Welcome Back to Breakfast with Lisa & Josh!

Hi, everyone! Lisa here, bringing you today’s newsletter.

Soundtrack for this newsletter: Pua Līlīlehua - Keola Beamer

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Wanna know a secret?

I used to hate traveling.

Seriously.

I used to be the person who would rather stay in the comforts of my own home with the couch with its perfect years-in-the-making butt indentations, watching re-runs of Friends instead of a life of adventures and hostels and beaches in Thailand.

And it wasn’t just me not wanting to travel - I used to judge others for traveling. (Serving myself some humble pie right about now. :))

When I would hear people talk about their perfect summers in Spain or their lazy cafe days while studying abroad in Prague, I’d nod but just think they were not-so-humble bragging. At the time, I felt like they were just fleeing real responsibility and being kinda… selfish. The questions screamed loudly in my head, but I never dared to say anything out loud - why would anyone leave home? What about their family? How could anyone keep a job if they’re always on vacation? How could they even afford it?The truth is, I just didn’t understand any of it.

Anyone else recognize this place?!

I’m a first generation daughter of two immigrant parents and traveling for fun was never really a thing.

For my parents, a big trip was, well, moving to the US for the first time. Talk about OGs of #solotravel. My mom moved when she was in her 20s and my dad moved much earlier when he was just 5. Both of their immediate families stayed behind, as was the way back then. Reflecting on it now, the bravery and forethought to do something like that in search of a better life is staggering, and something I take for granted far too often.

For my family, traveling usually consisted of short weekend road trips, taking the occasional trip to visit family or that one time I spent a month in Taiwan as a part of a study/exchange tour. Traveling was something you got to do only if it made sense and was attached to something more “responsible.”

Being a daughter of immigrant parents comes with a certain set of responsibilities. Making sure your family is ok was priority number one. I know that sounds vague, but that’s because it is and sometimes all encompassing. For me, this equated to making appointments and getting my parents to the doctor on time, transcribing all letters/texts/emails and making sure they were grammatically sound, reading many an instruction manual to fix things around the house, serving as translator and peacemaker, amongst many other roles. (Travel YouTuber didn’t exactly fit in with the list of duties 🙃)

I felt selfish to want to do something just for me, and like I needed to work for it, to earn it before I could go on my own.

It was always really hard to explain to other people that every single decision I made involved my family.

It was a constant battle between finding the “me” and taking care of the “we.”

So I took little trips, hidden under the “responsible reasons” to travel. There were those little getaway trips to Utah and Arizona when I had a conference to attend the next week or a weekend in Boston because I had an interview that coming Monday. I never could take an international trip, especially by myself. I’d felt too guilty to leave home.

Then, one day, I saw a job posting in Hawaii, and felt such a strong pull towards it that I had to apply.

I didn’t actually think I’d get it and even if I did, I didn’t think I’d actually move there. It felt like such a leap from my current life…but I applied anyway.

I couldn’t actually go, right?

My parents were getting older...and what if I’m away when…[insert every possible worry someone could have...]

And then, somehow, I got the job. 

I was over-the-moon excited, and also terrified to tell my parents. Their response was exactly what I was worried about.

I still remember my dad saying “wow, so now you know you can get a job anywhere, really! Including here,” not so subtly hinting that he wanted me to stay close and be with the family.

After a couple of days of ruminating on the decision, I had decided to go. Before I told anyone, my dad left me a voicemail, “Lisa—you should go. Your mom and I were talking…and well, had we both never left, we never would’ve met, had this life that we have now, never would’ve had you.” I wish I still had that voicemail.

It was never easy to leave home, even as a kid, even just for a few days - pangs of guilt and that nagging worse case scenario always kept me close, just in case.

As a child, I’d rarely go to sleepovers. When I was going to spend a Christmas break snowboarding in Colorado, I called to cancel my flight the day before I was going to leave because I was afraid this would the be the “last Christmas.” In college, I spent most of my weekends driving home, thinking “I’ll have more time with my friends later. I won’t have as much time with my parents.”

