Welcome Back to Breakfast with Lisa & Josh!

Soundtrack for this newsletter: Toto - Drax Project

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Quick note: We have a new podcast called Travel Support Thursday! The 2nd episode is out today, check it out if you want - link here

https://youtu.be/oW6IToTnF0s

Do you remember how summer break felt when we were kids?

It felt like those 3 months lasted a lifetime.

There were high highs, and low lows. Everything just felt amplified, important, life-or-death almost.

Every day was filled to the brim with opportunities.

It felt like being truly alive - a dozen weeks where anything was possible.

Unlimited time, unlimited energy, nobody telling you what to do and where to go (kinda.)

Close to zero responsibilities. All your favorite people around you all day every day.

Every single day was Saturday.

Total, and complete freedom.

That’s what quitting my job to go on a trip around the world felt like. 

Little me on summer break, believing that anything was possible.

Same vibes, 30-ish years later.

It’s like having a year-long summer vacation.

It’s intoxicating, (for me, on my first one, I took this idea a bit too literally) wonderful, terrifying, all-encompassing, lonely, celebratory, exhausting, extraordinary, adventurous, breathtaking, heartbreaking, blindsiding, staggering, and, above all, sublime from start to finish.

It’s like condensing all the feelings, experiences, highs and lows, and personal growth that you might have over a typical decade of your life into just 365 days.

On my first solo trip around the world over 12 years ago, I’d never felt so alive—like truly, completely living each day—for such a consistently long period of time.

Whew, trim that chest hair, yeah?

That’s the best way that I can describe the feeling of actually leaving for and being on the trip. But as with any highlight reel, that’s not all to the story. There’s all the lead up to it - all the sacrifices, the letting go, the doubts, the regrets, the endless goodbyes, the feeling of inching closer to something you’ve been working so hard for, the pit in your stomach when you actually walk into that final meeting to let your boss know that you’re quitting to travel - there’s so much life in there.

This is my attempt at summarizing the full emotional and logistical journey of a person who was just daydreaming of traveling the world to putting the plan in place to make it happen, executing on the plan, leaving for the trip, being actually on the trip, and the hardest part of all, coming back home.

I think and hope that many parts of this journey will ring true to anyone who’s left behind an old life to pursue a new one.

Everyone’s timeline and experience will be different, but I believe that there are some universal experiences in this process.

Here we go - 

THE EMOTIONAL TIMELINE OF QUITTING YOUR JOB TO TRAVEL THE WORLD

2 years before THE TRIP:

The idea. 

You probably see someone on TikTok or YouTube doing a little song and dance or going ga-ga over the freshest baguette sandwich in front of the Eiffel Tower, and wonder, probably aloud in the middle of a shopping mall or on your couch:

“How in the living f* did they afford to do that? They just left their jobs, and are traveling all around Bangkok and Tokyo and Rome and Buenos Aires? They must be some trust fund kid or had a cushy big paying job or somehow escaped college without a billion dollars of debt. There’s no way I can do that, no real people actually do that.”

This is the beginning of the journey, always. It starts with a relatively poisonous mixture of jealousy, admiration, righteous anger, and a stark feeling of the inherent (and very real) imbalances of the world. (Which then follows with a healthy dose of guilt, of course.)

This is the “I’m so mad that my life isn’t like this, and I’m going to dig as deep as I can to figure out why I can’t live this life so that I can feel better in my own life” phase. I don’t mean that to be insulting or belittling - it’s just exactly how I felt, and what I said, once I saw other people living out my dreams.

I, initially, secretly wanted it to be impossible. 

Me watching YouTube, furious that no one is sharing their secrets.

Also in frame - cute sleepy kitty, so how could I be that mad?

I wanted the idea of quitting my job to travel the world to be so far flung, so ludicrous, so unattainable that I didn’t have to even try, that I didn’t have to worry about starting down that path. It would have given me a sense of peace that my dream was so far out of reach that I shouldn’t even bother, because then I wouldn’t have to feel the inevitable regret at not making it happen for myself.

This initial anger, resentment and general guffawing at the seemingly endless stream of people on social media that were out there living the life that I wanted to have slowly turned into a new obsession.

This obsession was the nonstop watching of travel content to decipher EXACTLY HOW all of these people made it happen for them. There were so many travel content creators out there giving super vague, feel good-y, motivational but ultimately useless tips.

There were a very few that took the time to show how they did in excruciating detail. I watched every single thing they made, like a man possessed.

It all centered around one, all consuming question that I just couldn’t find an applicable answer to:

“No, really, HOW did they afford it? I’m going to watch every video on the internet about this until SOMEONE answers me honestly here.”

