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- Reflecting on Chaos
Most people write reflections at the end of the year, zooming in on the last twelve months. But the past two years have been so chaotic—two layoffs, countless pivots, and an astonishing acceleration in technology—that I decided to look at a bigger chunk of time to reflect and identify the things that were consistently true and meaningful
The Tech Job Market: A Rollercoaster of False Signals
The post-COVID tech job market has been nothing short of chaotic. During the pandemic, companies misinterpreted growth spikes caused by unique circumstances—remote work, heightened online engagement, and a global need for distraction. When the world began returning to in-person life, demand fell off a cliff. The result? Layoffs, hiring freezes, and unprecedented competition for job seekers.
Personally, I was shocked by how impersonal the process became. Even with strong referrals, I struggled to actually talk to a human. The market was so oversaturated that companies relied heavily on rigid checklists and screening tools. I ultimately realized I was wasting a lot of time trying to go down the traditional job hunting route and took a pause to look at the situation with more of a first principals lense.
Lesson learned: Don’t let a broken system define your worth. Instead, adapt. Learn new skills, consider different roles or types of engagements, and keep moving forward.
If you’re feeling stuck or just trying to figure out how to navigate this market, check out my post on the rise of generalists and how to use AI to stand out as a candidate.
Side Hustles for Sanity and Stability
I was laid off just 5 weeks before my scheduled paid parental leave for the birth of my 4th son. I am what you would classify as a “high performer”, so this came as a total surprise. At the time, I was totally reliant on my full-time job to support and provide for my family. I knew the severance would go fast so I started thinking about the problems I needed to solve:
Support my wife and family as we bring a new baby home.
Replace my income and pay the bills.
Replace benefits OR make enough additional income to get my own
Maintain sanity.
While I would have loved to land a comparable job with great benefits, I didn’t want to put all of my eggs into one basket. I started talking to the people I have enjoyed working with the most over the recent years and quickly found a great opportunity with Nova.
I had worked with the team a bit at Automattic and loved their unique approach for driving adoption of the .link gTLD through partnerships. I’ve been working with that team for over a year now and not only has the extra income been a huge help, the work gives me a chance to leverage my full set of skills with great partners like Gravatar, Dub.co, Heylink.me, and many others.
Not every side hustle looks the same. Sometimes it’s a bit of consulting, sometimes it’s small projects here and there, and sometimes it’s building something of your own. There are some great companies that started out as side hustles. Not ready to build a product or business? Try building an audience.
Take Elena Verna, Peter Yang, and Oji Udezue, for example. All strong product leaders wo are investing in building their own audience in different ways.
Lesson Learned: Find a way to diversify your income and improve your resilience to what can be a very volatile and unpredictable world.
A few tips to help you get over the mental box of a 40 hour work week
Put the appropriate amount of time, energy, and focus into your full-time job (if you have one) and focus on delivering real business value.
Determine your needs and goals.
Do you need income now or are you trying to build something up over time?
Are you trying to build new skills to increase your value in new ways or are you trying to leverage skills you already have?
Find a way to open up enough time to add more value in other places/ways.
Wake up earlier.
Work a little later.
Prep your meals for the week.
The list goes on.
Just start. Most people have worked out how to do something, and stop just short of starting. Take that big scary step and start building your own “thing”.
AI Product: Learn Now or Get Left Behind
I didn’t plan on going back to agency work, but I had a unique opportunity pop up to lead product for a company that was building native AI SaaS products. I made the choice to deal with the things I didn’t like about agency work in exchange for a chance to build innovative products with the new technology that would undoubtedly change the entire industry. While I had been involved in some AI evaluation and planning work at Automattic, I hadn’t really been hands on with building, and I knew that experience would be important.
Working with the Engineered Innovation Group introduced me to end to end AI/ML development. I worked on everything from the core architecture and APIs to prompt engineering, designing for non deterministic experiences, and mapping out agentic workflows. In just a year, I gained more practical knowledge than I had in the five years prior, and I “collected” more hands on experience building AI products than 90% of other product leaders in the industry.
One of the most important take aways from building with AI, is that the “laws” of experience design are change drastically. While we’re all used to building very deterministic and general experiences, AI enables us to go the opposite direction with non-deterministic experiences that are highly personalized to the individual.
The “book” on how to design and build with AI is being written right now, so the only real way to learn is by doing. You can’t comprehend what’s possible for your customers/users if you don’t actively use and test the technology yourself, so get out there and start playing around. Check out my guide to prompting if you want to skip ahead a few spaces on the gameboard.
Lesson: By the time we are ready to ship the thing we’ve been building, the user’s expectations and definition of what a good product looks like will be drastically different. The companies that win will be the ones who show users what better looks like before they find a reason to define it on their own.
Other Observations, Lessons, and Thoughts
You will do your best work when you’re excited about what you’re doing and when you believe that your contribution to it matters.
Don’t hesitate or procrastinate when it comes to eliminating the things that waste your resources e.g. time, energy, headspace, money.
Push yourself to learn something new, improve the way you do something, or apply something you know how to do in a different way.
Your ability to do anything well, relies on your ability to feel good. Eat well, hydrate often, sleep, exercise, and decompress. Self care is important and it does impact how others see you.
You will always have something you “should” be doing. Make the time to do the things you want to be doing.
Don’t underestimate yourself. Become more aware of your unique strengths and lean into them with confidence.