How to Work & Travel 365 Days a Year Without Going Insane

How to make remote working
a permanent lifestyle
A S A P I O S E S S I O N
*How to travel and work 365 days
a year without going insane
@thedesignnomad / melewi.net

Travelling for 7 years
Just got back from a roadtrip in ! Belize
40 countries and counting!
In the last year:
" New Zealand
# Australia
$ France
% Italy
& UK
' Iceland
( USA
! Belize
) Belgium
* Netherlands
+ Denmark
, Sweden
- Switzerland

Melewi
T H E T R A V E L L I N G D E S I G N S T U D I O

We design awesome products for users
and businesses around the world
Team of 8 people from 7 countries
Just turned 5 years old
Clients in 5 continents, 48 countries
Millions of users globally

2010
now
😄
/
😄
🎉
😋
🤗
😋
/

2010
now💥 😭
😫
💥
💥
💥

2010
now💥 😭
😫
💥
💥
💥
😄
/
😄
🎉
😋
🤗
😋
/

2010
now
* disclaimer: this is not my best lettering work

2010
now
But first, what’s a digital nomad?

2010
now
But first, what’s a digital nomad?
Someone who can work without the
need to be in a speciﬁc physical location
Someone who posts really
annoying photos like these ones
(sorry 😅)
(and who works digitally 7)

2010
now
Defaults to diversity
Global experience
Choose where you live and work
Not be tied one spot and having to be constrained to that
Build a routine and lifestyle that works best for you

2010
now
Create a life that you run,
not one that runs you

2010
now
The Realistic
Truth
Common
Misconceptions &

2010
now
Misconception
1
Truth
I just gotta ﬁgure out
how to get ‘work’ going
Once you’ve gotten ‘work’,
you still have to ﬁgure how
to keep it going
The ‘life’ part can be just
as (if not, more) tough
2of

2010
now
Misconception
2
Truth
My life is going to be
perfect and amazing
This lifestyle has ups and downs
- the highs are amazing, but the
lows can be REALLY tough
2of
(an “Instagram” life)

or if that ship has sailed, then:
how to make remote working a permanent lifestyle
How to travel and
work 365 days a year
without going insane

1How do I
get started?
P A R T 1 O F 3

1
This is the most daunting step
It’s a brand new world full of unknowns
It impacts your entire life
Of course it’s scary!
But it doesn’t have to be scary all at once

1
You’ve got 2 options:
Get a remote job
Be your own boss
Strike 4D yay!
Let’s ﬁgure out what works best for you

Which option do I choose?
how do I get started?
P A R T 1 O F 3

I’m okay with instability
I value stability
I don’t mind selling
I hate the thought of selling
I prefer ﬁguring
things out on my own
I prefer learning with
guidance / mentorship
I don’t mind working
across different roles
I like focusing on
doing the work
1
3
2
4
BOSS JOB BOSS
BOSSBOSS JOB
JOB
JOB
A few things to think about

I don’t mind selling
I hate the thought of selling3 JOB
I’m okay with instability
I value stability1BOSS
I prefer ﬁguring
things out on my own
I prefer learning with
guidance / mentorship2 JOBBOSS
I don’t mind working
across different roles
I like focusing on
doing the work4 JOBBOSS

I prefer being
accountable to myself
I prefer being
accountable to someone
I want to be a
jack of all trades
I want to be really
good at one thing
I’m able to cope with
emotional stress well
I’d prefer as little stress
as possible in my life
I like managing
people or projects
I hate managing
anything but myself
5
7
6
8
BOSS JOB BOSS
BOSSBOSS JOB
JOB
JOB

I prefer being
accountable to myself
I prefer being
accountable to someone
I want to be a
jack of all trades
I want to be really
good at one thing
I’m able to cope with
emotional stress well
I’d prefer as little stress
as possible in my life
I like managing
people or projects
I hate managing
anything but myself
5
7
6
8
BOSS
BOSS
JOB
JOB

The real question is:
Do you want to be your own boss?

