👋 Hey, it’s Diana! I’m so glad you’re here for this Operations Optimist newsletter. Each week I dive into questions about building operations functions, fundraising, and startup life at large. Today I’m sharing my take on loneliness, especially the kind that creeps in when I work remotely.
Even though I’m on maternity leave, I still recall how lonely remote work could feel. Honestly, I have mixed feelings about it. I love the flexibility, yet I miss the office buzz and a clear divide between work and home.
Over the past five-plus years, during which I’ve worked from home, coworking spaces, airports, and everywhere in between, here are the approaches that helped me.
Fighting the blurred lines
For me, the hardest part has been setting boundaries. My mornings lost their rhythm without a commute. With no firm quitting time, work tends to bleed into everything else. So every hour feels like work, and that cuts into time with family, friends, exercise, and so on.
What helped was drawing lines both physical and mental. I carved out a dedicated home office and blocked non-work hours on my calendar. I even split devices, my laptop for work and iPad for downtime. When my cutoff time hits, I try to close the laptop, leave that room, and mute notifications. These small rituals help a lot, though without discipline they can fade fast.
Crafting moments for connection
The good thing is that if you work remotely, so does your team. I set up informal rituals to spark interaction: a weekend-stories thread on Slack, a water-cooler chat for hobby talk, and a channel for everyone’s latest binge-worthy TV pick. These tiny routines take almost no time but create micro-moments of connection. My team also used Donut chats to pair up for quick one-on-ones with an icebreaker question.
But as an extrovert, I still needed more. So I tried coworking spaces to meet new faces, signed up for executive coaching to focus on personal growth, attended meetups and local tech events, and caught up regularly with friends who also work remotely. None of these alone solved everything, but mixing them up over the years scratched that social itch.
Changing perspective and leaning into it
I’ve learned that remote work suits people who already have a solid social network and career foundation. That wasn’t me at the start. Mentorship was much harder online. Back then, I would have been better off in an office.
Once I built a network, established my career, remote work became easier. I kept work at work and found social time elsewhere. Acceptance made all the difference.
Honestly, remote work doesn’t fit everyone, especially if you’re a true extrovert. It can feel like a forcing function. But if you stick with it, you might as well reap its perks. I found it ironic that I could work from from anywhere in the world, yet I spent most days in my apartment. That paradox led me to experiment: a month on an island, a few weeks in a country house. Changing my scenery kept me energized.

That’s it. These are the approaches that helped me fight remote-work loneliness:
Drawing boundaries both physically (separate rooms and devices) and mentally (scheduling)
Creating moments for connection both with your team and through startup events
Embracing change of scenery to reap the benefits of flexibility and travel
All in all, I haven’t discovered a universal cure for remote-work loneliness, but I’ve learned to manage my expectations and emotions. And this mindset has carried me farther than any single trick could.
What works for you? I’d love to hear from you!