The Imperfect Spontaneous Trip (Liveblog)

“I’ve made a huge mistake.”

The craziest part of this spontaneous trip was that I spontaneously moved to Portland a month later! It literally changed the course of my life. Here’s how it went down.

WEDNESDAY, Nov 5th 8 PM (EST) 

Have you ever thought, “what if I just packed my bags right now and went somewhere?” I’ve had that thought quite often, and this time, I’m pulling the trigger and I’m (digitally) bringing you along with me! 

I’m going to Portland tomorrow and staying for one week.

…but I shouldn’t. Interestingly, this spontaneous trip has a high chance of failure. Here’s why I might be making a mistake…

Reasons I Should NOT Go (Imperfections)

  • I decided to go tonight at 8 PM on a whim; my flight leaves at 5:30 AM tomorrow. That’s EIGHT HOURS notice before I have to leave for a one week spontaneous trip across the country (Jacksonville, FL to Portland, OR). 
  • I returned from LA three days ago and I’m still tired from that trip. My only pair of jeans still has LA dirt on them (that is not a euphemism, haha, it’s literal dirt!).
  • I’m flying standby and we’re approaching the holiday season. Standby travelers only get on the plane if there are empty seats, so I risk not making my flights and getting stuck in one of the airports. Even if I make my flights to Portland, I might have trouble getting back, which means some brutal sleepless airport nights. It could even end in me buying an expensive flight home out of desperation.
  • The flights don’t even look good. There’s maybe a coinflip chance of making it through on standby tomorrow. An airport sleepover looms large.
  • I’ll be stuck in Portland for Thanksgiving? It’s possible. It’s a risk I’m taking.  
  • I don’t have warm clothing, I have Florida clothing.
  • I want to finish my book on imperfectionism before the year’s end. Traveling around with intermittent wifi is not ideal for that!
  • I don’t know where I’m going to stay yet. I made sure to commit before I even looked at places to stay. I’ll be looking for a hostel somewhere in the city center.
  • I’m not mentally prepared to go across the continent again and deal with the logistics of travel.
  • I just bought groceries today! Poor avocados…
  • A stray cat could bite me at any point in the journey. Loose cats on a plane?
  • I have two phone meetings tomorrow.
  • I have to get up at (freaking) 3:30 AM to make my flight.

But here’s the thing…

I’m writing my next book on how to be an imperfectionist, and the core idea behind the book—something I really believe in—is that when we take decisive action toward something good, its value can overcome a slew of imperfections that surround that choice. This trip is unplanned, I’m unprepared, I haven’t done research on visiting Portland, and the situation is simply ripe for something to go wrong. It’s the most imperfect trip I’ve ever dared to take, so it will be interesting to see how it turns out!

There Are Reasons To Go, Too

  • Problem-solving exercise: Suddenly, I have a lot of details to work out, and it will be a good exercise for thinking on my feet and doing my best to make this spontaneous trip a non-catastrophe. I’ll be live-blogging it on this page so you can see how it goes!
  • Proof-of-concept for my upcoming book: I’m excited to test out the entire premise of my book. If the spontaneous trip goes horribly, it won’t discredit the book, because I may gain even more that way. Just like muscles, we grow by overcoming resistance. Whatever happens, I’m going to learn something.
  • Comfort zone explosion: Suddenly, I don’t have a bed tomorrow. That’s not very comforting! But I’ll find one, even if it means contorting my body around airport chair armrests.
  • See Portland! Yes! I’m most excited to see the city’s walkability and public transportation (I like the idea of being carless, so I may move there one day if I like it), and of course, the food. 
  • Demonstrating my power of choice: I like doing things like this because I’m proving to myself that I can and will break my own rules. It’s good to surprise yourself because it expands your belief in what you can do.
  • Instant memory: I’m never going to forget the night I decided to spend a week in Portland on the whimmiest whim ever.
  • Traveling is a top priority for me, so this is great. Traveling, however, is not urgent like doing laundry or eating groceries before they spoil. This is a good example of making it urgent by sacrificing other urgent tasks in order to do it. 

That’s it for the introduction. I’ve got some work to do! I’ll be updating this page so you can join me in my travels! I’ll likely include some pictures too!

