The Funny Thing About Traveling Alone: 50 Connections Along The PCH
There’s something funny that happens when I tell people that I’m traveling alone. A few months ago I was telling my friends about a road trip I was getting ready to take down the Pacific Coast Highway.
Until the point they realize I’m going solo, they’re so excited and fire a dozen questions at me:
“Where are you going? What’re you going to do? How long are you staying?”
And then they ask, “Who are you going with?”
And I say, “No one. “
And then the sequence of questions stops. It’s like they can’t go any further in this conversation until they clarify that I did in fact mean what I just said.
So then they ask the same question in a bunch of different ways:
“You’re not going with anyone?”
“You’re going by yourself?”
“You’re not meeting up with someone when you get there?”
And then even when I patiently repeat myself and confirm that yes, I did just say what I just said, it’s like they don’t even know where else to go in the conversation, they're kind of stuck on this point.
I find it kind of funny after a while because I grow to expect it, but what I’ve found is there are two main concerns behind that awkward stump ini the conversation, two main concerns people have about traveling alone.
The first is a concern around safety. And I get it, in my case, I’m a girl in my twenties, traveling alone, sure, there are some extra things that I need to worry about that a man might not need to have at the top of mind from a safety perspective
But I also travel everywhere alone, even around my own neighborhood. It’s not like I’m going to let that fear keep me from leaving my apartment.
But the second concern is where I believe the root of this resistance comes from. It’s this fear of, “Won't you be lonely?”
And the way they ask that — or, better said as, the way they ask that without actually asking that — makes it seem like they feel bad for me, like I’m doing something so depressing that they feel like they should say how sorry they are for me.
I can always tell that these people have never gone on such a trip.
So I can understand if maybe their idea of traveling alone looks like literally not speaking to or coming into contact with another human being for days at a time, like it’s some kind of silent retreat.
The funny thing is, I would bet that I make more connections on a trip traveling alone than they would if they went with their partner.
It just kind of happens.
So let me tell you about the 50+ connections I made on my 4-day trip down the Pacific Coast Highway.
Some of them, you’ll notice, are with new people I’ve never met before, some are with friends from back home who for one reason or another still present there with me, and some are from people I’ve never actually spoken with. I define a connection in this piece as a moment shared between two beings, a special moment, one that might be utterly insignificant, but still meaningful and memorable, a moment of seeing, and/or being seen.
50 Connections Along the PCH
Lady driving my Lyft: This encounter was memorable because we were in such different mental places at this moment. The woman driving my Uber was so excited to talk about where I was going (I guess when it’s cold in Cleveland, everyone’s looking to vicariously live through you when they hear you’re going to Cali). Meanwhile, I was actually in quite the opposite mood and was just worried about making my flight on time and trying to wrap my mind around whether I forgot anything that I wasn’t anyone pleasant to actually talk to.
TSA agents: I had forgotten that I brought my pepper spray with me, so my baggage set off the alarm to be further screened at security. However, when the agents looked at my bags and looked at me, they passed over it with a minimum of concern. I wonder if this would still be the case if I wasn’t a white girl? (Fun fact: in the course of the whole trip I went on 3 different planes and security checkpoints round trip, and none of them caught my pepper spray. Here’s to feeling safe…)
Ramit Sethi (finance expert and Author of I Will Teach You To Be Rich): No, I didn’t actually meet with Ramit on my trip, but there was a moment his work was alive and consciously there with me. My flight there was a redeye with a connection layover in Las Vegas. It didn’t take me long into the first flight to think back on Ramit Sethi and how he explained what’s the value/cost of things compared with the value of them. In this case, I was hunched over my seat trying to get an ounce of rest and quickly thought of him, and how little “savings” I was actually getting with this cheaper flight.
Las Vegas Airport Staff Lady: I’d done some research on how I was going to survive this layover and actually get some sleep. The secret was going to be this gym at the airport that had a lounge in it with no music playing that I could crash for a few hours. The only thing was, this gym was the hardest thing to find, almost as if they didn’t want anyone to know about it. I asked this one staff lady for directions there, and she was so taken aback by the question, (apparently it’s weird for someone to even know about it, because it’s normally just staff who use it) that she insisted on walking me there. (And it was closed. -_-)
The car rental guy in San Francisco with the broken arm: Once I finally got to San Francisco to pick up my car rental. The checkout guy was telling me how he broke his arm doing some work around the house (however that happens?). He warned me about all the car break ins in San Fran lately and at this point, I trusted him enough to believe the best deal he suggested for the prepaid fuel option.