The money part was just so far away for me - I had less than $0 saved when I started, a low paying job, and the dream felt like it was more than one lifetime of work away.

But still, I kept digging, and the questions kept coming:

When you’ve been searching for 3 hours and still can’t find an answer.

“How do they ever get a job again after just quitting like that? Aren’t they going to burn their careers to the ground?”

“How do they not die out there while traveling the world? Isn’t is dangerous?”

“What do you even pack for something like this? How can you prepare?”

“How do they know where to go?”

“Won’t they run out of money? What if they get robbed?”

“Is what they’re doing even legal? Can you just go from country to country indefinitely? Do you need visas for that?”

“What do they do with their mail while they’re gone?”

Every single one of them had different stories and backgrounds - some of them were independently wealthy, trust fund kids, crazy high paying job-havers. (Some were easier to spot than others.)

But, actually, they were the exception, most people were not actually THAT wildly rich, and many had even less than I did when I started.

Their stories invariably hit these major points:

1. They made the decision that they were going to free up the space, money, and time in their lives to quit their jobs and take a gap year or something similar.

2. They scraped, sacrificed, saved, started side hustles, sold everything, and, when the time was right, quit their jobs.

3. They somehow managed to go on the trip that they always wanted to, even if it ended up being a slightly compromised version of the initial big dream, but they were ok with that.

“Well, crap.” I said to myself, after binging 200+ hours of travel content, deliriously trying to find the answers.

“Maybe it is possible.”

This is just a picture of me looking delirious and dumbfounded. Mostly at the fact that eating vegetables is possible while traveling.

At this point the idea is just that - an idea. It hasn’t gelled into reality yet.

These things take a while to fully sink in.

1.5 years before THE TRIP:

The plan.

Six months of nonstop consuming of travel content later, you’ll very likely be somewhere between exhausted, disappointed, and very, very ready to do something.

You will have watched at least 41 travel budgeting videos.

You will have watched at least 15 travel packing videos.

You will have watched countless travel videos titled something like “Is (Insert City Here) Worth The Hype??” Or “24 Hours in (Insert City Here)!” (we’ve made that one before!) or the classic “13 TIPS TO KNOW BEFORE YOU GO TO (Insert City Here)!”

You will have likely consumed at least 1 book about how to quit your job and travel the world.

Hopefully it’s the one I’m writing :)

You’ll be watching these videos at work instead of working. You’ll be sneakily consuming travel content on your work breaks.

You’ll know exactly how the metro systems work in at least 10 big cities around the world, and you haven’t been to any of them, yet.

The obsession has gone too far. It’s time for action.

Packing video #12 on the road to too many.

This is how you know that you’ve gone too far in the learning process, and that it’s time to make a real plan.

It’s time to create a real exit strategy, to bust out an Excel or Google Sheets spreadsheet, (you can use our trip planning spreadsheet for this! if you’re reading this, it’s already in your inbox, from when you signed up) it’s time to start making this into a reality.

Enough dreaming. Enough watching other people live the life you want to live. 

Enough of watching the same videos and listening to the same podcasts by the same people who invariably go to the same destinations as everyone else (guilty.)

It’s time to stop dreaming.

It’s time to make whatever changes in life are required to be able to go and eat noodles in Tokyo, see the pyramids in Cairo, dance in Buenos Aires, and run with the bulls in Pamplona.

Most importantly, it’s time to commit. 

It’s spreadsheetin’ time.

Don’t tell my previous employer, but in this phase I spent significantly more time on the clock researching ferry schedules in Thailand than I did doing my actual job.

You’ll be spending a lot of time in Google Maps looking at all the beautiful places you’ll go. You’ll be pricing out theoretical flights way, way in the future just to get a real idea of how much it costs to do the trip you want to do.

You’ll have 92 Booking.com tabs open trying to get a good idea of how much a hotel or hostel costs in Rome in the offseason.

Maybe your dream trip is 3 months in Europe, and you want to go to every single capital city.

Or you want to travel for a full year, hitting 30 countries and going all the way around the world.

Or you just want to take that honeymoon that you’ve been putting off for too long.

Awesome, price that out.

Look at every single hotel.

Find every single flight, train, or ferry.

Figure out how much a meal costs there.

Account for public transportation costs.

Find everything you’ll spend money on, no matter how small.

Put it all in a spreadsheet.

The most important thing to know that in this phase, you enter it slightly frustrated, a little overwhelmed, and ready to put in the work to plan your trip around the world.

