The State of Remote Work | #152

Checking in on what remote work tells us about work

September 4th, 2021: Greetings From Fuli, Taiwan. We’ve been doing a bit of travel through southern Taiwan. Definitely one of the coolest parts of Taiwan I’ve been to. Here is a view of the golden needles in bloom outside one of the rooms we rented and scootering through the greenest rice fields I’ve ever seen.

Greetings to all the new subscribers! There are nearly 4,700 people now. I’ve decided it might be fun to share some goals for people to support the newsletter if they want to, so I’m setting a goal of 5,000 subscribers by the end of September. If you’ve enjoyed the newsletter I’d love it if you’d share it with a friend or your social media network.

I also have several updates on Boundless and the newsletter at the bottom!


#1 The State of Remote

At the beginning of the pandemic, I argued that companies who committed to long-term remote were looking at a free strategic option.1 The base case for everyone was confusion and muddling through, so by choosing to invest in remote-first capabilities you could build for the future without the competitive disadvantage you might otherwise incur.

While the smart companies have leveled up, a large chunk has chosen to muddle. Friends at these companies report endless announcements, updates, tweaks, and backtracking. At these companies, people are also spending their day’s chock full of zoom meetings, performing industrial-era office work in front of a laptop. What a wasted opportunity.

One thing I realized in consulting was that you don’t have to have good ideas to stay in business. Sometimes a business model moat, industry trends, or regulations are good enough. Yet I am still a bit shocked that 18 months into a pandemic with endless amounts of information on how to make remote working work, there are CEOs making unforced errors like the CEO of the Washingtonian who wrote a public editorial in the Washington Post which seemed like it came from the 1990s:

Those who work from home probably won’t have FOMO, they will just have MO. The casual meetings that take place during the workday. The “Do you have three minutes to discuss X?” These encounters will happen. Information will be shared. Decisions will be made. Maybe if you are at home you’ll be Zoomed in, but probably not.

These make for great stories but it’s not worth wasting too much time on it. These companies will be left behind eventually.

The bigger story is how much things have shifted. It is hard to notice unless you are looking at it through the lens of common knowledge. Two years ago all-remote working or even working multiple days per week was a taboo idea. Too silly to even mention. Now everyone knows that everyone knows it is not only possible but might be a better strategy.

We are never going back to a day in which serious business leaders will be starting with all in-person as the default starting point for how to run a company.

Four Big Themes I’m Watching

With the lens of remote, I’m excited to continue exploring three big shifts in this space:

More experiments: The most interesting thing to me is the explosion in the number of experiments for how we work. This is the part that journalists don’t give a damn about. They’re more interested in pushing some both sides nonsense about fully remote versus fully in-person. No serious company has held the extreme in-person position in 10+ years. That debate is fake news. I’d love to see more written about how companies are experimenting with working remotely. In the meantime, I’ll be covering it here.

Information & Power Dynamics: Remote aligns with a deeper shift under the surface, a complete change in how people share information and communicate, which means the way power is distributed in an organization is much more dynamic and up for grabs than in the past. This is likely what gave employees the power to push back on the CEO from above and urge her to not only backtrack everything she said but apologize for even writing such thoughts in public.

Apple was one of the earliest companies to go remote and has likely built a lot of capability in doing so. They were in the news a couple of months ago because a little more than a thousand employees put forth a petition arguing for permanent remote-work options. This fit in the news narrative well and got amplified as an uprising at Apple. Nonsense. That group represented less than 3% of corporate employees and the real, more interesting story was that Apple was already permanently shifting to a 3-days in-person schedule.

That’s a pretty big shift! Apple was known as one of the most controlling employers and is deciding now that almost all corporate employees can be remote 40% of the time. How did this decision get made? What were the learnings from them starting so early and working remotely?

More Options For The Self-Employed: For self-employed freelancer/creator/coaching types like me, the shift in stories has enabled me to imagine new possibilities in terms of what I might work on over the next few years. More companies will likely be open to finding people to work much more flexibly in the past and in part-time roles. One challenge many long-term freelancing types face is that they are often in a sort of underemployment - where they would love to work with teams and companies in a deeper way but have no interest in full-time employment. Now smart companies are going to be forced to be much more creative with how they deploy talent.

New People On The Pathless Path: While there has been talk of many people quitting their jobs I think the bigger jump will happen in 2-3 years. In my book, I’m writing about how the stories we tell ourselves about how leaps happen tend to hide the truth. What I’ve experienced and seen in many others is that there is a dramatic event and then a period of recovery followed by action. In my case, a two-year health challenge was the dramatic event. The pandemic will be that experience for others. Some people move through these phases remarkably fast but almost always go through them. It took me about 3 years from recovering to quitting my job. If you’re looking for signals in your own life pay attention to when you start doing any of the following: side gigs, making new friends, personal makeovers, new habit small experiments, travel, writing online, and so on...

All I’m saying is watch this space.

Still More To Go

Because of Delta, all the smart companies have gotten 3-4 more months to continue to learn and get better at remote. If you’re at a company that is still playing office in front of a laptop, you should probably try to change jobs ASAP. If you’re a company leader at one of these companies, there’s still time.

A new story is emerging.

+For another good perspective on what this means for the labor economy, opportunities, and compensation, Dror Poleg has a great piece in the New York Times.


#2 Some Updates

August Break & Writing: I took most of August off from the newsletter and ran a few guest issues. It was a nice break. I’ve been writing a few hours for my book each day and have made a ton of progress. It’s morphing into something I’m excited about. I’m writing a book for the same people that like this newsletter. I also hired John Adamus to help me shape the book into a final form and it’s been great working with him so far. He has a number of resources on his site for writers.

Guest Issues: If you didn’t get a chance to read there here is Lauren on Digital Nomads, Pam on Career Models, and Nick on The Challenges Of Social Media. It was a fun experiment and I’m open to future guest posts but will only accept finished drafts for submission going forward.

Future of Boundless: We now have almost 4,700 people which is both terrifying and exciting. This newsletter remains the thing I’m most excited about though I sense I’ve been holding back a bit because I’m channeling a lot of creative energy into the book. I’m planning on doubling down on the newsletter after I launch the book and am hoping to continue to experiment with fun ways to turn this into a sustainable part of my work. If you have any feedback or requests for topics for me to go deeper on I’m all ears.

Sponsors: I’ve had a couple of companies reach out about sponsoring the newsletter and have been pretty hesitant so far but am brainstorming ways to do it in a way that might also benefit readers. One idea is to take a percentage of the money and use it for grants for creative projects. I’m also thinking about how I might use tokens and even NFTs to reward some of the early supporters of the newsletter. Still seems very early in the crypto world but I’m watching with an open mind.

#3 Support Boundless

I am focused on building a life around exploring ideas, connecting and helping people, and writing. If you’d like to support me directly the best way is to consider becoming a paid supporter of the newsletter.

Get 10% off forever

Alternatively, I use and love all of the following services and they give me 30% of all revenues from people that sign up. If you plan on launching a course or e-mail list and you end up using my affiliate code, I’ll gladly spend an hour helping you get set up and answering questions. Just let me know!