Muir Woods security person: Upon trying to enter Muir Woods, the parking lot security guy told me how online reservations and parking reservations were needed to get into Muir Woods, which I didn’t plan in advance, thinking I could just do it in person. But I thought, no biggie, I have my phone, I’ll just pull over real quick. Only thing is, there was no reception on that whole hill. The guy advised me to drive all the way to the top of the mountain (10 minute drive) to find service. There was no service. So I drove all the way back, and then he recommended driving all the way to the bottom by the beach. It was super frustrating but I got a kick out of thinking what he must be thinking, literally seeing my car pass back and forth circling this entrance, all because I couldn't find reception.
Staff person at the gay bar: I unknowingly walked right in just as they were closing, and the bouncer unapologetically turned me right around, and gave me that look that said, long night and I’m just trying to get outta here and go home.
Disc jockey playing oldies on radio: It was too late to actually go anywhere else in the city that Thursday night, so I decided to take a drive around downtown San Francisco. The disc jockey on the radio played oldies songs, and there’s one that I fell in love with: Blues Run the Game, by Jackson C. Frank. I ended up finding it on YouTube and playing it on repeat as I drove around that night.
Girl I matched with off one of the apps: We never got to actually meet up, but it was interesting to chat with someone who was also from a super religious background who was finding her way to accept herself as a queer woman.
Nightly check ins with Jen back home: My nightly check in buddy back home! Before I left for my trip, she asked me the most simple, yet profound question, “Why are you taking this trip?” And what I landed on were a couple reminders I wrote to myself for why I was there: Have fun, relax. It's an adventure. Some simple advice for vacation and for life. I’d send her a picture of me with that index card at different places along my journey.
Location Sharing with a different Jen: There was that friend from home who I shared my location with on my phone. “Just in case I die or get kidnapped,” I’d told her. Just knowing she could see where I was made me feel so much safer.
Daniel, celebrating a year since COVID: A year ago I was staying at Daniel’s place when we first heard about social distancing. Crazy to think how the time goes by.
Coworkers: I thought of my coworkers who all thought I was crazy for how I’d said I was afraid to die on my trip. I guess they’d have reason to think I was being a little extreme, but it was a totally valid concern, in my book.
Friend who describes vacation as relaxing: Funny how some people see vacation this way, which I realize is incredibly difficult for me to do. No time for relaxing, there’s just too much adventure and fun to be had!
Phone call from friend: The next morning I was on my way down the coast of Route 1 to officially embark on my road trip. Maybe just an hour outside of San Fran, a friend called me to talk about something, and was saying how bad she felt for “bothering me” on my trip. Meanwhile, the reception was crappy, so I pulled over at the nearest place I could so we could talk, and randomly, I ended up stopping at . It was this magical overlook that honestly was one of the best stops I had on the whole roadtrip. I still don’t know if it was just because of the excitement of it being my first view of the coast, or if it really was the best spot. It doesn't matter. Either way, it was wonderful, I was so giddy, and I wouldn’t have stopped if not for that phone call.
Owners walking their dogs on the beach: This trip was my first time away from Luca solo. Nevermind the emotions of that, that time was a pretty depressing period for me. I hadn’t been able to walk with her in months because of her injuries and recovery from her first surgery, and she was just about to get a second surgery for another torn ACL. When I saw those owners walking their dogs on the beach, it reminded me of how I won’t want to lose sight of what a gift it is to be able to walk my dog.
Friends watching Luca: This made me think of my friends watching Lou, and how they’d been so kind sending updates and photos. I was so afraid that I wouldn't even be able to enjoy my trip because I’d miss her or feel guilty for not taking her. But I can say that both Luca and I definitely enjoyed those couple of days even apart.
Locals at the post office: I make it a point to do postcards whenever I travel. So I stopped at the post office to drop off my postcards and took a photo in front of it. I got so many weird, confused looks from the locals, which was funny. Tourists don't really go to post offices. I do.