And you’ll know that you’re done with this phase when you have a clear idea of the trip you want to take, how much it costs, and a big ole spreadsheet to back it all up.

It’s all about getting it down to one final number.

That way…

You know exactly what you need to cut back on to save up enough money.

You know exactly how many months of paychecks you’ll need before you quit your job to travel.

You have a clear goal.

I think it was the great, OG Casey Neistat who said, “Without a goal, you can’t score.”

Now we just have to get there.

I don’t know which I love more—a whiteboard brainstorming

session or a good spreadsheet…

1 year before THE TRIP

Clearing the way.

This is where the real fun begins.

Going on the trip is inevitable, it’s merely a question of how long do you have to wait to get there.

You’re committed, you have a clear goal, and you just need to cut out the things that are slowing you down on the way to it.

This is my favorite phase of the journey by far. 

It’s the part where you get to show just how badly you want it, and every single day feels like significant progress.

How we kept ourselves accountable back then.

(Lisa should’ve probably drawn this poorly

shaped money thermometer thing, not me.)

This is the part of the journey where your friends start to ask you “Hey, you haven’t come out for drinks with us for a while, is everything ok?”

You will answer this with “Why don’t you just come over for dinner or drinks? I’m not doing the bar thing right now.”

You will have said “No” to going out to dinner enough times in a row that people will just stop asking altogether.

You will have started inviting people over for dinner at your place instead.

You will have started cutting back all extra expenses.

You will have moved to a cheaper cell phone provider.

You will have gotten rid of more unnecessary subscription services than you even remember signing up for in the first place.

This isn’t just about cutting back, you will have started finding ways to make more money.

This was our every Sunday—meal prepping on a budget.

You will have potentially started flipping furniture on Craigslist for extra cash.

You will have asked your boss for a raise. 

You will have sold off that record collection that you never listen to anymore and put the money into a Vanguard Index Fund.

Yes, everything is ok. More than ok. 

Heads down, focused on the goal, making big sweeping changes to the way you approach everything in your life.

To the outside world you have bunkered yourself in, rarely being seen in social situations, hard at work at something most will not understand.

How many $5 rotisserie chickens does it take to take a 1 year trip around the world?

When you tell people your plans, they’ll be mostly supportive, but also confused. 

You’ll hear a lot of:

“Oh wow, that’s amazing! But why throw away a perfectly good career?”

“Aren’t you afraid of being broke forever, and never being able to get another job again?”

“Aren’t you worried about getting robbed in (insert place here)? I’ve heard that happens all the time!”

“Just come out for ($20) cocktails, you’ll be missing out on so much if you don’t!”

“Why do you have to quit your job to do that? Isn’t 2 weeks of vacation every year enough?”

“Aren’t you afraid of telling your boss that you’re leaving?”

All of these are absolutely valid fears - dreadful FOMO mixed with a feeling like you’re potentially going to tear down your entire life by making this one choice.

Fear of the unknown. 

Uncertainty if you can pull this thing off in the first place.

But also, absolute certainty that you have to at least try. 

You have to give it a real shot, or else you’ll be opening yourself up to the worst case scenario of them all - 

Friends don’t let friends have regrets.

It’s a tug-of-war between the old you and the new you. Two enter, only one may leave.

You are a caterpillar inside its cocoon, slowly changing into the beautiful world-traveling butterfly that you were always meant to be.

This phase is all about getting the things out of the way that are slowing you down in pursuit of your trip around the world, and using that space created to add in things that will get you there faster.

This phase is about progress in every aspect of your life towards one singular, massive goal. 

The next one is about letting go.

6 months before THE TRIP

Letting the old you go, to make room for the new you.

This phase is when you’ve officially gone too far to go back. This trip is happening, and it couldn’t come fast enough.

Everything in your life has changed. 

Where before you spent $100 on a sloppy night out with your friends, you now use that money to buy an underpriced-and-dirty KitchenAid stand mixer off Facebook Marketplace.

You spend 15 minutes cleaning it up and taking better photos than the last seller, and you sell it that same day for $150.

Your Amazon orders per month are down to just the bare minimum. Things you don’t use are no longer accumulating, they are disappearing.

Costco, and its glorious $5 rotisserie chickens, are familiar old friends.

You’ve cut off that crazy-expensive Verizon / AT&T / whatever phone plan and replaced it with a $15 per month plan from one of those great budget cell phone providers.

You’ve cancelled so many monthly subscriptions, you might not even have any left. YouTube has tons of free movies and shows, and there’s hundreds of other sites that do too.

