The Power of Self Education in TechFeatured

We learn best from our own mistakes and no experience is truly a waste on the path to successBobbilee Hartman @@bobbileehartman epitomizes the nontraditional success that has become common in the tech industry today. Now an independent entrepreneur and a Developer Evangelist at Square, she has evolved from an artist to a software engineer to a member of the outreach team at her company. She has done so without the support and accompanying rigidity of a formal, degree-earning education. In an industry where women in STEM continue to search for a foothold, Bobbilee’s journey is inspiring and encouraging. Luckily, I had a chance to interview Bobbilee myself. The path to a software development career doesn’t have to involve a computer science degree anymore.Bobbilee studied photography and business in college and had every intention of becoming an ad buyer at an ad agency to use those skills afterwards. Graduating during the Great Recession, however, made achieving that goal far more difficult than was expected. Due to most companies’ cost saving and downsizing goals, ad agencies all around the country were eliminating the ad buyer role. Although the position eventually returned to the market, at the time, Bobbilee needed to find a different path.Even so, many of the skills she learned in her classes were transferable and highly valuable in her future career. For example, she often needed to talk to the subjects of her photos to get permission to photograph them for class and doing so required that she be comfortable approaching strangers. In her current role as an evangelist, this is particularly useful for striking conversation with potential users or simply better understanding her audience.Learning software development isn’t easy without the background, but there are many resources in place today to help career changers get there.After finishing college in 2011, Bobbilee started working for a small startup in a marketing and design capacity. Owned by a family friend, the company was a great fit based on the several marketing and design internships she’d had in college. She picked up some web development basics from her colleagues and followed it up with a one-day Ruby on Rails workshop. Web development turned out to be empowering and fun. “I love how organized the process is. You’re always learning new things and it never feels like work - more like you’re playing games and problem solving all day. It’s interesting and difficult for a lot of people to understand, so in a way you feel empowered to take on the world and solve big problems. I love that I can help so many people in the world with this skill,” she says. At the workshop, Bobbilee volunteered to act as a photographer for the upcoming Ruby conference. The conference made it possible to meet some great developers who told her about a 4-month coding program in Chicago. They said so many great things about it that she had convinced herself to go by the end. The program was very challenging and Bobbilee didn’t find herself at the top of her class. Still, upon completing the curriculum, Bobbilee landed a job as a junior developer, which she quickly followed up with her first job as a software engineer at Intuit in San Diego.One of the most valuable resources for learning something completely new is enthusiasm - from the student and their potential mentors. With this resource, over the course of just a few months, Bobbilee was able to completely change her career into a technical role that better aligned with her interests. This enthusiasm continued even after she found success while still working full time with her role as an instructor at, an online bootcamp school where she mentored for five years afterwards. She worked with 5-10 students at a time and had as many weekly mentoring calls scheduled. With this experience, Bobbilee had the opportunity to amass an enormous amount of mentoring experience and develop her own expertise further. Sharing is caring - possibly the most impressive piece of her career is Bobbilee’s independent events projects.The enthusiasm for sharing her knowledge and experiences led Bobbilee to some of the most impressive feats of her career: the founding of Rails Camp West Coast and Lodged Out. Rails Camp was a concept from Australia that she had heard about and wanted to see in the United States. In 2014, she started her own chapter to take conferences outdoors and to the next level. After working in web development for some time, Bobbilee found herself unhappy with her work - and the people around her were noticing. She was often asked if this was really what she wanted to do, and she always said that it was. Over time, however, she came to realize that working on her own was getting isolating in the workplace and she was spending a lot of time outside of it at events and meetings. She needed to communicate with people more and Rails Camp was a great way to do it.About Rails Camp West, she says, “There is no agenda at camp. You can play outside and hike or swim or rock climb. Outdoor activities are different at every event. You can also play board games or work on computer and pair program with someone. You can teach each other new things, participate in karaoke at night, and attend fireside chats. Some folks come to practice their big conference talks, so there might be a short workshop, discussion, or impromptu talk going on in the afternoon. 