← Part 2: Contribution
Part 4: Iteration →

How to live: Adventure

Play the game?

My good attitude about work and the ASA continued through the year. Along the way though, I started getting the sense that the company wasn't going to continue the exam support. To be a real actuary, you need these exams to get an ASA. We worked in the satellite office, so we were second-class. There were only seven of us there, compared with the dozens at the hub offices in Chicago and New York. Taking a quick break to stretch my legs on the office balcony while studying for the predictive analytics exam, I realized that this might be my one shot at this last exam I needed. The company might not give you the time off to study for another chance. You could get stuck here. You'd better try. (How to live: scare yourself out of complacency with daydreams about dead ends.)

Use a high-vis vest at the office to help others know when it's time to talk.

I was eating some sesame Ezekiel toast one morning when I got the email. Congratulations! I'd done it. I'd made it in time. The company took away all but a token amount of exam support and study time two months later. And they rejected my bid at a transfer to one of the hub offices. Nothing personal, we just can't have people moving from the satellites to the hubs you see. (No, I don't see, but I'll nod anyway as I work out my next move. Working hard has given me ammunition, so I can also say no.)

I was much more interested in participating in the job search after getting my ASA than the one during my summer of despair. This time there was no weird situation to explain away. True that I'd taken a circuitous path here. But at this point I was a solid contributor and I had the shiny ASA. I knew my way around Prophet, even though I'd never aspired to be good with that actuarial software. Slipping away from my desk into conference rooms on the floors of the office where nobody knew me for interview calls felt right. One day I got the chance to sneak out not for a phone call, but for a beer with some of the guys from another company who were in town for their annual meeting. Since I had some clout, the little remorse I had about ducking out calmed down, and I met with them by the pool. A different kind of job -- technical sales. Working remote most of the time, and traveling to do presentations across the country. That would be how to live, but maybe just temporarily as I finished up saving my FIRE fund.

As talk of this scary new "corona virus" started bubbling, I had three job offers to consider. The company could say no to me, but working hard at following the path had given me some symmetry. I also said no.

Leaving felt fine. I respected my boss. But working there was no longer how to live.

The Compound

Covid was ramping up and the office was emptying out. The lease on my apartment had expired, and I'd moved in with Mom so I could keep options open during the job search. Meanwhile, David showed me the vacant 1970s-era singlewide trailer during a tour of his new property. Here's what I could do: Work remote from his place until the job offer at the new place is finalized. Live in the trailer. Shelter from the pandemic and any potential chaos it'll cause, staying away from shared HVAC systems in apartment buildings so I don't get sick. Because who knows how bad it'll be to get covid?

Three months into my first pandemic, I closed one company's laptop for the last time, then opened a new one the next Monday.

It wasn't long into covid when getting ready for work one day, I spontaneously broke down. I barely slowed down going through my morning routine while setting a top-ten record for hardest sobbing of my life. The world is falling apart! But I haven't lived yet! And clearly things are just gonna keep getting worse and worse. This covid thing, this is just a taste of what's to come.

Can you tell yet that I am a paranoid person? I think a lot about the things that can go wrong. When the 2020 protests started getting out of control, I wondered how likely and how soon it would be before people would start being rounded up. Would it take another few years? Would it happen this summer? Pay your reparations, someone would scream at me as four others kick my ribs into my lungs. That's not how to die, but it might happen anyway. Crazy? Well, the Holocaust happened less than a hundred years ago. And society seems to be headed in the wrong direction when you look at it from the wrong angle. Maybe this covid thing is a spark that will make things really ugly.

The new job was fine, by the way.

I started taking walks in the woods behind the house. Hearing about the people in cities trapped in their apartments, I felt grateful that David let me move into a place that had its own little trail. On one of those walks, I heard a podcast with Daniel Schmachtenberger. He validated my concerns about all of the problems we're facing. We're in a bad situation. It's not just covid. It's... everything. But rebuilding the world and trying to fix the problems (even if we don't succeed) is how to live. It'll take all our capacity.

Antsy again

A year into covid now. Closing the distance on financial independence thanks to the lockdown (on my spending), the cheap rent, the good salary, and investment returns. The whole time, I'm getting less interested in my work. I'm not desperate like I was in the summer of despair.

Now I'm feeling two things.

I still want to make a contribution to the world. Not necessarily in that solo way like before. I could be part of a group dedicated to fixing some of the problems that Daniel listed on my forest walk day. Actuarial work at this point is like that of a botanist studying some cool leaves while a forest fire is breaking out a mile away. The world needs you to firefight, even though the leaves are interesting. The leaves need saving. The world needs saving. The world needs you to save it.

