04 - How to Quit Your Job, Travel, and Do Whatever You Want

Freedom, Almost



January in The Bay Area isn’t special. It doesn’t get cold, the sun sets at 5pm, and everything feels out of place due to people slowly recovering from holidays.

This January is different though. The world is my oyster. Or my legume. It’s at least something that opens up into the unknown.

What’s on the agenda for this year? I’ve got a ticket to a show in Dublin (Ireland, not California) on May 5, 2012. That’ll require a passport. How long will I be gone? I’ll have to figure that out along the way.

On January 2, 2012 I walk to the local court house to apply for a passport. I mention I’m planning on visiting Europe for the first time. They advise me to renew my driver’s license before I leave (it was expiring this year). My passport arrives three weeks later. Easy enough.


Next up: waiting. The only future plan is a show one evening in Ireland on May 5. That’s so far away from January to not need planning yet. I wait. I work on some side projects. I enjoy not needing an alarm clock. I use the running trail beside my apartment every other day (another benefit of living in the south bay).

Then, the middle of February rolls around. I meet someone visiting The Bay Area who, conveniently, happens to live in Barcelona. I mention I’m thinking of moving around and they half seriously invite me to stay at their place in Barcelona.

Barcelona person returns to Barcelona, but we keep chatting online for a while. Long story short: I decide to stay with them in Barcelona over the summer.


Now we get to the meat of initial travel planning.

First up, I renewed my driver’s license.

Next up, find the best way to save money while traveling. Start reading http://thepointsguy.com/ every day while going through a backlog of his posts too. He keeps up with all active credit card promotions, points program specials, discounts, and limited time specials.

Based on TPG, I upgraded my Amex card to Platinum which had 50,000 bonus signup points (after meeting spending requirements), applied for a Chase Sapphire Preferred which came with 50,000 points (after meeting spending requirements), and opened frequent flyer accounts with all airlines I end up using.

Note: There are hundreds of high quality travel sites. Don’t get overwhelmed reading them all. Pick a few relevant to your situation and keep up with their latest posts.

The Amex Platinum yearly fee is steep at $450, but it did come with 50,000 points (worth $500 with lazy spending), it refunds global entry application fees ($100), gives you $200 worth of airline credit for incidentals, has no international currency conversion fees, and the card can be used as a pass-through to your bank account in overseas ATMs (this comes in handy later).

Amex Platinum is great if your life is full of international travel. You can always cancel it when you’re done.

With pre-planning done, get to work on actual planning. My only constraints were I needed to be in Dublin on May 5 and Barcelona afterwards. Everything else is open.

While planning a hop to Dublin, it seems silly to not visit London too. So I’m looking for how to get a few days in London, then a flight to Dublin for a few days, then Barcelona for three months, then back to San Francisco.

Intermission — Planning Travel

Planning Flights

Planning flights online is frustrating. There’s no way around it. There are endless numbers of combinations of airlines and layovers. Not every online flight search site can even find the same combination of flights at the exact same time.

For planning flights, use Hipmunk, http://matrix.itasoftware.com/, southwest.com, and your credit card provider’s travel interface (either Amex or Chase at this point). You’ll usually be rewarded by your credit card bank by booking directly through their site, so don’t book on Hipmunk.

Remember: southwest doesn’t list their flights on flight search engines. You can only book southwest through southwest.com. They have great fares for US travel.

Keep a notepad to jot down airlines, flight numbers, dates, and times as you search. You can’t always re-find the same combination again. If you find something you like, write it down.

Sometimes it can be tricky if you find the perfect combination of flights on one site but then need to book through a different site – the same combination may not show up right away. Usually you can narrow your search criteria on the non-conforming site since you know what you want (specific times, specific classes of travel, specific airlines), but you need to keep all details along the way to make it happen.

Planning Housing, Hostel Edition

Concurrently with your airline search, you’ll want to plan for a place to live. The name of the game here is hostels. Use http://www.hostelbookers.com/ for finding, checking availability, reading reviews, and booking your hostels.


Americans aren’t familiar with modern hostels. Here’s what you need to know.

A hostel is basically a hotel with bunk beds. A typical shared hostel room sleeps four to eight people. Outliers will have twelve or sixteen people in a room. If you have a little more money, you can book private rooms at hostels or even a two person room, but you have to pay for both people.

Most hostels have an “economy dorm” rate too. “Economy” here means the room will be cheaper than other rooms because it may face a noisy street or have windows opening to a street with loud bar traffic until 2am. Economy rooms typically sleep eight to sixteen people (four to eight bunk beds).

How should you manage room sizing? I prefer six person rooms. Four people is too few. Six people in a room decreases your chances of getting a room full of duds. More than six people in a room makes everybody just feel distant and unapproachable. Forget trying to meet anybody in a twelve or sixteen person room – the entire room will change every day.

A quick note on how booking a hostel room/bed: The deposit you pay to the booking service (in this case, hostelbookers.com) is deducted from what you owe the hostel, but the hostel does not get any of it. It’s fully kept by the booking site. Some hostels allow you to book directly through their own website which can be better because: they may not charge a deposit and if they do charge a deposit, the deposit goes to the hostel so they can help make your experience better. There are a few cases where you will want to use an external booking service though. I’ll get to those situations later.

Why hostels though? A hotel room will easily cost you $60 to $300 per night ranging from really bad to medium quality. A hostel bed will cost you $10 to $50 per night ranging from medium quality to really good. If you want your money to stretch as far as possible, you’ll be able to sleep in a room with a few other people.

