The dream versus reality of traveling for one year are similar and different than my expectations. Today I’m going to jump all around the map for an exploration of finances, heath insurance and our relationships as we begin to unravel the past twelve months. This is a departure from the recent Thailand posts and a little more information about our life in general as we approach our one year anniversary of exiting the corporate life for a life of travel and adventure.

Please don’t misconstrue this post as complaints. These are just the realities of our experience. Yes, we know we’re lucky to be able to travel for a year. Yes, we know we’re fortunate. We also know that we’re making difficult choices that allow us to live like this. So come on, let’s dive into the dream versus the reality.
Living the dream…well….maybe…I guess
One of my friends recently told me “you’re living the dream!” I found myself wondering if he realized how much stress the actual “living” of the “living the dream” contains. I’ve certainly thought that other people who embark on this kind of event are “living the dream” but I didn’t give any real thought to what the reality of it looked like. The reality is slightly different than the dream.
We spent six or seven months hiking the Pacific Crest Trail last year and then four months caring for our parents.

Now we’re sitting in Thailand trying to process what happened last year and what’s happening to us this year. We’ve certainly gathered no moss during the past twelve months. I assumed that our travels would be full of rest. Wrong! I think I’m more tired today than I was a year ago!
A calculation of the level of “road weariness” didn’t factor into my equations about traveling for one or two years. I guess I didn’t think we’d become road weary, and yet we are worn down. We just returned from a grocery store. I must have searched for fifteen minutes for shaving cream. Shaving cream! I don’t mind looking for “stuff”, that’s part of travel. I’m just tired of always looking for something.
The dream versus reality of traveling for one year: The old life keeps creeping back in
We’ve racked up more frequent flier miles and hotel points than I expected to accumulate during the past year and…wait for it….I was finally bumped into Marriott’s Lifetime Platinum membership level. I’m not sure what happened that opened the magic gates, but at 994 total nights Marriott welcomed me into the Lifetime Platinum club. We need to rack up another six nights so that I can begin saying “Oh, I’m a bit above 1,000 nights in a Marriott.” Not that anyone would care…but still…it’s just a few twitching bastions of a discarded corporate life.
Going Away Dinner Reunion Lunch
It’s crazy to think that it’s been a year since I said goodbye to my job. The picture on my left was my coworkers. I’ve stayed in contact with one or two of the folks in the image. The image on the right are the fellows that I worked with when I joined the company in 2002. Adam is the last man standing. Oh the stories…but I digress. I’m still in contact with almost everyone in the picture on the right.
I keep tweaking LinkedIn to give me fewer and fewer job notifications. Do I really need to know what jobs the LinkedIn algorithm thinks are well suited for me? It’s been a reminder, sometimes several times a day, that LinkedIn believes I should be thinking about employment. I don’t need to follow all the LinkedIn rock stars at this exact moment, however I’m not sure that I’ve found the right balance between completely disconnected and slightly removed from the workforce.
A year is a long time…
Perhaps the main difference between our current journey and other journeys is the time duration. When we’ve traveled out of the country before on pleasure we haven’t been gone for longer than five or six weeks. The duration of this trip forces us to deal with issues at home, like bill-paying, that we’ve not had to deal with in the past while on holiday.
There’s been an awful lot of “life” for us to begin to process during the past month now that we’re in a less stressful situation. I miss the comforts of home, our own furnishings, our own food, our dog, our family, our friends. We have each other out here, and while it’s good, we miss being at home too.
The dream versus reality of traveling for one year: Established Relationships have begun to erode
The time we’re spending traveling takes us further and further away from the established relationships we have with our friends and family. The travel is wonderful, but it comes at a cost. We can feel the difference in our close relationships. It’s understandable though. The lack of proximity dictates a lot about the type of relationships we will or won’t have.
We tried to get together with friends when we blew through Portland in December and again in January. We failed miserably. Not for a lack of interest, but just for a lack of energy and a desire to maximize family time. We also wanted to see our PCT friends, both in Oregon and Washington, but we failed.
