Remote Work Works — Just Not at Every Stage of Your Career

The company I founded over two decades ago went fully remote in 2018, thinking we were ahead of the curve. We’ve maintained our “Great Place to Work in Canada” designation twice since then. Remote work has delivered real benefits, especially for team members with young families.

But I keep coming back to something. Work arrangements that make sense at one career stage don’t necessarily work at another. I see three distinct phases.

Stage one: Early career (Don’t do remote)

When my family ran our shop in the Congo, I learned business by watching. I saw how my parents’ demeanor shifted when customers walked in, how they handled complaints, the subtle art of reading people and situations.

At my first job after graduating, I was using a tool incorrectly. My boss saw what I was doing and stopped me. “No, no, no, you don’t do it that way. You’re going to break this.” That two-minute interaction saved me hours. This doesn’t work through a screen.

My kids can’t see any of that now. I’m behind a closed door on video calls all day. When we used to have an office, my nieces and nephews would come over and see us having meetings. They’d absorb how professional relationships work just by being around.

This observation-based learning is how business skills actually develop. You don’t just learn procedures — you absorb judgment, timing and the hundreds of micro-decisions that make someone effective in their role.

We used to hire from universities through co-op programs. Students would work with us for four months, and if we liked them, we’d offer full-time positions when they graduated. Those co-op students learned as much from overhearing conversations as they did from formal training.

That pipeline doesn’t work the same way remotely. We can’t observe how people are working in that natural mentorship way where you notice someone struggling and offer guidance.

You can’t learn to read a room through Zoom or absorb professional norms by watching boxes on a screen. The subtle skills — when to speak up, how to handle conflict, how to build trust — come from being physically present.

For people starting their careers, being in a group environment matters. That’s when observation builds the foundation for everything that follows.

Related: He Spent $3K to Start a Side Hustle That’s Eyeing $1M Revenue

Stage two: Mid-career (Remote makes sense)

Then life shifts. You’re starting a family. Suddenly, the flexibility of not commuting becomes enormously valuable. You need to be there when a kid gets sick or to make it to school events during those years when it matters most. Maybe it’s one parent working from home while the other goes to an office. Or parents alternating days. The key is having the flexibility to make arrangements that work for your situation.

This is where remote work delivers its greatest benefit. For parents with young children, the flexibility can be transformative. These are often people who’ve already built their professional foundation through earlier in-person experience. They know how to work. Now they need space to execute while managing life’s demands.

There’s a tradeoff worth acknowledging: remote workers often have less visibility when opportunities arise. If you’re not in the room, you’re not there for the spontaneous conversations that sometimes lead to new projects or responsibilities. Many people in this stage knowingly accept that tradeoff—they’re prioritizing family during these crucial years, and that’s a valid choice.

Stage three: Late career (Don’t do remote)

But there’s a third stage worth considering. Eventually, your kids reach a certain age. Family demands shift. Maybe at this point, experienced professionals should spend more time in group environments again.

I was talking to someone about this framework yesterday. He challenged me on the middle stage. “We managed to commute and raise kids when they were three or four years old. We did it all.” Then he paused. “But yeah, I can’t stand being home all day. I want to be out with people.”

We’ve spent decades building expertise. We want to be around the energy and problem-solving that happens when people work together.

Not for their own learning — they’ve built their expertise. But because the early-career workers need someone to observe. The co-op students need experienced people around to learn from. The mentorship that used to happen naturally through proximity needs experienced professionals to be present.

If everyone who knows how to do the work is remote, where do the people learning the trade get their observation time? Someone has to be there for them to watch, to learn from, to absorb the unspoken parts of professional practice.

Nobody wants to be “forced” back in the office. But experienced professionals have something to offer that early-career workers need: the chance to learn by watching people who actually know what they’re doing.

Related: Why Are Remote Work Trends So Different in the US and UK?

A framework still taking shape

We’re fully remote now, and our team is distributed across the country. Going back to a traditional office setup isn’t realistic or something we’d want — we’d lose significant benefits we’ve gained.

But I’m thinking more carefully about matching work arrangements to what people need at different points:

• Early-career workers need proximity to experienced professionals for observation and learning
• Parents with young families need the flexibility remote work provides
• Experienced professionals benefit from group environments to provide mentorship that early-career workers need

When experienced professionals work alongside early-career people, both benefit. We can read body language, know when someone’s stuck. But it’s not one-way; early-career people bring fresh perspectives and new tools. When you mix these generations in person, something pretty amazing happens. It ultimately brings value to a business.

This isn’t solved. We’re experimenting with ways to create learning moments more intentionally for different stages of career and life.

Remote work isn’t going away, and for many situations, it’s clearly better than the alternative. But choosing between “fully remote” or “fully in-office” misses the fact that the future of work requires us to be honest about what people need.

Different people need different things at different times. And preserving learning through observation — really seeing how a business works — means that as business owners, we should be thinking beyond one-size-fits-all solutions.

The company I founded over two decades ago went fully remote in 2018, thinking we were ahead of the curve. We’ve maintained our “Great Place to Work in Canada” designation twice since then. Remote work has delivered real benefits, especially for team members with young families.

But I keep coming back to something. Work arrangements that make sense at one career stage don’t necessarily work at another. I see three distinct phases.