2020

2020. What a year. What can be said that hasn’t been said a thousand times already? Let’s just skip past that and jump into how it was for me: I was laid off. I considered consulting. I got a new job. Becca got a new job. Optimizely was acquired. We got a new car. A dog. Moved to a larger house. Basically, we transformed our entire life. And thankfully no one close to me passed away from Covid.

A lot happened, good and bad, which pushed me to grow in many ways that I didn’t expect.

Career

The lay-off from Gladly forced me to take a step back and re-assess my career, the path I’m on, and what will keep me satisfied. I started pursuing independent consulting as a way to have a more flexible work-life balance, and make space for multiple simultaneous projects, but I couldn’t get it off the ground.

My hypothesis was that early-stage startups often struggle to attract design talent and successfully integrate them into their development processes. The founders usually aren’t designers, so they don’t know how to run the fledgling design org. They’re too small to have a full-time head of design, and the designers they do attract are usually too junior to know how to set themselves up for success. This felt like a gap I could fill. (It still does).

But what I was trying to do was too ill-defined. Plus I was starting from scratch during a pandemic, when many companies had frozen their budgets, selling to companies that don’t have much money anyway, so there were headwinds against me. And then Becca was feeling less stable at her job, so I went back in-house (ultimately at LaunchDarkly).

Deciding to go back in-house was a bitter pill to swallow, in all honestly. I was hoping to build a more flexible work-life balance where I was more in control of my time. Going back in-house felt like a sacrifice to that vision. (Also, I didn’t want to be new again, since this would be my 3rd job 2 years).

Instead, though, I changed my mindset going into my new role. My job doesn’t have to be my sole creative focus. I can make space for other projects while also having a full time job. The key, for me, is to not expect work to fulfill all of my creative urges, and to reserve energy for projects outside of work. In my previous jobs I would pour all of my energy into them, but that’s not healthy. I need to build time into my life for creative activities that aren’t work related. This mindset shift, and being more attuned to my energy level and not taking on too much at work, has helped a lot.

I still think there’s opportunity to fill the design-leadership gap, so I’m still feeling it out. I learned that it’s better to lay the ground work for future growth and jobs and income streams while you’re doing other things, so I’m doing that now (in addition to side projects, creative hobbies, etc.).

Side projects

Being unemployed — and quarantined — gave me space to re-kindle my love of side projects. I regularly had side projects in my 20s, but then they dropped off when I went to grad school, focused on my career, ramped up my social life, and got married.

I re-discovered that I love having a project to work on slowly, deliberately, over a long period of time. It gives me an outlet to try new ideas on, emerging technologies to experiment with, and learn new skills (or brush up on old ones). Although I regularly try out ideas that inform decisions in my day job, that’s not the primary reason I do them. I primarily do them to scratch creative itches.

In contrast to work, I don’t feel rushed or pressured to get anything done. I don’t have deadlines. There are no stakeholders to please. No internal politics to navigate. I approach them as something fun to work on. I can just follow creative urges as far as they take me, without worrying if it will pan out or not.

There were 2 main projects I worked on:

• Center, a personal CRM to help you stay in touch with your network. I’ve been working on it with my buddy Omar, who started it a couple years back. It struck a chord with me since I was managing my network and consulting leads in Notion, which was serviceable but not great. I got sucked in and started helping out on product strategy, design, and frontend coding, which I’m still doing today.
• Invisible Ink, which is a writing app that doesn’t show you what you’re typing or let you backspace or edit. You can only write. Why would I build such a monstrosity? The idea came from Vernacular Eloquence, which cited studies showing that people who wrote without seeing their writing ended up with better arguments, and prose that flowed more naturally. Why? Because writing is actually reading and writing, where you write a few lines, re-read it back, edit it, write some more, repeat. This gets in the way of developing your line of reasoning.
• Bonus third one: writing on this blog. I wrote 13 posts last year, which is more than the past few years, but not prolific. I like having space to think and write, and am building that into how I spend time outside of work.

Going into my new job with side projects in the hopper has helped me establish a better relationship between my job, creative ambitions, and side projects. I used to want my job to be the be-all-end-all of my creative outlets. But it can’t be. I realize and accept that now. I like writing, hand lettering, programming, graphic design, watercoloring, and more. No job will scratch all of those itches. So I like being in management, and leading teams, so that I can empower people to do their best work in my day job, but save creative energy for my own personal projects outside of work. It feels like a good balance so far.

Creative confidence

By far my biggest growth in 2020 is my newfound creative confidence.

This primarily came from the Artist’s Way, a 12-week program to help you strengthen your artist’s voice. It has helped me be more attuned to what my muse is saying, and given me the confidence to follow it wherever it may lead. This is true both for my personal projects, and my job.

In personal projects, I’m less afraid to follow whatever interesting design idea, lettering idea, writing prompt, etc., that I have. Is it pleasing to me? Do I like it? That’s the main thing that matters. I used to be more concerned with, Is this the right way to do something? Is this how other people would expect me to do it? Instead I am more confident listening to myself. I now use my internal compass as a guide.

This is true in my job, too. I’m more confident pursuing the course of action I see as correct, based on my prior experience and understanding of the field. In the past I’d be more worried about it being the “right” thing, or what my boss expects. Now, not so much. It’s very liberating.

Routine

The routine of quarantine can be dull and repetitive, but there’s aspects of it that work for me. Every morning when I wake up, and I know I’ll be home all day. Home for work. Home for play. Home for side projects and dinner and chores and so on. Home home home. This simplicity means I don’t need to think too hard about what my day looks like. It’s like wearing the same clothes every day — it’s one less thing to think about, so you’re mentally freed up to focus on more important things.

I of course miss seeing people and having in-person events, going to restaurants, seeing live music, and so on. I will welcome those back into my life when they’re ready. But for now, I’m embracing the aspects of routine that work for me.

So ya. 2020, I won’t miss ya. But your hardships pushed me to grow. Now here’s the door.