Hostels are not hotels though. You’ll get clean sheets, a pillow that’s probably pretty hollow, and a mattress of unknown sleep ability. Some hostels have great memory foam mattresses while others have mattresses with springs you feel all throughout your sleep.

Most US hostels will have a towel for you to use, but some expect you to bring your own and charge a towel rent fee if you want to use one of theirs.

Bathrooms and showers will either be in your room or in the hallway. Hallway bathrooms with showers have configurations of: two to six toilet stalls with two to six shower stalls and four to eight sinks. If you bathroom is in your room, it’ll look like a normal bathroom. Most hostels have hallway showers with doors that shut for privacy. Some have gym style showers with curtains for privacy.

All hostels I’ve seen accept credit cards for payment. Some hostels may charge an additional $5 fee for processing a credit card, but if you’re already spending $600 for two weeks that extra $5 won’t bankrupt you.

Hostels range in size from small converted houses with four rooms to entire city blocks with hundreds of rooms. Each hostel will have a different feel based on staff presence. Hundred-room hostels will be staffed 24 hours with front desk people and service staff. Five room hostels usually have one 24 hour desk person who will handle all problems. Some hostels don’t have 24 hour front desk service, but someone who works there sleeps at the hostel so you can wake them up if anything serious needs attention.

Hostels are either independently owned or part of an organization. The largest organization is Hostelling International (HI) and its international counterpart Youth Hostels Association (YHA). Hostels under those organizations are membership organizations and they require you become a “member” of their organization to stay. Membership just means paying them $15 to $25 for a yearly pass. If you don’t pay for a yearly membership, they will add $3 per day to your stay.

If you are staying at a HI hostel, I recommend booking through hi

Simultaneous Bookings: Airlines and Hostels

Availability is the name of the game when traveling. You have to match your airline availability with your housing availability. You don’t want to arrive with nowhere to go, do you? You also don’t want to pay for a place to stay when you can’t get to it.

Should you book your airline before your hostel or your hostel before your airline?

You should do both! Browse your hostel options on hostelbookers while browsing your flight options at a few flight search sites. Find a good middle ground of availability of cheap flights (usually Tuesdays are safe for cheap flights) and available hostel rooms.

I prefer to book flights before booking housing. If you’re visiting popular areas, there will be multiple housing options and, at worst, you can stay at one place a few nights then move to your more desired place when it opens up.

Note: Hostels have limited availability and can be extremely popular during peak travel times. If you book through hostel bookers, you’ll be paying a 10% reservation fee. Sometimes if you book directly through the hostel’s own website they won’t require a deposit and will allow you to cancel your reservation with no penalty. It can be advantageous to book your hostel first then figure out flights if you aren’t paying reservation fees (then you can change/modify/cancel your reservation if your flight search doesn’t pan out).

Most hostels have their availability schedule up in multiple: their own site, their third party booking sites, and possibly a parent organization site too. Sometimes each site shows different availability! If the dates you need aren’t available directly with the hostel, check hostelbookers.com. If your dates are not available there, check their parent organization. If all of those don’t have availability for your desired room type, change room types or try a different local hostel.


Finalizing Plans

What were we trying to do? Oh, right. I’m trying to plan a trip to London, Dublin, Barcelona, then back to San Francisco.

There isn’t much of a story at this point. It’s just hours of work. You must become one with the flight schedules and connections of the airlines in your price range.

Most online flight search sites have a multi-city search option you can try for more-than-roundtrip flights, but multi-city searches sometimes don’t include all options or inject odd airline preferences when other combinations are cheaper or at better times.

You’ll need to try combinations of one-way flights and multi-city flights to see all viable combinations of flights under your time constraints. After a while you’ll start to recognize the airline schedules and rates since they are fairly common over time.

Try to book your flights at least two weeks before you need to travel. Sometimes you can wait as late as eight days until you need to fly and still get a good rate. Booking less than a week before you need to fly will make the fare more expensive, and booking less than two days before you need to fly with make the fare much much more expensive.

Also for booking: remember to use Tuesdays. Tuesdays tend to be cheap flight days. Try to avoid flying on Friday, Saturday, or Sunday.

Play along at home by finding a cheap set of flights between San Francisco, London, Dublin, Barcelona, then back to San Francisco for a month away from today.


I ended up booking San Francisco to Atlanta on US Airways for $177, Atlanta to London then Barcelona to San Francisco on US Airways for $1,271, then London to Dublin and Dublin to Barcelona on Are Lingus for $330.

See what happened there? I had to split out the middle of my trip on a different carrier for better pricing. No multi-city search site would give me a sane entire trip between SF->Atlanta->London->Dublin->Barcelona->SF. All the charges got billed to my Amex Platinum to help meet the spending requirement to redeem 50k points in the future.

The same day I booked these flights, I also applied for Global Entry online. Global Entry costs $100 (refunded completely if you pay with Amex Platinum) and asks the US government to check your background so you can use expedited TSA-Pre security lines (no shoes off, no jacket off, no belt off, no computer out of bag, no liquids out of bag) and you get to skip Immigration lines when returning to the US. Instead of using the Immigration line, you go to a kiosk, scan your finger prints (at least four of them), fill out your customs declaration on screen, then you get a paper receipt to take to customs.

Final Pre-Flight Checks

after booking flight, seattle, changed flight, storage unit, blah blah blah

Next: 05 Freedom, In Bullet Time