Leading like Star Trek’s Chief O’Brien remotely, remote dev for 15 years

1. Hey, can you please introduce yourself?

I’m Ryan Wilcox. I’ve been a professional developer for the last 15 years or so, most of that remote (except one stint at full time every day office job and one project that wanted me in the office half time). Most of my day-to-day work finds me being one of the lead engineers for a mid-sized replatforming project. 

This role, the way my day job runs it, finds me with lots of leadership work, while still plugging away at the lines of code level of work. One day I may find myself writing Node.js, Python, or helping to maintain our Jenkins pipelines. Another day may revolve around driving some architecture change across the project with solutions architects, the product owners for our various teams, running our backend developer’s special interest group meeting, or talking to developers 1:1 to understand what boots-on-the-ground challenges the team really has. 

2. What motivated you to choose remote working?

I went to college at Rochester Institute of Technology in Rochester, NY, about 2 hours west of where I grew up. I was lucky enough to be given two choices: take a DBA position for a small manufacturing business near Rochester, or go into business for myself, as I had found a 15-20 hour a week consulting project from a friend.  

I decided to go into consulting for myself, move back home, and leaned heavily on remote work to get clients – it’s a good trick when you can get it, big city money and small town expenditures. I ran out of money at least three times, but I know it would have happened much, much sooner in a higher cost of living location.  

Remote work is a great economic equalizer, giving a larger range of opportunities anywhere to people from anywhere. Save our small towns: work remote! 

What motivated me to work remotely
What motivated me to work remotely

3. What were your initial months like? Did it live up to your expectations?

Starting a remote business was unique, especially in the mid 2000s, and with a little (and only a little) capital. Technology has improved a lot since then: Want an email address and calendar system? Get Google Docs. Code hosting? For cheap or free on Bitbucket/Github. 

Yet some problems are still the same:
– How do I find clients?
– How do I put together standard workflow practices and paperwork?
– How do I communicate with clients easily e.g. keeping them up to date on billing or how far along their project is? 

Add to that, remote working challenges everyone faces:
– Equipping yourself for the work
– Finding a place to do it
– Understanding when you have to make a change because things just aren’t working 

Starting a remote salaried job, many years later, meant those business related problems went away and I could focus on the technical side of the work. I had solved the remote challenges. 

I did write a blog post about the remote working tools I use – some of those are still good, common sense, some of them have gone by the wayside and have been replaced. 

4. How did you find remote working roles?

As a remote consultant I was never very good at finding roles. A lot of projects in my career I’ve stumbled upon were either because I was at the right place at the right time, or becoming known for a niche thing, or being on the right job boards. 

In the last six-ish years there have been great strides: 

  • Remote freelancer markets (highly recommended if you’re as weak at the marketing and sales part of consulting as I was!)
  • Remote focussed job boards, or 
  • Positions looking to hire “talent no matter where we find it” (one of the reasons I took my current job)

5. What have been the best, good and worst aspects of remote working for you?

I did remote consulting, had enough of that, got a remote job at a (very small!) startup. Then that startup was bought out, and the buying company wanted to relocate me to work onsite. I did that job for 3-4 years and then got a fully remote job again. Remote working was really nice, and the office gave me a perspective of the other side too. 


My wife went back to school this fall, which meant I had to help more around the house. Remote working gave me flexibility here: drive the kids to school if I had to, take a 10 minute walk to pick them up at the bus stop, use my lunch hour to clean a room in the house, etc. Even (and I don’t recommend this part, but it happens especially now) watch the kids while working. (Sometimes this was setting up and working on the dining room table while watching them play in the living room. Other times this involved turning on a movie, walking into my office and hearing them scream). The ability to support my family and my wife this way came in very handy.  

Now “watching the kids while working” is a lot of people’s current, long term, reality, with COVID-19. Normally I’d call that an anti-pattern of remote working. Nowadays – like during this once in a century global pandemic – nothing’s optimal. Be kind when your fellow human’s child wanders into the frame screaming because she can’t find her favourite stuffed toy, as has happened to me on occasion. 

Watching the kids while working
Watching the kids while working


My office situation (working remotely) is so much better. Even when I had a “big” cube at work (in-office), it wasn’t that big. And for a few months when I had to go in an open-office type arrangement, I spent most of my days literally hiding anywhere but my desk.


Unfortunately, one of the worst things for me (and countless others) is a COVID-19 reality. Before COVID-19 I would try to get out of the house at least three times a week (even if just to grab lunch or coffee!), and work from somewhere else at least one afternoon a week. Just to see people, see something that wasn’t the inside of my house, deal with the isolation, you know. 

For me, COVID-19 turned that reality completely on its head: that’s no longer an attainable lifestyle (living my best quarantine life). On the contrary, the house is filled with everyone and there’s remote schooling which effectively means I have more than enough people around.

I do absolutely feel the pain of those isolating by themselves, but in the before-times I had an outlet. 

“Most people don’t believe something can happen until it already has. That’s not stupidity or weakness, that’s just human nature.” 