9:37 PM (EST) 

Flight: Booked

Airport Parking: Booked

Hostel: I called the hostel as their site showed no availability. Luckily, there was some availability when I called! I’ve booked all days but Saturday, which was filled up. I’ll have to find a place to stay Saturday and then come back to the hostel for the last three days. It’s not perfect, but that’s the theme of this spontaneous trip anyway, right?

10:14 PM (EST) 

Now that I’m all booked, I’m feeling proud of myself for doing this. This is how imperfect action is—at first it seems crazy, but once you dive in, regret is rare because you’ll realize how much imperfect forward motion beats passive living. I have to pack now.

11:37 PM (EST) 

I’m packed now. I should get 3.5 hours of sleep. I’m super excited! We’ll see if that lasts when I get to the airport and think, “Here again?” (Actually, I love airports, so it might be more like, “Here! Again!”)

11:45 PM (EST) 

Goodnight! 🙂


6:52 AM (EST) 

Are you kidding me?

As I got in my car to go to the airport this morning, I quickly punched in the address for airport parking into my phone. It had trouble loading, so I reset it. I reset it again and again, but something was wrong. Meanwhile, I was desperately trying to remember how to get to there by memory, because my phone had no internet, no maps, and not even a phone function. This was with the phone showing full bars on 4G!

Of all the things to go wrong, it was my cell phone, which had not had a single similar problem in the many months I’ve owned it.

I nearly canceled the spontaneous trip then and there, as my phone (with internet) is how I access my reservations and how I get around (with Google maps). And I wouldn’t even be able to call the parking service to pick me up from the airport when I got back. 

But in the spirit of this spontaneous trip, I decided to go anyway and figure out how to make it without a working cell phone. People used to not have the luxury of cell phones. Some of them managed, right?

After making a few wrong turns and freaking out a little bit at my dwindling time cushion, I did find my destination later than desired. The shuttled dropped me off at the airport 35-40 minutes prior to takeoff, which sounds fine, except that standby travelers have to check in 30 minutes prior to the flight or else they can’t fly! I had only a few minutes to spare when my ticket was printed.

I easily made this first flight. There were 60 empty seats. And as I sat on the plane, I tried the internet one more time, and for the first time since last night, the internet worked! That was a special moment. After all of the unexpected drama, I was on my first flight and my phone was working fine.

Now I’m trying to figure out how to get to Portland, OR today. The flights look iffy; I might have to get creative. I’m going to try going through Seattle first. If not that, perhaps Minnesota or a 3 flight jaunt that begins with Salt Lake City. 

8:07 AM (EST) 

Missed Seattle. Doh.

3:09 PM (PST) 

Well, I made it. I type this in The Northwest Portland hostel, located right in the heart of Portland.

I worked with a kind flight attendant to figure out that Minnesota gave me the best chance to make my flights. And sure enough, I made my flights and arrived in Portland at 1 PM Pacific. This was a resounding success since I had counted on sleeping in the airport!

Part of the reason I came here was to check out their public transit. I’m interested in the carless lifestyle. I was pretty impressed with the MAX light rail—it was $2.50 for a 2 hour ticket all the way up to $26 if you wanted a 7 day ticket (or $1,100 for a full year pass). Being carless here—which seems absolutely possible—would save a huge amount of money over owning a car. I could go on a rant here about how many hidden vehicle costs there are, but nobody wants to read that.

3:55 PM (PST) 

Another reason I wanted to come here was the food, and so far, my high expectations have been blown out of the water. The first thing I did was visit a “healthy fast food” place called Freshii, and got a delicious bowl of rice, quinoa, steak, pico de gallo, black beans, and other stuff. This is the type of place that’s hard to find in Jacksonville Beach, FL (my current place of residence). 


While that was great, it wasn’t mind blowing or anything. But what I saw next was! Food carts.


I’ll have to get a better picture than the one shown here, but there were about 30-50+ food carts all in a row. Yeah, that many. You could get food of the following types: German, Thai (I saw several Thai carts, and Thai curry is my favorite food), Mediterranean, Indian, Polish, Vietnamese, Hawaiian, Brazilian, and more. And these are all in the same place! For a lover of good, simple food of varying types, this is unbeatable. I want to park a cart there and sleep, so I can wake up and eat at these places.

