Allison Rosen
Jun 10 · 6 min read

I have been a virtual employee of Upside Business Travel for a year and a half. I came into this virtual life thinking “OMG THE FLEXIBILITY” and a lot less about “OMG THE HOURS ALONE.”

Actual footage of me in my apartment

Both are true at different moments, and it’s important to be ok with that if you’re going to choose a role where you’re not based in the central office, or virtual 90% of the time. But just because you’re not in the office all day doesn’t mean you can’t be wildly productive and keep your sanity. Here are a few tips I’ve learned that have helped me strike a balance and be effective, even from afar.

Build an Internal Network

I came to Upside from very large, structured organization with a clear delineation of responsibilities from team-to-team. At this start-up, everyone is really on your team, which can be an incredibly tricky set-up for a virtual set person. Who do you go to when you can go to anyone? Who’s the right someone when you can’t see who’s free or who’s out sick or who’s got headphones on and has a “if you talk to me, you will destroy my train of thought and I will never forgive you” face on?

Oh, were you working on something?

You go to your network. Set yourself up with a few people (some on your team, some on other teams) that are receptive to a quick “hey, you got a sec?” And make it a few because sometimes that person does NOT have a sec, or sometimes they’re the headphones person on snooze mode. And that’s ok, because you can ping someone else.

Also, spread these people across functions throughout the organization if you can. So if you have a customer experience question, you have a customer experience person to start with. He or she may redirect you, but that’s fine with you. You want the right person, and your network can help you find that person.

Speak UP

Picture this. You’re on a call. You’re alone. You’re listening to the UberConference twangy, country hold music for the 3rd time. It’s 3 minutes over the call start. What do you do?

Welcome to at least 3 minutes of my day, every day. When this first happened, I was sad. “They forgot about me,” I thought. And while sometimes they were just looking for a conference room or having trouble with the dial in number, other times I was right that they totally forgot, and that didn’t feel great. People should remember, but sometimes they just don’t, and you just have to roll with it.

I try to check every meeting at the beginning of my day to make sure there’s a dial in. I integrated my UberConference number into my calendar so I wouldn’t forget. If there is one and they forget to call in, I slack entire channels instead of just one person to remind them.

[insert trumpets here]

Once you’re on, it can be hard to get a word in edgewise. Group meetings are the hardest for this, but (similar to being a woman in any business meeting) you just need to speak up for yourself. Sometimes I need to talk louder or over people to be heard. Often times, I have to tell people to get closer to the speaker. Yes, it can disrupt the flow of conversation and yes, it makes me feel like I’m nagging, but is the alternative better? The alternative is adding no value, tuning out, and missing things. A little “hey, I can’t hear you, and think what you’re saying is important so want to make sure I know what’s going on” is much better than disappearing because you’re not physically there.

Build Yourself a Schedule

I live in a studio apartment in New York City. It is one room that houses every single item that I own. I had to buy a wall mount with a swivel for my TV because I A) didn’t have room for a piece of furniture to put it on and B) needed to have it move from when I was watching on my loveseat (not enough room for a full couch) to when I was watching it in my bed. All of this to say, I don’t have a lot of space.

When that already multi-purposed room suddenly also became my office, I took a turn to the over-side-of-whelmed. It wasn’t only that my physical space that was suffocating, it was that I never knew when I could shut off. Did I wait until my boss’ little green light when to gray? Did I wait until everyone’s little green light went to gray? Did I stop when the work was done (which it never is)?

One thing I learned quickly was, if you don’t set boundaries, no one else will do it for you. So I built myself a calendar, and asked for a WeWork space. I don’t always go to it, but I always have the option to get out. I block off my lunches, I plan excursions. Remember that flexibility that was so exciting? You have it. When you’re in an office, you and a friend will go out for coffee at 10am. So, go out for coffee! Call your mom! Swing by the grocery store when no one else is in there! Go to the gym! It’s ok to step away for a moment to catch your breath. You have your phone, if the world is on fire, you’ll know it. And you’ll be much more productive after taking a moment to reconnect with yourself.

The other thing about building a calendar is that you also have to give yourself an end of day. In an office space, there’s a general vibe to the end of the day. You can feel when people start easing out and shutting down. When you’re virtual, you don’t have that moment. So choose one. I check in with myself at 6pm. I assess what’s left on my “to do” list, and decide if I need to keep going, or if it’s time to start closing up. Sometimes, if my brain feels fried, I may log off a bit earlier. In a fast-paced company, someone is always going to be on, so just choose when you think you’ve accomplished all you can for the day and SHUT IT DOWN.

Visit the Mothership

Will travel for brainstorms.

I’m lucky enough to work for a business travel company, so planning travel to Upside’s HQ has never been a fight. And while we are living in a virtual-friendly world, and I am a virtual girl (read that to the sound of Madonna’s Material Girl, please), there are some conversations that are just easier in person.

Brainstorms or high level strategy meetings are more beneficial when you can see body language and run the room. If you’re virtual, make sure that you have some built in time to go to the HQ and check in. It helps you feel a part of the crew, check-in with your network in person, and run those meetings that will really help you get to the next step in whatever you’re working on.

Yes, it can be a cost to the company, but the company likely factored that in somewhat when they hired a virtual employee. Don’t be afraid to ask for what you need, and make sure you make the most of that time when you have it. You were hired to be the most impactful and effective employee that you can be, wherever it is that you are.


Does a flexible work life with unlimited PTO sound right for you? Upside is Hiring! Check out our Career Page for current postings.

Upside Team Blog

Our goal is to be the best travel company on earth. Our strategy is our culture.

Allison Rosen

Written by

Upside Team Blog

Our goal is to be the best travel company on earth. Our strategy is our culture.

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