The Guide to Working Remotely

15 min read


  • Selling remote to your boss
  • Find out if you are a remote worker
  • Everything you need to know about working from home
  • Coworking spaces
  • How to avoid getting depressed
  • Accounting stuff from working remotely
  • Tools that will make your productivity
  • Tools that will break your productivity
  • How your coworkers should contact you

You probably read this book.

DHH Remote

No. It’s not an REM album.

“Remote Office Not Required” is a book by 37 Signals.

I read half of it and skimmed through the rest.

It’s not a “Recipe boook” or a “how to in 10 steps”.

It’s a book about “Why”.

This is the Guide to “now what”, “how do I”, “in 10 steps” sort of…

1. Selling to your boss

Time to do some quick math.

The almighty TI

  • You spend 1 hour commuting each way. Total 2 hours per day. 10 hours per week. 40 hours per month.
  • You spend $50 a week in gas.
  • You get sick once every 2 or 3 months. Therefore losing 4 days. 32 hours.
  • Coworkers make you lose 2 hrs a day. 40 hours per month.

Let’s say you get paid $50/hr.

Every month your company is losing:

$5,800 a month

If you are top notch. Let’s say you get paid $100/hr just to make math easy.

Your company is losing

$11,400 every month

Let’s say that again.

Eleven thousand four hundred dollars.

Scrooge is losing lotsa money

I would do the same face if an employee tells me I am losing $11,400 a month on him/her.

Before you pitch it to your boss. Don’t say “I did this math and your are losing…”.

Don’t do that.

Lookup an article from a prominent source.

The Harvard Business Review would be a good one. Or MIT or Stanford…you get the idea.

Don’t show your boss an article you saw on Wired or US Weekly.

Sneak a copy of the Remote book

Don’t just show up at your boss’s door saying “Hey I read this book about…we should do it”.

That won’t fly.

Give it as a gift

  • Your boss’s birthday
  • Your boss’s wife’s birthday
  • Your boss asks you for ideas for gifts
  • Christmas (might be funny)
  • Labor day (might be sarcastic, not so funny)
  • Any holiday (use your best judgment)
  • Send anonimously to your boss’s desk (kinda creepy)

The truth is that the math doesn’t lie.

$11,400 a month is a lot of money.

2. Are you a remote worker?

You are not a remote worker

You work in an environment where you need to ship products to companies. Shipping and receiving, quality control, operations.

You work in sales interacting with customers all day by phone. Sales people need “the pump” and the competition of other sales people to get that “competitive drive”.

You have an internship program where you need to train people. You are either the trainer or the intern.

Not a remote worker:

Jobs that require physical presence

  • Receptionist
  • Student advisor
  • Intern
  • Food service
  • Child care
  • Maintenance

Lookup the “telecommuting guidelines of Berkeley”. They are common sense…to most humans.

You could be a remote worker

  • Writer
  • Editor
  • Programmer
  • Marketer (that one of the Marketing stuff)

Think about this…

  • Can you do your job individually without depending from other people 100%?
  • Can you do your job from anywhere? from any time zone?
  • You only need internet and a computer?

You could be remote.

Remote doesn’t mean “work from home” only. It means “work from anywhere”.

Say you live in Rome (New York). And you move to Rome (Italy) for a month. Can you do the work there?

You are definitively remote potential.

NOTE: Work individually 100%

The only way to work individually 100% is when you are a writer. You are writing books and you only do that. Like I am writing this post. I don’t depend on anybody to write it. Although that’s extreme.

If you are a writer, probably you have an editor, a publisher and all those folks in the writing biz. You need to answer to them. Unless you are a reclusive hermit.

Work individually in a team

If you have team members I assume you are working towards a common goal. Sales goals, shipping code, customer satisfaction goal?

Can you do 8 pomodoros straight up without interruptions? (Lookup “pomodoro technique)

You can be remote.

3. Working From Home

NOTE: Working Remotely doesn’t imply Working from Home ONLY

Working Remotely means working from anywhere not only your home.

It means:

  • A coworking space
  • The coffee shop (read Starbucks)
  • The train (if you hackatrain)
  • Your backyard
  • The library

If you decide to work from home. This is exactly what you need:

Aeron ergonomic chair

  • Home office with a door that you can close
  • Desk
  • Standing desk.
  • Aeron chair (don’t be cheap here)
  • 3 computers. A desktop (PC or MAC), a laptop PC, a MAC. Wireless mouse, wireless keyboard.
  • Ipad, kindle
  • 2 external monitors larger than 23 inches…and the cables to hook up to computer.
  • Printer/scanner a fast one.
  • Noise cancelling headset
  • Noise cancelling headphones
  • File cabinet. A good looking one small.
  • Fireproof lockbox
  • Desk lamp

We are talking about $1,000 for desk and chair. $3000 to $4000 in electronics.

Why is this important?

You are sitting in front of your computer all day.

You need the best ergonomic chair out there. They are not cheap. Your back is worth much more.

You need good computer equipment and backup computers in case they break.

You will need a portable laptop if you work from other remote places.

You will need an ipad/kindle or smartphone if you want to read a book in the park. Unless you read paper books.

Got a meeting with a local client? Bring your Ipad.