Disclaimer: I haven’t tried the food from the carts yet, but I bet it’s good. CNN declared Portland the world’s best street food, after all.

5:56 PM (PST) 

I’m going to an “art walk” now with the hostel folks. I’m not really into art unless it’s beautiful nature drawings, but they said a key phrase: “free food.”

FRIDAY, Nov 7th 10:33 AM (PST) 

Hostels are great. 

The art walk was pretty fun. The first few didn’t have much food other than a basket of clementines. But then we went to two in a row that served us free wine and cheese! Oh, right. The art? I’m not very artsy, so a lot of it was boring for me. I thought these were kind of interesting:


What I did enjoy was talking to two guys from New Zealand. This trip was their first time in the USA, and they said it seems similar to New Zealand so far (but that Canada is even more similar). I’ve always wanted to visit New Zealand, so I asked them a lot of questions. Also, one of my favorite shows is “The Flight Of The Conchords,” which is about two New Zealand guys who go to New York and try to make it as a band. One of the guys said “yiss” in the same way that Jemaine on the show does. It was awesome!

11:17 AM (PST)

One reason I love hostels is because of the diversity of people you meet. I’ve been talking to Richard from Scotland for a while and now a guy from Australia. If you’re traveling solo especially, go to a hostel. The atmosphere and culture of hostels makes it really easy to meet and socialize with people.

Anyway, last night ended with a burger and beer with a guy who retired here. I got back at 11 PM (PST), so I had been running and awake for almost 24 hours. That always results in amazing sleep for me (this despite sleeping in a room with two guys I’ll nickname “The Snorlax Brothers”).

 11:25 AM (PST)

Two guys—a Scot and Australian—who know a lot more about history and politics than I do are talking world politics next to me. It’s pretty interesting. Since I’m a member of the Apathetic political party, I think I’m going to go head to downtown now and see where the wind takes me. Ciao! 

 11:11 PM (PST)

Whew. That was a tiresome 12 hours. I went with an Australian guy to the Japanese Gardens nearby. It was pretty stunning (pictures below), good conversation, and a lot of walking.


Then we went to the food carts. I started with a lamb gyro and then got pumpkin curry (I was hungry). These food carts are amazing! Spontaneous trip success!

$5 gyro from a food cart (it was authentic and delicious!)
My $5 gyro from a food cart (it was authentic and delicious!)

Immediately after we got back at 4 PM, a group from the hostel was going out for happy hour drinks and we joined them. The next 7 hours were a fun combination of beer, mixed drinks, sushi, and ice cream. There’s an ice cream place here with a line going out into the street called “salt and straw” with ridiculous ice cream flavors. I sampled “turkey.” Yeah. Turkey ice cream. I ending up ordering the pumpkin pie instead.

So I’ve met a lot of interesting and cool people so far, and it’s weird to think I could be at home right now, but chose to do something a bit crazy. I could get used to this sort of thing. I like Portland, but honestly, I was in love the instant I saw those food carts. 

SATURDAY, Nov 8th 10:45 AM (PST) 

It was a decent night of sleep despite the rampant snoring around me. Before I went to sleep, I met my bunkmate Tom, a 68-year-old expat with the hair of a rockstar living in Argentina. We talked about books and traveling for a while. 

When you travel, you’ll see there are other travelers constantly on the move. Right when you think you’re well traveled, you meet someone who has been everywhere. But it’s not about how many places you see, it’s about how the experience and culture changes you. And this meshes well with Mark Twain’s famous quote (my favorite quote ever):

“Travel is fatal to prejudice, bigotry, and narrow-mindedness, and many of our people need it sorely on these accounts. Broad, wholesome, charitable views of men and things cannot be acquired by vegetating in one little corner of the earth all one’s lifetime.” ~ Mark Twain

One thing I struggle with is social cynicism, and that is especially the case with typical “hangout” activities (i.e. drinking at bars). I enjoy alcohol, but I struggle to join in on the “let’s get hammered together” way of thinking. I don’t see this as a bad thing, as alcohol is a mild toxin, depressant, and impairer of judgment. Wow, I must sound like the life of the party now… 🙂

I had 3 beers, 14 pieces of sushi, and 2 gin/tonics over a period of 7 hours last night. It was a great time that included interesting, fun conversation. But underneath the fun was cynical person who wondered why we we’re playing shuffleboard as a drinking game instead of actually keeping score. Drinking games are a strange social ritual to bring a group closer through forced mutual drinking. It bothers me some because the point of drinking games is to give up control over how much you drink. 