You’re look at your bank account not as an indication of how much money you can blow this month, but into a departure countdown. Every $500 buys you another week of freedom. Only a few thousand to go until you get on that plane.

You’ve learned how to invest your money into index funds or another reliable, low-ish risk investment so that your money will grow not only while you’re waiting to leave, but as you’re traveling.

The day we went from me having my own apartment to 3 people in one place. Gotta love roommates :)

You’ve practiced the conversation you’re going to have with your boss when you tell them that you’re quitting to go on a trip around the world in your head dozens of times. You’re ready for it.

You eagerly await every new email from Scott’s Cheap Flights (now called Going), and you’ve already booked your first flight of your trip. Turns out, if you’re patient enough, you can find one-way flights to Europe for under $200.

Sure, let’s kick this thing off in Rome. Why not?

FOMO is no longer a monster that keeps you up at night - it is an old friend, acknowledged with the same amount of respect that you give a mosquito. Hear it buzzing, see it’s there, swat it away, go on with your life.

At this phase, Lisa and I were so excited to kick start our travels

we decided to convert our car into a little camper.

Much like our #vanlife days, this was kinda short lived too.

Your career is no longer you - your job no longer defines who you are. You know, down to the hour, exactly when you’ll hit that magic number in your bank account that means you can safely quit your job, and do whatever you want.

You are starting to feel the freedom.

You feel like Neo, finally seeing the Matrix of your old life for what it really is - an illusion. Jobs, careers, money, work stress, familial guilt trips, decades of unspoken expectations, and indeed, time itself - all an illusion built to keep you going on that one-safe-path that you used to cling to so dearly.

The curtain is slowly closing on the old you, and opening up on a new act - the new you.

The world traveling you.

The about-to-travel-to-20-something-countries-in-a-year-you.

The does-whatever-it-takes-to-get-there you.

The unafraid you.

3 months before THE TRIP

Everything must go.

It’s so close you can taste it.

The pasta in Rome, the baguette in Paris (yeah, I said it), the massaman curry in Thailand, the sushi in Japan.

The only thing between you, and that, is a bunch of stuff.

So you buy your new home for the next year - a 30-ish liter backpack or carry-on suitcase, and pack it full of just the stuff you need where you’re going.

You’re picky about what goes in there, but, invariably, you pack too much. You read packing lists online.

You realize quickly that they’re equal parts useful and absolutely bonkers.

“Do I really need a water purifier for Europe or Asia?”

No. No, you do not.

“What if it’s raining?”

Then you’ll buy an umbrella. They sell them everywhere.

“Do I need to bring a separate GPS tracker in case my phone doesn’t work?”

No. You’ll just ask someone for directions. Leave it at home unless you’re trekking in Nepal.

Even then, probably leave it at home.

“What if I forget something?”

Then you’ll buy whatever that thing is, wherever you are.

Wasn’t about to bring this big ole suitcase, unless it came with this guy.

After going back and forth at least a hundred times about what to bring, and realizing that 80% of it is just clothes, you’ll close up your suitcase or zip up your backpack one last time.

Everything else you own is now for sale. 

It starts rapidly disappearing.

You forget you even had most of it in the first place.

You’ll go out and talk to a travel doctor, and they’ll get you all the necessary immunizations that you need for wherever you’re heading to. It costs less than you think.

You double check that you have your passport, and that it has enough open pages and is good for the duration of your trip, and at least another 6 months on top of that.

You book that first night’s hotel wherever you’re going, being careful to not book too much more. Flexibility is everything on a long trip.

Who knows who you’ll meet, or where you’ll end up. That’s the whole point.

You’ll schedule that innocent-looking meeting on your boss’s calendar titled “Monthly Check-in,” which is actually the meeting where you inform them that you’re quitting in a month or two.

Wow.

You take a deep breath in.

You have that meeting.

You tell them you’re leaving, fearing the worst. Will they just fire you immediately? Will they hate you? Are they going to yell at you?

Instead, they thank you for giving them so much time to prepare for your departure, and for offering to help train whoever is coming in to replace you, and for documenting your current job and workflows so thoroughly to make the transition easy.

They tell you that you’re welcome to come back anytime, because of how great of an employee you’ve been.

The meeting ends with them asking all about your trip, where you’re headed, how you planned it. They’re excited for you. Probably even a little jealous.

You finally exhale.

It’s all going to be OK. 

1 month before THE TRIP

Freedom and fear.

At this point it’s 50/50 if you’re still employed, or not.

If you are, you’re spending all your time helping transition yourself out of your role, and preparing your replacement to step into it.