If yes, go for it! /
If not, go get a remote job ☺

How to get a remote job
P A R T 1 O F 3

As with applying for any job…
Show your value and experience
Show you’ll be a valuable employee
Invest deeply into a few options, don’t gun for as many as possible
Understand the desired outcome the business has for your role

Understand the power of social proof
Make sure your LinkedIn is decked out and has recommendations
Any references you have will really help you

Tough competition
High demand (remote job-seekers), low supply (remote jobs)
Competing on a world stage now
Do NOT make this about how much you want a remote job

Do something different to stand out and be remembered
Show your effort, interest and commitment
Stand out from the crowd

Show you understand the challenges of remote
working + you’re fully ready and equipped to handle it
Are you planning to travel?
How will you work?
Are you good at self-
managing and organising?
Will you communicate often
and clearly with your team?
Do you take initiative and
ownership, or will someone
have to watch over you?
Are you responsible
and reliable?
Do you have a handle on
timezones and online
communication?

How to be your own boss
P A R T 1 O F 3

What business do you want to be in?

Immediacy
“I need to be
earning cash asap”
Easiness
“I should be able to get this
without too much difﬁculty”
Potential
“I feel this has a high
potential to succeed”
Competition
“I’m prepared to
face competition”
Scalability
“I think this could
be really big”
Managing
“Will most of my
work be managing?”
What business do you want to be in?

Almost deﬁnitely not solo
Multiple skillsets
Management / selling focused
Product based
Product-based: B2B
IMMEDIACY
EASINESS
POTENTIAL
COMPETITION
SCALABILITY
MANAGING

Almost deﬁnitely not solo
Multiple skillsets
Marketing / selling focused
Product based
Product-based: B2C
IMMEDIACY
EASINESS
POTENTIAL
COMPETITION
SCALABILITY
MANAGING

Mostly solo
Usually one hard skillset
Production focused
Service or time-based
Service-based: Freelancer
IMMEDIACY
EASINESS
POTENTIAL
COMPETITION
SCALABILITY
MANAGING

No longer solo
Multiple skillsets
Management focused
Service or time-based
IMMEDIACY
EASINESS
POTENTIAL
COMPETITION
SCALABILITY
MANAGING
Service-based: Agency

How to get started
(for Freelancer / Agencies only, sorry product people)

You’re selling your services to a segment of businesses
You’re asking them to trust you and pay you

Who are your customers?

What do they really want?
What do they value?
What frustrates them?
How do they think?

Pretend you’re an actor in a ﬁlm
Who’s your character?
Mimic them
Research them
Talk to them
Be a creep without getting arrested

Leia Organa
“Darth Vader destroyed Alderaan (my home planet),
and is taking over The Galaxy. I will not sit still for this!
I need to defeat him. But how?!
If only there was a way to destroy the Death Star and
defeat the Empire once and for all…”
N A M E
Q U O T E
A G E T E C H - S A V V Y F R U S T R AT I O N ( S ) G O A L ( S )
/ 5
21 5
The Empire destroyed
her home planet
She doesn’t know how to
destroy the Death Star
# K E Y W O R D
Bold
Leader
Courageous
Princess
* because she’s
from the future To defeat the Empire
To restore democracy
within the Galactic
senate

Representative snapshot of your target audience
It should not represent one sole customer
Perhaps a different demographic is a better ﬁt for you?

How to find customers?

Meetups
Coworking spaces
Cafes
Make an effort to stay in touch
Keep directing people to your website!

LinkedIn is a really powerful tool
Build a compelling proﬁle
Reach out to people and get to know them
Again! This is a not a ‘hit-as-many-as-possible’ approach
Take time to build a relationship and trust

You should always be communicating and proving your value
People work with people who they trust to get results
You need to show you can get results
And you need them to trust you

What your value proposition?

WHAT services are you offering?
HOW do you work?
WHY should I hire you?
WHY should I buy from you?
WHY should I work with you?

