Table of Contents

It feels like just the other day I announced I was leaving Asana to pursue freelancing. Now, almost eighteen months later, I'm taking a break from my freelancing career as I search for the next step on my journey through life.

Full disclosure, I actually started this sabbatical in September 2021. I've been enjoying myself so much that I've neglected writing this until now. What can I say? I've been enjoying my lack of responsibilities.

This is a big shift, so I'll share what I've been up to for the past eighteen months, and where I'm headed.

Where I've been

Fortunately, I've had a successful second stint as a freelance web developer. One measure of "success" is that I never had to search for work and instead relied on connections I made throughout my career to find projects and clients. Having a steady stream of leads allowed me to focus on running my business and executing client projects.

Specifically, I would like to give a shout-out to Casey Martin, Kelsey Aroian, Vanessa Koch, Tony Mingo, Natalia Kowaleczko, and Michael Spradlin who all helped me find client work during this time. Thank you all so much.

During the past eighteen months, I've completed fifteen client projects. Cranking out this much work wouldn't have been feasible (or advisable) by myself, so I must express my deepest gratitude to Jaime Hernández—my friend and closest collaborator—who worked tirelessly with me on countless projects. I'd also like to shout out Nels Andereck and Rob Schneiderman, two friends I met while working at Asana, who I also collaborated with during this time. I've loved working with you all.

On average, I launched a new client
project every 36 days. Whew.

Surprisingly, I took home more net income freelancing than working in-house. Comparing these is difficult, as the former requires paying more taxes for self-employment and benefits while the latter provides non-income compensation such as stock options, insurance, and other perks. Nuance aside, the income potential for freelancing provided a delightful surprise.

I also learned a lot during the past eighteen months. Working on so many projects with various stakeholders and collaborators, competing priorities, tight deadlines, and requirements forced me to improve all aspects of my professional skillset. I improved my communication, became a project and people manager, and bolstered my core competencies as a web developer.

Much of my learning happened as I struggled to communicate with so many people, missed deadlines, improperly prioritized work, and used the wrong tools for the wrong job.

Learning through failure is difficult but necessary.

Lastly, I worked with several wonderful clients while freelancing. I became connected with collaborators and stakeholders who I now consider friends through our working together. These people were typically patient, communicative, and empathetic, making them great collaborators. It's hard to ask for a better experience when working with others.

Looking forward

I'm going to take some time over the next year to continue engaging in my daily practices, cultivate areas of interest, spend time with friends and family, travel, and see where the world takes me.

Instead of focusing on my actions being a means to a financial end, I'm going to allow them to be the end in and of themselves.

What happens when my focus isn't on earning money and, instead, on the authentic enjoyment I receive from whatever I'm doing?

You will doubtlessly see me around these parts as I continue writing and publishing whatever I'm thinking about, learning, or building. Writing is one of my favorite practices and one where I will continue to invest a great deal of time.

If you want to stay up-to-date with whatever the hell I'm doing, subscribe to my newsletter and get this nonsense delivered straight to your inbox whenever I feel like sending it.