Here's the second thing: nihilism. Why bother? It's all probably going to hell anyway. You're just one person. What could you possibly do to help shift the direction of this slow-rolling disaster? Instead of fighting a hopeless battle, have some fun on the way out. Or at least do something more practical than what you're doing now.

You've been into living simply and you've felt deficient in making real things with real utility. So lean into the minihouse build with your friends. If you do that, then you'll get more skills that you'll need to live in one of the many upcoming disaster scenarios.

You felt a spark that time you went deep into reading about life aboard sailboats. The fantasy of sailing away with America in flames behind you off to New Zealand is pretty compelling. (Nothing bad could possibly happen in New Zealand.) So go and learn how to sail.

You've enjoyed rock climbing before. So go and try to get good at it.

Neither contribution nor nihilism involve continuing as an actuary. And the boss is leaving anyway. He's the one that's been holding everything together at work. Now a lot of the responsibility is going to fall on you, but you've spent the last year merely doing... fine, but not getting better. Definitely not enough to be ready for him to be gone. The house build is stalling too because you're not putting enough effort into it.

"Be the change you want to see in the world." I chuckled when I saw the cliche on a sign at the coffee shop while writing another one of those journal entries that ended in the decision to leave stable employment again. I'm not up for helping the world yet though. I'm gonna focus on those couple things that are interesting to me now. I'm gonna finish the fucking drywall that I've been taking so long on so we can put this minihouse build behind us. I'm gonna learn to sail. I'm gonna climb. I'm gonna live, because I'm not sure whether I'll be able to for much longer. Yeah, maybe the forest fire is breaking out. For now, I'm done studying the leaves, and I'm also ignoring the fire. I'm just walking away.


Free once again after acting the actuary role for a few more years. I had been slacking on my part in building the minihouse, but now there's plenty of time. I start showing up at our little home building jobsite more regularly and for longer than before. I move embarrassingly slowly with the drywall work, wondering how bad the mistakes will be. But at least I'm moving. Seeing David move faster on the other parts of the build motivates me to continue. There's not much else to do with my time, so I'd better keep moving.

Eventually, the drywall is nearly finished. Just one thing left. One huge thing. A long day with the texture gun. Up and down the ladder for hours, Mixing mud, filling the hopper, splattering goop everywhere as I aim for the walls and ceiling. Pulling that tight mechanical trigger for hours, asking more of my forearms than ever before. It felt like the only day in my life that I'd actually worked. There were question marks around it before. Would I tap out on this project when it got hard like I did on my failed Habitest? Drywall texture day was a vote in favor of not giving up.

Before drywall though, firmly roll the flashing tape.

Paint, flooring, trim, kitchenette, fixtures, watching the other guys do the more complicated stuff like HVAC and electrical and plumbing. Working with their dad on the siding, wondering what the other timelines with my dad might have been like. Hitting some deadlines, missing and resetting some.

I moved in to the loft even though downstairs was still a construction site.

Then one day, I finished screwing the ladder together on the back deck of the big house. Took the temporary OSHA-disapproved loft ladder and put it away, hanging up the new ladder that I'd made out of three eight-foot studs. And the minihouse was done. (Well, done enough.) Now what?


That whole time, I was also learning how to sail. It started in June 2021, while I was still an actuary. Shirking my work one afternoon in the backyard hammock, I was reading a Bucky Fuller book. One time, I heard that how to live is to do what gives you energy. Oh! Here's something! I'm probably not gonna be a pirate like Bucky here is talking about, but there's always been something drawing me to the water.

The next few weeks were filled with videos and books about sailboats. Then a meetup to join the Sunfish fleet on one of the lakes nearby. Accidentally getting that one-seater Sunfish speeding along on a beam reach felt magic. Then an airbnb in Sanford for a month so that I could be a bike ride away from the Wednesday evening races. I made a 8.5 by 11 sign with a sharpie. Two words: "Need Crew?" 70-something Richard waved me over, and I had a spot in the races for the next few months. Then a weekend course with the U-Sail boat club, eventually renting out the 21 footer by myself. Taking friends out on "my" boat felt great, even though my first time trying to heave-to didn't go according to plan. Took Mom out on a birthday cruise. When some spray came over the high side, she said "wooo!".

Now with the minihouse done, it was time to take this sailing thing a little further than the local lake. I made an account on crewseekers.net. It didn't take long before I was on a zoom call with Captain Lauren. She needed one more person to fill out her crew for her upcoming trip from Key West to Burnt Store Marina in Southwest Florida. "Can you pack light?" she asked. "Hang on a sec," and I darted across the living room of the minihouse to grab my backpack. It's the size bag you'd see any high-schooler carrying. "This is the only bag I took on my two-month trip to Budapest."