‘WHAT’
I sell UX & UI design
services to startups
‘WHY’
We work in close collaboration with
startups to create intuitive and engaging
products their users will love

Value proposition isn’t about what you’re doing, or how you work
It’s about the value that the client or customer will receive

How to build trust?

A clear methodology of working

This is a game of leveraging!
Find customer Do great work Leverage that
Add to portfolio
Get a recommendation
Update your website
& LinkedIn

Add to portfolio
Update your website
& LinkedIn
Add to portfolio
Update your website
& LinkedIn
Add to portfolio
Update your website
& LinkedIn
This is a game of leveraging!

2How do I
keep things going?
P A R T 2 O F 3

2
So now you’ve gotten some work
The rest is simple right?
Wrong! (sorry 🙊)
Working remotely has challenges more than getting work
Whether you’re a remote employee or an entrepreneur

2
Remember that many things you never
thought about will be things you’ll have to
Whether it’s timezones, or cultural
misunderstandings
Over or underworking
Internet or infrastructure issues
Routine or discipline issues

Working as a remote worker
P A R T 1 O F 3
how do I keep things going?

So many unknowns!
Don’t panic!

Common Issues,
Simple Rules & Guidelines

Time management
“Wait, you want all of
this by your morning?”
Communication
“Argh I don’t think they
understand what I’m saying”
Deadlines
“Their morning
deadline is 2am for me”
Work relationships
“Wait, is my boss
unhappy with me?”
Typical problems at work get exaggerated in a remote setting

Unpredictable
infrastructure
“My wiﬁ isn’t working,
I’m screwed”
Visual communication
“Wait, I don’t understand,
can you sketch it out?”
Lack of easy / immediate
access to things
“I need X now but where do I ﬁnd
it, and why is no one online?”
And of course, there are new problems too

Do these things to mitigate them
Test the wiﬁ
(run a ping test)
Have data as a
backup
Find a coworking
space
Always use
earphones
Always switch
your video on
Back things up!
Often!

Over-communicate
Type things down; don’t rely on memory
Schedule things in advance
Set reminders to keep things visible
Explicitly talk or ask if there’s something wrong
Speak up!
Do these things to mitigate them

Dropbox
For any
and all ﬁles
Google Docs
For any live documents and
systematic organisation docs
Slack
For all internal
conversations
Notion
For project
management
Invision
For design mockups,
prototyping and feedback
RealtimeBoard
For any visual / strategic
planning + virtual workshops
Tools We Use
Hubspot
Sales pipeline
Harvest
Time-tracking
and invoices
Trello
Tracking anything!
MixMax
Email plugin

Running a team as a boss
(or like a boss)
P A R T 1 O F 3
how do I keep things going?

Working remotely is already tricky
Running a team remotely is trickier

Lack of visibility
“What’s happening
with the team?”
Team culture
“Where’s the
team spirit?”
Team organisation
“No one seems to know their
role and place in the team”
Managing a remote team brings new problems to solve
Roadblocks
“We need this by
tomorrow but it’s the
wrong timezone”
Single points of failure
“X has gone missing,
we’re all dooomed”

Central point to keep track of things
Visualise as much as you can
Organise consistently
Label for easy reference
Centralise information
Melewi

Have some overlap with your team
Or with your clients
Have it ﬁxed as much as you can
Dedicate the other time to work
Plan your time
Melewi

Keep things accessible all the time
Access shouldn’t be only when a
speciﬁc person is online!
Some labelling conventions are
good; keeps everyone on the
same page
Keep things accessible
(& backed up)
Melewi

Melewi
Explicitly lay out
how you work
Everyone on the
same page
You don’t have to
repeat yourself
Structure how
you work

Always put meetings down
So you never have to rely on
remembering or manual timezone
calculations being right
Plot in everything - including non-
work events and quiet work time
Schedule & let the tech
do the timezone math

Full team standup
Mondays to Fridays
3pm SGT
Rain or shine
Go through all projects statuses
before doing stand-up (done
yesterday, doing today, obstacles)
Melewi
Schedule
consistent
catch-ups

Sales Team Catch-up
Every Monday & Wednesday
Go through statuses on everything
Melewi
Schedule
consistent
catch-ups

Set to recur every 1 - 4 weeks
So nothing slips or gets forgotten
It’s a system that prevents reliance
on people to remember things
Melewi
Schedule
consistent
catch-ups

All those real-life lunches, coffees,
water-cooler chats don’t happen
naturally remotely
But they’re important
So schedule them in!
Schedule fun
hang out time!

