Freelancer’s Field Guide

A How-To on Living in a Modern Nomad’s Paradise

Greetings, and Salutations!


In this living document, I will maintain a compendium of ideas, techniques, actions, and data which will hopefully ease the trials of a new, or experienced freelancer/nomad. I aim to create a discussion with and help build the global community of freelance and remote workers.

I am now working towards the goal of spending an entire year (2017) outside of the United States, while paying off my entire student loan balance ($42,320.10) and working less than forty (40) hours a week.

I love this lifestyle. It’s full of challenge and intrigue, romanticized ideals and beautiful, harsh realities. Here’s what you need to know about me in seven words: Non-traditional problem solving creative with vicious wanderlust.

I can’t live in routine for too long. After a seven year career in professional kitchens, I monetized my long-time web development hobby into a full time position in early 2015. Six months later, I decided to leave the traditional office world, around my 25th birthday. Next year I’ll celebrate my 26th birthday in France, with an exquisite, extensive French culinary experience. The moral? Write your story. Nobody else will.

How, you may ask, can I afford such a luxurious lifestyle free from the modern clutches of e-corp? It’s simple. I follow two rules:

  1. Our Surrogate Asian Stepfather’s advice: To save money and life a rich life, cut spending across the board, and only spend huge on the things I truly value. Pay yourself first.
  2. No more yes — either Hell Yeah, or no. I only do what I truly believe in. Derek Sivers is a huge influence on my philosophy of living. I recommend all of his work.

For me, I choose to passionately chase all manner of new cuisine, freedom from a regular work schedule, consistent, interesting challenges and exciting new experiences. This describes a rich life for me.

Read on to find out more.

(Note: there are referral links peppered throughout this article, because I’m not the 1%. If you’re offended by this, click lightly)

Principles of Progress

Here I explain what larger values will guide my daily routine. These are mine: Growth, Experience, Love, & Energy. Yours may be different!

Life brings with it a lot of big decisions. Where do I want to be? What do I want to do with my limited time? How do I get from here to there?

Principles are the guide posts for goals and actions. I’ll build goals from these principles directly.

Growth is a result of gaining experience. I know I have gained life-levels when I’m jumping out of my comfort zone. I also know health and wealth are gained through discipline and growth. I anticipate losing all sense of my comfort zone many times in the coming year, as I’ve never traveled internationally. Growth also requires challenge, so as a rubric I will ensure my goals are built upon some ideal just without my reach, in order to consistently propose a challenge. Without a challenge, life stagnates.

Experience brings happiness and growth. Life is a journey, and routine can be damning. A large chunk of the human population can travel nearly anywhere on the planet in a reasonably effortless manner. I find this fact astounding. I recognize the immense luck of being alive right now, so I feel a drive to find connection with humans and gain empathy. Experience is a cool way to slow down time. So I chase new experiences. Experience has also taught me discipline and brought wisdom. Above all, however, is the experience of love.

“Monotony collapses time; novelty unfolds it” — Josh Foer

Love is the root of Everything. I’m not hyper-spiritual. I’m a hedonist and I thoroughly enjoy sin, but I self-identify as Chaotic Neutral. Through it all, I love. I never allow myself to prejudge, or exclude unnecessarily. I tend to be alone and like it that way, but I love myself and this planet, and want to see all of it that which I can. When I play music, I feel a deep love for the universe. When I look into another’s eyes, and have a meaningful conversation about ideas, I feel love for humanity. When I cook and eat, I feel love for the natural environment that allows me to exist. Love is all you need.

Energy can take many forms. Kinetic energy is most valuable in the morning — if I get a brisk walk or jog in before breakfast, my day shows increased returns. Building systems to harness my natural energy cycle and patterns is key to success. Flow energy comes mid morning, about 3 hours after I’ve woken, and I can generally get two or three deep-focus sessions in a day, in which I can tackle heavy-hitting problems that require contextual cognition beyond simply returning emails or writing commit messages. Focusing on increasing my energy will have compounding returns. Momentum builds with regular expenditure of energy. It’s impossible to build momentum (for a project, a relationship, a conversation) without putting in regular effort. Practice makes perfect.

Time Management: The Playbook

Here I will detail how I plan, organize and execute actionable tasks and develop ideas into reality while responsibly managing my allotment of time on Earth.

Manual Work

The bulk of my billable hours are spent programming. I thrive in isolation and love coding through the night. It’s a brilliant way to solve problems. Deep-diving into hard programming problems takes immense focus and discipline, without frivolous distraction. I’m constantly trying to build checks-and-balances systems to reduce distraction and increase productivity. Please, share your experiences with me! Let’s learn together.