When our PCT hike abruptly ended we were left in a weird head space. We didn’t celebrate. There was no one to celebrate with. Our friends and families offered a few kind comments, but they didn’t really (through no fault of their own) understand thru-hiking or have the same experiences that we had. So we really, really wanted to connect with fellow hikers during our time at home. Even here today, 7,500 miles and five months away from the PCT, it still feels incomplete. I wish we had someone to talk to about it. Someone who understands trail life and post trail life.
The dream versus reality of traveling for one year: The finances….
As we’ve moved further away physically and mentally from “home” I’m trying to “close up shop” on a few loose items. In an effort to maximize our income last year we worked until the last second, ran around like chickens with our heads cut off for a few weeks (Idaho, Colorado, Oklahoma, California) and then started hiking the PCT. There wasn’t much time for finesse.
For the first time in about a year I’m taking a hard look at what’s coming directly out of our bank account. We pay everything possible with a credit card that gives us air miles and then pay the credit card off at the end of each month. We had cell phone applications that I’d purchased over the past year but no longer need. LinkedIn Premium. (If I’m not looking for a job do I really need to drop $65 a month on that one?) Weather apps, storage apps, too much insurance, Garmin, Audible, additional cloud storage…and the list goes on. So, I’m trying to clean up a bit. Really just starting to spend time on “us” again.
Cleaning up these kinds of items leaves me feeling quite guilty. Guilty that I’m somehow cheating on our parents in beginning to shift my primary focus back to our lives. It’s needed and necessary, but that doesn’t make it any easier.
Looking at our finances isn’t as challenging as I expected it to be. We have only what we have, because we gave up our incomes. What is challenging about our finances is downgrading our spending habits. We’re eating out a lot. Yet we’re trying to eat out at cheaper places (200฿ versus 2000฿) when we can. In the past we wouldn’t have worried about that so much. We heard rats in the wall at our last hotel in Bangkok. In a prior life we would have gotten worked up about it and switched hotels. Today, well, switching hotels costs extra money. The rats weren’t actively running across our sheets, so, we can live with it.
The dream versus reality of traveling for one year: Health insurance
We’re trying to figure out how to move forward with health insurance; keep what we have (at $1500 a month) or downgrade to more of a catastrophic coverage policy. I asked my Cobra representative what exactly my health insurance policy covers in South East Asia. Deafening silence was their response to multiple queries. I ended up pulling my previous employer into the mix for some help with obtaining coverage responses. I was on the phone for two hours one morning (around midnight Thailand time) talking with with several insurance representatives. In the end, the existing coverage in SE Asia was really only reimbursement coverage for a catastrophic injury.
Once we learned that juicy little nugget of information, we picked up travelers health insurance that will cover us in SE Asia. It’s about $800 for four months of coverage for both of us. Not too bad! We did find that the plan will also cover us when we return to the US, provided we’re more than 150 miles from home. (Sorry kids! We’ll be hanging out in Eastern Oregon so that we have functional health insurance when you visit us from Portland.)
Great insurance coverage = Great Doctors!
Dr. Jonathan Lowy Laurie Sinn, RN BSN Dr. Ralph Damiano
We visited my Cardiac Surgeon (Dr. Damiano) and Cardiologist (Dr. Lowy) before leaving the US. Both report that my heart is doing just fine. Dr. Damiano said that I’m a “picture of good health”.
My primary GP (Dr. Moynihan) helped prepare us (and support us) during our thru-hike attempt and South East Asia preparation. When I started looking at ACA plans I couldn’t find any that cover either of my cardiologists and only one that covers my GP. Good God!
Less insurance coverage = less choice
I’ve had a boat load of dedicated specialist care from physicians over the past few years. It’s difficult to think about walking away from that level of potential care. The whole “pre-existing” health care business in the US is just a complete cluster. We did laugh that one of the insurance plans stipulated that pre-existing conditions also include any current medication that you’re taking. High blood pressure? No coverage. High cholesterol? Why that’s a pre-existing condition too!
We’re leaning towards completely dropping Noelle’s Cobra coverage and keeping mine through October. In October I can roll over to a Affordable Care Act (ACA) catastrophic coverage plan that will cost about the same as what I pay now, but give us annual deductible of about 16k a year. We’ll figure out the details before the end of this month.
