My career story

I recently took a leap and quit my software engineering job to start a custom carpentry business. Since I can remember, I’ve always been the type of person that loves making things and software seemed like an exciting and profitable way to pursue my passions. I grew up helping my dad maintain and improve his rental properties which sparked my interest in construction and remodeling. I loved the satisfaction of building something with my hands and showing it off to friends and family. My dad always encouraged me to pursue my own business in high school and early college. I was drawn to work for and learn from other people, but he instilled a belief that working for myself was the right approach. I always felt a deep sense of loyalty to my dad. I felt that he had taught me so much and I knew that he worked hard to succeed in his own career. I always felt he knew and understood things I hadn’t yet learned.

My Junior year of high school, I was diagnosed with testicular cancer. It’s one of the most treatable forms of cancer, but at the time, I knew nothing about it. All I knew was that people died of cancer. I never felt like my life was at stake, because my doctors assured me that I caught it early and the treatment was very effective. I was a little scared and bewildered as everything seemed to happen all at once, and I had no idea what treatment would be like.

From surgeries, to chemotherapy, I was spending more time at the hospital than I ever anticipated. I fell behind in school and I began to wonder if I would ever catch up. It was the first time I had been pulled away from my day-to-day life and forced to reflect on who I was and what I was doing. I still struggle to describe the intensity of my emotions at the time, but I fell into a deep depression. I was unhappy with the person I felt I was becoming. I felt like I was coasting through life on autopilot. I was making decisions about my future on superficial information. I was too willing to give up on things that were hard or didn’t feel right. I wasn’t dedicated or passionate about anything. I was devastated by the idea that I would live a life without meaning. When I finally pulled through my depression, I vowed that I would master woodworking. It was the only thing I had stuck with, even if my effort and interest that far had only been half-hearted. I decided this would be my passion and I was convinced that I would discipline myself to master the craft.

For a long time, I did spend a lot of time woodworking. I read and watched everything I could. I got a job at cabinet shop called, “We’re Innovative,” and learned enough to start my own small business building furniture and other custom cabinetry. I was proud of myself and what I could create.

As time went on and I started college, I struggled with the idea of choosing a career. I really wanted to grow my cabinet business, but my dad encouraged me to pursue something bigger. He was a software engineer and naturally encouraged me to follow in his own path. I was reluctant at first. The idea of sitting at a computer all day was the most dull thing I could imagine. I loved being active and on my feet. I also loved working with people. I liked helping people. I was doing great in my psychology electives, but my dad convinced me I wouldn’t make enough as a counselor or therapist. As usual, I listened to him without question. I didn’t so much as look at how much a therapist earned in a year, hell, I didn’t know how much I even needed to earn. Like many college students, I had never lived on my own and had little understanding of the cost of living.

Eventually I took a few programming courses and was hooked. I loved it. It was so creative. It was like being in my shop, building something, figuring out how to bring an idea to life. As I developed more interest in software, I started to pay more attention to the software I used everyday. I vividly recall seeing someone using a feature on a MacBook in one of my classes and being impressed my the elegance and simplicity of the Mac interface. I visited a store and fell in love with their software. I worked all summer to save up and buy my first MacBook. It was my most prized possession for several years. As I learned more about Apple’s business and development philosophies, I quickly became enamored with the company. To me they were the most iconic intersection of art and technology that I had yet encountered. I really wanted to work at Apple, but I knew little about what it would take. I spent my college career thinking I had to become an exceptional programmer to land a job with Apple. I never really took the time to do any research into what their culture was truly like, what they looked for in employees, or even so much as challenge myself to understand whether my approach was inline with my true strengths and values.