In order to track my clients, work, notes and other outstanding tasks, I maintain a monolithic task list in emac’s org-mode, using David Allen’s Getting-Things-Done method. This isn’t a solution for everyone, and I’m not a productivity expert, but it does fit my needs well — learning new software and having the chance to extend it as I see fit is priceless. Besides, for productivity there isn’t much that can make you do something. It’s about picking the task you need to complete, and focusing your energies until it is complete, then repeating that process. Everything else is fluff.

That said, here’s a rough outline of how I keep my life in order.

Once a month I take about two hours to review my overall life goals, including financial budgetary projections/actual numbers, general progress and intuition about my next few weeks, and overall mission. I treat this as an informal, self-meeting in which it’s okay to move tasks around or flat-out delete side projects or low-priority tasks if I feel they weigh me down.

For me to put a task on my action list requires a stirring reaction of “Hell yeah,” else it drowns in non-existence. I simply can’t live with cruft.

Once a week, almost invariably on Sunday evenings, I spend an hour reviewing the past week’s progress and planning the next week’s task list. This Getting-Things-Done review cycle helps keep my focus between large, long-term projects and shorter-term contexts. Some other things I do on a weekly basis:

  • Housekeeping for business — do I need to follow up on any non-development related business tasks? This includes finding new business. More on that below.
  • Financial Bookkeeping — I aggregate and track every penny, and usually do a weekly finance session, which never takes more than an hour.
  • Laundry — My laundry is lightweight and anti-microbial but it requires regular washing. Life is mundane sometimes, too!
  • Family — It’s nice to call your family, if you can. They probably miss you.
  • Meal Day — I cook most of my meals by myself, because I thoroughly enjoy the process of cooking. It saves a lot of money, but once a week I make sure to treat myself to a special meal of sorts, either with friends or solo.

Each week, I review what business I have in the pipeline and where I need to fill gaps. Sometimes clients fall through, sometimes I get sick, etc., so I want to keep a steady stream of “good” projects. First step is defining good in my terms:

  • Willing to pay my rates.
  • Has a clear idea of what work needs to be done, in actionable terms
  • Understands the project and has at least one manager/stakeholder/decision maker who is savvy enough to discuss details with.
  • The project has to be somewhat interesting — I don’t often turn down work for this reason because I find every problem interesting, but as I grow I’m sure I’ll specialize and reach for more complex problems. For now I’m in the trenches.

About half of my work is repeat business from clientele who were happy with my performance, and the other half is new business. Of this new business, I’d say 75% is from either cold-emailing businesses I’d like to work with (small businesses in need of website uplifts) or applying for contracts on Upwork, Freelancer and reddit’s /r/forhire.

Once a day, I update my tasks for the rest of the week and adjust if I feel necessary. I keep a zero-inbox and reply instantly whenever possible. I honestly don’t do a ton of email, outside of clients. Currently I use gmail but am transitioning to a mutt-based email workflow. At the end of my day, I make sure to not leave any unfinished tasks on my list by moving them to when I’ll think I’ll be able to complete it. Over time I’ve gotten much better at estimate my time this way. A typical week’s task list looks like this:

Slightly Censored due to NDA

Many times a day, I’ll update and take notes in my file. I always have this in an open emacs buffer on a workspace, and frequently clock-in and clock-out of tasks, adding notes and prioritizing.

My morning starts with a bit of light exercise, meditation and then a slow breakfast. I like to read stimulating medium-format content after eating, and then begin work on my tasks for the day. Last night’s review session left me with a crystal clear idea of what needs to be accomplished today, so I’ll ignore emails and knock out task #1. Then I usually take a break to catch up on news (quickly, five minutes or less to browse headlines and save any I deem crucial-to-consume with pinboard).

My best work happens in this mid-day block, and after a nice lunch I’ll get one more good work sesh in before I retire to leisure, nightlife, hiking, reading or music.

Software Help

Tasks are generated by a human (usually me) and reworded so as to be directly actionable. When they’re on my list I always try absolutely my hardest to finish it to the best of my ability.

I keep track of billable time using org-mode clock in and clock-out on a per-task basis. This file will live on, allowing quick text or tag-based searching. Agenda-mode is really cool.

I track my computer usage with RescueTime — I spend a lot of time on this laptop and need to make sure that time isn’t squandered.

I retroactively and manually track time I’ve spent in general terms (by the 1/2hr) on Google Calendar. here’s what a typical week looks like:

Yeah I cloned out some stuff, so what? And I don’t like sleeping before 2am.

I’ve built about a dozen different calendars and summarize what I actually accomplished here. This acts as a wonderful visual journal of where my time is generally going.

