Finding your own personal product-market fit: From designer to engineer to startup founderFeatured

It’s always been difficult for me to define exactly what I do. Growing up, I always had an interest in tech, design, and business, but wasn’t exactly sure what that meant as a job. Rather than try to pressure myself to define it, I prioritized following my curiosity, taking big risks, and working with interesting people. From there, I trusted that I’d figure something out.I grew up in a university town in the midwest, which allowed for plenty of opportunities to learn and explore. In college, I struggled with that same pressure to choose my major and chose, instead, to follow my curiosity. I declared my major at the last possible minute, choosing Advertising, which had two years of core curriculum. This allowed me to take a year to study abroad and another year to take classes that sparked my interest; mostly film, design, programming, and studio art.My first exposure to startups was during my design internship at Wolfram Research, where I got to participate in the launch of Wolfram Alpha. It was exciting to see a small team of scientists, engineers, and designers come up with something interesting, and launch it to the world. I knew that was the energy I wanted to be around. I didn’t have much work experience, so I still had no idea what that meant my “job” should be.Shortly after college, I took a big leap and moved out to San Francisco. Without really knowing anyone, I traded rent for web design at a tiny 4-person startup, and worked my way through various freelancing gigs, agencies, and publishing companies, mostly just saying “yes” to interesting challenges that needed to get done. Eventually, someone I met at SXSW mentioned that the startup she was working at, Square, was looking for engineers who had a design-mind. I had been programming since I was a kid, and had a few web developer gigs, but had never heard of “front-end engineering” before. It sounded kind of scary to suddenly call myself an “engineer”. I decided to follow my curiosity and trust that I had the skills to figure it out. Square was small, and seemed promising at the time. I had seen it around the city and was excited for the opportunity to work on something that was helping small businesses and artists. I joined as the second front-end engineer, and the second female engineer in 2011.A few years later, and dozens of exciting product launches, I had fully burnt out. The 16-hour days and revolving door of managers got to me. While I didn’t know much about burnout, mental health, or self care at the time, I knew I needed a break.Finding your ‘next big thing’ is hard.I wasn’t ready to jump straight into another full-time job where I was firing on all cylinders. I had developed an interest in painting, and decided to move to New York to take some classes. I had a lot of fun with this and it definitely helped unwind my pancake brain. Eventually, I decided that making art was a thing I enjoy doing for fun, and not something I wanted to depend on for my living. I started taking on short-term freelance work, doing a mix of design, engineering, research, operations, and product for companies like, Facebook, and Intercom. All of these were fun projects, but again, I struggled with what I wanted my “job” to be.Thinking back to how I’ve always made decisions, I went back to prioritizing curiosity, risk-taking, and working with interesting people. I thought about the challenges I faced at multiple points in my life: burnout, impostor syndrome, working through creative blocks, figuring out career moves, and isolation with creative & personal projects.I started asking friends how they worked through these challenges, if they had a magic wand, what they might need to help get them through it. Almost everyone I talked to had some project or idea they wanted to work on, but had a million excuses for why they couldn’t. They struggled with time, money, accountability, anxiety, and structure to make it happen. I heard over and over that they just wanted a person who had been there before to listen, hold their hand, and help them figure out how to make decisions. Find your own personal Product-Market FitI recently learned of the concept of ikigai. What do you love? What does the world need? What are you good at? What can you get paid for? This concept can apply directly to making a successful startup and finding your own personal success.Personally, I love making things & helping others. After talking with friends, I realized that everyone could use more help in working through their career, business, and creative challenges. These are things I can help with, and areas where I know people who can — why not build a product that can facilitate this at scale? Now I just had to figure out whether people would pay for this. I spent the better part of a year listening, learning, researching, and prototyping. Through this process, I learned about the concept of coaching. I’ve since had the opportunity to work with a handful of coaches and in hindsight realize how much of an impact it would have made to work with a coach earlier on. I also learned that most coaches today are discovered through word of mouth. There isn’t a trusted brand or centralized place to find the right person, and it’s especially difficult to find coaches who have had hands-on experience that align with your goals. Many companies are beginning to offer coaching support for their employees (where was this five years ago!), but there are still so few resources for solo-entrepreneurs and individual creatives to get the support they need.Recognizing the impact that access to coaches who have “been there before” could have for enabling more inspiring, creative work— particularly for people with the least amount of access and support— Walden was born.Trust breeds confidenceStarting a startup, a business, a creative project, or side hustle is hard. I’ve found that the more pressure I put on myself, the more I tend to doubt myself. When I doubt myself, my confidence goes out the window. Without confidence, I feel stuck and frustrated, and usually can’t get much done. I’ve hit these walls countless times during my journey of starting Walden.By shifting my focus back to those initial drivers— following my curiosity, taking risks, and surrounding myself with interesting people— trust & confidence in myself becomes easier. It takes a lot of help and support from friends, mentors, coaches, and colleagues to find and maintain your ikigai— whether it’s for your own personal journey, your career, your business, or your projects. I’m still learning and figuring a lot of this out. In the meantime, I’ll continue to remind myself (and others!) to stay curious, take risks, work with good people, and trust themselves.Madelin is the founder of Walden, a coaching platform for creatives, solo-entrepreneurs, and side hustlers to get the support they need to launch their next big thing. She’s worked as an engineer, designer, and product lead at tech companies such as Square, Facebook,, and Intercom.
Loved this post and also love what you're building at Walden!
Thanks @tingtingluo!!
This is amazing - so articulate and inspirational. Thank you for sharing Madelin 🤗
Thanks for sharing, Madelin! This part realllllly resonated with me: "By shifting my focus back to those initial drivers— following my curiosity, taking risks, and surrounding myself with interesting people— trust & confidence in myself becomes easier." This is the biggest balance for me in an early, early stage startup - trying to get the thing off the ground. So much is up in the air and the reflex reaction is to add pressure to the mix, which has the exact opposite effect as I'd like it to. Thanks for the reminder that I'm not alone!