This document provides advice for running a remote business and living a digital nomad lifestyle over an extended period of time based on the author's 9 years of experience. Key lessons include establishing consistent communication windows for the remote team; codifying processes, knowledge, and company culture; planning travel, work, and personal schedules; and prioritizing social, physical, and mental well-being to avoid common issues like isolation that digital nomads face. The author advocates for automating systems and routines to bring structure that prevents reliance on individuals and helps teams and lifestyles feel sustainable long-term.
5. I was a freelancer for a year
Discovered being a "digital nomad" by accident
Soon had too much work, and had to hire
Didn't want to stop travelling, so okay, remote team it is then…
digital nomad
9+ years
lived in
3 countries
travelled to
40+ more
13. Um, I thought she said she was gonna do it
Isn’t this what the client meant though?
Wait, we didn’t discuss this yet…
No, I don’t think so. Yes, that’s what he said!
Wait... I don’t think you can do that
Err, that’s definitely how it’s done
What????
oh no
15. 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)
Schedule
consistent
catch-ups
17. 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
Schedule
consistent
catch-ups
18. Have some overlap with your team
Or with your clients
Have it fixed as much as you can
Dedicate the other time to solo work
Plan your team’s time
20. So many things we never stop to think about because we’ve never had to
Others we haven’t stopped to question
For example, how do you learn from someone?
A lot of the times, by imitation...
So what happens if you can’t observe to imitate?
24. Hey Mel, where do I find the McD sitemap?
Hey Mel, is Rumen working today?
Hey Mel, we’ve got this new lead, what should I do?
Hey Mel, what should I tell everyone about days off?
Hey Mel, who should I ask about this?
Hey Mel, do you think I should shave my head?
Hey Mel, our accountants are asking us what our monthly expenses are?
Hey Mel, where do I upload this file?
Hey Mel, Hey Mel, Hey Mel...
omfg
28. 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)
37. No one is in the same room!
There’s no physical space to help you create the right “vibe”
How do you have a culture without easy access to each other?
How can you assess morale and camaraderie?
The same issues with working remotely exacerbates team culture problems
39. Why
Why are you doing
what you’re doing?
(Simon Sinek does a much
better job of explaining this)
Values
The judgement of
what’s important
Attitudes
A way of thinking or
feeling about something
Behaviours
The way you conduct yourself
(particularly with others)
40. Explicitly communicate those values + corresponding attitudes and behaviours
Leave them somewhere visible
So you can revisit them
And your team can revisit them
Always refer to them
Always use them to help assess if you’re sticking to your values
43. Don’t rely on just you
All those real-life lunches, coffees,
water-cooler chats don’t happen
naturally remotely
But they’re important
So schedule them in!
Designated
Hangout Fun-time
44. Make spaces for them
Automate involvement
Reminders don’t have to
just come from you
Doing it
asynchronously
45. Team culture is about having a
shared approach to certain things —
both good and bad things
Help everyone get on the same page
React the right way
Teach everyone to
have similar responses
47. Schedule individual chats with every member of the team
Create opportunities for the new person to get to know everyone
Make the first step to familiarity a priority
Assign other team members to make them feel welcome!
52. 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!
53. 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
54. 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
55. 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
Use tech for timezones
+ Make space for life
61. 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
63. 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
65. 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!
67. 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
69. 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!!
71. Feeling lonely and isolated is one of the biggest digital nomad problems
Humans are social creatures!
72. 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