Reskilling vs Upskilling: Lessons From My Developer to CTO Journey
In the fast-paced world of technology, staying still means falling behind. As someone who’s journeyed from a junior developer to a CTO over two decades, I can tell you the only constant has been change.
The secret to not just surviving, but thriving, in this ever-evolving landscape?
👉 Upskilling and reskilling.
These two powerful concepts have been fundamental to my growth and honestly, to my survival in tech.
My 20 Year Journey Through Tech
I started my career as a junior developer bright-eyed and hungry to build. Fast forward twenty years, and I’m now a CTO, responsible for strategic decisions, leading teams, and driving product vision.
This wasn’t a straight path. It involved constant learning, uncomfortable shifts, and many deliberate choices. Every role and project pushed me to acquire new skills and, sometimes, completely reinvent myself.
What Is Upskilling?
Upskilling is about advancing your abilities within your current role or domain. It’s leveling up your existing strengths and going deeper into your craft.
Real Developer Examples:
- A backend developer learning microservices, performance tuning, or switching to a more efficient backend language.
- A mobile developer exploring advanced animations, accessibility, or cross-platform frameworks like Flutter.
Tech Trend Example:
- AI engineers diving deeper into transformer optimization and model fine-tuning are prime examples of upskilling in 2025.
- Upskilling helps you stay relevant, master your field, and prepare for higher responsibility within your track.
What Is Reskilling?
Reskilling is the process of learning entirely new skills to switch to a different role, domain, or career path.
Real Developer Examples:
- A manual QA tester learning JavaScript and Cypress to become a frontend automation engineer.
- A developer transitioning into a Product Manager role to focus on customer needs and product strategy.
- A senior IC moving into people management shifting from writing code to mentoring and leading teams.
Tech Trend Example:
Reskilling from frontend engineering to DevOps/cloud infrastructure is a major trend, driven by demand in cloud-native environments.
Reskilling vs Upskilling: Who Needs What?
Knowing which path to choose depends on your career goals and where the industry is heading. Here’s a clear comparison between Reskilling vs Upskilling:
| Aspect | Upskilling | Reskilling |
| Goal | Deepen skills in your current role | Learn new skills for a different role |
| Focus | Advanced tools, frameworks, techniques | Entirely new domain or skill set |
| When | When staying in your current track but want to level up | When changing roles, e.g., dev to manager |
| Example | Backend dev mastering microservices | Manual QA → Frontend dev, Dev → Product Manager |
| Outcome | Greater efficiency, expertise, and role growth | Career shift, new challenges, broader opportunities |
So if you want to master your current craft go with upskilling.
If you’re pivoting roles or shifting direction reskilling is your move.
This comparison is at the heart of the reskilling vs upskilling conversation.
My Personal Experience: When I Had to Upskill and Reskill
For most of my journey, I was in constant upskill mode:
✅ Learning cloud technologies
✅ Exploring new frameworks
✅ Understanding systems architecture in depth
This allowed me to stay relevant, remain hands-on, and gain credibility with technical teams.
But when I stepped into leadership, I had to reskill:
💼 I had to shift from building things to enabling others to build.
🧠 From solving code-level problems to solving people and process challenges.
📊 From feature thinking to product, business, and growth thinking.
Neither path is optional. As you grow, both become essential.
Common Traps That Block Developer Growth
Even the most talented developers fall into traps that limit their progress:
1. Fear of Leaving the Comfort Zone
Sticking to the familiar even when your tools or methods are becoming outdated.
2. Tutorial Hell
Consuming tons of courses without ever applying or building something real.
3. Title Chasing
Focusing more on job titles than building the actual skills those titles require.
4. Waiting for Permission
Expecting your company to provide training instead of owning your own growth.
Conclusion: Build a Learning Strategy Before You Need One
My journey is proof that learning isn’t optional in tech it’s a career necessity.
Whether you’re choosing to upskill or reskill, what matters most is that you stay deliberate. Stay curious. Be honest with yourself about where you are, and where you want to go.
🚀 Don’t wait for disruption prepare for it.
🔁 Revisit your learning plan often.
🎯 And most importantly, know when to upskill and when it’s time to reskill.
👉 If you’re a startup founder or team leader looking for guidance on building stronger technical teams, feel free to get in touch with me always happy to connect.
