San Francisco I’m leaving you and become a digital nomad. The Preparation.

Nate
13 min readSep 8, 2016

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San Francisco, I love you but I am preparing to leave you. Photography by Me, take from Coit Tower.

Preparation leads to better execution. After all the planning I’ve done, I must admit this was probably the most exhausting and scary part. I had to re-learn, re-organize, and re-test everything.

Here is the list of things I had to prepare:

  • (Re) learn how to pack stuff for a nomadic life
  • Digital nomad essentials and nice to have items
  • Mentally preparedness

(Re) Learn How to Pack for a Nomadic Life

The biggest difference between traveling for a vacation and living nomadically is how to pack for a trip. Packing for a vacation is much simpler and easier. I only cared how many clothes I’d need and everything else I can just buy at the destination. Also, I could just stuff everything in the luggage without thinking about organizing them. If I packed like that for my nomadic trip, my journey would have been much more difficult.

Packing for a nomadic living is definitely challenging and requires a balance of art and science. If packing too much, the bags are getting heavier and my back hurts. If packing too little, I had to buy more stuff at my destination.

1. Pick the Right Backpacks or Luggages

Living nomadically requires travel light and being a minimalist. Therefore, it is essential that I would not check any luggage, which leaves me with a maximum of two bags (one carry-on and one personal item).

A regular carry-on luggage gives me a big space. However, it is not easy to carry around and there is an overhead weight. On the other hand, a regular travel backpack would work fine for a short trip. However, it would not work well with a longer trip due to its smaller size and most of them are top-opened, which made it challenging to properly organize things. I didn’t want everything to pop up like a pop corn whenever I opened it. This led to my search for the right backpack for this trip.

Side-open backpack provides more space like a carry-on luggage but with less overhead space.

My criteria(s) for picking a backpack are:

  • Be able to open sideway like a carry-on luggage.
  • Big space and many compartments
  • Laptop compartment should be closest to my back
  • Adjustable and durable straps
  • Zipper-compatible with locks
  • (Optional) a bottle compartment
(Left) Tortuga Air Backpack as my primary luggage. (Right) Duffel bag as my secondary luggage.

My Primary Luggage: Tortuga Air Backpack

I’ve seen some people using a camping backpack. If it was working well for you, stick with it. There is no one-size fit all. After I’ve researched many backpacks, I ended up purchasing Tortuga Air backpack. It is definitely pricey, but I think it’s worth the investment. It may not be best for everyone. At the moment, it is working fine for me. I am using it for packing important stuff like a working laptop, daily clothes, and electronics.

My Secondary luggage: Small Duffel Bag

I’d been using it as a main carry-on bag for most of my vacations, but not this time. Its length is around 20 inches, which is able to fit a tripod nicely. I am using it for packing my personal items, jacket, shorts, books and essentials. Occasionally, I used it to offload stuff from my primary backpack.

2. Re-Learn How to Pack

I was initially naive about this. I thought the right backpack would solve everything and I was wrong. Having the right backpack is only half of the battle. The rest is absolutely up to me and it requires a ton of works. I’d been re-packing my stuff every single day prior taking off for my nomadic trip. It was very exhausting.

Here is some of the tips I’d like to share:

Tip#1: Clothes. Roll them

Don’t fold them but roll them unless you use them as bubble wraps — protecting some of the electronic devices. I also put it in between any gap I found.

Tip#2: Use Cube Organizers Responsibly

While using a cube organizer definitely helps organizing stuff in a proper place, if not careful, you’d end up having less space than you would. Each cube organizer requires a little bit of extra space. It may be small but every centimeter counts. I limited a maximum of two fully packed cube organizers per bag. I had two for my primary luggage and one for my duffel bag. I also packed a couple of empty cube organizers for carrying toiletries and dirty clothes at a co-living space or hostel where I stayed.

Tip#3 Rather be thin than thick

Although I could stuff a lot of things in my backpack by expanding its compartment, there would be a tradeoff for doing so. I’d rather having my backpack packed thin and leave some room inside the compartment so that the backpack has a room for its flexibility. Thick backpack tends to pull a weight to your back. To make a backpack thinner, it requires a lot of re-organization.

Tip#4 Cheap Solution for Protecting Your Electronic: Tupperware or Plastic Ware

Tupperware or plastic container would provide some water resistance and act as a shield or cushion for your electronic devices while they are in your backpack.

Tip#5 Offload Non-Important Stuff to a Secondary Bag

I’d rather gain my arm muscles than testing my spine’s strength. In short, too much stuff in a backpack hurts my back.

Tip#6 Only Pack What You Need and What You Will Use Frequently

Determining what you need is easier than determining what you will use frequently. Sometimes it was hard to know if I was going to use something frequently. I did not know exactly which items I could live without until I left my first destination for the next one. For instance, I brought a power extension cord along with me thinking that I’d have been using it frequently. It turned out I didn’t use it that much.

Tip#7 Don’t Pack Jeans and Jacket, Wear Them!

Don’t pack them. Wear them on the day you travel. It is usually a sign that you overpack your stuff if you have to pack them.

