My Pandemic Origin Story

Bonnie Kate Wolf
13 min readNov 5, 2021

March 2020 — I lost my job. Here’s how I went from unemployment to making $600,000 a year. This story focuses on HOW I landed jobs and contracts, not so much the work I made while there. Let’s jump back in time a bit.

It was Christmas-time 2012 and I needed a job because I was studying for my bachelor’s in illustration and college is expensive. Even though I went to college in the UK (where education is much cheaper than the US) it still cost a lot to support myself in London. I managed to get a job as a Christmas temp on the shop floor at Lush Cosmetics in the Victoria Station shop, making £10/hour. I spent a few months telling people about lotions and learning how to take care of my skin. After my contract ended, I was able to switch shops to a more central shop on Bond Street. A couple months in, I saw a post in the Facebook group the Lush employees shared.

“Looking for a graphic designer”

I sent in my information: I work on the shop floor. I’m studying illustration. I want to be a graphic designer.

They brought me on to design a book. And they paid me £40/hour which was 4 times my shop floor pay. I started working out of the press office instead of on the shop floor. I got to direct photoshoots. I worked with hair stylists. I got to test new products. It was literally a Cinderella story.

While working for Lush, I was also working on my bachelor’s, and then my master’s. Towards the end of said master’s, I wanted to stay in the UK, so I needed a visa. I applied to work at Usborne Publishing. I started working there as a designer, designing children’s books. I got to use some of my illustration skills, but mostly I was a designer.

They told me after 3 months, I would get a visa. That was 3 months before Brexit happened. Because of the uncertainty of Brexit, the company couldn’t hold onto me. I had to move back to San Francisco.

My final project for my masters at the Chelsea College of Arts

It’s now January 2017 and I get my first job in tech. A recruiter had contacted me through LinkedIn and found me a job at SurveyMonkey as an internal brand designer for ~$70k/year pro rata. They want someone who can design spaces and do brand work. During my master’s, I had designed a ‘room’ made of craft objects, which I am told is what gets me the job. I’m laughing to myself that my love of textiles and crafting got me a big girl tech job.

This contract lasts 6 months, and I move onto Square.

My dad was working there at the time (in IT, not design), and was able to refer me. The recruiter, Alex Benson, was very much a champion of me and my work. My work was not quite good enough, though, to be honest. He told me I might be able to do visual design there if I started as a production designer, so that’s what I applied to do. I was curious about what production design was, and I loved organizing things, so it felt like it might be a good fit.

I later found out from my manager that I wasn’t a top candidate. I had some issues with typography in my portfolio that he didn’t love. The recruiter (who I’d been lucky enough to meet in person) told him to give me a phone interview. So we did the phone interview, and, apparently, I endeared myself to him rather quickly. The hiring manager gave me some specific feedback on my portfolio. I made the changes he asked for.

I came in for a portfolio review. When I showed work, the team asked if I’d changed my work since I applied — I said yes I had, based on the feedback from the phone interview. As it turns out, that basically cinched my offer. They loved, not that I had made better work necessarily, but that I knew where all my files were and then took the advice to improve myself. That job paid $98k/year plus ~$40k in stock (over 4 years).

I was able, between my relationship with the recruiter, and my own desire to be better, to get an offer for a job that I wasn’t going to be considered for. That hiring manager, Chris “CJ” Ereneta, is now one of my favorite humans on this planet. We’ve gone to comedy shows together with his family. I’ve been to their house. We play DnD together. These are the kinds of relationships that enable you to grow as a person and further your career and your personal happiness. They aren’t common, but CJ and I built a bond that transcended my job at Square. Claudia Ng, who was essentially my production design mentor, taught me an enormous amount about tech, production, representation, and humor. She and I are also still friends. Those relationships are very important for your happiness and your career.

Illustration I made while at Square, which was animated

After 1.5 years on CJ’s team, I had to tell him I was moving on. There was a lot of crying while reading thoughtful emails. I had an offer from OpenTable to be a senior brand designer.

In the last 6 months of my time at Square, we had a lot of internal changes that were frustrating to me, so I allowed myself to look at other jobs. A recruiter on LinkedIn found me, liked my work, and suggested I come to OpenTable. This was by far the most “traditional” job search I’ve ever had. I did the interviews, did a design test, and accepted my offer. I was very excited to make more money ($140k/year plus stock) and to be a senior brand designer.

A notebook I designed while at OpenTable

While at OpenTable, I got to help them on a number of projects, but it was obvious after a year that it wasn’t the right place for me.