I’m just being transparent about my inner Debbie Downer. I enjoyed myself very much, and that’s why I think my inner critic may be wrong. Connecting with people is significant, and if a ridiculous drinking game helps to achieve that, then perhaps it shouldn’t be judged by it’s “bare” components—loss of choice, social pressure to overdrink, and a poor excuse for a “game” as no score is kept. 

Thoughts On The Spontaneous Trip

My experience last night is a microcosm of this spontaneous trip, and of life as a whole. It was a night full of imperfections—such as “turkey ice cream” and my internal debate on the value of drinking games—but that did not take away from the value of the experience. As everyone ages, I hope it’s most common to recognize the imperfection in everything we see and do, and then to embrace it as is. 

For an analytical person like me, I wonder if this is a more difficult task. I wondered if while I was contemplating the implications of drinking based on shuffleboard performance, everyone else was thinking, “this is fun!” I’m not implying that I’m superior for questioning it. On the contrary, I’m implying that I’m the one who needs to learn to downshift my analytical engine. And this imperfect night on this spontaneous trip is exactly the type of experience I need to accomplish that.

And that takes me back to this choice to dive headfirst into this spontaneous trip. It was less comfortable in every way, but discomfort is the best path to growth. Eating ice cream with turkey in it was very uncomfortable.

11:45 AM (PST)

I’m off to the farmer’s market they have every Saturday. I’ll probably meet up with a new friend there. 

6:24 PM (PST)

The timing didn’t work out to meet Mike, so I spent today alone. It was still pretty awesome. The farmer’s market was incredible—they must have had 50-100 vendors and much of it was organic food. 

farmers market

After that, I walked across the bridge to the Oregon Museum of Science and Industry.

I walked across the bridge on the left.
But before I crossed, I saw this scene. Man and dog battled for at least a minute. Theory: the dog wanted to keep possession because the guy threw it out really far into the river.
On the bridge!

There was a lot of cool stuff in the Oregon Museum of Science and Industry. My favorite part was a section of mind puzzles and brain teasers. After a few hours there, I walked back over the bridge and the sun was setting; it was spectacular.


I got some unexpected good advice from unexpected places today:

New rule: if you see Don Ho, you must ask him to dance.

 8:07 PM (PST)

I’m chilling at the hotel now. I was going to meet the hostel folks for another pub crawl, but I’m tired. I might meet them later on. I’m on the 15th floor with a great view! 

portland city view

When I took the elevator up here, I noticed a floor was missing. Can you spot it? Someone must be superstitious!


Tomorrow, the plan is to watch football in a bar or restaurant. I’m also going to trek a mile or so back to the hostel. This worked out pretty well, actually. Being alone in the hotel tonight will give me better sleep and help me to recharge for the last half of this imperfect, but great spontaneous trip!

SUNDAY, Nov 9th 5:49 PM (PST) 

Today exists for relaxing. I watched the Lions beat the Dolphins and came back to the hostel, where I’ll spend my final three days. I’ve been hanging out in the common area, talking to people who come in, writing, and reading. It’s not going to drop anyone’s jaw, but it’s been quite enjoyable. 

I’m still debating on whether or not to go to the pub crawl tonight.

MONDAY, Nov 10th 10:36 AM (PST) 

The reason I was debating the pub crawl last night was because I did Saturday’s pub crawl and didn’t enjoy it too much. It was one of those “underground” bars where it’s loud and everyone is standing up. I don’t like having to shout, so I found the whole setup to be awkward. Of course, I don’t really go to bars much, so maybe it’s just me? My thought is that if it’s a loud place, there should be dancing involved. Otherwise, it’s just harder to communicate with people, which is weird because talking to people the whole point of going to bars (aside from drinking, I suppose).

