Remote Work: What Actually Matters After 5 Years of Figuring It Out

I’ve been working remotely on and off since 2018, but it was really the pandemic that forced everyone, including me, to get serious about it. Now, five years later, I’ve learned that most of the articles about remote work focus on the wrong things.

They talk about fancy virtual reality meetings and AI-powered collaboration tools. But honestly, the biggest remote work challenges I’ve faced had nothing to do with technology.

The Real Problems Nobody Talks About

Problem #1: The context you lose when you’re not physically together.

When you’re in an office, you pick up so much information just by being there. You overhear that the marketing team is struggling with a campaign, so you know why the client is asking weird questions about analytics. You see that Sarah looks stressed, so you check if she needs help with the deployment.

Remote work kills that ambient awareness. You have to be much more intentional about staying connected to what’s happening.

Problem #2: The meetings… dear god, the meetings.

I swear, when people went remote, they decided the solution to everything was “let’s have a meeting about it.” I’ve been in Zoom calls where eight people spent an hour discussing something that could have been a Slack message.

Problem #3: The loneliness is real.

Look, I’m an introvert. I thought I’d love working from home all the time. And mostly I do. But there’s something about human connection that video calls just can’t replicate. The casual conversations, the shared frustration when the coffee machine breaks, the celebration when you ship something big.

What Actually Works

After years of trial and error (mostly error), here’s what I’ve found actually makes remote work… work:

Documentation Becomes Your Best Friend

At Rocket Money, I started what became a company-wide documentation initiative. Not because I’m a process nerd, but because when you’re remote, you can’t just tap someone on the shoulder and ask “Hey, how does this work again?”

We documented everything. Not in some formal, corporate way, but like we were explaining it to a smart colleague who just joined the team. Decision-making processes, technical architecture, even the quirky workarounds we used.

Best thing we ever did. New people could onboard faster, decisions got made quicker because the context was written down, and we stopped having the same conversations over and over.

Async Communication (But Not for Everything)

Here’s what I learned: not everything needs to be discussed in real-time. Status updates, feedback on documents, progress reports, these work great asynchronously. People can respond when they’re in the right headspace, with thoughtful answers.

But brainstorming? Problem-solving when you’re stuck? Complex technical discussions? Those still work better in real-time. The back-and-forth, the building on each other’s ideas, the “wait, what if we tried this?” moments, they’re hard to recreate with asynchronous tools.

The Right Tools Matter (But Not the Ones You Think)

We didn’t need VR meetings or AI assistants. We needed Slack for quick questions and casual chat, but with clear expectations about response times. Notion for documentation, because it’s actually pleasant to write in, unlike most wiki tools. Calendly or similar for scheduling, because coordinating meeting times across time zones is painful. And good audio equipment, seriously, invest in a decent microphone. Bad audio makes everyone miserable.

Building Connection When You’re Apart

This was the hardest part to figure out. How do you build relationships and trust when you’re not sharing physical space?

Some things that worked for our team:

Regular one-on-ones that aren’t about work. I started doing 30-minute calls with team members just to check in. How are they doing? What are they excited about? What’s driving them crazy? Half the time we’d end up talking about their kids or a book they read or some hobby project.

Shared virtual spaces. We kept a Slack channel called #random where people would share random thoughts, interesting articles, photos of their lunch. It recreated some of that office banter.

Celebrating wins together. When we shipped something big or hit a milestone, we’d have a virtual celebration. Sometimes just a group call where everyone had a beer or coffee and we talked about what went well.

The Stuff That Doesn’t Work (Despite the Hype)

Virtual reality meetings: Tried it. The technology isn’t there yet. It’s distracting, the headsets are uncomfortable, and it solves problems that don’t actually exist.

Always-on video calls: Some teams try to recreate the office by keeping video calls open all day. This is exhausting and weird. People need space to think.

Over-monitoring productivity: Tools that track your keyboard activity or take screenshots of your screen. If you don’t trust your team to work without surveillance, you have bigger problems than remote work.

What I’d Do Differently

If I were starting a remote team from scratch today, I’d focus on three things:

1. Hire people who communicate well in writing. This matters more than technical skills for remote work.

2. Establish clear boundaries. When is it okay to interrupt someone? When do you need to respond to messages? What deserves a meeting vs. an async discussion?

3. Plan for connection. Don’t assume team relationships will develop naturally. You have to be intentional about creating opportunities for people to get to know each other.

The Reality Check

Remote work isn’t going away. But it’s not a magic solution either. It requires discipline, intention, and yes, some good tools. But mostly it requires remembering that behind every Slack avatar is a human being trying to do good work while also living their life.

The future of work isn’t about better technology, it’s about better ways of working together, regardless of where we happen to be sitting.