50-65 people attend every year and there is no application process you just buy a ticket on the site.”At the same time, Bobbilee started working on the idea for Lodged Out, “which is an umbrella over the whole idea of unplugged retreats.” As demand for her retreats grew, she was able to expand further than just engineers. “Now I run them for all types of people and I collaborate with people, partner with other brands, and companies hire me to run off sites that are unplugged at lodges and summer camps.“I did 5 total events last year, and I’m doing 3 this year (including rails camp). Every event is different in size (anywhere from 20-60), and develop hype differently. I’ll email past attendees, post on Instagram, and email other folks who I’d think would like to come…and that’s about all I have time for in terms of marketing right now. Next year will be different though!”While there are some sponsors whose contributions go to outdoor activity fees, diversity and inclusion, and t-shirts, the events largely pay for themselves through ticket sales. Bobbilee treats them as nonprofits and contributes all revenue back into operations.In addition to growing her experience and understanding of her work as a software developer and indulging her interest in unplugged retreat events, these entrepreneurial ventures also made is possible for Bobbilee to become an events management expert. This further opened several doors for her.Sometimes, an independent project that starts out as a hobby can impact and change the entire course of your career.Although Rails Camp and Lodged Out did start out as side projects, they helped Bobbilee build an expertise in an area that would help her land her next job at Square, as a developer evangelist. The job requires far more than just software development skills. On a day-to-day basis, Bobbilee writes blog posts, makes YouTube videos and other content, and helps spread the word among developers about Square’s expansion from hardware. “We've always had people know us for our hardware, but what some people don't know is that developers can add payment forms to their website or mobile app as well as build custom apps for Square sellers. They can also customize our point of sale readers using our Square Reader SDK.” she says.Her entire career up until now, from her education in photography and business to her experience as a software engineer, events entrepreneur, and even coding mentor have prepared Bobbilee for her work today. As nontraditional as the path has been, it has only positively impacted the quality of her work.As for the future, Bobbilee says, “Rails Camp will stay the same forever. It’s perfect, sells out every year, and people love it the way it is. I will never bring in more people to that event because the magic is in the small group size. Lodged Out growth is geared towards private events. I will most likely add another person to the team and we’ll grow the private sector together.”A major issue that women in tech face today is imposter syndrome - moving past it will be an enormous step toward true equality and workplace diversity.Imposter syndrome is unsurprisingly common among women in tech, and Bobbilee has been no different. Especially without a certain formal background, it can be easy to feel as though the people around us know far more than us and we simply don’t belong in the position that we’ve been given.The thing is, very rarely are positions simply, “given.” If you have a job, you’ve probably earned it by giving a great interview. Bobbilee’s advice?“Try to rest your mind for a minute and say to yourself, they've just read a little bit more out of a tutorial or a book than me. It's not that they are smarter than me in any way. It's literally just that they've tried a couple things, got an error, and they learned from it."At the end of the day, we learn best from our own mistakes and no experience is truly a waste on the path to success. Swati is a writer, digital strategist, and brand enthusiast. She is currently a tech startup Brand Story Consultant with Plotline and is also passionate about gender equity in tech, abolishing the phrase, “marketing bullshit,” and making startup growth strategies accessible to all entrepreneurs. She consults pro-bono for small businesses and nonprofits and writes about things that matter (and things that don’t) in her free time.Want to be featured in an Elpha Editorial? Tweet or DM us with your details!
Love this! I am a firm believer in the power of a complementing a traditional "hard skills" background (i.e. business) with more humanities-based "soft skills" such as art and photography.
Great article. I especially appreciate this as I'm currently going through a career transition myself. I'm taking tech courses through Skillcrush and completely changing my career path, which before, was in banking and very far from anything 'tech-y'. Definitely, I have to be willing to make mistakes and not be the best at everything from the start. That will come with time.
Great story. Thanks for sharing! I love the advice that it's not that people are smarter in any way, it's just that they read more or had more experience. This is something I'm starting to realize and it makes such a huge difference to constantly feeling like an imposter.
This was one of my favorite takeaways too! It’s a question of experience, not intelligence. Which is why, when I catch myself saying, “Ugh, a better developer/founder/whatever than me would think this problem is SO easy,” I reframe it as: “Future Me is going to think this is SO easy, because she’s done it before.”
Thanks for sharing! This is a great post, with super helpful takeaways especially for those looking at next steps in their career. Always being open to learning, and knowing it gets easier as you gain more experience is key.