Friend who suggested stopping at Montana de Oro: This was a cool way of feeling connected with folks back home. They’d tell me their favorite spot on the highway, and I’d go check it out and explore. There was that one little cliff there that I climbed and only after the fact that I realized that was probably not the safest or smartest decision that I’d made. But I made it up okay, so it was alright.
Coyote at Montana de Oro: I remember the coyote that stared me down like a hawk. And I saw it and it saw me and it knew that I saw it seeing me and I'm sure I was much more afraid than it was.
Woman from Avon Lake in the Big Sur gift shop: This was totally random to meet someone thousands of miles away that is just 20 minutes away from you back home. This woman moved there just for the summer to work at Big Sur, but now she has a boyfriend there in California, and she doesn't know if she wants to move back. She suggested I check out Pfeiffer Beach since I was already so close to it.
Toll booth lady at Pfeiffer Beach: So I went to Pfeiffer beach. There was a parking toll lady to get into the lot, and somehow in the 15 second encounter I had with her, I made a joke that had her rolling as if I said the most hilarious thing ever.
Connor, my rock enthusiast friend: A friend of mine is obsessed with rocks, so I thought of him as building a couple cairns and collecting a few cool striped Cali rocks to send to him for his collection.
My friend who always says “Holy Moly Batman '': So there was a tipi someone made at the beach with sticks, and a Batman action figure standing up against it. This made me think of her. I took a picture to send her.
Fisherfolks and the 10-year-old daughter: There were these fishermen at Pfeiffer beach. They showed me how they dig for these worms (which looked like snakes) and sandcrabs to use as bait. They tried to convince me they weren’t scary by letting me hold one (those things had spikes), to which I screamed nervously. The 10-year-old laughed at me and showed me how it was done by someone who isn’t afraid of snake looking things that move and have spikes.
Hotel check in guy: He told me how he wasn’t going to charge me the $50 security deposit. When I asked why, he said it was because I looked trustworthy. And I wondered if he would have had the same first impression of me if I had been a different race or gender.
The car that passed me: The next day was a long driving day, and I remember this one car who passed me on the one-lane highway. I forgot that we were allowed to do that here, and it totally caught me by surprise. But it made me want to try it too.
The car I wanted to pass but I didn’t: Then I had my moment to pass someone else, and to be honest, I tried really hard, but I couldn’t do it. It was never quite the perfect moment, and then I decided it wasn’t worth all the stress and just stopped trying.
Film star on the side of the road: There was some filming going on as I was driving along Route 1. I remember the actor, dressed in a suit, who looked so unimpressed with the beautiful sight that was surrounding him. I wonder if being so unenthused was part of the scene he was filming, or if he really felt that unimpressed with the view.
Monterey lady at the jewelry booth: There was the lady in Monterey selling her jewelry outside at one of the booths who told me about how much she loved the whale watching trip from one of those local tours, and encouraged me to take advantage of the opportunity.
Dad: There were these cool swords in Monterey that I had to take a picture to send to my dad. He loved them.
Senior couple at the parking lot: They couldn't figure out the parking meter machine and were so stressed out. “Technology!” they said. I helped show them how to use it in just a couple seconds, and they were so incredibly grateful.
Famous Van-life Instagrammer: I could have sworn I saw this woman’s van that I’d followed online. I could be wrong, but it was really cool to feel like I was seeing it in person.
The average person leaving his driveway near Big Sur: I pulled over near Big Sur to take some photos near the side of the road, and there was a hidden driveway with a resident pulling out from their house just then. I waved, they waved back. I wondered if the view got old for them, or if there’s anyway it’s possible for them to still see it the way that I saw it, fresh and eyes-wide, for the first time.
Big Sur Police: A mudslide happened and washed away part of the road through Big Sur just days before I got there. At the end of the highway was a police officer who I tried to convince to let me walk closer to see the actual mudslide area. He didn’t. But he did show me some cool pictures of it and tell me about what happened and how they handled it. There was no detour, just a 45-minute drive back up north to the nearest exit. It was still worth it just to get those photos and talk with him about it.