People aren’t around to
notice things unsaid
Make the unnoticeable
and invisible explicit and
available
Melewi
Say things explicitly

3How do I
‘sustain the sane’?
P A R T 3 O F 3

3
The point of this lifestyle is to live a lifestyle you like
It defeats the purpose if you’re stressed out and don’t enjoy it
This means routines and boundaries help you!
This means being consistent and conscious about things outside of work

Feeling isolated
“I feel lonely”
Feeling unsupported
“This is hard, but I’ve no
one to talk to about it?
Want for community
“I don’t feel I’m part of
something bigger than myself”
Feeling overwhelmed
“There is so much to
keep track of….”
Cultural shock
“What???!”
Getting used to new
“I don’t know how to
do anything here”
Common digital nomad problems

How do I ‘sustain the sane’?
P A R T 3 O F 3
Plan, Organise
& Systemise

Standardised Packing Lists
& Essential Travel Info

Kindle
Lipbalm
Cables &
Earphones
Battery Pack
Earphone
Adaptor
Pen
Tickets
& Visas
Passport (yay
Singapore!)
Everything You Need To Survive Flights

P A R T 3 O F 3
Work-life Routine

Yay freedom! You get to decide
But because there are no rules set for you
It’s too easy to let one thing or the other slip
Unless you put in some simple rules for yourself
Some routine isn’t a bad thing!

Plan out your work time
Plan out your personal time
Plan out your days off (e.g. weekend)
Stick to it!
Think sustainable and long-term

:
Singapore
"
New Zealand
;
Europe
Quiet work
Personal time
Team overlap Team overlap
Personal time
Quiet work Quiet work
Team overlap
Personal time
Create a
schedule for
yourself

P A R T 3 O F 3
Staying Sane & Healthy

Go slow!
Travel slow - 1 month at one spot is the minimum
Start out working remotely at home, then start travelling
Find a good place to stay, you need to feel safe and secure
If you’re tired of travelling, stop
If you want to travel again, start
Listen to what your body and brain are telling you

Don’t forget friends and family back home
Carve out and schedule time to stay in touch
Get out there and meet new people
But it’s admittedly tough to build long friendships / relationships on the road
But keep trying
Take initiative
Find places people hang out at
Be friendly!

Working out regularly on the go is tough, but it’s important
Digital work is a sedentary lifestyle
Take walks, do body-weight workouts, ﬁnd a gym
Eat healthy! Don’t operate on holiday mode

Get travel insurance!
And other insurance too
Make sure you’re saving
Make sure you’re still contributing to your
country’s social and healthcare system (e.g. CPF)
Pay your taxes!!

Feeling lonely and isolated is one of the biggest digital nomad problems
Humans are social creatures!

Feeling overwhelmed will likely happen
Any taboo about it not being okay to have
a tough time psychologically is bullshit
Talk to someone - a therapist, a
psychologist, a psychiatrist
You have remote options
Consistency is important

1 2 3 4 5Remember these
5 things if nothing else!

1Getting started is
only half the battle
O N E

Work-life balance is extra
important when you’re remote
T W O
2

3Organise and systemise to
keep sane amongst the chaos
T H R E E

4Reflect and introspect,
stay connected
F O U R

@thedesignnomad
M E L E W I . N E T

Want moaaaar insights?
M E L E W I . N E T / N E W S L E T T E R

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Community Group
C O M I N G S O O N

How to Work & Travel 365 Days a Year Without Going Insane

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