Deciding to be Self-Employed
After years of working as a Software Engineer at various companies, I found myself at a crossroads where the benefits of self-employment began to outweigh the risks.
The Catalyst
After leaving InVision, I’ve struggled to find an organization I enjoy working at. It’s rare to find good pay, meaningful work, work-life balance, and an async culture. I’ve changed jobs several times over the last few years trying to find all four, with not much luck.
Last year brought a series of personal challenges. I was diagnosed with type 2 diabetes, requiring significant lifestyle changes and ongoing management. Shortly after, I suddenly lost a grandparent, which forced me to confront mortality and what truly matters in life. Last December, my oldest cat started requiring heart medication four times a day, adding daily caregiving responsibilities.
Being able to work remotely is critical to managing my own health and household obligations. The flexibility isn’t a nice-to-have; it’s essential for maintaining my health and caring for loved ones. The frustration with corporate environments, confidence in my ability to deliver value, and the pressing need for flexibility in my personal life pushed me toward self-employment.
I’ve decided to stop doing the same thing over and over again and expecting different results.
The Plan
Over the last few years I’ve been tinkering on a plant monitoring project. The project grew to the point where I needed to form a proper business. In 2024, I took several months off to recoup and work part-time on Plant Ranger. Part of this work was forming Digital Buttes LLC with Kali and Conant to build Plant Ranger.
We hired a graphic designer to create a logo, style guide, and icons for Plant Ranger. And paid to have the b-parasite device tested so that I could sell them in the United States. To de-risk the failure rate of the devices, we decided to sell unbranded (without a Plant Ranger shell) programmed to work with Home Assistant. Since October we have sold over 100 devices.
After adjusting for tariffs at the beginning of May, I’ve learned that hobbyists are less willing to pay $25/device (was $12/device). This pricing challenge forced me to rethink the business plan, at least for the short-term. I’m not a hardware person and finding a hardware person in Eugene is difficult. Plant Ranger’s value is in the data ingestion, processing, smart watering notifications, and recommendations.
I’m exploring integrating Plant Ranger with Home Assistant. The integration will send data from all plant sensors supported by HA and display Plant Ranger alerts and recommendations in Home Assistant. Home Assistant’s developer API is complex. All of this is going to take months to build, launch, and grow.
I still need to pay bills. To do this, Digital Buttes offers IT contracting and consulting services. I landed my first contract in early May and am committed for at least the next several months. My biggest fear right now is lead generation. Kali and I are iterating on business cards & marketing and I’m going to start attending Eugene and Portland networking events.
If your team needs help updating applications, migrating to the cloud, containerizing workloads, or implementing DevOps/GitOps practices, please reach out to ryan@digitalbuttes.com.
The Future
Over the last two months, I’ve found that I enjoy the increased freedom. I’ve started running 2-3 times a day and am slowly improving my mile time. Ochkam, the sick kitty, is doing as well as can be expected and will be with us for a while longer. I’m talking to my grandmother more often and trying to be more present.
Contracting part-time has taken a lot of my stress away. I think the improvement is a mix of only working 25 hours a week and not having to worry about fitting in to the company culture. I’m helping the org solve specific problems and only those problems.
I continue to add features and prepare to launch Plant Ranger. Next week I will be making a proper home page and working on the Home Assistant integration. Lead generation will be my primary business concern for the foreseeable future. I’m a little nervous but a lot less stressed. I don’t know how it will turn out, but I know I would regret never trying to make a go of self-employment.