You Never Forget Your First
In honor of Valentine’s Day, our team reflects on memorable career moments.
Life is full of monumental firsts, and Valentine’s Day stirs up memories of the romantic variety: first crushes, first dances, first kisses, first loves — you get it.
While we relish a good love story, we’re a business, after all, so we’re inspired by career-related firsts: the places you started, the moments that changed your path, the challenges that seemed insurmountable until you did it.
Here, the WOTW team shares unforgettable career firsts.
You never forget your first…
… work website.
“The very first website I had was built by a small, Arkansas-based team. It was a simple site for my clothing store with little more than an address and list of vendors. Never in a million years did I anticipate that my future business would be to solve a lot of the problems I faced as I grew that website into an e-commerce store!”
— Mallory Ulaszek, co-founder/lead project manager
…site design.
“I didn’t think I’d end up being a web designer. I dreamed of it and studied informatics in school, but quickly learned I’m better suited for front end development than backend. This came to light when I was working with my college mentor. He was a great professor and liked me because I was able to talk to people, tell a story, and also code a Twitter bot. He oversaw my capstone to secure my Informatics minor. At the time, I was convinced I was going to lean into fashion and pitched the idea that I could build a website for a small boutique I was working for. He agreed and after copious amounts of research (my type-A mom would be so proud), I landed on Squarespace.
Looking back, the site was painfully simple — and not in a cool, minimal way. I’m sure I used a too-round sans serif and my images were far from optimized. The only custom code I used was to change colors for some of the headings. But it was my first actual site, and the first time I realized I could really pursue my back-burnered dream of being a web designer.”
— Alex Lucke, developer/social media manager
… tech support call.
”My first job in tech was at an e-commerce development company. On my first day, the CEO welcomed me and walked me into ‘design,’ which was one guy in a room with two desks. He pointed at the empty desk and said, ‘First thing you need to do is learn the software. Tech support, line 2.’ It was terrifying at first, having no reference, thinking this person was relying on me to help them, and I knew nothing. I truly believe that day forged my interest in a good user experience! I solved their problem by the way, and the rest is history.”
— Eric Anderson, developer
…cyber attack.
“We were working with a client who could not believe we could get his site launched by the end of the week. We promised it was doable and assured him it would happen. Come Friday, there was a major domain breach that took down basically everything online, including Amazon, Netflix, Spotify, and of course, Squarespace. I was SO scared to tell this person we couldn't launch his site after all. It turns out his wife was a high-level technology reporter and had been reporting around the clock as it happened, and he was totally OK with it. We got his site launched the next day.”
— Kelsey Gilbert-Kreiling, co-founder and lead developer
…job, in any industry.
“My first job was at a bagel shop, which was half bagel shop, half frozen ice/custard stand. During the day, I'd clean the front area of the bagel shop and at night, I'd serve custard and frozen ice to teenagers and families. The only part I'm glad I never had to do was wear one of those stupid paper hats.”
— Justin Mabee, developer
…time asking for a raise.
“I was 13 years old, working under the table at my Dad's sporting goods store in the Detroit suburbs. I assumed I was a shoo-in for a 25 cents an hour raise, as I was trying to save up for something from dELiA*s catalog. Imagine my surprise when my own father said, ‘No!’ He was a fair man, but also liked a good teachable moment.
’Why do you deserve this?’ he asked. ‘You can't just ask for it. Prove your worth. And ask for more than what you would be happy with so there's room to negotiate.’ I quickly went home, typed up a formal letter bulleting all the reasons I deserved this raise. Letter in hand, I returned and tried again, this time with success! Lesson learned. And these days, I always ask for at least 50 cents more.”
— Emily Schwartz, project manager
…huge mistake.
“I had just started working for a glossy magazine in Chicago, and I got to write a big feature on this new restaurant group, run by two partners and a big-name chef. I nailed the feature, was so excited about it — until their PR person called me when it came out. Turns out I spelled one of the partner’s names wrong throughout the entire article. I was mortified. But I learned an important lesson: fact-check, fact-check, fact-check — and from more than one source.”
— Molly Each, marketing editor
…time getting fired.
”I don't think I've ever told people about this because I'm so embarrassed. In 2011, I graduated from college and moved to Chicago. My Acura was packed to the gills with everything I owned: a side table, trash bags of clothes, and my old bike on a Craigslist-purchased rack precariously attached to the trunk.
With minimal job prospects, I snatched up the first job I was offered: a nanny position for two toddlers with behavioral issues and a helicopter mom. She told me that I wasn't allowed to be on my phone, a directive which I promptly ignored. (I know, I'm not proud.) I was super homesick and lonely and honestly, hanging with two toddlers all day is boring as hell. (I'm a mom now so I'm allowed to say that). My screen was my only escape from the blah moments of the job. The boys' mother would often sneak up and peer behind corners to check if I was on my phone. We all know how the story ends — I was fired. But I would like to think that low point led me to put myself out there in a bigger way. I started temping downtown, which led to one job, which led to another. I'm better for it.”
— Katie Stipanovich, operations manager
…career epiphany.
“My first job — in the event industry, totally unrelated to web design — actually hired me because they were really impressed by my Squarespace website. It was basically my glorified resume at the time. I eventually quit that job with no plan but to find a work-life balance and a career I loved. Flash forward six years, the answer was there all along, giving me little signs along the way.”
— Shelly Morse, developer
…leap of career faith.
“The first time I realized I could make it out on my own, I mentioned to a group of former colleagues at lunch that I was contemplating it. Their eyes widened and they said, “If you do, we will be your first client.” A huge win, but still it was risky, and I lost a lot of sleep before the leap. Once I was out on my own, I looked back and realized that my whole career was a risk. Not even a full-time job is a sure thing. I’m so glad I took things into my own hands.”
— Kishya Greer, developer
…big career change.
“2020 was the worst. It served up heaps of unfairness, from the least extreme (like having to wear a *gasp* mask) to the most (lost jobs, homes, family members). But what it served up to me was the realization that I did not want to be a stay-at-home parent. Turns out I desperately missed working. I love my kids, and my husband, and my home. But they are a LOT.
So for the first time, I took real action to change my career. So here I am, at the beginning of 2021, starting a new journey. While it’s hard, I’m doing my best to savor all the moments — even when my kids are climbing the walls and my husband’s on a Zoom call two feet away and my brain is fried and the world feels like it may be ending — because I’m working.”
— Anna Potter-Malone, project manager