That one client from work: There was a client that I thought of driving through the hills of Big Sur. The one who guessed where I was going before I could even tell her, but then she couldn't believe that she guessed it.
Rebecca Solnit (Author of Wanderlust: A History of Walking): I listened to this book along my drive, and it was mind boggling to me how much history there was in walking. She talked about people walking hundreds of miles, and I couldn’t help but think of walking the entire Pacific Coast instead of driving it like I was doing.
Mom: At one point I called my mom during my trip and shared something with her that made her laugh. This was a great moment because until then, I just got the vibe that she was a nervous wreck about me traveling alone and that I needed to convince her that I was okay and not to worry. Then in that moment, it actually felt like we were enjoying the trip together.
Venice Beach skaters at sunset: There were the skaters of Venice Beach. And you can tell the comfort that they had that, while I'm here today and viewing them today as if they are my spectacle. This is their backyard that they're in every day. And I am just another person who was here today, gone tomorrow. They were skating and a whole crowd of us was watching until sunset, when the skaters were having a hard time seeing and were about to get ready to leave. Just then, I pulled out my phone and turned on the flashlight to point at the ground in front of me so the skaters could see where they were skating. Moments later, everyone around the park did the same with their phones, illuminating the whole area so the skaters could keep skating and so we could keep watching. It was such a magical moment of us all being in it together.
Girl with the drug dealer boyfriend: As I was watching these skaters, the two girls next to me were talking about the one girl’s drug dealer boyfriend. I remember how funny it was that I couldn't escape overhearing the conversation because I really wanted to see the skaters and there was no other open spot to watch.
Muscle beach fellas: I love muscle beach, and every time I’m there, I’m either the only, or one of just a few girls that are there, which makes us stand out a bit. I don’t mind though. And I always find it funny the looks on those guys’ faces when I whip out a few reps. Next time, I need to muscle up!
Houseless person playing drums in the tent corner: There was someone playing drums in a tent near Muscle beach. I stood by and just listened, because I could understand-- there’s something about drums that takes you away. And I felt like I could relate with that person so much in that moment.
Venice beach gift shop lady: She could tell I needed validation about the shirt I was debating picking out, and she gave it!
Friend who bought me dinner: I asked a friend of mine where he’d suggest stopping to pick up a nice dinner for my final night in town. He recommended Gjusta. I took his suggestion and totally splurged on myself. Then, he asked me to send a pic of the receipt, and he paid for my meal. Even though he wasn’t there, it felt like we had dinner together.
Waiter at Gjusta: Part of that splurging is definitely due to the awesome waiter that was at Gjusta. He helped make recommendations for which smoked fish to try, which I’d never had, and talked up the carrot cake and golden latte enough that I got both of those too. Yes, they were each amazing.
My former boss: Mark would always say how he did his best work at 35,000 feet because there were no distractions, and no one there to bother him. I always find I do my best writing and thinking on plane rides too, so I always think of him.
Baby crying on the plane: When a baby cries on the plane, why is it that no one ever feels sorry for the parents?
The mountains: I really did connect with those mountains while I was there. They kept me company and oh, wow, did they speak to me about all the fear I have that’s holding me back. (I wrote A Promise to the Mountain from this experience.)
Taxi driver back home: There's my taxi cab driver from the airport. A 60-something year old retired guy from Slovenia. Don't ask me how I get all this information in such a short span of time, it just kind of happens. He was sharing his thoughts on the world, about how when he was my age he could sleep for days, but how you don't sleep much when you’re as old as him. He shared some quotes that he said were from Kant and Nietzsche. Then, he said something about “our winter of discontent” that was so beautiful and I said, “Wow, I guess I really need to read up on those philosophers more, huh?” He replied with, “Oh, that was Shakespeare.”
Me: Beyond any of these connections, I connected with myself in new ways. The planner side of myself, the giddiness, the fear, the excitement, the awe, the pull, the tiredness, the setting the day with intention, the not settling, the being deserving part, the splurging part, the explorer part, the not needing to share it to feel good about it part.
Anyway, the next time someone tells you they're traveling alone, don't feel bad for them. They won’t be lonely. Ask them to tell you a story about what happened and who they met along the way. They’re bound to have stories to tell.
That’s the funny thing that happens when you travel alone.