Photo by Karsten Winegeart on Unsplash

Getting Comfortable With The Uncomfortable

Dennis Field
3 min readFeb 13, 2022

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At my core, I am a builder. I love building and shipping things to the masses. Sometimes these are small things like a new blog post or a small piece of communication in Slack; other times, they come in the form of an extensive program or product that will be sent to a whole company. There’s always a bit of anxiousness whenever I ship something, and depending on the risk tied to that project, the feelings grow. I can’t change that, but what I can do is prepare.

Where do I prepare? Outside of work. Over the last 4–5 years, I have shipped one major project a year. Some people call these types of projects side-projects. I like the think of them more as labs or creative spaces that I go to learn, try new technologies, and meet inspiring people. More importantly, though, these spaces are where I take my most significant risks. They are my training grounds to learn, grow, bet on myself, build confidence, get humbled, build strong empathy for the process and people. It’s where I learn to respect the journey of creating something.

As a result of putting in these hours, I can draw on these experiences whenever I need to do so at work. The end results of these personal projects have varied. Some are thriving, some I’ve sold, some I’ve just closed up, and others I’ve yet to decide what I’m going to do with them in the long-term. A few have produced some passive income, but most have not. That’s okay because the learning has been priceless.

I’ve learned that no two problems and audiences are created equal. By investing time into these projects, I’ve created a set of tools and built resilience that I can draw on anytime I need to when at work. It helps me network internally empathize with the business and the people I work with because, in some ways, I’ve seen variations of what they’re going through in my own world. I tried to solve similar challenges myself.

Work is hard. It’s damn hard. However, just like an athlete, I try to care for my health by sleeping well, eating well, and building in some activity in my day. I also ensure training and practicing on my “side projects” are scheduled into my week. I prefer early in the morning or late when lights are down and I can focus. This regular training helps me familiarize myself with the feelings, challenges, and obstacles so that I’m prepared and confident whenever they show up at work. Although they may come in a different scheme, I can recognize the similarities and get comfortable in the uncomfortable quicker.

Here’s a list of some of the projects I’ve built over the years. All have helped me learn something or continue to do so.

Thank you all who have supported my ideas and taught me so much over the years! Your support as a customer, user, follower, or even a critic of my projects has helped me grow well beyond the project itself.

This post was originally shared on my personal blog.

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Dennis Field

I’m a designer solving People challenges @InVision. I also wrote a book that helps other designers reach their goals. Learn more: http://bit.ly/1fAgk4