So 20+ years of thinking almost exclusively about the “we,” I finally did something for me and I moved.

I felt truly free to be me, for the first time in my life. I made friends who became family, I rediscovered my love for nature, hiking, and the sea. I was sure I had found my forever home.

Then, the worst case scenario happened.

My dad passed away, unexpectedly.

Anyone who’s lost a parent or any loved one knows what this feels like… for some reason, I felt worse that I was away. Guilt, anger, sadness. How could I have let this happen?? As if I had any control.

When anyone passes away suddenly or unexpectedly, a common reaction might be “life is so short and so unpredictable.” And maybe you’d think that the reason I started to travel was because I wanted to seize the day, live my life, because YOLO.

But for me, it was this realization that that I had spent most of my life up until that point living like my dad was dying, even when he was alive and well. I had spent my entire life worrying and preparing for that day, but in reality, nothing could actually prepare me.

After picking myself up the best way I knew how - staying busy, working non-stop, confiding in close friends, emerging into the world at times for the gym, counseling, some more “responsible” trips, and months of binge watching Terrace House - I finally took my first solo trip to Japan when I was 31 and it was incredible.

I stayed in hostels for the first time. I tried ramen in Japan for the first time. I went sightseeing alone. I went on hikes alone. I sat down at restaurants for dinner myself (Japan is really great for introverts like me.)

It was all incredibly exciting, lonely, beautiful, and incredible. I would do it again in a heartbeat.

It made me realize—I actually did like traveling all along and it turns out, I’d been making mini decisions all throughout my life to get to this point — from solo hikes in HI to trying new foods in New Orleans, renting a SUP for the first time in Antelope Canyon. All of those decisions were actually me testing the waters, silently saying “I like to travel.”

It was also then that I first started to realize that how many of the decisions in my life were made with my family in mind. And while I can love and appreciate my value for family, I realized I needed to find space for me in the “we” mentality.

Don’t get me wrong, it wasn’t all so one-sided.

I love being who I am and where I come from. And I love my parents and who they raised me up to be. Because of them, I share love for different cultures, a desire to try new and delicious cuisines, and like learning different languages.

Because of them, I am fiercely independent and have a desire to care for others. They provided for and loved me in the best way they knew how, in a country they were just trying to understand and find their way in. Because of them, I even get to do this—travel and have a home-base!? The dream.

Travel for me started off with the desire for freedom, independence, trying to separate myself a bit from familial obligations and responsibilities.

But it’s turned into so much more than that.

This life of travel has afforded me the ability to appreciate different cultures, incredible food, and incredible people, who even though we seemingly come from very different worlds, aren’t so different after all.

Our wonderful friends at the Giving Tree in Chiang Mai. Imm left her hometown to learn massage therapy—traveling to Bangkok, where she learned to take the train for the first time, then to Korea and China, all to learn different forms of massage, eventually coming back home to start her own business. She hopes to make her daughter’s dreams of going to university abroad come true someday.

What a superhero.

I don’t think I’ll ever be the person that makes decisions solely for myself…that’s just not who I am, and that’s ok. But the Lisa who hated traveling taught me to let go of a lot of the fear and responsibility I held on to for so long and to live for myself a little bit more. Turns out, it is possible to find and do things that I love, but also still be there for my loved ones.

And as it turns out, traveling doesn’t have to be selfish after all.

Today

Spoiler alert! We made it all the way to Santiago—all 170+ miles from Porto. Currently relaxing, editing, and still eating lots of bread.

The (Near) Future

Back to Hawaii :)

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See you next Sunday…ish :)

- josh (and lisa)

Oh, and if you want to learn how we afford to take all these trips after quitting our jobs last year, you’ll likely be interested in our Skillshare course on Travel Hacking and Frequent Flier Miles.

It’s been really taking off lately, but we still have a few uses of this link left for those of you who want to see the class for free. It comes with a free month of Skillshare, which is more than enough to watch our class and any of the other great courses on there!

Check it out here: https://skl.sh/lisaandjosh02221

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