If you aren’t, you’re spending your time meeting up with everyone you’ve ever met, telling each one about the trip you’re about to go on.

You talk about how long you’ll be gone for, what you’re most excited about, how you’ve considered starting that YouTube channel or travel Instagram page or podcast you’ve always wanted to make. You talk about how you want to spend 1 month here, 3 months there, only 2 weeks here.

They’re equal parts excited for you, and baffled as to how you managed to pull it off.

This is exactly how you feel, too.

More wow.

This is a time of saying goodbye. Not just to essentially everyone you’ve ever met, but, officially, to the old you.

You say the words “Just fly out and join me wherever and whenever you can!” over and over, instead of saying goodbye.

You give them an extra big hug goodbye, just in case they don’t.

Most won’t.

Saying goodbye is hard.

It never gets easier.

It would be concerning if it did.

The one thing you do notice is that your friends and family are all of the sudden incredibly supportive of this choice you’ve made for your life.

Where maybe they used to question your plan, saying things like:

“Aren’t you worried you’ll be poor forever?”

“What if you can’t get a job again later?”

“Why do you need to travel for a whole year?”

They now say:

“Wow, that’s amazing! You’re going to have such an amazing time!”

“You’ve absolutely got this, I feel like you’ve been a world traveler this whole time!”

“How can I do it too?”

Everyone’s got your back now that you’ve put in the work to make your dream come true.

My original OneWorld RTW booking for my first trip. All booked with points.

It looks boring, but I was so, so proud to get this.

You’ve changed literally every aspect of your entire life, slowly making changes to make room for this one audacious goal that you’re on the precipice of.

You realize that they had your back the whole time, but were just worried about you.

You also realize that you had to believe that you could do it first, before you could expect others to.

You spend the last few weeks in a bit of a haze. You feel directionless, a bit depressed.

The trip couldn’t come fast enough. But also…am I ready?

Saying goodbye sucks.

It’s important.

But it sucks.

The day of THE TRIP

Exhilaration and uncertainty.

It’s time. It’s finally time.

You’re carrying everything you own in a tiny backpack or suitcase.

You make your way to the airport.

Nothing feels real yet. This might all come apart before it even begins.

“It’s too big of a dream, it’s too audacious, I don’t deserve this” you incorrectly tell yourself.

You nervously hand over your passport to the check-in agent, half expecting them to call your bluff on the whole thing and send you back to your old life, post-haste.

Instead, they smile and hand you your one-way ticket to Rome, and say “Have a nice flight!”

“What have I done??” You ask yourself, one last time. The nerves and uncertainty take over.

“Did I plan well enough?”

“Will my money last?”

“I have no idea what I’m doing.”

One step at a time.

Every day from here on out is Saturday.

It’s up to you to decide what to do with your never-ending weekend.

This might be the first time in your life you’ve had total autonomy in your own life.

You start to realize that it’s equal parts exciting and terrifying.

It’s all up to you now.

You take a deep breath in.

You hop on the plane.

You watch 14 Avengers movies.

You land in Rome.

You get lost on the way to your hotel, and a nice Italian man helps you find your way, and points you to a great pizza place.

You drop off your stuff, and go to order that pizza.

You take your first bite of pizza in Rome. It tastes like happiness.

You finally exhale.

You’ve got this.

Your adventure is off to a great start.

You’ve got this.

You’ve earned this.

Today

In case you missed our latest Youtube episode, we're bringing back Travel Thursdays! We always love hearing from all you--whether on YouTube, IG, or through this very newsletter.  And we equally love tackling all of your travel questions together. We don't always get to answer each one, so we're bringing back Travel (Support) Thursdays to try to do just that. Leave a comment in the Travel Thursday video and we’ll try to answer your travel questions!

And in case you are interested in listening to these episodes, they will also be available as podcasts on a podcast platform near you!

The (Near) Future

Your questions, every Thursday, wherever we are in the world--Travel Support Thursday, here we go! :)

Don't you worry--our "3 Days in X" series will keep coming your way! Meat sweats, Spa Land, $100/day budget—it will all become very clear soon.

Our Latest Videos

Travel (Support) Thursday returns! In this episode, we answer your questions about travel credit cards to get miles and points, how we choose where we travel, and get into the nitty gritty of our YouTube financials and whether we make enough to keep traveling indefinitely.

24 hours in Seoul never feels enough, but we sure tried to do it all.

The much requested Kyoto and Osaka video. Come and get it :)

See you next week…ish :)

- josh (and lisa)

Oh, and if you want to learn how we afford to take all these trips after quitting our jobs 3 years ago, 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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