My last year of college was extremely difficult for me. I spent what felt like all my time studying and researching. I was so out of balance that I eventually had an anxiety attack and thought I would have to drop out with only a semester left. Luckily I had supportive friends and family that urged me not to give up. I stuck it out, struggled through what no longer felt in line with my values, and graduated with a bachelors in computer science. There’s a lot more to the story of my last year of college and the months after graduating, but I eventually started an internship at a small software company with an enticing mission to change the world by improving business sustainability practices. It was my first office job, and a huge learning experience. I had no experience in how software companies were run. I was ready to learn everything I could absorb. It was engaging for months. I was excited by the prospects of creating software that could help fulfill our mission. I felt like I was learning quickly and for the first time, I was getting paid to work on intriguing and challenging problems.

The excitement and optimism didn’t last long. Within a few months, I began to realize how different my values were from the engineer I was reporting to. He seemed to have an obsession with technology and well architected and efficiently written code. On the surface, that seemed normal for a software engineer. I often felt inadequate, and doubted my own beliefs and potential. I found myself more concerned with whether we were building the right things, rather than whether we were building things right. He wanted the code to be right, and I wanted the solution to be right. I had no first hand experience with other software companies, but my intuition was telling me that this company had the wrong approach. I felt strongly that we needed a more customer-centric approach, than a technology-centric approach.

I regrettably stayed with this company for several years trying my best to rally support for my views on how to improve our product. I knew early on that I wouldn’t stay with this company for long, but I wanted to continue learning and persevere through the struggles I faced in order to prove that I had tried my best. I wanted to ensure that I could land a “better” job when I finally decided to leave this company. However, in hindsight, I ignored something I truly believed even before I began working at this company, that working with a great team was far more important early in anyone’s career than what you’re working on or how much you’re earning. Our dysfunctional team dynamic was preventing us from achieving great things, and I knew this early on.

I also truly loved working with our Program Managers. I felt they were my true peers and they were a huge reason I stayed with the company for as long as I did. Their jobs were much harder than mine. They had to work with our customers first hand to solve their problems and make up for our less than helpful platform at the time. I did everything I could to help them. At times I thought I would get fired for ignoring my supervisor and doing what I thought was right. I wanted them to be successful and efficient in their work, but not everyone on the dev team felt the same way. To some, the PMs filled a role that was viewed as a necessary evil on the long road to building a platform that would eventually provide their services in a fully automated way. I never saw it this way. I always believed that one of our strengths was that our customers were able to interact with a real human who understood their problems and went above and beyond to take care of them. I believed we had to do everything in our power to support our PMs.

After several years of fighting my intuitions and trying to cooperate in what I believed was a dysfunctional organization, I finally gave in. The same lead developer that I reported to early on had re-written a large portion of a project I had worked on for months. I discovered the changes when I started a task to add a feature to the service. The code had become incomprehensible. The naming conventions made no sense, new patterns and been applied, and the latest features of the project framework had been utilized in ways that took days to understand. I was done. This had happened a number of times before and I pleaded with this developer NOT to re-write anyone’s work without consulting them directly and coming to an agreement on the changes he felt were necessary. This developer made my contributions feel so worthless, that I saw no possible way I could continue to work in that environment.

In the final months leading up to the decision to really start looking for a new job, I had been debating a career switch to a product manager/owner role. I was convinced I would be much better at managing people than anyone else who had been in that role at our company up to that point. I was just afraid that would be the end of my programming career and there would be no way back. Again, only in hind-sight was this a ridiculous assumption. It’s not much different from saying, if you don’t start out in the right career, you’ll never be able to switch, yet people switch careers all the time. It’s hard, but it’s far from impossible. Instead, I landed a job at a small email marketing company that was expanding into digital content management. I would be leading a new project to develop a platform for organizing and selling digital content. I found a way to make this company’s goals align with my own. I saw this as a chance to finally pursue my own ideas without being impeded by another developer or a culture that stifled creativity.

I started this job feeling stressed and insecure. I was taking on something I had never done and I honestly wasn’t confident I could pull it off, but I was willing to give it all I had so long as there was no “red tape” to slow me down. In the first several months of this job, I was learning far more than I had in years at the previous company. I was desperate to learn everything I needed to know to make this project a reality. I was making what felt like good progress, but I was also being asked to do extremely technical work I was completely unfamiliar with. I put those aspects of the project aside and focused on the parts that were most interesting to me, the management and organization of content. I wanted to make something different and incredibly easy to use.