3. Secure your belongings

Living in an urban area has taught me a lot of things: no matter how safe the place looks and how nice and friendly strangers seem to be, always watch your belongings and be aware of your surrounding — I am not saying you should be pessimistic. Theft is always a crime of opportunity. You should never let that opportunity opened.

Locks are the best tool for theft deterrent — keep in mind nothing is 100% theft proof. Therefore, I never travel without a lock especially when I stay at hostel, guest house, or co-living space. I always carry four TSA locks, one combination lock (for a locker), and a screw gate carabiner.

You should have ones too and most importantly don’t forget to lock up your stuff and carry lock-keys with you.

In addition all traditional locks and keys, here is other device you can use to protect your belongings:

Screw-gate Carabiner

I never thought of any usefulness of a carabiner and I always thought it was for a camper until now. Thanks to this article for a lot of useful tips. A screw-gate carabiner with a couple of rings becomes very handy and is a perfect combination.

The way I use them is I attached the screw-gate carabiner with a ring to a compartment where I think I’d open frequently. You can see how I used it in the photo below. They can provide a functionality similar to a laptop lock for your backpack. It slows down a person who’d want to open your bag and (hopefully) makes you realize what‘d be happening to your bag sooner. However, they are NOT a theft-proof (and nothing is). Therefore, always be aware of your stuff.

Screw-gate carabiner attached to one of the ring and a zipper. Quick access but also provides a layer of protection.

What I pack:

My main luggage:

  • Essential clothes for 6 days (i.e. socks, underwear, inner clothes)
  • 4 T-shirts
  • 2 shirts (I wore one of them)
  • Working laptop + charger + work related accessories
  • Personal laptop + charger + external hard drive
  • Medical supplies (i.e. allergy medicine, contact lenses, ear plugs)
  • Important documents
  • Essential electronic items

My secondary luggage:

  • Polytech jacket (nice jacket or blazer) — I wore this too.
  • Sun glasses and eyes glasses
  • One pair of short Jeans — I may consider removing this, but for now I’ll pack it for a tropical/summer weather.
  • TSA liquid items (shampoo, spray, toothpaste, eyes drop)
  • All essentials (i.e. toothbrush, laundry bag, organizers)

Digital Nomad Essentials

Besides packing obvious essentials, here is the list of my essentials:

Hotspot Device

Almost everyone needs Internet to work (and live) and it is what make a living nomadically becomes possible. There is no doubt I would need one just in case there is no wifi nearby or I need to do work on the road. Tethering to a smartphone works but there are reasons you’d still need one. I used Karma Go as a backup, sometimes as a primary, source of internet. It is small and fit a shirt pocket. There is no doubt hotspot data is expensive. Therefore, I purchased it as needed. I only used it for checking email, work-related (i.e. push/pull from GitHub), and surfing web. So far I haven’t used up my 1 GB data yet. As long as I did not use it for watching any movie/TV subscription service (i.e. Netflix, Hulu), my data usage should be under control. There is also an alternative option to Karma Go: Internet-Go, but I haven’t tried it.

Power Bank for Mobile Devices

Living nomadically means that I’ll be frequently on the road and mobile device is obviously an integral part of my daily life. I always carry a power bank in my daypack. It becomes handy in many situations where I did not have immediate access to a power outlet.

USB Charging Station

I used this one. Since I was doing mobile app development as a part of my job, I had to carry many testing devices. It became a hassle when I had to find four or five power outlets for charging my devices. Instead of doing that, I just plugged all my usb cables into this power station and I only needed one power outlet. Even if you didn’t carry that many mobile devices or electronics, I’d suggest having one. It’s generally very useful when traveling with more than one electronic devices and also you could share your available USB charging slots with your friends or fellow travelers.

USB Charging Station

Portable External Hard-drive

I used Western Digital My Passport. It is compact, small, and has password-protection available. I re-formatted it and re-partitioned into two drives: one for storing copies of important documents and another for importing photos and videos from my mobile devices and camera. I also setup password protection and encryption with a software that comes with the drive so my data becomes a brick if it went missing. It currently provides sufficient protection for me. Some people may argue WD password protection is useless and prefer something with a stronger encryption. Therefore, I’d suggest you use whichever can give you a peace of mind.

Medical Supplies

Self-explanatory. I bring allergy medicine, Tylenol, eyes drop, and first-aids kit with me.

Emergency Contact Cards

Download here from RedCross, print, fill out, and put it in each of your bag and your wallet.

Packable Daypack

Carrying a traveling backpack, a carry-on luggage, or a duffel bag while exploring a new area is overkilled. Therefore, I used a packable daypack after I settled my stuff down and I’d like to explore the area. When I no longer need it, I can just fold it back into a small pocket and it did not take up any space. I usually packed it with a bottled water, snack, map, and a jacket. I’d suggest packing a sunscreen also if visiting a beach during a hot summer day.

My packable daypack Instruction. Small and compact.

Secondary Wallet

Yes, you read it right. I have a secondary wallet with its contents similar to my primary one, but with less stuff. It only contains what I need. I carried it with me instead of my primary one whenever I went exploring unfamiliar area and visited a place where I knew it’d be risky or my instinct told me ahead of time it wasn’t right.