Two weeks later, Chelsea and Michelle (the rest of the crew) picked me up from the tiny airport in Key West. We'd finish up supplying the boat, then head out the next morning for two days at sea. My berth on the SV Escape was the table/bed conversion in the salon. I fell asleep that night all sweaty and with a smile on my face.

Copiloting the boat with Michelle at 2:30AM as Chelsea and the Captain each slept down below was a lifetime highlight reel moment. Now free from concern about the storm that fizzled, we watched the moon rise and kept clear of the fish traps.

Joy wells up in me the next morning as we close in on Fort Myers Beach. We're on the same approach that I had taken with my boat mechanic dad when I was 11, 12, 13. He's been gone for over a decade now, and now sailing into the Pink Shell is the closest I've gotten to him in years. Then I have to take a break from laughing in between tears on the foredeck to heave the dinghy we're towing over to the port side. "Use your brute strength!" the Captain shouts from the cockpit. Not something I hear very often.

Docked again, talking with Michelle over tea in the cockpit. How to live? Pursue a life of adventure, like what we're doing now? Or find a way to contribute through some kind of knowledge work? It's a false dichotomy, she points out. Yeah, to ramp up you'll have to make some sacrifices in the short term. But it's possible. (She was living it right in front of me.)

"Matt, you'd do well in Northern California," Chelsea added after joining us. That stuck with me.

But before that... More sailing.

Back to crewseekers. Five more messages. Another videocall, this time with Brooklyn Bob, the 60-something Australian with a scheme to sail from NY to the nearest possible Sydney. (Turns out there's a Sydney in Nova Scotia.) It'd take a week, give or take, at sea with no stops for 1,000 nautical miles at 5 knots. I have no business as his only crew on his two-berth boat given my lack of experience But we ignore that through our excited banter and big smiles on the zoom call.

I pack light again, wearing the recommended boots to the airport to ensure that a backpack is all I need. [Picture of me at the airport with my boots on] Within five minutes of meeting him at the dock in the outskirts of Brooklyn, I hold a fastener in place on the outside of the cockpit's fiberglass as he glues from the other side.

A few days on the water pass. We've gotten into the routine, keeping the boat moving east. Bob makes some fried rice and vegetables. I watch the waves as the autohelm steers the boat. Dolphins swim with the boat for a few minutes. We share dinner in the cockpit, and I breathlessly go through the sound signals I read up on earlier. My turn to clean up, I do the dishes while trying not to slam into the walls as the boat rolls me around down in the salon. I fail, bang my leg on the cabinet, wince, then smile. Could be worse, much worse, so be careful, okay?

Up on the foredeck now, in Bob's spare oilskins to keep me warm and dry. The swell is huge behind the boat. The bow rises and falls slowly and rhythmically into the water with a period of about eight seconds. I smile as gratitude for this adventure washes over me.

Not shown: bruises from my first few times doing dishes while the 27-footer rolls side to side.

I learn from Bob as we go. He teaches me about navigation. He shows me how to navigate around the groups of container ships and fishing boats we sometimes find. He shows me how to tie up the halyards with the special kind of line he uses for them. We tend to the misbehaving bilge pump by manually priming it together. It's frustrating, but it feels like an achievement every time we get it to suck out the gross bilge water. I admire how agile he is, moving with stability on the foredeck to work the lines (like when we need a jibe preventor). Many other 60-somethings have given up on using their bodies like that, but he hasn't. I imagine myself living like him when I'm that age.

(Later in the trip on the phone with Canadian customs, we give our birth dates. Turns out he's 81, not 60-something. Wow.)

We're closing in on St. Peter's Bay, Nova Scotia at 4:30AM, motoring now because the wind has died down. The combo of the scent of pine trees (how can I smell them from this far away?), sleep deprivation, and the sunrise with perfect clouds made me a little teary. Bob described it as he looked up after tying the mainsail to the boom: "Magical."

Three nights of well-earned rest at the marina before we continue for the final short leg to Sydney. He and I laughed as we sped up to a jog on the way to dinner at the Bras d'Or Lake Inn. We weren't going to miss it twice in a row.

The fun from the trip to the restaurant fades as the dinner conversation gets tense. Bob is annoyed with my ambivalence about how to live. He wants the best for me, but it seems to him that I'm not on the path to get it. I turn from the window overlooking the lake back to him, and his eyes bore into me. "Matt, get off the fence and make a decision about what to do. Otherwise you risk wasting your life." I'm silent for four seconds as we hold eye contact. "Bob, you're right."

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Part 4: Iteration →