Basking in the glory of Config

In February 2020, I spoke at Config 2020. This is where things started to change. I had joined Twitter a few months prior, and people knew who I was because of an article I wrote for Or at least, they wanted to know if they didn’t. I spoke about illustration systems, something I’d worked on at Square and OpenTable. I met a lot of product designers, including Jon Kerwin (who was at Thumbtack at the time) and Lauren LoPrete (at Dropbox). Both of them worked in design systems and I was enamored with both Figma and design systems in general. Jon referred me to Thumbtack after I found out they were hiring.

Did the interviews. Got the offer. Was stoked to start in April 2020 as a senior brand designer. Pay was $140k + stock, so the same as when I was at OpenTable.

Then COVID came along.

My job offer was rescinded by the VP of design. They’d rescinded everyone’s offers. I had already quit my job at OpenTable, and I wasn’t going to swim backwards. For the first time since Brexit, I was unemployed.

It felt horrible. I knew it wasn’t my fault, but I knew that finding a new job was going to be rough. Every day Twitter was abuzz with companies cutting their staff. I felt it was going to be impossible to compete with people from Airbnb and Uber. Talented people lost their jobs.

So I posted to Twitter.

Screenshot from Nov 5, 2021

Within hours, I had hundreds of likes, something I was not familiar with. I had people emailing me, trying to find ways to help. It was surreal. I went from (I felt) an internet nobody to someone people really wanted to support. The transparency I had displayed resonated with folks. People helped me find a good number of contracts that paid between $250-$25,000. Most projects were for $5000 on average because I was mostly taking brand design work.

I worked with Cyd Harrell for the California government. Meg Robichaud brought me to Lyft for a couple months to help with a project. I designed emails for Simple Health with Matt Ström. I helped redesign a campaign for Segment with Angela Haddad. I created illustrations for Rocketblocks with Kenton Kivestu. I spoke at Fitbit and Iterable. I worked with Gary Williams at Caviar. I designed A LOT of icons for various companies.

While doing all of that, I started building my twitter network, since that was where people wanted to talk to me. It is impossible to mention every person who helped but it was a lot of people. I felt the entire world was on my side. I still do. Build yourself a network of trustworthy, talented people who will support you and your career. Do the same for them.

Illustration I made for Oura that was never used for anything but I love it anyway.

While freelancing, I was job searching. Here’s a list of jobs I was rejected from:

Illustrator at Facebook
Art Director at Medium
Visual Designer at Brex
Senior Brand Designer at SquareSpace
Illustrator at Robinhood
Brand Design Lead at Slack
Designer Advocate at Figma
Creative Director at Oura
Senior Email Designer at Square
Senior Marketing Designer at Instacart
Product Illustrator at Coinbase
Communications Designer at Instagram
Product Illustrator at Lyft

If you read that list and are familiar with my CV, you’re probably thinking “But BK, you already worked with Square, Lyft, Figma, and Facebook. Why did they reject you?”

It is disheartening to be rejected from places you have already worked, or by people with whom you already have a relationship. But those roles weren’t right for me — I am more entrepreneurial by nature and I’m a bit of a dreamer. I don’t like to be told I can’t do something or that I’m not experienced enough.

Iconography I designed for Oura

I had been working at Oura for part of 2020 and towards the end of the year they asked me to come on as a full-time illustrator. I was so excited. I loved the brand. I loved my team, especially my manager. They offered me $115,000 without any stock. I was shocked because that was way less than I was making while contracting there. I managed to negotiate up to $120,000 (still too low, but we were in a pandemic and I was desperate and scared). A week or so before I was meant to start, my manager told me they were rescinding my offer — they wanted to focus on getting a web designer with that headcount. So, for the second time in 2020, my job offer was rescinded and I was back to freelancing. I feel no resentment towards Oura, my team, or my manager. I did great work there (including their icon set) and I learned a lot about brand design.

In 2020 I made pretty great money freelancing and contracting — about $150k over 9 months. For someone who was recently unemployed (twice) in a pandemic, that felt pretty darn good. By the end of the year, I had designed more icon sets, and decided it was time, after talking with my mentor Meg Lewis who I also met on Twitter, to focus my efforts solely on product illustration and icon design. She gave me some great advice: you can always change your business and revert, but you can’t take chances if you don’t let yourself. I started marketing myself as an icon designer (my true love).

