Adventure, Sea Kayaking, The Great Adventure, Travel

What I Fear Most About The Kayak Trip

Photo by Éole Wind.

When I get to Texas I will give up the bicycle and switch to boat. Every leg of my Adventure must be powered by my own body, and the Gulf of Mexico will be done paddling.

Here is what I fear most about the kayak trip.

  1. Running out of water. The first 200 miles after crossing into Mexican waters there will be no one. The first town is Tampico and until we reach that there’s nothing but deserted coastline. Not even farms. I always wondered about that on maps and now a more experienced kayaker has confirmed it. 200 miles could easily be 8-12 days of paddling and it will likely be the toughest part of the whole trip. Obviously, being alone heightens the risk in many ways but the most urgent one is water: we have to bring our own and ration carefully, with nowhere to take on more fresh water on the way.
  2. An accident. People have so many fears for me on this trip such as hurricanes, storms and cartels. We won’t be out in hurricane season, we will stay ashore if there are severe storms and the cartels just aren’t known for preying on kayakers. But every morning we are going to have to paddle fiercely to break through the surf and get out to sea, and every evening we will have to ride big waves back to shore like surfers. There’s so much potential for something to go wrong during these crucial, wind buffeted times—especially with rocky shores. It’s a matter of training and experience, knowing how to handle your kayak, but the training curve is steep.
  3. Personality conflict. This is the first leg of the Adventure where I’ll have co-adventurers and the idea of companionship sounds great. I’ve also been warned, and seen firsthand, how friendships can suffer under extreme stress. We will be living off rations, physically exhausted with daily discomfort and dangers. That makes people mentally tired and grumpy. Little things become big things. Everyone will look to me as the expedition organizer to keep things together. Will we get along?

These fears don’t hold me back. To me, fear is something to give you consideration: it says here are the issues you need to address. Right now is the time to make plans and preparations so that these risks will be minimized. We will learn to deal.

What I Want Most

Despite the above I look forward to this trip with happy excitement. There are many things I look forward to: days at the beach training, the thrill of riding a wave, paddling into small fishing towns, eating street food after dark, seeing dolphins leap beside me.

It will be good.

But of all the things I hope to see and experience on this trip, there’s only one thing I want the most:


I believe adventure is a life-changing practice, and I want to share it with others. There must be more people out there who have the bold or reckless spirit to commit themselves to the journey; who have a quest without, perhaps, a cause. How many times I’ve experienced great joy (or hardship) in private moments on the road—and wouldn’t the joys be sharper, the hardship lighter, with strong-hearted companions?

To adventure is not to find heaven, but to discover earth; it is to fall in love with our fickle, wonderful world and her many highs and lows.

I’d like to meet the kind of soul that takes a chance on the love affair.

Right now there are two individuals tentatively planning on joining me. That makes three of us putting paddles in the water this winter, three of us crossing the face of the sacred earth.

I wonder if there are more of us.

If you’re interested in joining the Adventure you should email me. We’re training in Corpus Christi, Texas this fall, then paddling 1,000 miles to Coatzacoalcos, Mexico. Interested? Email me at [email info removed—adventure is over!] Not sure yet? More information here

Please tell others.

Personal Development

I was afraid and I kissed her

She looked out the window and I was scared. We had flirted good and well but she doesn’t date co-workers. Here we were in her apartment, the pot smoke thick, the small talk thin.

She was stoned but she knew what she was doing. Come see the view on the porch. Winter in Minneapolis. Balconies aren’t for winter, they’re for summer and trapping boys.

So the question: do I kiss her and how? Every man knows this moment. She did her part and led you somewhere you can make a move, because she’s into you. Or maybe she’s not into you, so why are you on her porch? Because she actually shows guests the view in winter.

What if you kiss her and you weren’t supposed to? Then are you a rapist? Rapists are the worst! Or will it be like a sitcom and you’ll both make an excuse to get out of there and then you’re friends for two seasons and then you elope.

There is no one to tell you what to do and the clues are a joke. You just have to move.

So I moved.

We ran out of conversation and I pushed her against the wall and looked her in the eyes and our lips were together. It probably seemed very romantic and confident because I moved slow. But I moved slow because I was afraid.

She moved with me. She kissed back. Then we were kissing, we worked together on that kiss.

