Working Remotely: How To Do It Right and Why


from Entrepreneurs Unpluggd

Last night’s Entrepreneurs Unpluggd event Working Remotely: How To Do It Right and Why in Chicago brought together a room full of people and four speakers exploring what it means to work remotely. Here’s a round up on the big ideas in case you missed it.

Jason Fried/37Signals

We’ve shared before how 37Signals works remotely. In a new book, REMOTE: Office Not Required, founder Jason Fried considers the question of working remotely from both the employer and employee perspective.

Over and over, the big message of wherever you work: It’s the work that matters. People worry if they can’t see you working they can’t know if you are working. He says it just doesn’t matter, you must look at the work.

it’s the work that matters


  • Real, unified culture is built around communicating online and all major decisions are made online. “Everywhere we talk we have fun.”
  • Chatrooms dedicated to discussing all manner of topics from projects to pets enable people getting to know each other better and faster. Jason argues new employees are able to feel more integrated into a company culture faster through remote work.
  • You learn to read one another’s written cues as well as non-verbal cues. And you can always get face time when you need it.
  • Flow is better because people are interrupted less and opt in to a conversation rather than just being tapped on the shoulder.


  • Opting for remote workers means a company has the option to hire more better workers.
  • Teams thinking of adding a remote worker to first try it out as a team by testing things and building things, developing the habits to support a remote worker.
  • Everyone gets the same interview depending on position and look for people who have worked collaboratively and/or remotely
  • Remote teams should prioritize people who are self-motivated, good time managers, deal with themselves, are all around managers of 1.

Sam Rosen/Desktime

Sam offered a parallel account to Jason’s, that of the power of place, but one that also supports the idea of remote work through coworking spaces.

“the office” doesn’t work anymore

By described what a not-good-enough separation of work/home looked like and some less-than-friendly looks from cafes, he said his first experience in remote working at coworking space as “filled to the brim with a bunch of rad people” and that it had, delightfully, reliable internet. In coworking, he found community. And in coworking, he sees the future of work.

  • Technology means we no longer are tethered to our desks and globalization combined with that technology means teams look different and are in different cities, time zones, continents.
  • “The Office” doesn’t work anymore for workers or the way young entrepreneurs build businesses.
  • An overwhelming amount of space and money involved in commercial real estate. Yet shadow space and ass-to-seat time makes it inefficient and archaic. Demand is for just-in-time spaces like coworking spaces, cafes, and office spaces with room for outside workers.
  • There’s a reason we work in each of the places we work (bed, home office, Starbucks, cool cafe, coworking space which changes over time.
  • When people want to be with people, a coworking space means being around people who can teach you things. Spaces have different cultures and foci. Find one that works for the way you work.
  • Perceived issues of safety/security trump real incidents of that kind of community trust being violated.
  • Remote working/coworking is still in its infancy. Our kids are not going to realize that’s not something that happened before. Our job, as people who cowork or understand coworking, is to get the word out, show that this is an option, this is an idea, this is the future.

Andee Harris/Bedroom Chemists & Syndio Social

Andee shared how selling a company changed the way she thought about entrepreneurship. She always thought entrepreneurs want to build something to sell something. Now wonders if, maybe, entrepreneurship is about building something, grow it, and then continue growing it.

innovation, collaboration, trust, openness, and boundaries

Her remote working tale was a bit more cautionary.

  • Her first business (Emerging Solutions) was built on transparency and having passion, trust, openness, boundaries.
  • She wanted to support a more balanced life for her and her employees, which means having great energy during the day and keeping that alive when you get home, she wanted a more balanced life for herself and her family.
  • Remote working didn’t work for her company as it grew and was sold. She sees it as a failing of Jason’s point that you must build the culture early and support it. “We did not have the mechanisms in place.”
  • Some companies may work better together. She argued that to learn other parts of the business, to be a leader, you need to understand the whole business from a holistic perspective.

Jeremy Neuner/NextSpace

Jeremy says we’re on the cusp of a once in a century shift. How, where, why we work is changing. In his book Rise of the Naked economy, he explores this shift from work being a place to a state of mind.

He looked to integrate Jason’s points about the power of remote working with Sam’s about the power of shared space by sharing how Andee’s push for balance matters. He argues remote and shared working are not only NOT mutually exclusive, they are symbiotic.

work is an ecosystem of places

  • Smart phones (1 in 10 people on the planet now have one) is the most rapidly adopted technology in the history of the species.
  • Tech has evolved faster, and we have adopted it faster, than we have evolved. We’ve evolved to be a social, collaborative species. Technology allows us to be mobile and be entrepreneurs anywhere, we have to figure out how to balance that with what fundamental humanity demands from us.
  • We have the tools to work remotely, stay innovative, be creative, and stay connected.
  • Weighing flow against fundamental humanity allows us to know where we need to work that day.
  • The greatest challenges we will face, for both business and society, will require us to have mighty collaborations and to come together in many different ways.
  • Work is no longer a place. Work is an ecosystem of places (Sam’s bed/office/cafe/coworking space).
  • The big questions are where and how am I going to work today and what do I need to get done today so that so that I can be happy, productive, innovative, creative, successful. You decide where you are going to be more awesome.
  • Entrepreneurs are inherently good at not taking no for an answer and that should help fuel the rise of the naked economy and remote working.