The Anywhere OS: Preface

The Anywhere OS: Preface

Hey there! I’m Luke. I want to kick things off by sharing why I wrote this book.

My story (2013-2019)

My experience working remotely started almost a decade ago. At the time, I was a recent college graduate who moved to Boston, Massachusetts, in search of finding an “interesting” job in technology, but my wife and I planned on leaving as soon as we could. I knew that living in Boston was a temporary home and the only way I could leave was if I could take my job with me. I wasn’t willing to move to another location (especially somewhere more rural) if I wasn’t able to work on interesting things.

Six months after the move to Boston, I started working remotely as a contractor for a startup based in Silicon Valley. At the same time, 37 Signals (now known as Basecamp) released a book called: Remote. This book shaped my thinking and reinforced what I felt. If I work from a laptop, and my laptop can go anywhere, why do I need to live in Boston? Why can’t I relocate to a place where I want to live and still do meaningful work?

I discovered that working from anywhere had a lot of promise, but it also wasn’t easy. At times, I felt lonely working out of my tiny apartment. Some days I didn’t know what I was supposed to work on. I didn’t really know my coworkers or my boss well, either.

Despite the challenges, I couldn’t shake the feeling I had working from that 500 square-foot apartment. The freedom and autonomy was addicting. I felt like I was living in the future.

As my career advanced, I worked for a few different distributed companies in a variety of roles (individual contributor, team leader, executive) and was able to move out of Boston a few years ahead of schedule with my wife, who could also work remotely.

We ended up moving to Portland, Maine, and noticed an instant improvement to our quality of life. We didn’t have to spend two hours a day commuting, we lived closer to family, and were in a place that we wanted to be. Work no longer dictated where we lived.

At the time, I worked for a startup based in Nashville, Tennessee, and we would travel down and spend winters there, escaping the snow and cold in the Northeast. The entire time, we would regularly ask ourselves, “Is this real life?”

But working remotely still felt way too tough.

At every distributed company I worked for, I would repeatedly run into the same problems. It was difficult to answer questions like:

  • What are people working on?
  • Why does my work matter? How does it fit into the bigger picture?
  • Who are my coworkers? Are they people or robots?
  • Why am I spending my day sitting in boring meetings?

This itch drove me to start Friday (the company, not the day). I saw a need in the market and wanted to explore ways to help.

When things started to get interesting (2019-present)

I worked on Friday as a side hustle for a while, growing the idea enough to discover that there was an opportunity worth pursuing. I quit my day job in September 2019, raised a small amount of funding, and was able to hire a few engineers to explore possible solutions.

At the time, there was a growing number of companies (especially early-stage startups) that were struggling to hire in cities like San Francisco, New York, and Boston, so they were increasingly building distributed teams out of necessity.

Working on my startup accelerated the pace of learning. I was able to see what other companies were doing, but I also had the opportunity to share the lessons I learned after working remotely for several years. We could also take the lessons learned and build software to help.

At the time, about 2% of the US population was working remotely. Many investors were curious about this nascent market, but it wasn’t large enough back then. Remote work was a nice-to-have, but not a must-have for most organizations.

Then COVID-19 hit.

Approximately 10 times as many people are working fully remote now. Organizations are cutting back on office space. Numerous companies have shifted their operations to a work-from-anywhere model. Most research indicates that most companies will adopt a hybrid approach moving forward.

The way we work has changed.

2020 completely changed the face of work. As a result, many of you are trying to chart a new path into the unknown.

Why I wrote this book

I wrote this book because I couldn’t find a practical how-to guide on how to run a business and lead a company from anywhere. Existing books are too theoretical and not actionable enough. After COVID, many of you don’t need to be convinced that working from anywhere is the future. What you want to know is how to make this new approach actually work.

I’ve spent almost a decade working remotely. I’ve learned many important lessons from our customers. I’ve see what works and what doesn’t. I’ve also spent a ton of time reading through decades of research on how to work on distributed teams.

At the end of the day, I concluded, “why don’t I just write the book I wish I had.” And here we are!

About the co-author, Aisha.

I’d like to introduce you to Aisha Samake, my co-author for this book. Aisha has been working at Friday as a content marketing intern from Northeastern University for the past few months, and has written her own books in the past. I thought it would be useful to have her share her perspective, especially as she’s new to working from anywhere.

Aisha was working part time at her university when COVID hit, and she had to quickly shift from working in an office to working from home, while navigating online classes. Throughout the book, Aisha will share an employee perspective on the topics covered so we can unpack the advice from a variety of angles.

Ready to jump in? You can start with chapter 1 where we talk about the history of the office.