Ten Bad Things Are Going To Happen, And Then You’ll Get There

Illinois Factory
Factories and steel mills span for miles next to the rails in Illinois.

I spend a lot of time planning trips before I set off. Hours and hours are spent checking maps, spreadsheeting what I’m carrying, organizing travel reservations, and obsessing over photos of my destinations.

Mere minutes after I leave, something always goes wrong.

Part of travel, and especially part of independent and extended travel, is the inevitable destruction of your beloved itinerary. Here are my suggestions on learning to “embrace the suck” while traveling at home and abroad.

1. Mother (F———) Nature

When it comes to things beyond your control, few challenges exist as mercilessly as weather. When I visited San Diego for the first time, they had the most rain they’d seen in 5 years. For extended travel, it’s absolutely essential to assume you’ll get the worst weather and allow yourself to be delighted when it (usually) goes better than that.

Don’t sit in your hotel room when it rains. Bring an outfit that stays warm when wet like synthetic sportswear, put on your raincoat, and push on. Some of the most exciting moments I’ve ever had were in the worst conditions, because being able to say “I did it anyways” is a great boost for your morale on good days.

I like to look at weather as a challenge rather than a disruption. When Hurricane Sandy hit the Northeast, Jim and I went bucket-list camping on the highest mountain in Massachusetts, and being in a stone cabin amongst near-freezing temperatures and a constantly howling wind that pushed rain against our faces like needles was one of the best experiences of my life.

Solution: Do Stuff Anyways

2. Things Break

On my tour of the Northeast in 2012, my friends Jimmy and Max both had bikes from the late 1970’s and I had a touring rig from 2011. I spent a lot of the trip stopping into bike shops to get my bike fixed. When we arrived home after 1,500 miles of riding, I tried out Jim’s bike and found his gears to be miserably misaligned and desperate for maintenance. I couldn’t believe it.

“Jim, how do you ride this thing?” Jim just shrugged. It didn’t bother him.

Embracing imperfection is a good way to maintain sanity, whether its with a car on road trips or just the zipper on your suitcase. Take your time finding solutions, and invest to mend problems the right way or avoid them in the first place. Don’t get attached to anything; your travel supplies are a means to an end. When your travel experience is controlled by the frustration of a broken cell phone, you’ve lost.

Solution: Ignore what you can, and never let the things you carry own you.

3. Canceled Flights

I had a plane ticket to Colorado for $99. New York City and Denver were both hub cities for Frontier Airlines and their bike transport fee was $75, far lower than other airlines. I booked 2 weeks in advance for a Saturday at 8AM. I thought I was a plane-booking savant, and I was lucky enough to have a ride to the airport with my Dad.

On Friday, November 1st, a man with an assault rifle shot up Terminal 3 in LA, another hub for Frontier, and my Saturday morning flight to Denver was cancelled. We found out 20 minutes before arriving at LaGuardia, a four hour drive from home.

The lesson I learned is to always plan a backup. Since I had no way to stay in New York overnight and then get a 75lb bike box into the airport alone, we decided to drive back and wait for the next ticket. I wasn’t grounded permanently, but I was in a car for 8 hours without actually getting anywhere. If I had taken a taxi or a bus, I would have been up a real creek. Thanks, Dad.

Solution: Plan for your flight and the 3 flights after it in case of a cancellation.

4. Sickness

I shouldn’t have trusted clam chowder from a bar in Albany. There wasn’t even a sign out front that said “BAR,” just a string of neon beer advertisements. I was there on a train layover with my new friend Mike, a 26 year old carpenter from Connecticut who was starting his life over in Spokane, WA. I didn’t want to look fussy, so I wolfed down clam chowder that looked pre-digested and tasted awful. Five hours later, I’m violently ill and completely motion-sick in a train car in upstate NY, with fifteen hours to go before Chicago.

When you’re facing an illness while traveling, the temptation is to resign yourself to complete misery. These kinds of situations will really test you. The second you feel illness coming on, you need to start making a game-plan.

I let myself rid my body of whatever seafood menace was ravaging my stomach and then found water at the train’s café cart. Despite feeling like I was just going to lose it, I knew dehydration would ruin me the next day, so I slowly forced down sips of water over the next few hours. I drifted in and out of sleep for the rest of the night, picking away at the water bottle until I’d finished it. In the morning, I was over it and back to health.

Take that Tylenol, drink water, eat bananas and oranges, put lime juice in and on everything, and don’t eat anything questionable in content. Trust your instincts. Don’t take chances. If you get motion-sick on flights and trains, eat foods you’re intimately familiar with rather than taking a chance with something new.

Solution: Get yourself better, and take preemptive action.

5. Fatigue

I have to admit, I’ve turned into a little bit of a masochist from cycling. Embracing fatigue in the same way you embrace weather keeps you a lot more positive while traveling, because inevitably, you’ll miscalculate a flight layover or get yourself lost, and your day will get longer by several hours

Decisions get significantly more difficult when you’re tired. Few things are more stressful than wandering unfamiliar places at night, desperate for a hostel or hotel room, surrounded by suburban sprawl and traffic. You can try and mitigate this with good planning (good luck) but a better solution is to keep yourself from looking at the situation negatively, even though every fiber of your being will be screaming against that.

Mantra. Chant one. “This is going to make a great story” is my personal favorite. Get yourself thinking about how great it’ll be on the other side of fatigue, and get through it.

Solution: Visualize your finish line.

6. Bugs

Ah, insects. Universally despised by everyone except entomologists and beekeepers. When we camped in the center of the urban wonderland of Haverhill, MA on a bicycle tour through the Northeast, we were feasted on by mosquitos. They were relentless.