The dream versus reality of traveling for one year: Adding new expenses
I broke down today and picked up an annual subscription for VPN software for our phones and laptops. We’ve experienced multiple instances of American websites or applications not working correctly due to the web/app host blocking Thailand IP’s. Go figure. We’re handling banking and healthcare so it’s critical that we can access all our “stuff”. I hadn’t even factored in VPN software into our budget. It’s only about $100 a year, but still…
We picked up a subscription to mail postcards to my mom. We can populate the postcards with our own travel pictures. Since my mom has no access to our blog or social media, this seems like a nice way to keep her somewhat up to date on our travels.
Anyway, we’re trying to keep a tight reign on our finances. It’s challenging though! I’ve been drinking Chang beer when we eat out. It runs anywhere from 70฿ to 100฿ for a “big” beer. I’ve been eyeballing the Deschutes beers at many places for about 350฿ for a “small” beer. I have no idea why Oregon beer is so popular here, but I’m working to avoid it just to save a few extra ฿.
We did pick up local cell phone SIM cards for about $10 for a month of unlimited txt/data. Noelle has switched her txt’ing over to Messenger. I’m popping the old SIM card out and putting in the new card every day. This allows me to continue chatting with my old phone number. I did look at at AT&T plan for Thailand and laughed at the price of about $140 a month per device (6GB).
It cost us more when we purchased our phones “unlocked” in 2019, but the extra expense will pay for itself within a few months in SE Asia. Last week I throttled Noelle’s existing AT&T plan down to the cheapest option and I’ll do the same for mine in two weeks when the monthly plan is up for renewal.
The dream versus reality of traveling for one year: Do I miss my old life?
The job: AKA Gainful employment
We’re just about half way through our planned two year “gap year”. I’m not sure where I thought I would be mentally at this point. I’ve come to realize that I actually do miss some aspects of my old job. The time away has given me clarity on what aspects of my old job I miss and what aspects I don’t miss. I hope to gain more clarity as we proceed on our trip. At the end of this adventure we’ll need to make decisions about how we wish to proceed, or not proceed, with our professional lives.
Our material possessions
Hiking the PCT was very eye opening in relation to what material possessions I really “need”. It was odd to recognize how much “stuff” we’ve accumulated that we don’t actually need. We have two very full storage units in Portland. We went to the units in January to grab some clothes. The first visit was pretty depressing. I may have dropped a “F-bomb” when we opened the storage door. So much stuff. How to even begin wading through it all?
When we sold our house we sold or gave away about 50% of everything we owned. Looking at our storage units was a stark reminder that we have a long way to go. At the very least, we need to consolidate down to one storage unit to save ourselves a few hundred dollars a month.
I miss having a space of our own that we populate with “our” stuff. I believe that we’ll pare our belongings down even more when we finally settle down. (Sorry kids, we’re still keeping the furniture!)
Friends and family
I miss hanging out with our children on a regular basis. I want to see our friends. Perhaps I’m missing the “home” more now than I did while we were hiking. Definitely dealing with grief might be easier in the confines of our own “space”.
I’m trying to be better about reaching out and connecting with friends/family/old co-workers now that I have somewhat dependable internet connections. I’m making an effort anyway, but I suck (in the best of times) at making new friends.
Today, as I write this, we’ve left Bangkok and are staying on the island of Ko Tao. I’m glad to leave Bangkok. Truthfully (just between you and me) I really didn’t like Bangkok all that much. It’s such a conundrum of wonderful street smells mixed with the smell of shit. Amazing sights intertwined with the homeless living in the streets. I think perhaps, for me, less would have been more. Perhaps a week or two weeks max.
Solitude
Bangkok is too much chaos for my taste. I’m seeking less people and much less noise. The PCT was silent most of the time. Just me and the crunching of my feet on the trail. Bangkok is the polar opposite. The PCT may have completely rewired my brain in relationship to what I’m seeking in adventure. Even sitting in Bangkok, what I really want to do is pull on my shoes and load up my pack and go for a really long hike.