Ear Plugs

Co-living space such as a shared room will occasionally have noise issue from either your neighbors or outside. Wearing ear plugs will help alleviate most unwanted noise issue, especially if you were a light sleeper. However, they are not a sound-proof. If the unwanted noise is actually from a person within a close proximity, nothing can save your uninterrupted sleep. Worst comes to worst you will have to politely ask the offender to quiet down. Most of the time the offender just had no idea how loud he or she was or just simply had no common courtesy.

Airline Mileage Membership or Travel Loyalty Program

If it was free to apply for an airline mileage membership (i.e. VirginAmerica Mileage Member, etc) or travel loyalty program (i.e. Expedia Plus, etc), I’d suggest you do it. It’d help you cutting travel costs down the road (i.e. free ticket, free discount on hotels, perks and etc).

Digital Nomad Nice to Have Items

I would highly recommend them, but they are not necessary.

TSA Pre-check

If you fly domestically a lot from major airports, I’d suggest you apply for one. It costs me $85 USD (as of 2016) and it is valid for 5 years and so far it has been worth every penny. Once my TSA Pre-check application was approved, I was assigned KTN (Known Travel Number) and I used it whenever I booked a flight (more info: TSA FAQ). At the airport security check, I didn’t have to take off my shoes, my jacket, and I didn’t have to pulled out my 3–1–1 liquid bag. There is also a special lane for TSA pre-check. It expedited the entire security check process at least by half or more. Therefore, I no longer had to wait for too long at the security checkpoint. LAX airport is one of the major airports I had benefited from having this.

Cloud Backup

Having a secondary source of backup besides the external hard-drive is always a great idea whether it is DropBox, Box, CrashPlan or etc.

More resources for preparing and packing

Mentally Preparedness

Start living nomadically and working remotely wasn’t just about constantly changing my physical presence. I also had to mentally prepare myself for it. I valued my own space and privacy the most and I had that luxury when I was living by myself in a tiny studio room in San Francisco. In a process of becoming a digital nomad, I had to realize I’d no longer have a home base and some of my privacy would need to be sacrificed when co-living. Also, anxiety would likely be running high on traveling days. Therefore, it was essential for me to be mentally prepared.

Here is my abstract version of mentally preparedness:

Knowing Yourself

Knowing what work for you and what not. For instance, am I more toward introvert or extrovert spectrum? Do you need a moment alone with yourself once in a while? Any specific time you need to go to bed?

Acknowledge Yourself

Everyone has a weakness. Be able to acknowledge and accept your own weakness is usually challenging. For instance, will you feel comfortable co-living with strangers for a long period of time? Will you be able to sleep comfortably on a floor or couch every night? Will you be going insane if living without any social contact?

Know Your Boundary and Limit

Knowing what your acceptable level is and what level you couldn’t compromise. For instance, (in the extreme case) how long can you live without internet and still feel fine?

Here is my concrete version of mentally preparedness:

Simulate Nomadic Living

Living nomadically was meant to be an absolute minimalist. I simulated living in a digital nomadic life style during my final week at my apartment in San Francisco. My empty apartment became my training ground. I was pretty much living with ONLY essentials and things I packed — No TV, No cable Internet, sleep on a floor, refraining from taking any phone call after 11pm and all clothes I wore were from my backpack. It was sort of extreme, but it was necessary. I initially felt I was camping in my own empty apartment. After my second day doing this, it wasn’t too bad. I did this for about three days although I wish I had done it for the entire week. I learned what’s working for me and what’s not. Basically, I learned more about myself and my limit.

My training ground (empty apartment) just a day prior taking off as a digital nomad.

Reviewing Itinerary And Details

Since this wasn’t a vacation, I re-reviewed my itinerary and destination details: what nearby, bus stop, time to check-in (if any), contact phone number, and how to get there once landed, prior I actually took off for my first destination. Stress and anxiety during the traveling day are probably higher than most days. Therefore, I tried to get all the details breaking down into manageable steps, especially when it comes to how to get myself to a destination. If there were things I had to do, I put them on a high priority reminder (i.e. confirmed with AirBnB host a day prior and let the host know my estimated arrival on the travel day).

Always Have a Plan-B

Things are not always going according to a plan (i.e. flight delayed, cancellation, etc). Having a rough idea of plan-B would help alleviate your concern and anxiety. Making a TO-DO list if plan-B needs to be initiated will help you stay on track. For instance, I’d write down if my flight was delayed, I would message my AirBnB host about it.

Now I am Ready to Roll to my 1st Destination

My next article I will talking about my digital nomad journey to Hollywood, California — How I live, Co-Live story, How I work, tips and trick.

By the time I finished writing this article, I’ve already finished my 1st month of living nomadically. If you like my story, please support it by clicking a little heart icon below or share this article. I’d be greatly appreciated.

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Nate

I am #DigitalNomad #EntrepreneurEngineer #Musician and #Artist. I love sharing and talking about my experience and journey.