A few years ago when I was at Clubhouse I blogged about our process of becoming a geographically distributed team. In that case, the first stumblings towards global domination were not made to acquire talent but rather in an attempt to retain talent vital to our team (talent = people we really loved working with and didn’t wanna lose!). In that article, I outlined some of the ways we tried to bridge the gap and some of the things that were still just tough.

I’ve also written about some of the reservations I have about working from home, especially as it pertains to underrepresented people in the workplace.

Since moving to Nylas and serving on the top-notch leadership team here, I’ve been even more privy to some of the business-side challenges of having a team where people are working from all over the place. SO I thought I’d pull together a quick blogpost of my learnings.

Things to Consider Before Opening Up Satellite Offices or Having Remote Teammates

People In Other Places Are Often In Other Timezones Too

I know it sounds obvious, but it needs to be stated. If you employ someone somewhere else, their day may overlap with yours a lot, a little, or not at all. You need to think about how that’s going to affect everyone’s ability to get things done. If your SF-based team is making most of your decisions synchronously in meetings or Slack, how will that affect your support folks in Berlin, your UX designer in Medellin, or your developer in New Zealand? Will they have to work odd hours just to keep up with HQ or can you start relying more on async tools?

When working across large distances across the globe, it is important to establish a baseline in every area for when they should be online and working and when they should stop and go live their lives. While you might sometimes need a teammate to work before or after their formal working hours, it is useful to know, clearly define in the calendar, and respect those agreed-upon working hours.

If you’re going to be working across significant time differences, I recommend trying to move meetings to times that work better for people and leaning more heavily on tools like Clubhouse and email that allow people to communicate on a more humane timeline.

Flights and Hotels Are Expensive

Cohesion across teams does require some amount of time spent together in fleshspace. Getting people together often means flights, hotels, and expensed meals. Just make sure you have the money for this — and that you earmark it especially for those purposes.

A/V Is An Investment…Good A/V Even More So

I am of the opinion that videochat software is painfully immature and being relied on too heavily for important communication. I use videochat every single working day and it is very much in the “can you hear me now?” phase. This is unfortunate because around the world in so many contexts people rely on it to make crucial decisions (read how Skype Trial has tragically become the norm for US immigration court).

Despite videoconferencing’s weakness as a replacement for “the real thing”, it is what we got. So doubling down to make it work is important. Headphones, good mics, fast wifi, and good webcams can cut down the distance between co-workers and enable you to have vital conversations with less muffle, crackle, and static.

When these all fail you — as they inevitably will — try to keep your teammate’s phone number nearby and just call them on the phone. I’ve had so many hours wasted fighting with videochat. Don’t let that be you and your team.

Employing People In Other States and Countries Can Be Costly and Time-Consuming

Different states and countries have different employment regimes. If you intend to employ people there, you will need to be in compliance with those requirements. HR companies like Gusto can likely help you with red tape, but it will still require some time and money to make sure you are following the rules of (and engaging the insurance market of!) the state or country where your fantastic new potential teammate lives.

Benefits Can Be Lopsided

If your company offers special perks to people in the office, you’ll need to carefully consider which of those you can/want to extend to people working from home or a satellite office. Things like free lunches and free office massages or whatever are often there to entice people to come in to the office and stay there. They tend not to be as feasible to make available to people who are working from home.

It is important to think about offering a benefits regime that doesn’t cause lopsidedness or ill-will when your HQ folks and your remote folks compare their cards.

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None of this is intended to discourage you from doing what you need to do to attract and retain great people for your company. The last 10 years of my career have been spent working in organizations and teams that span state and national borders, and I’ve rarely had to rule someone out because of their location.

Remote workers do work; geographically-distributed teams can and do work—even on a small scale. They just work best when you go in with your eyes open to the challenges.

I’ll be honest: I don’t love my job and I don’t think I’ve ever truly loved any job I’ve ever had since I began my working life in earnest. Don’t get me wrong. I’ve had several lovely work environments in beautiful offices with truly fantastic co-workers — many of whom I still count as my closest friends — but I’d still not call that loving my job.

No, I’ve had jobs from unbearable to perfectly survivable, and the older I get, the more I realize that here in late-stage capitalism, a job I love is not the goal, –being able to put time and money and resources into things I want to see flourish is. I don’t do what I love, I fund what I love.

By this I mean, I am a donor of my money and time and skills. I currently do unpaid work for at least five different groups and give money and/or advice to dozens more. I don’t work on the front lines of any efforts to cure the sick or free the encaged or smash the empire, but I do my best to give to groups that do. And I’m finally coming around to realizing that funds and funders matter.

I recently facilitated a dinner event attended by people from both the commercial and nonprofit spaces, and I noted a distinct snootiness towards people who hadn’t committed their lives to radical struggle defined as working in a cooperative or a foundation-funded NGO. I’ve encountered this sensibility throughout my journey as an independent activist/organizer and it’s lame and wrong. The “revolution” will no more be funded by large non-profit donors than it will by Silicon Valley venture capitalists.

The truth is that the struggle has and will always require a diversity of tactics, as well as a diversity of funding and energy sources. The more we radicals understand and accept that, the easier it will be to start building cultures and structures of support that help us better share responsibilities and promote self/mutual care.

Activist guilt, that feeling that you constantly should be doing more for the movement, is real. Survivor/thriver guilt is real, but so is activist/organizer burnout and illness. If we embrace a model of funding what we love rather than doing what we love to death, we just might move our lives and efforts into balance, and begin modelling that new world we seek.