There are so many shopping malls in Bangkok! We’ve been to several of them in search of aftershave. You wouldn’t think it would be so difficult to locate aftershave huh? I finally found some Burberry that smelled OK but was crazy expensive. After a lot more searching I found some Gillette aftershave that smells tolerable, but is definitely cheap. I now smell like a teenage boy after his first shave. Anyway, the shopping malls are packed with people. Literally we walk into them and I want to turn around and walk right back out.
The dream versus reality of traveling for one year: Saying goodbye to family
Clyde, AKA Cupcake
I’m trying to come to grips with the death of Noelle’s dad Clyde, I called him Cupcake, and placing my mom into an Alzheimer’s center. I fear I’m not doing well, at all, with this adjustment. Some days I’m consumed with thinking about them.
I had a good relationship with Clyde, I loved him dearly. Meeting Clyde later in my life, a bit past my formative years, allowed us to have a different relationship. More a relationship of equals than a relationship of father-in-law and son-in-law.
Spending time with him during his last days was incredibly difficult, but also rewarding.
At one point a few days before he passed I had to break down the reality of the situation to Clyde. While he was the one dying, it wasn’t all about him, so he just needed to hush up and let the rest of us experience his upcoming passing the way we wanted to experience it. Clyde laughed really, really hard. That’s the memory I’ll choose to hang onto about Clyde, his laughter and big smile when I told him that his dying wasn’t all about him.
I hope that I’m as good a sport at the end of my life as Clyde was at the end of his life. Somehow, I doubt it. Godspeed Cupcake! Tell Jackie her favorite son-in-law said hello!
Estelle, AKA Mom
I’ve called my mom, Estelle, three times since we’ve been traveling here in Thailand and two or three times before we left the States, after leaving Colorado Springs. It’s so very strange. I’m still trying to learn my moms new “schedule”. I call the Alzheimer’s center and a nurse will answer the main number. Sometimes it’s a “good time to talk” and other times it isn’t a “good time to talk”. I decided that I’ll talk to her no matter what, even if the nurse says shes having a bad day.
It’s so different than calling her at any other point in my life. I could call my mom at her house at any time and talk with her. I can hear her distinct voice in my head saying “hello” when she answered the telephone. Now, well, I don’t have the luxury of that kind of easy communication. I need to hope that the nursing staff answers the phone, that my mom is nearby, that she’s available to talk, that she’s willing to talk and that I’m prepared with something to say.
Now I’m trying to communicate and punch through the heavy fog of her vascular dementia. It’s not like a regular conversation though. I’m trying to avoid questions that will drive the conversation into the “third rail”. The third rail is a comment or question that will be upsetting to her. It’s hard to know what those questions may be on any given day, so I’m taking more “at” my mom than I’m talking “with” my mom.
I’m telling her about our “vacation” in Thailand. Telling her little antidotes that I hope will amuse her. I’m worried that my prattling is just me trying to make myself feel better at her expense. It’s a dawning recognition that my mom can’t care for me and communicate with me in the same way that she has in the past. The fulcrum of our relationship responsibility is now firmly in my jurisdiction. I need to meet my mom where she’s at, not try to have her meet me where I’m at.
The dream, my dream, of my mom living in an Alzheimer’s center was that she would like living there. I would visit her and she would walk me around the facility and introduce me to her new friends. The reality of the situation is far different than my dream. She doesn’t like living there and she wants out. She’s not shy about saying that she wants out either! I did laugh (silently, deep inside) one day when I told her that “it seems like a nice place to live”. She immediately offered to let me stay for a few nights, locked in, while she walked out the front door. Ouch!
The wrap up
How do I possibly wrap up this past year? Quitting our jobs, thru-hiking, back packing, my brother’s divorce, the death of Noelle’s dad, moving my mom into a memory care facility, moving my dad into an Independent living facility, bouncing around South East Asia, detaching from a stressful job, writing a blog for you to read, not worrying too much about the future.
How’s this for a summary? “In 2019 I walked away from my career, financial security, my children and grandchildren, in the pursuit of a different kind of happiness. A happiness that isn’t rooted in what kind of car I drive, what kind of house I own, or how much money I have in the bank. I have never felt this raw, yet so very much alive.”