Tools of the Trade

Here I will detail every item I own and travel with. I try to strive for minimalism, and simplicity in living. I choose my environment carefully and prepare diligently. This list is indubitably geared towards a modern society with functioning Internet and electricity. If TSHTF, I’ll keep track on paper what becomes obsolete and update when I can.

These recommendations represent my personal gear list and may not be applicable to your situation. Each product linked below I have personally used and can wholly recommend in general.

Physical Goods

Luggage — your new home

  • Daypack: New Outlander 35L Packable Daypack— this pack fits the bill for me to carry either a ton of water in a bladder, or my laptop and journal with a light extra layer. Packs very small for fitting in the Tortuga.
  • Main Carry On: Tortuga Travel Backpack— 44L and the perfect carry-on. This is the best backpack a digital nomad who is me can buy. I’ve tried others, but the Turtle perseveres.
  • Compression Sac: Sea-to-Summit 22L lightweight pack — Honestly I may ditch this, I never really need it.
  • Packing Cubes: eBags 3pc packing cubes — nothing special here, just a useful set of cubes to zip and organize my clothing into.


  • Pants: Levi Men’s 504 — Some people don’t fuck with denim. I do. I think a dark pair of quality jeans are more valuable than air. One pair lives on my walking-sticks nearly every day. The other, in my bag.
  • Shorts: Quiksilver Everyday Union Stretch — comfortable, quick drying, high quality. I don’t often dress formal. I do have a pair of blue Dickies that come with me as well.
  • Base Layer: Icebreaker Tech — if it ain’t broke don’t fix it. I just got these and they are a serious upgrade to my skin-feels. The Internet wasn’t lying, Merino wool is the #greatestofalltime. Three t-shirts and two long-sleeve have served me in varied climates. Layering is key!
  • Undergarments: Ex Officio Men’s Briefs — Game. Changer. I know they’re pricey, but damn it’s worth it. Grab three pair and rotate, they don’t get too dirty because Merino. I hope the ladies have something that feels as good as these do, day in, and day out. I threw out every cotton whitey-tighty I had and upgraded my undie game. Now the goods are wrapped in a cloud.
  • Fleece: Columbia Steens Mountain Full Zip — I actually don’t have a fleece layer yet, although I plan on purchasing this one before Winter falls. I do have a light-weight pull over hoodie that works well as a mid-layer.
  • Shell: Marmot Precip XL — Wonderous, ultralight, bone dry. Works as a windbreaker or as a top layer to keep the elements out. Never dissatified with a Marmot product.
  • Socks: Smartwool PHD Crew— Again, Merino wool takes the stage. Ultralight, smell-free and extremely breathable. No qualms, except the price. I don’t mind paying more for quality and value — frugality isn’t always about low prices. I have five pair of crew cut and one pair of long hiking socks.
  • Footwear: Merrell Chameleon Prime Stretch Hiking ShoesShoes are a personal item that are very important to get right. Try a few pairs, don’t be afraid to order and return. These fit me perfectly and have lasted many years in regular use, and seem to be holding up fine in heavier nomadic-type use (more walking and hiking than before)
  • Extras: A nice Merino wool buff by Buffera has endless uses, and I like my Ray-Bans. I also have two flannel shirts, a polo, and a pair of lightweight running shorts. And a generic leather belt & bi-fold wallet.



  • Passport + 3 paper copies + digital copy
  • Visas + 3 paper copies + digital copy
  • Travel Documents (Tickets, boarding passes, itinerary, etc) + paper copies + digital copy
  • Insurance Documents + 3 paper copies + digital copy
  • Health Records + 3 paper copies + digital copy
  • Cash, ~$200USD in local currency
  • Debit Cards, 2 separate banks
  • Credit Cards, three separate accounts