As I was hesitant to go again to last night’s pub crawl, I figured I needed to go, if only to stretch my comfort zone. I went and had a blast, though. We went to bars where we could actually hear each other speak and there was ample seating. 

I really enjoyed talking with everyone. Compared to the average person, travelers seem to be extra friendly and sociable. I suspect this is due to a traveler’s exposure to so many people and cultures. It has a way of balancing out one’s perspective of people and the world.

Later today, I’m going on a hike with the hostel group. I’m pretty excited! I tossed around the idea of staying here longer than my initial plan, but I don’t know. My productivity has gone down because I’ve been out and about. For this spontaneous trip, I have paused my mini habits to focus on the experience and this liveblog. I think I’ll reinstate them today, as they’re meant to be doable even when on vacation! 

Will I Move To Portland?

One of the lesser reasons I came here was to see if this is a place I’d like to live. After my experience so far, I can say that I would enjoy living here. The food scene is great (apparently, nobody in the world loves these food carts as much as I do). I would not need a car here, either. That would mean more walking and biking, and that’s fantastic! This type of daily activity is an underrated component of health.

I don’t care for the cold weather, but with the right clothes, I don’t suspect it would be a huge problem. 

7:24 PM (PST) 

Yeah, I totally missed the hike today. I thought it was later than it was. I’m quite disappointed as I really wanted to hike in Oregon. Blech.

What I did instead was walk a lot around the city and look at some apartments. I’m going to try to look at another apartment tomorrow. Essentially, if I can find the right place, I’ll probably move here for these reasons:

  1. The food is great. The apartment I hope to see tomorrow is only TWO blocks away from a few dozen food carts and less than a mile away from Whole Foods. It’s in the perfect location.
  2. I don’t want to own a car. First of all, I’m the opposite of the guy who waxes his car. Second of all, I dislike driving in general. Third of all, cars are deceptively expensive to own—insurance, gas, maintenance, and taxes! Consumer reports says that cars cost—at the very minimum—$5,000 a year to own.
  3. Walking and/or biking. I love the idea of walking or biking everywhere, and this city is great for that. I prefer to walk above all, and this location has a “walkscore” of 100 (the highest possible). If I need to go to the airport, I’d just hop on the MAX light rail which goes directly there, which would be right outside my front door in this spot. For comparison, right now I have to drive 30 minutes and pay $4 a day to park my car at a long-term parking spot whenever I want to travel.

7:39 PM (PST) 

I’m a bit scared that I’ll like the apartment. Because if I do, I might have to move there, and fast. I’m the type of person that can’t really wait to do something like this if I know it’s what I want. 

The weather here could be a thorn in my side, but I’m honestly not sure how big of a factor it is. I’ve always preferred warmer weather, but is the cold weather enough to take me away from the pleasures of great food and having no car? Decisions can be so difficult sometimes!

8:59 PM (PST) 

I’m just thinking how strange it is that this spontaneous trip has me considering a huge life change. 

TUESDAY, Nov 11th 

Too busy to write anything!

WEDNESDAY, Nov 12th 4:31 PM (PST) 

I submitted my application to rent out a “micro studio” apartment in Portland. The place is only 200 square feet, which will nudge me to become even more minimalist. Which means that yes, I am planning on moving to Oregon (and soon!). 

Yesterday was so much fun, with the highlight being that I met two readers. First, I went to Multnomah Falls with John, who is the hanging basket guy in Portland. He’s an awesome and genuine guy with a passion for the outdoors. After that, I had dinner with Wes, who works in IT. Our conversation was a great combination of business and life, with plenty of laughs along the way. 

It’s cliche, but I’ve met so many fun and interesting people on this spontaneous trip. And as imperfect as it seemed when I decided to take off, I can’t imagine not doing it now. I would not have met April, Elisa, Tom, Ed, Dan, Bret, Danielle, Liz, Wes, John, Adam, Jacob, Eddy, Shae, and Alex (among others…. Hello if any of you are reading this!).

The Decision To Move To Portland

As long as my application is accepted—and it should be—I’m moving to Portland. It’s a rare opportunity that overcomes some of the objections I have.