Office with a door

If you live with somebody else…your girlfriend/boyfriend, partner/husband/wife, relatives, any human or not. They will assume you are available. Just cause you are home.

“Do the laundry”…but I am working…”but you are home”

“Can you please do XYZ”…but I am working…”you are home so…”

“Can you watch the kids”…but I am working…”well you are home”

Teach others that you work from home

They need to respect you working from home.

If they don’t.

You CANNOT work from home. Simply cause they will interrupt you every 5 minutes. And you are back to interruption land.

Seek other places to work like the mentioned above.

The Coffee Shop with the weird foam

You don’t have a home office

This will not work:

  • You work from the dining room
  • You work from your bed
  • You work from a spot where they will interrupt you…even if you tell them not to.
  • Your home office is used for guests to sleep. If your guests are there for a short period. Seek other temporary work place.
  • Your kids are home all day. It will break your heart when your tiny one wants to play with you and you say no.

You cannot work from home.


4. Coworking spaces

I worked from home for 2 years…

Then I looked for a coworking space due to the above reason (read heartbreaking)

Working from home all day every day will make you lose it if you don’t interact with the humans.

You will become a hermit and you will get depressed. More about this below.

There are a lot of coworking spaces opening up all over.

I coworked in Chicago for like 3 years. Officeport. The Coop. Ravenswood coworking. 1871.

Here is my review about coworking in Chicago

The main benefits of coworking are:

  • Working remotely from home doesn’t work out every day
  • Meet humans
  • Make friends
  • Go to local meetups

Going to local meetups

If you are working from home is hard to go to local meetups.


You get lazy.

You need to commute.

It’s dark out and you are already home.

You need/want family time.

Half home Half Cowork

You should do half and half…or a few days here and there.

If you work remotely you don’t need to go to an office every day. A coworking space is an office.

A coworking space where you need to commute for an hour each day is not fun.

But if this is the only way to meet people. Then do half and half.

Although remember that you might go back to minus $11,400.

You could do:

  • Work a few days from home a few days cowork
  • Mornings home, afternoons cowork
  • A cowork schedule where there is no bad traffic

5. How to avoid getting depressed

Working remotely can make you into a hermit if:

  • You don’t go to at least a weekly local meetup
  • You don’t shower
  • You don’t make an effort to meet humans

Your schedule

  1. Wake up
  2. Take a shower
  3. Get dressed
  4. Have breakfast
  5. Commute to home office
  6. Do Pomodoros
  7. Emerge from home office. Take break
  8. Into home office.
  9. Have lunch at noon. No later than 1:30pm. Cook it and bring outside or go buy lunch outside and eat it there.
  10. Back to office. Work til 4pm. Break
  11. Work til 6 to 6:30pm

Make this your ritual. very important:

Take a shower > Get dressed > Have breakfast > Take a walk outside at least once

Little things will hint that you are losing it such as:

  • Not showering
  • Not shaving (if you are a clean cut male)
  • Not knowing if it’s cold or hot outside (losing sense of weather)
  • Not remembering what you had for lunch
  • Not remembering last time you talk to a human face to face
  • Working from your bed

Your schedule could change if you decide to cowork:

  • Beating traffic at 7am or 11am
  • Going to cowork in the afternoon so you can then go to nearby meetup

6. Accounting stuff

If your company is not in your city you need to get advising about complying with your state taxes.

If your company has never hired someone remotely from your state probably they don’t have a clue they need to pay for XYZ. If this is the case you need to get advise from a local accountant. Hopefully your company will pay for this advise.

This is very important stuff.

7. Tools that will make your


Gmail and google docs.

Collaborate on google docs is very easy. You can see and edit the same document at the same time.

Skype with a nice headset.

Buy a Skype number so they can call you from a phone to your computer.

Webcam for webchat. Very important to see your teammates, clients, others.

Nothing beats body language.

Dropbox to share files. If Google Docs not enough for you.

Basecamp to share projects, tasks, etc

OnepageCRM to share CRM stuff or use whatever other CRM

Citrix sharing screen stuff.

If you are a programmer, probably you know you can share screens with ssh to a remote server. Get a VPS, setup an environment and have you and your sidekick ssh to it. Plenty of tutorials out there. A good one on the Tmux book by Brian Hogan.

8. Tools that will break your


  • Your TV
  • Your Xbox/PS/whatever Nintendo like
  • Eating lunch at your desk
  • Youtube
  • Being a DJ on Spotify
  • Facebook

If you are working from home and you are taking breaks. Don’t use these to watch TV or play video games.

If you are the kind of TV person that likes marathons of shows. Unplug the TV while you work.

9. Company expectations

Can you set your own schedule?

Do you still need to go by 9 to 5?

Can you work 11 to 7?

It depends on your company.

To gain trust you must be available.

  • Get a skype phone number
  • Give them this number and your cell phone

You can be reached like this:

  • Skype phone
  • Skype chat
  • Cell phone
  • Whatsapp
  • Text
  • Email

It’s important to let your company know you are available.

When to contact you

Since you need to focus and you need to get things done

  • Ask them to send you an email if it’s not urgent.
  • Ask them to text you if it’s important.
  • Ask them to call you if the world is ending.

It’s important to set your boundaries. Set your schedule. Your meetings and how they should interrupt you.

10. What’s next?

If you got any other working remotely tips please comment so I can list them here