Career Paths in Tech, Part 3: The Dynamic Path - Why Not Both?

After exploring both the IC and management paths in our previous articles, I want to share a perspective that might surprise you: the most enriching technical career path might be refusing to choose at all. Through my journey from early-stage startups to established organizations, I've discovered that the ability to flow between hands-on technical work and leadership roles isn't just possible – it's becoming increasingly valuable in modern tech organizations.

Breaking Down the False Dichotomy

Early in my career, I bought into the notion that you had to pick a lane – either continue deepening your technical expertise or transition into management. This binary thinking is so ingrained in our industry that we often miss the rich territory that lies between and across these paths.

Let me share a pivotal moment that changed my perspective. I was leading a fintech startup's technical team when we hit a critical scaling point. As the team grew, I naturally transitioned into a CTO role. But instead of completely stepping away from the code, I maintained a careful balance: architecting high-level systems while still diving into critical technical spikes. This hybrid approach wasn't just about keeping my skills sharp – it was about making better strategic decisions informed by hands-on experience.

The Power of Dynamic Career Design

What I've learned through years of switching between IC and management roles is that this flexibility offers unique advantages:

Better Technical Leadership: When you maintain your technical edge while developing leadership skills, you can more effectively bridge the gap between strategic vision and practical implementation. I remember leading a major cloud migration as a director – my ability to both understand the technical details and manage stakeholder expectations proved invaluable.

Enhanced Credibility: There's something powerful about a leader who can not only guide strategy but also roll up their sleeves when needed. As a fractional CTO, I found that my ability to alternate between high-level advisory work and hands-on development gave me unique credibility with both management and engineering teams.

Sustained Learning: The tech industry moves at a breakneck pace. By maintaining involvement in both tracks, you're better positioned to understand emerging technologies not just theoretically, but practically. This dual perspective is invaluable for making informed strategic decisions.

Real-World Applications of the Dynamic Approach

Let me share some specific scenarios where this fluid approach has proven particularly valuable:

Early-Stage Startups

In several fintech ventures, I started as a hands-on tech lead but had to scale into a CTO role as the company grew. The ability to maintain technical involvement while building management skills was crucial for:

• Making informed architectural decisions that would scale
• Building and mentoring engineering teams effectively
• Maintaining technical credibility while developing leadership capabilities

Fractional CTO Work

Working as a fractional CTO demonstrated the power of this dynamic approach:

• Monday: Deep diving into a client's technical architecture
• Tuesday: Leading strategic planning sessions with another client's executive team
• Wednesday: Hands-on coding to prototype a critical proof-of-concept This variety kept me sharp and ensured my strategic advice was grounded in practical experience.

Enterprise Leadership

Even as a director overseeing large technical teams, I found immense value in staying technically engaged:

• Leading technical spikes to evaluate new technologies
• Participating in architecture reviews
• Maintaining enough technical depth to effectively challenge and support technical decisions

Strategies for Building a Dynamic Career

If you're interested in pursuing this flexible path, here are some approaches I've found effective:

1. Create Deliberate Learning Opportunities

When in management roles, carve out time for technical work:

• Lead proof-of-concept projects
• Participate in hackathons
• Take on occasional technical spikes
• Stay involved in architecture reviews

2. Build Strong Support Systems

To successfully navigate both roles:

• Develop strong technical leads who can maintain momentum when you're focused on management
• Build relationships with mentors who have successfully balanced both aspects
• Create systems that allow you to step in and out of technical work without disrupting team flow

3. Master the Art of Context Switching

Learn to transition effectively between different modes:

• Block dedicated time for deep technical work
• Use documentation and knowledge sharing to maintain continuity
• Develop clear communication patterns for when you're switching roles

4. Stay Technically Relevant

Even in management positions:

• Keep your development environment ready for hands-on work
• Regularly review code and participate in technical discussions
• Stay current with emerging technologies and practices

The Future of Technical Leadership

I believe the future belongs to leaders who can dynamically adapt their role based on what their organizations need. Sometimes that means diving deep into a technical problem; other times, it means stepping back to focus on team development and strategic planning.

This approach isn't without its challenges. It requires:

• Exceptional time management skills
• Clear communication about your current focus
• Strong support systems and team trust
• The humility to acknowledge when to step back from either role

But the benefits – better technical decisions, more engaged teams, and more fulfilling careers – make it worth the effort.

Conclusion

The question shouldn't be "IC or management?" but rather "How can I build a career that leverages both technical and leadership skills effectively?" By maintaining flexibility and refusing to be boxed into a single track, you can:

• Make better-informed technical and strategic decisions
• Stay engaged and growing throughout your career
• Build more effective and innovative technical organizations

Remember: The most impactful technical leaders often aren't those who chose one path and stuck to it rigidly, but those who learned to dance between different roles, adapting their approach based on what their teams and organizations needed most.

Your career in technology doesn't have to follow a linear path. By embracing the dynamic nature of modern technical leadership, you can create a more engaging, impactful, and sustainable career journey.