See you on the trail-

It’s great to read your perspective. I retired this year butI retired early because I quit my job. Ethically I could do what my boss wanted and so I quit. I’ve never quit a job. It’s along story for another time but because I’m 63 and Bruce is on medicare already I really had to think about insurance.I did do Obama Care and although I hate Kaiser for assorted reasons it will work for 2 more years.I’ve been good at jumping through hoops and I’d recommend it.
Enjoy your time, that place your at looks amazing.
We used Kaiser in the past when the kids were younger and it was OK. We definitely believe we have a better “feeling” about our coverage with non-HMO plans. It’s nice to be able to immediately see a doctor instead of being routed through multiple visits to earn a coveted doctor visit. I have no idea how a HMO would work when we’re traveling like this!
We’re enjoying our time and trying to decide where to bounce to on our next stop.
So insightful. Your adventures seem to have provided you with clarity of thought and a deeper understanding of what is important. Your brain has soaked up so much beauty and large doses of reality and it shows on your face. Rock on Steve & Noelle! Thank you for sharing.
We’re happy to share our adventures with you. Thanks for following along!
I appreciate the honesty and the insights. Somehow I thought that this was your to be your permanent go-forward life; traveling, adventures (good and bad), etc. Is it really only for two years, and then back to a job (though with a much pared-down set of baggage)? But then there are always bills to pay, even at 200-baht dinners. In any event, you seem to still be doing things on your own terms, and that is no small accomplishment.
Really liked the part about Clyde’s death being “not just about him”. He must have been a hoot.
Perhaps we need another post about funding our lives as we move forward! Is it really for only two years? Honestly? We’re not sure. We’d love it if we could stretch this out for a bit, but we need to start generating some sort of passive income for that to work out OK. We’re working on it! 😉
Clyde was a hoot. We’ve laughed several times during the past few days as we discussed how wrong it is to tell someone that’s dying that it isn’t all about them! When in live is it ever MORE about you, than when your dying??? But that’s that kind of relationship that I was lucky enough to share with him.
About linkedin Premium, I am surprised you pay so much. Even by paying by month I was half the fee you are mentioning (and I am in Norway, not the cheapest country in the world…). One trick is to unsubscribe and then they will offer you a discount (half price) to stay. Also take the year subscription, it will be much cheaper 🙂
I took time off work for travelling from December 2012 to September 2013. That included section hiking on the PCT and road tripping. I went to NZ from Norway, stayed there for 3 months, then TAS for one month, then flew over to California 1st of April. Started the PCT, stopped, did a road trip all the way to WA state and down again, went back on the PCT. Then in July I had enough. I wanted to go home (my flat was then waiting for me in Norway). So mid July I flew home and enjoyed the rest of the summer here.
Before that trip, I was in expatriation with my work in France. I didn’t like it, but it was good money. So basically I had been out of Norway for 2 years. It was really a good feeling to come back. I first stayed with a friend a couple of weeks, the time to get back mentally and have all my personal stuff moved back to my flat (I rented it for a while). I really enjoyed being back in my flat and was SO happy I hadn’t sold it before I left!
IMO there is a day when one feels that it’s time to go home. I don’t think there is any reason to fight it. Even if it means that your trip will overall be shorter than what you told to people before you left. I don’t think that this matters so much. A good idea though is to get back when the weather is nice again 😉
Cheers,
Anne
Thanks for your post. We enjoy connecting with our readers!
I think this is one of the discussions we’re starting to have; when is “enough” enough? At some point we’ll be drawn back, happily, towards home, to rebuild our “other” lives and move into the next phase. We kind of view the traveling at this point as a section of trail that we’re hiking.
At the moment we’ve fleshed out our plans through the end of this year. Beyond that? Who knows. I did meet a couple while hiking last year who hike and travel full time. They shared with me that they never plan more than one year in advance. Thy found it too confining. I like that concept. They also had much, much deeper pockets than we have though!
LinkedIn was quick to offer me a 50% discount on the Premium membership if I joined again. I’ve declined…