It’s December 2020. We’re roughly nine months into the pandemic. I quit my job back in March and I’ve been ‘trapped’ in the spare bedroom trying to build a company ever since.
If you know anything about San Francisco, extra space isn’t a luxury that many people have. I love our home. It’s right on the park in San Francisco and accessible to every part of the city by walking, biking, or public transport. When my wife and I moved into our place in 2019, we didn’t expect to be spending so much time in it, nor did I expect I’d be starting a company 25 feet away from where I sleep at night…
What I thought it was going to be like
When I jumped ship and started a startup with my two friends, I had envisioned that I would wake up every morning, go for a run, grab a coffee, knock out some emails, and head into the office with my co-founders and maneuver our way through startup life. It’s weird, but I had this vision in my mind that I’d try a new coffee shop every week and blog about which ones were the best for getting emails done, relaxing, and having meetings. I was looking forward to walking 1:1’s. I used to have walking or coffee 1:1’s with my previous managers, which was just the best way to have open and candid conversations, rather than being trapped within the four walls of a conference room. I wanted to grab coffee with my co-founders, walk along the water, and talk about the things co-founders talk about. If I didn’t have the first two, I was looking forward to the impromptu whiteboard sessions. I'm a sucker when it comes to whiteboards. If someone on the team offered to do a whiteboard session, I would always be the first person to raise my hand. I love collaboration and thinking aloud… it’s when I do my best work. But, we all know that wasn't the reality.
What really happened
It’s no secret that COVID happened. I quit my job right at the beginning of the pandemic, so literally, all of my ‘dreams’ were crushed the week I started full-time. I didn’t even see my co-founders in-person until three months after the pandemic began.
In reality, I had my set-up in our guest bedroom while my wife was a few feet away in our family room. I spent most of my day staring at my screen on Zoom, talking to the team, investors, users, and advisors. I had coffee in hand, but it wasn’t the same. When I was stuck and felt like I needed that whiteboard, I just banged my head against the wall to try and think of what to do. OK, I didn’t hit my head against the wall (I didn’t feel like repairing drywall), but I lightly tapped my head against the wall waiting for inspiration to come.
Just like most professionals, it’s been tough to separate work and life. Several people hated their commute pre-COVID, but I loved mine. I used to walk to and from work, but ever since my wife and I moved, I started running or biking to and from work. My commute was my time to wind down, listen to a podcast, call my parents, or just clear my mind. Now, I walk 15 feet to my kitchen, cook dinner with my wife, and see my laptop staring back at me, asking when I'll come back. Since there aren’t many activities to do at night during the week with most venues, museums, and restaurants at limited capacity or closed altogether, both my wife and I just resorted to working after dinner. I'm running a startup; work is supposed to be everything. I agree. But, my wife is actually what's most important to me. When you can’t go out and explore and make new memories in the amazing city we live in, it’s taxing on your mental health.
Leading the team
Though we’re in a crazy time, and we all have to deal with staring at a screen, my co-founders and I need to lead a team and build. To help with this, we split apart our weekly meetings into smaller ones. We always have a weekly All-Hands. We reflect on last week, check in on our monthly goals, and prioritize for the week. Then, we have separate meetings per ‘focus’, one for product/engineering and one for marketing/sales. We do the All-Hands first, so we know what our goals and objectives are for the week as a larger team, and in the ‘breakout’ meetings, we can have more in-depth conversations around what needs to be done to accomplish our goals for the week. It’s not all done in one meeting because 1) Zoom fatigue is real, and 2) While engineering cares about marketing, time is better-spent building than worrying about the blog post topic of the week.
Everyone has standing 1:1s. We go into each meeting with 3-4 key topics we’d like to discuss. Typically, these are done on Fridays to reflect on the week and look forward to the following week. We use these 1:1s as a time to give feedback to one another and have open conversations. It’s a great way to ‘wind down the week’ and get excited for the following week. My favorite topic to discuss is ‘What are you most proud of this week?’ My advice – have 1:1’s with your co-founders and everyone else on the team. It’s essential to create that space to have open and honest discussions and learn from one another.
Embrace the wins (big and small) and acknowledge the failures or shortcomings. We have two Slack channels, #ice-cream, and #no-ice-cream-for-you. We use the #ice-cream channel to give each other shoutouts when someone went above and beyond, thought of an exciting idea, or made positive impact on a project or to someone on the team. The #no-ice-cream-for-you channel is meant to be a place for self-reflection. What was something you tried that didn’t go so well? We use this channel as a way to call out our own personal ‘failures’ show what we’ve learned, and say what we’re going to change moving forward. Companies always say they embrace failure, but many don’t talk about it enough. Since our team doesn’t interact in-person, we don't want failure to feel magnified to a single person, but rather as something we can all learn from. This Slack channel is a way to acknowledge that and embrace the fact that failure is OK within the company.
I always say to take my advice with a grain of salt. I’ve received great advice and some crappy advice over the years.
Get away from the desk. This one is obvious, but we don’t do it enough. I found myself staring at my screen or lightly banging my head against the wall for an hour, which was a waste of time. Now, when I get into that mental state, I’ll walk away from my desk and go outside for a 15-30 minute walk. I’ll listen to a podcast, call my parents, or do nothing. Then, I come back to my chair, completely recharged, and ready to go. Taking breaks are OK -- most times, that 30 minutes away from your computer is worth 5X the time you took to go on that walk.
Exercise. Regardless if you’re a co-founder, executive, manager, or an individual contributor, we all have stress. This stress can come from our work or personal life. I’ve always found a way to relieve my stress is to go out for a run. Most mornings, I'll go out for a run to prep myself for the day. It’s a great way to clear your mind and take in the beauty around you (and less screen time). Some days, I’ll go for a run at lunch to clear my blocked mental state and come back with a clear mind for the afternoon. It doesn’t have to be running, but you should always have something in your back pocket you can do that isn’t associated with a screen. Find a way to get the stress and doubt out of your mind.
If everything were what we expected it to be, life would be kind of boring. Like everyone else, I find myself learning new ways to cope with a world I’ve never worked in. In the beginning, I thought we’d be back in the office within 3-4 months (just like everyone else). As the months went on, it became apparent that it wasn’t going to be the case. So, I had to readjust. While it’s been crazy, challenging, and sometimes lonely, starting and leading a company in my spare bedroom has taught me more than I could have ever imagined.