  • Laptop: ThinkPad E560 — i7–6500U, 16 GB G. SKill 1866Mhz Memory, 1TB Crucial SSD, 500GB HDD — I need it to be fast, reliable and faster. This does the trick, and I run linux full time. I prefer Lenovo to Apple because I can update the parts myself, for less money.
  • External Drive: 2TB Transcend Drop Tested — Hardened, beefy and inexpensive. My kind of travel drive. I use this for both media storage and daily backups. I’ll probably get another.
  • Thumb Drive: 64GB Kingston DataTraveler — Nothing special here, used as a spare backup and boot drive with multiple OS distros on it.
  • Yubikey — I like to be secure and this helps keep the demons at bay.
  • Power Adapters — Aside from cell phone, kindle, fitbit and laptop chargers, I have this Kikkerland universal adapter. Super handy and tiny unlike most universal adapters.
  • Cell Phone: Google Nexus 6P 128GB — This is another point of contention for people. Just use whatever world-capable smartphone you’re comfortable with and make sure it works in the places you need it to. Google Fi has served my purposes very well — I’ve been around strong WiFi signals though. This phone is a beast and well enough replaces everything but the kitchen sink.
  • eBooks: Kindle Voyage — A beautiful device for reading long-format. PDFs I prefer on a tablet or my Nexus but aren’t unreadable on the Voyage. I get a lot of mileage from my Kindle.
  • Health Tracker: Fitbit Charge HR — I’m a quantification nut, and this has been a decent enough foray into wearable tech. I’d suggest something else, but it’s my only fitness tracker. After six months the casing starts to peel away, but otherwise it has worked well. Probably looking for replacement soon.
  • Earbuds: EchoBox Finder X1 Titanium — Holy bugger these things are nice! The price tag is a bit steep, but to be completely honest I was gifted a pair by a friend who works on this team. Shout out to the guys at Echobox for creating a solid five-star product. Earbuds are so lightweight I never get fatigued but they have a sound that rivals drivers in higher price brackets. I’ve used a lot of ear buds and these are bar none the best quality for price. Included customizable features are a nice touch, as is the hardshell carrying case.
  • Other: Eagle Creek eTools Organizer — for organizing eTools, of course.



  • GitHub — Source control and issue management. Crucial to my daily workflow.
  • House-sitting Communities: Nomador and HouseSitting.World — I’ll update this section as I gain more experience. I expect my first house sit via these communities in January 2017, check that then!
  • World Nomads Insurance — Relatively inexpensive, good coverage. Follow me and anticipate a deep-dive insurance analysis article in December 2016.
  • AirBnB — For when I can’t couch-surf, house-sit or hostel-sleep.
  • CouchSurfing
  • EarthClass Mail — Handles my paper-mail while I’m away. Lifesaver.
  • TurboTax — Doing my taxes with TurboTax isn’t free, but it is much easier and less stressful. Every January I enjoy doing my taxes, because I keep great records =)

Indispensable Software

  • Debian 8 Jessie is my daily driver. Mmmm, Unix. I used to use OSX, and I loathe Windows.
  • Firefox & Chrome are both heavily used in my day-to-day. Chrome is better when it comes to performance but FF is my best friend.
  • hledger is a great open source Haskell-based rewrite of ledger, incredibly simple command line toolset for double-entry bookkeeping.
  • RescueTime helps keep me accountable for my computer usage and provides an industry-best analytics dashboard. 10/10 will use again and again. I pay for premium.
  • emacs + orgmode act as nearly everything I want them to. emacs is my main IDE and I build all of my Rails apps in it. Read more about my Ruby workflow here.
  • Harvest is the best tool I’ve found so far for client invoicing and timesheets. I integrate with both PayPal and Stripe to facilitate easy payment methods for clients.
  • GitLab is my personal favorite repository management tool, I love to fiddle with the development kit in my spare time.
  • mutt for mail. Gmail is dead, long live gmail.
  • pass for all my passwords and sensitive banking information. I love pass.
  • Various system tools — I can’t live without f.lux, OpenVPN, vlc, and a bucketload of other small tools and scripts. See my dotfiles for more details.

Money Matters

I won’t say much on best practices here, but I will say it is important to have diversity in your assets and at least some “slush” money in case things go south. Budget is entirely dependent on you and your situation so my advice may be useless to you.

I can say I bank with a collection of online-only banks. I won’t list them here for obvious security reasons, but here are some good resources to reference on this matter:

Plenty of advice exists on how to be fiscally responsible. Do some searching, use common sense. Pick your Big Wins, and plan extensively for them. Don’t leave the country with $10 in your bank account, but don’t think it’s impossible to travel with less than $5000. As always, Your Mileage Will Vary.

As time progresses I promise I will update this section with a breakdown my processes and budgets, in an effort to remain as transparent as possible.

Travel Today, Not Tomorrow

Here I will occasionally espouse the details of my wanderlust and explain how this lifestyle need not be on the road, but is especially suited for it.

Introversion is a suitable personality type, to be certain, but I have found I tend to be extroverted when I’m around total strangers, so YMMV.

A lot of people fear resistance, or build arbitrary barriers. Screw that, I say. You want something? Plan for it, work for it, get it.

“Success is earned and not given.” — Me, motherfucker!

Work is a kinetic action that returns energy and reaction. Putting energy into something returns energy from that thing.

Some people will inevitably tell that you you’re wrong. It doesn’t matter if you’re explaining how you travel for yourself, or how being your own boss can be liberating. There are billions of people with opinions on this planet, don’t let them change your storyline.

We’re all on this rock together. Keep your stick on the ice. I’m rootin’ for ya.

— Keifer

If you liked this, find me around the web.