'I'll Never Work The Same Way Again:' One Co-Founder's Remote Work Experiments

There's a lot of talk about structure and boundaries, but there's something to be said for flexibility, and embracing the messiness of your "life's work."
'I'll Never Work The Same Way Again:' One Co-Founder's Remote Work Experiments
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Entrepreneur Leadership Network Writer
Co-Founder & CEO of Chatbooks
6 min read
Opinions expressed by Entrepreneur contributors are their own.

When my wife Vanessa and I started Chatbooks — an app that makes it easy to create family photo books — we quickly realized that the lines between work and family time were going to get really blurry for us. Talk at the dinner table often bounced back and forth between product decisions, problems at our kids' school, upcoming auditions, hiring questions, and who could get a bunch of friends to come over to pack boxes for a last-minute marketing promotion. 

When we started the company six years ago, the buzziest topics for startup founders were “healthy boundaries” and “.” But with a fast-growing and seven busy kids running around, that was never going to happen for us. Instead, we decided to treat Chatbooks like a family farm: We’d come and go, do our work, live our lives and stop worrying about where work stopped and life started. 

The almost complete integration of work and life that has become the reality for millions this year (including our at Chatbooks!) has been my world since 2014. As Vanessa and I have shared advice and rolled out new policies for our entire company based on our own personal experiences, we’ve landed on a few key efforts that can make working from home an amazing source of productivity and happiness for both companies and team members alike. 

Related: 10 Tips From CEOs on Working From Home Effectively and Happily

Recognize it is *not* going to be “like office life before, just on Zoom”

The first step in making this transition is to recognize that remote working life is just flat out going to be different. The things we value, the people we recruit and retain, and the ways we normally do the things we do — in other words, our company culture — will need to change. I know of one company that is requiring every employee to keep their video chat open (with a company-branded virtual background) from 8:30 am to 6 pm every day. That’s insane. Working “the way we always have, but now on Zoom” is bound to lead to and failure. 

Release the expectation of “9 to 5”

“Going to work” used to mean getting to the office around 9am and leaving around 5pm. But we already had some flexibility around this: As my wife and I juggled the afterschool activities of seven kids, there were plenty of times I left the office at 2pm, and returned to my laptop after the kids were in bed. With the move to an entirely remote team, we have encouraged our team leaders to release the notion of universal availability from 9am to 5pm, and instead trust that team members will get work done when it needs to get done. I’ve worked with individual leaders to enable this by scaling back the frequency of their all-, changing standup calls to written check-ins, and implementing “no meeting days.” As a company we still believe in contributing “Amazing Hours” to our company mission, but when those hours happen can be determined (mostly) by individual small teams and employees.

Encourage real breaks

In an office environment, there are natural breaks: grabbing a snack from the kitchen, or running into a colleague in the hall. But in a fully distributed team setting where Slack messages keep coming in hot, it’s so easy to feel trapped at our desks. Our bodies are not built for that many hours of sitting! We’ve encouraged all team members to use the “speedy meetings” setting in Calendar that automatically shortens meetings by a few minutes (instead of an hour, meetings default to 50 minutes, for example) to allow for a stretch or bio break between back-to-back meetings. We’ve also started to vocally encourage our team members to get up and get away from their desks regularly during the work day. Scheduling “Remote Walk-and-Talks” where the famous “walking meeting” now happens over Airpods in two different subdivisions, for example, has been a great way to break free of the glare of the Zoom on-camera light. 

Related: Survey Reveals 4 Transformational Remote Work Trends

Commit to deep work, in advance

But the real key that unlocks us from our solitary (or noisy) desks is embracing the power of “asynchronous work.” When work doesn’t have to happen at the same time for everyone, it makes it easier to prioritize the oft-elusive “deep work” sessions that can get crowded out by the noise and urgency of office life. As a leadership team, we have been encouraging more thinking, writing, and discussion in “async mode” in advance of (now shorter) larger group discussions. We’re relying more on workflow-management software like Flow to manage day-to-day project execution, and knowledge-sharing systems like Notion to process results and codify learnings. 

As our whole team embraces these distributed and asynchronous working habits and they become second nature, we’re seeing more productivity and happiness across the board. And we’ve been tracking it: In a recent team survey, 97 percent of team members said they were at least as happy at their jobs now as pre-pandemic, and two-thirds of our team members were more likely to recommend working here to a friend. 

Maybe all of these unexpected changes to our “working lives” are going to be good for us after all. By undoing some of the relatively new “go to work” norms that developed alongside the rise of the corporation, and instead sending us back in time to our little “knowledge worker family farms,” perhaps we can make peace with just working and living and simply embracing the un-compartmentalized noise and boundary-blurring satisfaction of doing our “life’s work!"

Related: Facebook Offers Employees $1K, Extends Work From Home Policy ...

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