My main objection is the cold(er) weather. I’m not a big fan. Add in the frequent rain and I’m less of a fan. But I’ve rarely had adequate cold weather gear, which obviously makes a big difference. While some people get depressed with too many days of cloudy/gloomy skies, I have always interpreted this type of weather as mysterious and interesting. I’m weird (but so is Portland).

Here are the core reasons why I intend to move there:

  1. The right spot: my location has every type of food I could want. There are dozens of food carts two blocks away. There is a Target one block away. There’s a Whole Foods a few blocks away. Street cars and the MAX light rail are one block away (I just hopped on the MAX and went straight into airport ticketing. It is an absolute dream for a traveler.
  2. No car necessary: I’m the guy who was going to ride his aging car into the ground. Cars are A-to-B tools to me, and I don’t like the huge costs and added stress they bring. I’ve always preferred to fly or take the train.
  3. Food: I’ve said enough about the food carts. There are a lot of other quality restaurants nearby as well, and healthy food is easier to find in general than on the East Coast.
  4. Minimalism & experiences over possessions: My current apartment is too big for me. I like the space at times, but my lack-of-stuff looks a bit silly in it. In a micro studio, I’m going to want to get out, and I have a huge, walkable/bikeable city waiting for me every day.
  5. Travel-friendly: At Jacksonville Beach (and everywhere else), I have to pay to park even a few miles away from the airport to get shuttled there, and then pay every day that I’m away. Now? Hop on the MAX and go straight to the airport (reading a book on the way). The unmatched ease of this will encourage me to travel more, which is scary considering my appetite for it.
  6. It will get me out of the apartment: If I move into this tiny little place in the center of a cool city (that doesn’t even have a kitchen!), I’ll be much more inclined to get out and do things. I need this. Right now, I’m in a fairly large one bedroom apartment in a location that has less to offer (and I generally drive everywhere here). This makes it more tempting to be a hermit, which is not what I want or need right now.
  7. A unique city: Portland has its own unique style and I think I like it. I mean, there was a 90s dance party on Saturday. Portland clearly gets it.

It’s actually really strange to visit a place for the first time and have it feel like home, but that’s exactly what it was like walking the streets of Portland. 

THURSDAY, Nov 13th 9:36 PM (EST) 

It’s been a week! I’m back.

Recap And Reflection

As I hypothesized, this spontaneous trip turned out to be amazing; I didn’t predict it would result in a life-shifting move. One thing I didn’t mention yet is how my social confidence grew as the trip went on. Confidence is largely determined by our comfort level in a situation. If you’re confident in making three pointers in basketball, it means you’re comfortable and not worried when you take the shot. 

After spending several days in the hostel environment of frequent social interaction, I became noticeably more comfortable with it. That made me more confident, and I know there are a lot of people who think they can think their way into more confidence, but thinking cannot replace experience. Living alone in Jacksonville and working at home hasn’t afforded me a great number of social opportunities, which has the opposite effect on social confidence, so this was really good for me.

I don’t mean to make you think I’m an awkward anti-social hermit by this commentary—I’ve always loved people and I enjoy talking to strangers; every person is unique. I’m saying that I’ve been less reserved, more open and more vulnerable with people, and have found it much easier to initiate conversation with strangers in this past week. 

 The Downsides

It wasn’t all perfect. On this spontaneous trip, I spent a decent amount of money (including buying overpriced beer in bars/restaurants). At this point, expensive restaurant bills seem to be a necessarily evil of being more social. In the long run, I like to drink alcohol with friends at home—it’s so much less expensive and still very fun.

But going out to a restaurant or bar can another dimension to the experience, and I believe in buying experiences over possessions. Perhaps it’s less an issue of value and more an issue of can you afford to do it. Some can and some can’t, but even as I can, I don’t want to do it excessively. I’m not going to be a penny pincher, but I won’t be reckless either. Moderation is really key here!

Another downside is that I wasn’t as productive. I mean, I did write over 5,000 words for this liveblog, but this isn’t a revenue-generating post. It’s just for fun. I didn’t work on my book as much as I would have if I stayed here. But this spontaneous trip will likely give me quite a bit more “fuel” for the writing engine, as the whole premise of this trip is the same as the book’s.

According to my experiences and all the research I’ve done, this phrase has life-changing power:

“This is imperfect, but here I go.”

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