Outside Insights: Fireside Chat with Derek Wood and Jeff Casimir

In our latest episode of Outside Insights, Jeff sits down with Derek Wood to talk about creativity, code, and what it really takes to grow a career in tech. Starting with Derek’s unconventional beginnings in art, alternative education, and hiding in bushes smoking cigs, the conversation moves into software projects and the future of the tech industry. Here’s a quick recap.

From Art to Software: The Nonlinear Journey into Tech

Derek didn’t start out in tech. His early days were filled with artistic exploration and learning in a nontraditional classroom. That creative foundation helped shape his unique approach to programming, even though the transition wasn’t always smooth.

“I didn’t know anything about programming... I was making it really hard on myself.”

He eventually found his way into software development through persistence, community, and a lot of trial and error. His journey reminds us that there’s no one path to becoming a developer, and that creativity is an asset—not a barrier—in this field.

Teaching and Learning: Why Collaboration is Key

One of the most powerful parts of Derek’s journey? Teaching. Whether mentoring others or reflecting on his own challenges learning to code, Derek highlights how collaboration and guidance can change everything.

“Demonstrating problem-solving is key. Don’t just focus on the code specifically.”

It’s a powerful reminder that tech is a team sport, and success comes from building with others, not in isolation. Whether you’re mentoring, pairing, or just sharing your work, learning is amplified through connection.

The AI Era: What’s Changing and What Stays the Same

With AI taking over the headlines, Jeff and Derek dive into what it really means for today’s developers. While tools like ChatGPT and Cursor are incredibly powerful, Derek emphasizes that AI can’t replace the nuance and empathy of human interaction—especially in user experience and design.

“AI can maintain a lot of context, but I’d still rather talk to a human.”

The key takeaway? Developers need to understand when to use AI and when to rely on their own judgment. Learning the fundamentals, practicing strong coding habits, and thinking critically are more important than ever in a world where tools are evolving fast.

Career Advice for New and Aspiring Developers

Derek drops some gold for anyone trying to break into tech—or figure out their place in it:

• Be persistent. The learning curve is steep, but it’s worth it.
• Find your niche. Not everyone needs to be a full-stack expert.
• Stay curious. Tech moves fast. The best devs are lifelong learners.
• Focus on users. Great software solves real problems for real people.
• Build in public. Your next opportunity might come from someone seeing your work online.

Whether you’re just getting started or considering your next move in tech, Derek’s story is a refreshing reminder that you don’t need to have it all figured out—you just need to keep moving forward.

Watch the Full Conversation

📺 Catch the full session here: Outside Insights with Derek Wood on YouTube

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