“Fulfilment,” Gustav Klimt

Balconies aren’t for winter and I was already caught, so we moved inside. There was a couch, the floor, some other furniture. I told her in advance that I didn’t want a relationship, because I’m a gentleman and that’s what gentlemen do in the age of liberation. She might have stopped, but I was no longer afraid. The chemistry was proven, she was in it just like I was.

(Fun fact: There are three types of women who don’t date coworkers, and all three of them will date a coworker.)

That time it worked out. Other times I failed. I went for the kiss once in Mexico and she jumped away like I had teeth mites. It’s not the rejection, it’s the uncertainty—the sense that you should know.

Most men hate this moment. I used to hate it. Because no one is going to tell you what to do, and it’s safer just to be be lonely and sad. Lonely is free. No one fails at lonely.

I don’t know if women have this same moment. Actually that’s not true—I know lesbians sometimes do, because I sort of lived with one and he had game. (He later transitioned to being male.) He had way better game than me. People don’t exactly go to bed at night wishing they’ll wake up as a trans boy—most trans boys don’t wish that—but if it came with game like that I would consider the offer.

But woman, man, trans, any human being has these moments. It might not be the kiss. It might be demanding a promotion or some respect. It might be anything.

You want to make a move and you’re scared as hell. You don’t know which choice will rip your heart out and eat it faster. No one can tell you what to do because they’re scared too.

Everybody wants to know how they can adventure without leaving their home town. There are a million ways to adventure and it starts with moments like this. Adventure doesn’t come knocking, the wizard doesn’t put a mark on your door, I’m sorry. It starts when you say it starts.

Here is the good news.

Every single time you move it gets easier.

That’s what I’ve learned. Any given time you make a move you might fail. But every time you make a move, the next move is easier.

Ask for a promotion and it’s easier to be the only one dancing. Whisper “Do you want to fuck?” and it’s easier to ask for a promotion. Sometimes you’ll fail but soon you’ll fail with grace. People dig grace. They come back to the graceful.

(What happened with the Mexican woman? We became friends. She wrote me a really nice note during the holidays last month. I tried to respond in Spanish. She once apologized for being “so rude” that night, which is very Mexicana of her. You don’t have to apologize for not kissing people.)

Good things don’t come to those who wait, good things come to those who tear through stacks of bad things like it’s a box of Cap’n Crunch looking for the prize at the bottom.

Push someone against the wall and kiss them.


This is What Fear Smells Like

Sometimes I wish my mother was more like Alexander the Great’s mother. His mom put his confidence above his mental health or the wellbeing of anyone in their kingdom. She told him he was a demigod and couldn’t possibly do wrong. I’m sure this is a great way to completely imbalance your kid and give them crippling social problems… but virtually everyone I know has crippling social problems anyway, so why not make it the fun ones.

My parents have always supported my choices, but it’s sort of a resigned support. They are not partners or advocates for anything I do: it just doesn’t make sense to them. Same thing for my sister’s big plans. So they tell us they are proud and wish us well on our crazy quests, and then we go off and do them.

I don’t really wish my Mom was any different. With all the broken homes and angry parents in the world, our little family came out alright. But I think we’re all of us handicapped in fearlessness. The level of anxiety and fear that people have in the 21st century does not correspond at all to the level of risk and pain that most of us face. We could use some Queen Olympia.

A certain level of fear is bred into us. The history of human development has been a shift toward more obedience, more settlement, more acceptance of authority. Biochemistry isn’t possible for nomads. All those centuries of sanctioning a settled, lawful lifestyle allowed us to make advances, but it comes with some debt to pay off.

Here’s what I thought I was afraid of. Starting two months ago I became terrified of my own Adventure. The whole plan began to seem overwhelming and completely crazy. I enjoyed being with my family and visiting longtime friends. I started to think I made a mistake.

I began to cling to my (temporary) settled lifestyle.

This always gets me. I have a soft spot for comfort and security. There are a lot of reasons I had a half-hearted marriage for three years, but it could all be summed up pretty well as “Drew really wanted to be married.” (I also blame the tequila, but still.) The reason I owned a house was similar.

So I always perceived a tension between my desire to adventure and my lust for security. That tension came to its boiling point in April. The reality of traveling through the Americas—danger, cost and discomfort—became my nightmare.

I did what I usually do. I dug in. I spent more and more time at home, reading, working and planning. I turned down options to go do fun and amazing things because I had to work harder to be as ready as possible.

Then I went on my kayaking trip. I didn’t want to go on the kayaking trip—sure I love Mitch, and I love the outdoors, but I had work to do! How could I give up a whole week and a couple hundred dollars when I had work to do?