2021 starts and I’m freelancing happily when I see a post from Josh Mateo about a gig at Netflix. Thanks to Molly Magnell for tagging me! Netflix is a dream company for me, and even though the job is more about Figma education and product design, I DM Josh. We start talking about Figma, and he offers me an interview. I interview with him, then with him, Jen Yee, and John Sullivan Hamilton. They tell me that some iconography is going to be needed at Netflix, so I’ll have a chance to keep making icons. I remember my time at Square, how taking a job that wasn’t exactly what I wanted led me to learn more skills. I accept.

While working at Netflix during the day, I’m freelancing at night and on the weekends. My clients are understanding that I don’t take many meetings and ask for feedback via Figma. I make Loom videos when I need to communicate with my face. Because I’m able to work my full 40 hours at Netflix while moonlighting as a freelancer, I’m able to more than double my income, rather than if I worked at Netflix alone. Of course, I am giving up some evenings and weekends and lunchtimes.

Iconography for Lyft

Let’s talk a little bit about how I got some of the projects I did. I like a list, so let’s do that.

State of California: someone reached out to tell me they were hiring, so I applied online with a proposal including a budget. It was accepted.

Literati: They found me on Twitter and emailed me.

Contra: They also found me on Twitter after I posted about looking for new clients.

BCG: Cold email from them. Not sure how they found me.

MURAL: Jess Rosenberg was the head of brand at Cloudflare (where I’d interviewed) and while she didn’t hire me there (because I declined the offer), when she went to MURAL to lead their brand, she asked if I could help them out. She’s now at Webflow and you bet we keep in touch.

Airbnb: A friend from Square (an engineer with whom I did acapella) told his colleague that I make icons, and that colleague was Matt Farag. Matt reached out, saying he wanted to hire someone for some icons who wasn’t a white man.

Lyft: I had reached out to Meg Robichaud (no longer at Lyft) before the pandemic to tell her I admired her and wanted to get drinks. We got a coffee near her office. When I lost my job the first time, she reached out because Lyft was looking to hire contractors impacted by the pandemic.

Brex: I believe someone internally must have mentioned my name to the new head of brand, Minou Sinios, because when they reached out for their icon set, they knew what they wanted.

Caviar/Doordash: I was on the same team as their creative director when I was at Square and he remembered my icon work from my time there.

All-Turtles: I interviewed here when I took the Oura job instead, and after losing that Oura job, they brought me on for many months as a contract art director.

Hopefully, you can see the patterns emerge. The important thing I have learned here is that you need to network. Find people on Twitter who do what you want to do — then ask them how they do it. That’s how Meg Lewis became my friend. Find people who hire people who do what you do. For me, that means product designers and creative directors.

My freelance contracts now average $20,000. If I can’t take a contract, I will try to pass it onto another icon designer. The largest icon contract I’ve ever had was for $145k (and we are still working on that one). The smallest icon project I’ve ever quoted was for $700 for a small gaming company. How does that all add up to $600k?

30% of my income comes from short-term full-time contracts, like my work with Netflix where during the day, that’s all I work on. I take these projects on, not because they pay the best, but because I learn a lot and I like to make new friends/connections.

65% of my income comes from budgeted freelance projects where I work with a company asynchronously (sometimes across many time zones) to help them build their icon libraries. Most of these projects are for product librairies. Those pay the best and are the most fun to do (for me) but require the most technical knowledge. Sometimes I do marketing icons or pictograms, but I’m moving away from that in favor of more product icons.

5% of my income comes from the money I’ve invested in Vanguard. My boyfriend convinced me in Feb 2021 to put my money from 2020 into some mutual funds, and they’ve earned me about $45,000 this year. The money I put in was pretty much only from last year — it isn’t a huge pile of money I’ve just sat on for years. I didn’t really have much liquid money before 2020.

An illustration I made of Taylor Swift in Figma. She’s my dream client.

My advice to anyone looking to start their freelance career is to specialize. As you can see, most of my money is from freelance contracts. When I was marketing myself as a brand designer slash illustrator slash icon designer, I didn’t get as much work. Hiring managers and project managers didn’t know what they’d get by hiring me. Now I market myself as an icon designer with a wide understanding of product and brand. Big companies can come to me because they know what they are going to get. It doesn’t matter what you specialize in — it just matters that you make it clear to the people with the money. Now, go get that bag!



Bonnie Kate Wolf

Illustrator who works in brand and product design. Clients include Airbnb, Square, Lyft, and Figma. Originally from San Francisco.