sacrifice for a cause I didn’t believe in. So I left.

It wasn’t a particularly hard decision, but changing my view of the world was hard. I was coming from a war zone, where everyone was fighting everyday – thousands of miles from their family.  Suddenly I was dropped back into a world full of feelings, caring about people, and sensitivity.  Political correctness had run rampant and it seemed like even the most innocent jokes offended somebody.  I wasn’t a saint nor soft-spoken, but everybody sure did seem overly sensitive.

Adventure Bet

Betting on me.

I quickly found out that you have to work to be awesome in the private sector – there’s serious competition (scattered amongst complete idiots).  So I went back to school – easily made Dean’s list (until I got bored) and worked hard at learning (easy – I love learning). After I finally graduated I found out about Venture Capital, Startups, and Technology Companies and how they can deliver such a staggering amount of wealth to founders and investors.

One of my professors saw a little bit of promise in me and passed my name along to a neat little startup run by some truly passionate people.  There I met friends that I have to this day, and there I also learned alot about how to not manage people, how to deal with difficult personalities, and the in-the-trenches truths about startup life. It was an amazing learning experience and I loved it, but couldn’t wait to get out of it.

Some time in Silicon Valley.

Stanford is expensive and really difficult.  Really expensive and really difficult. I actually had to study and actually had to do homework.  And sometimes, even with a bunch of work I wasn’t excelling – something I really wasn’t used to.  And it turns out I really need friends and colleagues to work through difficult problems, something I was noticeably lacking at Stanford.  Believe it or not, the people I was in class with weren’t on my level.  They weren’t lacking in intelligence, they were all smarter than me – I’m convinced of that.  They just couldn’t talk about some of the deeper things I needed – like: philosophy, the difficulties of working inside of an early stage startup, and the underlying philosophies that had defined life and death decisions (like the ones I faced in Iraq or 100 miles offshore – fighting sharks off of recently speared fish).

My classmates at Stanford were brilliant kids, with brilliant kid worries, and I was 28 wondering what I was doing there.  To complicate things, the classes I was involved in were clearly taught by the B-Team.  Don’t get me wrong – the professors were smart, well connected guys.  But it quickly become clear that my entrepreneurship professor hadn’t ever built a company (believe it or not) and that my comp-sci teachers were overwhelmed by the amount of student requests.

It turns out that Stanford Summer Intensives aren’t my learning style.  Another failure, not in grades, but in real learning.


Home from Adventure

Home, whatever that means.

So I returned home to find out that there weren’t any developers willing to leave their cushy jobs to work with me on developing the “next big thing.”  And it shouldn’t have surprised me – these guys had awesome work environments already, great salaries, and challenging work ahead of them.  And I was an unproven guy without easy access to capital or any real mentorship.

So I ended up taking the advice of others and took a job.  It turns out I was pretty good at the job and actually had a bunch to contribute.  I found that I understood and contributed to sales, sales strategy, and marketing but wasn’t a huge fan of sales as a career.  More importantly, I brought an attitude of getting shit done – and it turns out that’s a really rare thing in the business world.  The business world is full of meetings, and politics, and hot air.  I was able to bypass most of it and operated by being friendly and nice, but frank and proactive.

The banality of home.

Boredom.  The only way I could stay engaged was to push hard at my job – not sleeping much, not working out, staying plugged in all the time, and sacrificing everything but the job.  If I started to enjoy any other part of my life again – I’d find that my work wasn’t important.  That feeling – that what I’m working on isn’t important is something I really, really couldn’t stand.  I was craving risk, adrenaline and adventure again.

So I started a company on the side, with an amazing co-founder and we decided we were going to attack the construction space.  The chance of failure is remarkably high – something to the tune of 90% or more.  But I’ll be goddamned if that’s going to stop me.  At the time of me writing this, things are moving but we so early that any prediction would be foolish.


I had it, but it wasn’t wrapped around what I was doing in my day job. As a matter of fact, the stuff that I was working on (in my day job) was boring by any standard and was only really inspiring as it was a source of learning.  But when I was offshore, sailing, diving, fishing, spearfishing, exploring – I was really in my element.  If I was waiting on a monster wahoo to come in, or fighting off a shark, I was having the time of my life.

And even though I craved adventure,  I wasn’t prepared to make the monetary/professional sacrifice to move to something I enjoyed more.

Another Adventure Event

The Event.

I got a call from my sister, who was working in the Congo.  I had a habit of answering like a complete jackass, we had a great relationship – we laughed alot and  had so much fun that we were actually pretty embarrassing to be around. This one was different though, she was serious and tense – I picked up on it immediately.  Something was really, really wrong. The good news is that she wasn’t crying – so she was relatively composed and her life wasn’t in immediate jeopardy.

I’d prepared for this a million times over, she was in a sketchy situation and I was ready to drop everything, empty a couple of bank accounts, and go over there with the express intent of buying a couple of weapons and finding my sister.   I could operate with the best of them and I really didn’t give a shit – it was a lawless place, the kind I liked…  But that wasn’t it at all.

My Mom had a heart attack.  She was visiting my sister in the Congo when it happened.  Immediate grief and a sudden sinking feeling.

I’d already lost my Dad to work, stress, and a generally unhealthy lifestyle.  I couldn’t lose another parent that way.  The night I received the call, I couldn’t sleep.  I couldn’t do anything.  Completely helpless, I decided I wasn’t going to let work, other people’s opinions, my projects, my desire for wealth, or anything else stand in my way.  I was leaving to go sail and live a pure, simple life and I was taking my Mom with me.

So here I am, ready and (for the first time) willing to give up money and work to practice what I’m going to preach to my Mom – the value of time, following your passions, and experimenting with better ways to live.

If you’ve made it this far, I really appreciate your attention. I hope there was some value in the preceding words, that you’ll subscribe as I share my experience preparing for this transformation, and that you’ll stay with me as I continue to move forward.

I’d like to connect with you – and the easiest way to stay tuned is to subscribe by clicking here.

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