Even the greatest strengths, especially when they get over-used, eventually perform as weaknesses.

One thing to love about remote work is the (relatively) no-drama, no-bullshit work environment. I rarely engage with my colleagues about religion, politics, family squabbles or any other sort of potentially divisive issues. 

But what happens when the bullshit really matters?

Remote work keeps you focused on the latter, the work. And that’s part of what’s great about it.

I knew we had taken that idea a bit too far this past summer in London.

Prateek (our lead content strategist) and Tyler (our founder) had both flown 10 hours—Prateek from Mumbai and Tyler from Des Moines—for a week-long strategy session among the three of us. We were setting content strategy and editorial calendars for something like 16 clients. It was our very first time spreading the work beyond just Tyler and doing it together in-person.

Some weeks prior, Tyler and I had a tough conversation in which he conveyed his frustrations to me. 

I was missing internal deadlines. The quality of my work was flagging. At least one client had noticed. A change was needed.

Even as we pushed through client calendar after client calendar, things were still tense between us and I knew another conversation was needed.

On one level (the work level), the rationale was simple: I was spread quite thinly across nearly 10 different clients in my capacity as a writer. I was juggling a new and emerging role leading operations and the boundaries of the role weren’t quite set. I didn’t feel set up for success.

At least, that’s what was happening on the surface.

How to Survive a Cruel, Cruel Summer

Underneath the digital veneer was a much more complex picture. 

My elderly father was moving into a retirement community and I was struggling to support him by basically engineering that move from 3,539 miles away. It was too expensive to fly home during the middle of the high season in the summer. 

There was even a memorable moment when I was literally on the phone with the movers whilst attending a weekend music festival with friends. After his first month in the new place (which is lovely by the way), he fell and broke his leg.

I flew home to help out a few times over the summer, but the travel wore me down.

To make matters worse, my mother called me with some really heart-wrenching news. She was now essentially homeless and living out of her car. For the average person, this would be a shocking development, but for me, it’s par for the course because she has struggled with drug addiction her whole life.

If you want to take a stab at feeling utterly helpless, try getting a call from a parent who can’t even house themselves. 

I remember weeping openly in my uber ride back to the airport upon hearing this terrible news. The driver pretended not to see me and made nothing of it. I was grateful for this momentary and kind mercy.

I was spent just trying to get my Dad settled and now this.

When I got back to London the next day—my birthday no less—I tried to keep a stiff upper lip when the woman I was dating met me at Heathrow. Despite my best efforts, she could feel that something had shifted.

I could barely manage what was going on with my family back home. I didn’t have it in me to be emotionally present for our relationship. And I was likely leaving the UK for Mexico in a month or so anyway. I had stayed months longer, in part, because of our budding romance.

The great irony of vulnerability is that it pulls people toward you, not away from you.

The end was nigh, in terms of time and sentiment. We both felt it and it was awful.

So let’s tally all of that up.

An aging father with a broken leg just after a big move—check.

A mother without stable housing—check .

And one crumbling romantic relationship—check.

A true trifecta of personal turmoil.

Unfortunately, none of that can be neatly packaged into my weekly standup update in Slack.

At a “normal” workplace, you run into people at the watercooler and ask them how their weekend was. Maybe you head out for happy hour and wallow together over beers. (Sure, we’ve got a virtual happy hour on Fridays, but it’s just not the same.)

No one at work knew what was going on in my personal life and our work culture was/is such that it didn’t matter. But it did. A lot. Even as I write this, I know that some of our team will read this and learn about it for the first time and even that makes me nervous, though it shouldn’t.

After a few days of being cordial in London, I worked up the nerve to talk to Tyler about it all. It’s not easy talking to anyone, even your therapist (which I definitely was at the time), let alone your founder/boss.

I had to get past those feelings of being a victim to all of these circumstances largely beyond my control. I had to let go of the notion that these things somehow made me appear weak when in reality, quite the opposite was true. I worried too much about how different this would make me seem in comparison to my colleagues who all seemed to be performing well.

