Growing up, I was always the kid who did as they were told. It meant the world to get approval from other people, and I wanted them to be proud of me. After finishing school and starting my first job, it felt like I’d turned into a completely different person at work. I wanted so badly to be candid, say what was on my mind, be genuine about what I felt—but instead I forced myself to be polite and concise and to keep my personal thoughts and feelings separate from work. I constantly apologized for simply existing or asking anyone for support. I didn’t feel like I was allowed to be myself, as though it were inappropriate or unacceptable. It’s weird looking back on this now, because I considered myself to be outgoing even while being reserved at work. I always thought that was how you’re supposed to behave, and never connected it to all the years I never really enjoyed going to work.

Starting a new career during the pandemic meant that more of myself came through in my work, especially because there was no longer a physical boundary between my work life and personal life. Nevertheless, I still have a great balance of both. Being in product design at Dropbox has shaped who I am as a designer, and a lot of it comes down to letting my two halves overlap.

How it started

After an internship, I joined the company full-time in April 2021. All of my work here has been remote-based, but starting as a full-time designer was still challenging. As an intern, someone will hold your hand and show you how to function within your team, but as a full-time designer, the onus is on you to reach out and develop relationships with your team members.

At Dropbox, you’re empowered to own your career. Your manager and peers will provide support, but it’s on you to figure out where you need to grow, to ask for what you need, and to try new things. This was jarring for me, coming from a background of people-pleasing, because it meant my job actually required me to advocate for my own opinions and ideas. I imagine you’re thinking, “What a wild concept: being hired for who you are and the value you provide.” But it was hard for me to learn this, and it took a while to wholeheartedly believe it. If you’re thinking, “No way, that’s exactly how I feel right now,” then this post is for you.

Learning how to take up space in a virtual room

The experiences that stick out most are probably the ones when I struggled the most. With my first team at Dropbox, I had a hard time speaking up in meetings. I often felt that whatever needed to be said had already been said, so when anyone asked if I had something to add, I’d respond: “No, that all makes sense!” or “I agree with what __ said!”

My internship manager, Sandra Bilbrey, told me that even when I agreed with the rest of the team, I still had a unique perspective and helpful ideas to contribute. I think about this even now, because it helped me validate my reasons for being here. It feels risky to say something that might seem dumb or wrong afterward, but that’s the only way to do it. You must say what you think, mess up a few times, and be comfortable doing so. It’s like improv—if you don’t spit out all of your ideas, including the bad or incomplete ones, you’ll never get to the good ideas. In that same vein, good communication comes with practice.

Get comfortable with oversharing

In person, it’s easier to read each other because we have body language and other social cues for better understanding what’s being said and how someone feels. In remote work, if you don’t go out of your way to express what you’re feeling, nobody will ever know. For example, if you’re feeling crappy but you tell the team “I’m fine!”… we’re all going to think you’re fine. You may think the honest answer is something the team should pick up on based on your behavior or other cues, but in a virtual workplace it’s impossible for your team to know what’s going on when you don’t say what’s on your mind or what you’re feeling.

I had a close bond last year with Evan Leach, a designer on my first team at Dropbox. We quickly became friends, which was cool because I could say things like “I don’t feel confident about this direction” or “I have no idea what I’m doing and it feels like I’m making it up as I go.” That last one was fun because I learned that Evan, too, sometimes doesn’t know what he’s doing, and maybe none of the other designers do either, but we’re all just trying to figure it out. To build a bond, someone has to kick off by sharing more than the usual. It can be surprising how many other people are struggling with the same thing as you, but you may need to initiate this kind of sharing to find out.

To prioritize work, you have to prioritize people first

It seems counterintuitive, but those five minutes of chitchat before a meeting and those things we used to say at the coffee counter actually matter. In a virtual work environment, we need to reserve time for it. I can think of many times when someone has hurriedly rushed past the niceties and gone straight to “So, anyway, what are you working on?” We need to stop and allow some space for more casual conversations.

Some people may find it difficult to sit through the awkward pauses of Zoom, and some may find it difficult to talk about personal things. I think this comes from a belief that social chats aren’t inherently productive, but I’ll always argue that it’s time worth investing, because the way your life is going outside of work directly impacts how you’re able to show up for work. If you’re dealing with difficult things, you have extra stress on your mind. If great things are happening, maybe you’re performing a bit better. The more you learn about your team members, the better equipped you’ll be to assist them when they need it, and to celebrate them when they deserve it.

Creating space for vulnerability

I remember joining my first team and being a little intimidated by my project manager. He spoke really fast and was super on top of things, and I’d made it a mission to impress him. A few months into the role and after several 1:1s, I found he wasn’t as intimidating as I‘d thought and was actually very chill. One day he opened up to me during a meeting. He said he’d been dealing with the breakup of a long-term relationship, and that was why he hadn’t been more available lately. His vulnerability helped me understand him much better, and it was extremely gratifying that he felt safe enough with me to express it.

Sometimes these moments come naturally, and sometimes you have to create them. I talked with Ben Kowalski, who was a design manager for the Dropbox Mobile team, and he described an exercise in which people are asked to complete this sentence: “If you really knew me, you’d know __.” This gives people an opportunity to express as little or as much as they’d like, and makes room for sharing vulnerability.

Go on and overshare freely

I wholeheartedly believe that who you are outside of work directly informs who you are at work. You’re a whole person who can’t split into two. In a perfect world, we’d feel comfortable sharing seemingly minor personal details with other team members, but this takes work. Even something as small as sharing what you did over the weekend is a nice place to start. Creating moments to be vulnerable/emotional/genuine with each other goes a long way in a virtual workplace. I’ve been very lucky to have this with more than one team, and it’s a non-negotiable for future teams. Learning about the fun, sad, and uncomfortable aspects of people’s lives makes it easier and more fulfilling for me to support them in the work we do together.

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