We ate our beans cold and got in our bug-netted hammocks as soon as we stopped. During the night, I leaned a knee against my hammock’s net in my sleep and woke up with thirty or forty centralized bites on it. My knee looked like ground beef and itched for the next four days.

Jim woke up and said “There were three big mosquitos in my hammock, full of blood and trying to get out… I killed them.”

Bugs are going to happen. You’ll find mosquitos everywhere. Foreign countries always have their own variations of the swarm, along with a host of other creatures like snakes, scorpions, and creepy-crawlers. If you try and omit traveling to areas with unsavory wildlife, you’re pretty much limited to skiing.

My advice? A combination of defense and exposure. The DEET is to keep mosquitos at bay, although a bug headnet is a much better chemical-free solution. Even when traveling in summer, bring long pants for bugs. The exposure part is for your fear. I was terrified of bugs when I was a teenager, but enough interactions with them robbed me of the anxiety. When something big and spiky lands on your arm, just brush it off. You can totally scream (I do), but don’t let it get to you.

Solution: Get comfortable with your multi-legged friends.

7. Getting Lost

After I crashed my bike in Montreal, Quebec, it took me four hours to cover about 4 miles of distance. I got lost four times trying to find my way to a shop, eventually giving up and trudging the bike to Marie-Noelle’s house, the WarmShowers.com host I was staying with.

Only 20% of the problem is not getting where you want to go. I find that 80% of the anguish of getting lost is the frustration in the moment itself. Being stuck around industrial parks and auto body shops when you expected to be in a historic tourist-friendly utopia can lead to anger, depression, and self-doubt. It’ll be easy to berate yourself.

Mitigate getting lost with maps. That’s right; paper maps, not your cell phone. Visualizing more than the next left-right-left is a skill that needs to be developed with practice. Nobody is born a boy scout. Practice navigating using a compass and map whenever you’ve got some extra time to kill.

Solution: Channel your inner Magellan and avoid urban areas if you don’t have time to be lost.

8. Money

I’ve done it the wrong way; when something happens that doesn’t fall into your plan, it’s easier to just spend your way out of a problem. Buying a hotel room, a cab ride, a new bike part, or a ticket home is always a potential “last resort” that my inexperienced self would default to long before other alternatives had been exhausted.

It’s important to carry extra cash on you for emergencies, but consider all of your options before shortening your financial freedom with a bail-out. Conserving your money is like extending the amount of time you can spend doing what you want to do, rather than working. A solo traveler that works from the road is essentially trading time for time; getting work done means you can spend more time riding, exploring, and living apart from a major commitment.

Instead of taking an easier path, use difficulties where you could buy your way to safety as trial runs for serious danger. Pretend there’s no cab. Pretend there’s no hotel room. We all want to trek across some untamed wilderness or third world country someday, so why not use somewhere closer to home as a gauntlet?

Solution: Save your pennies, and look for alternatives. It’ll teach you priceless lessons.

9. Commitment

If you want to travel, and you want to do it for more than a week, you’ll need to make a commitment to it. Another paycheck, another bill, another “step” towards a fiscally responsible future is a hard noose to shake, but sometimes, cutting ties is exactly what you need to do for real personal progress.

Commit yourself. Commitment is the sign of a strong individual. The point of commitment is to pick a goal and stick to it. If you treat your trip like you would an anniversary with something unquestionable like a loved one, or a new job, or your mother-in-law at the airport, it stops being ethereal. Commit fully to your trip and stick to it, and don’t let the doubt creeping into your mind keep you from pulling the trigger.

Go ahead. Buy a ticket 4 months in advance. You’ll save a lot of money, but most importantly, you’ll keep your schedule clear so that your trip actually happens. Take “next summer” out of your vocabulary.

Solution: Pick a trip and stick to it.

10. Loneliness

I don’t notice I’m lonely until things get tough. When I’m facing any of the challenges above, being alone seems to double the stress, anxiety, hopelessness, and poor decision-making. There’s no easy answer for this; some people are born socialites, like me, and extended time alone can be tough.

I fight this in two ways. First off, I treat myself with respect. My tendency is to berate myself for mistakes and curse my bad luck when the going gets tough, so I make a concerted effort to cancel that line of thinking. Pretend you’re in a marriage; you can’t divorce your inner self, so learn to love yourself and tolerate your flaws.

Sometimes it’s too easy to hate myself. I’ve lost or forgotten my phone, shoes, sunglasses, tickets, and even a bike helmet while traveling. I challenge you to lose your helmet while on a bike tour. Being nice to myself is hard sometimes, but it’s essential to getting through the tougher days.

Second, I write. I keep a journal of my perspective on the past day every evening. Writing down my thoughts helps me focus on something other than my inward voice for a while. Thinking about what I’ve seen and done and who I’ve met goes a long way towards self-preservation

Solution: Love Thyself

Snowstorm Train

What’s the moral of the story?

Travel is never what you expect. Luckily, you can expect the unexpected, and your best weapon against the hardship of traveling’s worst headaches is the right attitude and the right perspective. You get to dictate how you react to adversity, and doing so with a smile and a bit of humor can turn your worst nightmares into the best experiences of your life.

Sticking to a travel guide and bailing when the going gets rough makes for boring stories. Get out there and embrace the suck.

7 thoughts on “Ten Bad Things Are Going To Happen, And Then You’ll Get There

  1. I was thinking of cycling somewhere for couple of months and your experiences helped me plan better. Keep writing and have yourself a fun trip in Denver!

  2. I’m not sure I agree with #3. As a person who hates planning, I’m lucky to have one plan. No amount of planning will prepare you for the unexpected. I think the solution for #3 should be, “be flexible and enjoy the ride.” Hey, you ultimately got to spend more time with your dad!

    1. That’s a good point. I like “Be Flexible” for everything about touring.

      And yes! It was great spending time with him. He and I have been driving buddies for years.

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