On the third morning of the week, Prateek was out at a meeting and Tyler and I had time to ourselves at the Airbnb where we were working. I told him everything that was resting on my heart and he took it in. His first reaction seemed to be shock that all that was happening and he didn’t know about it. We work so closely together. True to form, he focused on what could be done to help, if anything. There wasn’t much, other than hearing me out, and that much had been accomplished.

It was a kind and generous response. I expected no less and I’m not sure why I was so reluctant, in retrospect.

The great irony of vulnerability is that it pulls people toward you, not away from you.

They see their own flaws and frailties in whatever you’ve got going on. 

In some ways, they’ve been where you are at that moment. Hell, they might be going through something similar right now and are just oddly grateful to know that someone else at work is going through something as well.

The thing that struck me the most about the whole episode was the space-making that occurred. In a remote, digital environment, moments like that are a bit harder to achieve.

But they’re not impossible. And goddamnit are they necessary.

Building a Better Workplace Culture Through Small Wins

7 Tactics for Improving Well-Being on Distributed Teams

While I’d love to now tell a grand story about workplace transformation starting at that poignant inflection point, I’d be lying.

I’m not going to lie to you. Changing any workplace culture is a slow burn.

But I think what that moment gave us was greater consciousness, and again, space to begin thinking about how and why this stuff we call mental well-being in the workplace might matter. How it might look and feel and perform differently in our unique context.

That’s the other side of innovation, innit? (I’m turning British sometimes, I swear)

And the good news is that things seem to be trending in the right direction. 

We’ve been taking biannual surveys of the team, trying to capture their sentiments toward the worklife that we’re building together. The results look generally promising. 

Team survey results show that people felt better about workload, compensation, and quality of work.

The team seems to be feeling better, overall, about their workload, compensation, quality of work that’s being done. 

But, like everything, it’s a work in progress. 

When you’re dreaming up a next-generation collective of freelancers who are still freelancers but perform like an agency, there will always be corners you can’t see around and bumps along the road. This was a big one for us.

While this wasn’t a part of some big strategic plan to transform our workplace, we did make some interesting tactical changes that have proven effective.

Convene in person (at least) twice per year

There’s just no substitute for face time.

Now that our revenue allows for it, we’ve committed to bringing the team together (on a voluntary basis) at least twice per year. One retreat is designated as a “perk” trip, usually to an international location (like our last one in Mexico City) with fun amenities like the eco-retreat where we spent a few days together.

The Optimist at a team retreat in Mexico City.

The second retreat is more standard, usually to somewhere easily-accessible in the continental US (since most of our team are based there), but still an enjoyable location like our previous retreat in Nashville.

Wherever we go, people generally come away fired up about the mission of our agency and more empathic and collaborative in their work.

Hold gratitude sessions

At our last retreat, we got all kumbaya with it.

We went to a local park at sunset, sat in a circle, and each wrote one thing that we were grateful for or admired about every other person in the circle. We went around to each person and 2-3 people would share their gratitudes out loud with that person and the group.

Every person went home from that retreat with a pocketful of notes about how wonderful they are.

Sure, it felt corny. It also worked.

Designate a master of ceremonies 

I’m not sure how she keeps it all together, but Katy has figured it out.

Virtually every week, there’s a new taco-storm (we give virtual tacos which can be redeemed for gift certificates to celebrate people) for another team member. Usually, it’s a birthday, their “Opti-versary” (their anniversary having joined our funny crew), or they rocked it on some piece of content and got some great client feedback.

Katy on our promotions team keeps track of all of this and makes sure everyone feels celebrated throughout the year. It’s pretty remarkable to watch and takes so little effort on the rest of our parts to quickly celebrate our colleagues from afar then get back to work.

I remember my first few months at Optimist when my birthday passed and no one on the team knew about it. I felt a little tinge of sadness that I wasn’t close enough with the people I worked with (but hadn’t met yet) and that they didn’t know about my special day. And I’m not even big on birthdays!

But that’s the bullshit that matters.