Pretty easily.

A good policy I’ve learned: when you have an opportunity to do something unique, take it. So I went kayaking on Lake Superior. With someone I’d never met. And no money.


All the tension, fear and worry I’d been feeling melted away—not  just in the moment, as tends to happen on holiday, but completely. Even after returning home, and to this day, I feel a total calm about my impending journey.

Even though we’re bred to crave a settled, secure lifestyle, that is not who we evolved to be. From inside my little reliable box the Adventure was a dangerous, terrifying thing. It was easy to write it off and pull back from it. 8,000 years of Emperors told us to want houses, money and jobs. Traveling free spirits tend to get the stocks.

But when you explore, the horizon changes. Before the emperors were 500,000 years of walking wherever the hell you wanted to walk, of facing down predators with very little backup, of fucking and sleeping in the sun. That’s all we really want, and it’s the one thing Amazon can’t sell you.

Security makes us afraid. You can only fear what’s outside if you’re inside.

The whole time I was tense and afraid, I thought it was because of my Adventure. But it wasn’t. It was lack of adventure—it was four walls and a refrigerator that gave me something to fear.

What do you fear?

The Great Adventure

The Crisis Moment Before the Trip

Terror has struck. I knew it would happen sometime, turned out to be now. I’ve been so excited about the idea of my trip, I don’t spend much time thinking about the reality of it. But now I’m on the edge.

This week I took three days to literally lock myself in my room and work. I have a list the size of a painting of things to do before I go on the Adventure. I thought I would just lock out all distractions and work for a few days.

The problem with locking out all distractions is… you lock out all distractions. 

You need those distractions to keep yourself sane. Most people need to be distracted (Netflix, Facebook, video games) so that they don’t think about how they’re not living their passion. But what if you’ve decided, eff that noise, I’m going to go out and wrestle my dream down? Do you get a free pass?


If you’re wrestling your dream you’re doing the scariest thing: standing out, taking risk, trying the path that no one else has tried. You’re in the unknown, and suddenly you’re the only one responsible for how well you do. Then the questions start to come.

The first night it was worries about finances. Can I pay for all my gear, manage my monthly bills, and afford health care while I travel? What if I lose a client? What if I can’t put in the hours online while I hike?

This was a pretty big anxiety pill. But it was only the beginning. 

What Are You Doing?

The second day I got to a long-overdue item: contact consulates. A clever reader once suggested (thank you!) that I ask for letters of safe passage from each country. These letters are 0% likely to actually guarantee safety. But if I’m dealing with local authorities, an official seal and signature can be useful.

So Mexico… Belize… Guatemala… one by one I looked up each country. In addition to consulates I checked their visa requirements, how long I can be there, etc. The State department has lots of this info. And right next to it is the safety warning.


This is some truly horrible stuff folks. Have a look for yourself. None of this is new information to me, but reading it all in black and white—five weeks till showtime—has an effect.


I’m not going to lie. Here are some of the thoughts I had:

  • I don’t want to go.
  • The trip I planned isn’t possible.
  • I can’t afford this.
  • Do I even still feel passion about this? Is it really my dream?


I was so overwhelmed with doubts I had to lie down. I asked myself if I’ve ever been this panicked about something before. At first I thought the answer was no.


I remembered two times I felt this way. The first was the premiere night of the Stone Circle Study. I sat in a freezing, wet tent and knew I had seven weeks ahead of me, plus two people to look out for. The second time was at Teaching Drum school. It was so much harder than I thought it would be. Every day I wanted to back out and go home.

This running-away-terror, this inner rebellion, is something I know. I faced it those two times and persisted. The question is: was it worth it?

I thought about that.

Both of those times turned out to be pivotal moments. Moments that are more than memories, they inform who I am. There would be no Rogue Priest, no Drew Jacob—not as I know him—if I had gone home.

So, I decided, I’ll go forward.

Today I spent an hour in meditation. When I finished my meditation, I was at peace with my self-construed fate. At the end I heard this statement:

Your only duty is to live your personal legend.

All I know is I want to be the guy who met the gods. I can quit my walk at any time. But I have to at least start it.

Join the Adventure—Support the Walk!

If you enjoy reading Rogue Priest, believe in my journey, or just love seeing a spirited adventurer on the road, please consider making a donation to the cause. Your gift will help fund professional-quality equipment for the Great Adventure. It’ll keep me safe and help every step of the way.