Not long into the project, the CEO decided to shut down that side of the business and let several employees go. I was fortunate enough to stay on, and I was moved to the email marketing team. I was excited to work with a team again and I hoped that the dynamic at this company would be a 180 from the last experience. Luckily, it was. We got things done faster than I had ever experienced. Meetings were quick and there was always a decision maker that prevented us from debating a problem for hours without coming to a conclusion. When a decision was made, the team carried out the plans without complaint. It truly was a team effort here. I was excited to be a part of this team and this company. I felt like I was learning AND getting things done. I envisioned my career finally moving forward in a way that made sense to me. However, as time went on, I began to realize that even though I liked the way the company was managed and the people I worked with, I was feeling uninspired by our product. It wasn’t a game changer. It wasn’t making the world a better place and I really didn’t feel a sense that I was helping anyone, which by now I was very well aware was one of my core values.

I started to become more disengaged from the team and other coworkers. I was less interested in spending time outside of work with the people I was once excited to get to know when I started. I kept to myself and was far more concerned with my life outside of work. I started looking for jobs again, and the jobs that were most interesting to me required me to leave San Diego. I wasn’t ready to move because I was almost done remodeling the house I had worked on for the last few years. I spent my weekends and many weeknights pouring my extra time into this house to transform it from the neglected dump that it was when I bought it, to the beautiful little home on a canyon that it is today. I loved this house. It felt like the biggest part of my identity. It felt like the only tangible thing I had to show for my time over the last several years. I had also recently started dating my girlfriend and I knew she wanted to stay in San Diego as well.

The jobs I was finding in San Diego didn’t inspire me. I vowed to never again take a job for the money or the learning experience. I was deeply concerned with being motivated by the company, the product, and the people I would be working with.

After about a month of searching, I finally decided I would simply quit my job and start a handyman business while I figured out the next phase of my life. I did no research into what these types of businesses were making in San Diego, but I knew I could do great work and make enough to get by, so I dove in head first. I put together a website and a yelp page with the work I had done since I was in high school, and I had calls within days. I started to pick up work pretty quickly and I stayed busy. I wasn’t efficient though, and I was spending a lot of time buying materials, researching how to do new types of work I hadn’t done before, and trying to organize my finances. I was often stressed and near burnout, but I was extremely motivated to run my own business and find a way to make things work. I read more books and learned more new software than I had in years. I learned quickly from my mistakes and I felt a strong sense of control over my future. I wasn’t doing exactly what I wanted to do, but I had more control over my future than ever before.

I’ve recently shifted my focus away from general handyman work, which required all sorts of tools and supplies, to custom carpentry. I’ve always loved woodworking, but I didn’t have the shop space at the time I quit my job. I am incredibly lucky to have a loving and supporting girlfriend that encouraged me to pursue my dreams and did everything in her power to support me. We moved from the house I had been working on, to her house with a two car garage. The garage is now my workshop and I am just now beginning to focus on custom cabinetry and woodwork. Even though I have no employees, I’ve learned a lot about running a business. I’ve learned mostly the hard way, but the mistakes I’ve made have forced me to research and learn things I would not have been motivated to invest my time in prior to starting the business. Things like estimating, managing customers, and improving my communication skills where honed out of necessity to keep my business alive.

When I look back on my journey that brought me to where I am, I often feel like I spent too long in certain areas. I feel like I should have known and acted sooner when things were out of line with my values. It’s tough not to think this way, but I also know that I can’t get that time back and I’m determined not to make the same mistakes again. I’m focused on living by my values and intuitions and less by the values and intuitions of others. I’m excited for what the future holds and I truly feel like I’m on a path that will lead me to an even more fulfilling life. I’m learning to trust myself more than ever before.