Change how you onboard people

This is a constant moving target.

We’re always finding out that some new freelancers doesn’t have access to this or that important document or weren’t made aware of some ongoing practice.

When people feel lost at work, it just sucks.

Now we’re building a wiki to organize our knowledge management and doing more necessary hand-holding with onboarding calls. We know that people feel more secure and cared for when they’ve got the information and tools (and partnership) they need to succeed from the outset.

So we’re giving it to them.

Ask actual getting-to-know-you questions 

Our standups are another ongoing point of evolution.

They’ve gone from actual Google hangout calls, to Slack updates, to Asana updates, back to Slack and Asana updates.

Now we seem to have found the right mix. We ask folks to update their projects in Asana and coordinate with their team members on realistic timelines for work completion. And we also add in a fun getting-to-know-you question after they’ve dispensed with the work stuff.

This is important because all-business standups are off-putting. And it’s nice to ask thought-provoking questions to get your brain moving on Monday mornings. People find out what they have in common with each other and learn new things about their teammates they might not have otherwise discovered.

Don’t sleep on the power of standups for bringing people together over more than just the work.

Study up on the latest trends

Most of our team are voracious consumers of content.

We even have a #content channel in Slack where we share the stuff we’ve enjoyed on the interwebs.

As a bit of an experiment, I started posting more material about mental health and it opened the conversation up. We looked at the State of Remote Work report by Buffer where they call out some alarming trends.

The biggest struggles of working remotely, according to Buffer's State of Remote Work report.

Spoiler alert: People who work remotely have a hard time unplugging from work.

They’re also lonely and sometimes struggle to communicate and collaborate with their peers. Even with all of this connectivity and apps and devices to make us healthier, it turns out we’re still quite overworked and isolated.

Reading up about what was going on in the broader industry helped us benchmark how we were doing as a company. Sometimes you’ve got to zoom out in order to zoom back in on the challenge and get the right view of it.

Carve out dedicated time for mental health 

Just make the time. Schedule it. Send the invite. 

Show up. Turn your damn video on.

We took a cue from our friends over at Leapers (h/t for all the fabulous work they’re doing in this area) and booked a session completely dedicated to mental health. Just a few team members showed up, which was fine.

We talked a bit about our experiences in general terms and then used the time to just work together with our cameras on. As weird as it sounds, it was gratifying. Just hearing those voices and seeing those faces on the other end of the line made a small but measurable difference in our days.

The next step is probably integrating such conversations into normal practice and not making such a standalone “thing” but, we’ll get there. It’s a good start for now.

Why we’re optimistic about workplace well-being in 2020

Paul and his dad, enjoying much-needed bonding and down time.

Things have a funny way of coming full circle.

Dad’s leg healed up well, he loves his new apartment (more than he’ll admit to me but he told my aunt as much and then she told me), and we even got to go on a cruise to the Bahamas for Christmas.

Mom finally has a new apartment. And about that relationship…well let’s just say we’re on good terms and still support each other. 

After the crucible that was this past year, I’m grateful for all of the personal development and that I work in a place where I can immediately, flexibly, and creatively apply some of those lessons learned to make things a bit better for others.

That’s a lot more agency than most people have in their workplaces and I’m thankful for it.

I recognize that this moment of our collective reckoning with mental health isn’t unique to just Optimist. There are broader trends at play here.

But what last year taught me was the importance of making that space for another. Space to not always show up at 100%, to not always “crush it”, or be a friggin’ “rock star” or insert any other tech bro euphemism that strips people of any sort of natural human frailty.

Sometimes it’s space to just listen. Other times it’s space to say thank you and “I love this one thing about you.” Whatever space you’re making, don’t feel bad about it being a departure from our very task-oriented, remote work culture.

The greatest irony is that without that room for the so-called bullshit, the work wouldn’t get done at all. 

Follow along as we grow a new kind of agency

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Paul Perry

Paul Perry

I'm a principal at Optimist and lead agency operations. With a background in education and social impact, I help implement performance measurement, documentation, and steer the firm.

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