– Max Brooks, World War Z

6. What tools do you swear by while working remotely?

  • A good headset. Even a pair of Airpods is better than nothing. If you’re taking calls from a computer a cheap $20 headset may work for a couple months (but if you need mobile/tablet support, don’t cheap out). I spent (probably too much) money and got a good Jabra USB+Bluetooth headset in 2018, and managed to snag Jabra’s version of Airpods just before COVID-19 shut everything down. (I have no idea where to buy a headset. Probably easier to buy a time machine and pick a set up back in 2019).
  • A good whiteboard setup, preferably a collaborative digital whiteboard. MS Whiteboard looks really good for this, if you’re in the Office ecosystem. I have a few whiteboards and a whiteboard notebook in my office.
  • Slack’s reminder functionality. In a leadership position I sometimes have at least two conversations going on at the same time, while paying attention to various group chats, which makes a lot of context switching. Turns out, switching back and forth like that means I forget things. I find setting a Slack reminder on a point I want to reply to or a next action I should do reminds me to switch back to them and close that loop.
  • If you happen to work at a place with a highly restrictive VPN / proxy: a second machine (or tablet, or whatever) that’s just yours / you don’t connect it to work’s VPN, to stream music or video while you work.
  • A separate space to work. Even mail ordering a random small desk from Target or Amazon and putting it in a spare corner is better than working from your couch or your bed.  

7. Your most exciting/ hilarious experience since you started working remotely.

Closest I’ve come to doing something interesting with remote work was taking a working vacation to California. My team at the time was based on the East Coast, so I would use jet lag to my advantage: I would wake up at 5:00AM PST, go to my 9:15 Eastern Time standup, go about my work day – which extended to 2:00 PM PST (5:00 PM Eastern). Then I would go be a tourist for the rest of the afternoon and evening. 

I’ve been on the not so hilarious end of this too: having Hong Kong -> US East coast conference calls. There’s no way to slice that 12 hour time difference. 

8. What is your golden advice to a new remote worker?

  • Remote working is hard when most of, or even half of your team is co-located. In general this is an anti-pattern.
  • Remote leadership, I’ve found, isn’t bad. Although I’m a bad body-language and face reader, so people that rely on those tools are likely having a rough time.
  • You can probably hold that meeting without it being a video meeting. (I have a standing desk and dance and move around a lot – I’ll ruin your video conferencing software’s compression algorithms anyway).
  • Over communicating is important. One way I do this is to set a :sandwich: status just before I leave my computer for lunch. People will see that and know it might be an hour or so until I respond.
  • Time zones are hard mode. For your first remote job, try not to be in a vastly different time zone than the rest of your team. Even a 3 hour difference means you have half the work day happen without you, or without your team. (This is also a place where a business could be mature – if they have a history of remote work and the team is geographically scattered across multiple time zones anyway.)  

9. How do you see your career shaping up and your goals?

I grew up watching Star Trek. We have the management career track represented by Captain Picard (or Captain Sisko): officers reporting to them and direct reports, etc. In contrast we have Chief O’Brien: in later seasons of DS9 he’s given some on-camera helpers, but he’s not their boss, but the man who knows how everything actually works (sometimes in a literal sense). 

I’m currently in a position where I’m leading like Chief O’Brien: I coordinate how things actually work with the people that do them. I may mentor my developers, support decisions they’ve made and make sure there’s opportunities for growth. But I get to avoid performance reviews and arguing with people over salary raises and budgets. For me, the best of both worlds, and ideally I want to keep doing this style of work. 

Leading like Chief O'Brian from Star Trek
Leading like Chief O’Brian from Star Trek

I suspect more and more companies are realizing they need this dual career track: do you want to manage people, or lead by keeping your hands dirty? 

This style of individual contributor that leads other individual contributors is well supported by remote work. 

My favourite trick to focus a meeting or cause a group to come to a shared understanding of something? Share taking notes and screen share the notes. Or outline as decisions are being made. 

Sometimes coming to a shared understanding involves looking at code and doing some pair programming. It’s amazing what relatedly low tech solutions, of looking at text together, does. 

10. How do you expect remote working to evolve in the future?

On the tech side 

On the app side, part of me is looking for that killer AR office conference app. Would projecting an AR conference table of my current meeting onto my desk table be neat? Maybe. (Could it be a too expensive gimmick? Maybe) 

Agile rooms with stickies mirrored in AR: now that would potentially be useful. Holodeck style scrum rooms with thumbnail pictures of Jira tickets group around on the “walls” or in piles, perhaps? Current ticket systems are great at lists of things, but sometimes (maybe rarely, maybe frequently) you want the simple interface of (“throw this thing into a pile we’ll do the data entry to make the system happy later”). 

Maybe this is me desperately trying to find a use for AR tech. Maybe we’re not even there: maybe we just need a (video ?)conferencing setup as easy as a hyperlink (as easy as Zoom) with less of the security concerns… 

On the culture side 

I’m hoping that we come out of the COVID-19 pandemic with more jobs being offered as remote, or company cultures being more accepting of remote work. Companies that previously would never dream of being remote now have the infrastructure in place to support remote work. Or at least the acceptance of remote work, and hopefully the knowledge that we’re all trying out best in this situation. 

Before all this happened my personal rule of thumb was I would see 1 remote job for every 10 on-site jobs. I’m hoping that number goes up. 

11. Where can we follow you on?

Most of my professional work ends up aggregated on my LinkedIn page – be it postings on my personal blog or my old consulting company’s blog I can’t bear to shut down. 

My twitter (@rwilcox) is especially random lately, and Github (@rwilcox) used to be a reflection of what experiments I’m doing at the time. Now I have less time or energy for Github / code experiments but sometimes something interesting happens. 

Are you a remote worker too?
Would you like to share you story?
Just reach us at hrishikesh@remote.tools!

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