Chapter 9: What’s Next?
tsep career self-assessment skill-building network visibility job-evaluation
Status: Notes complete
Overview
Chapter 9 closes the book by turning the lens inward: how do you think about your own career as a staff+ engineer? The chapter argues that your career is a resource you must actively manage — not just grind away at hoping for the best — and provides concrete tools for evaluating where you are, what you want, and how to get there.
The metaphor is a trail map: you’re trying to reach a summit (your goals), but there are many trails, different ones suit different abilities and conditions, and the right trail depends on where you’re starting from and what kind of journey you want.
The chapter is deliberately personal and non-prescriptive. There’s no “correct” staff engineering career. But there is a process for being intentional about your choices rather than letting them happen to you.
Core Concepts
Trail map: A metaphor for career navigation — a representation of possible paths to your goals, each with different trade-offs of effort, speed, risk, and scenery.
Ability points: The idea (from RPG games) that you earn skills over time and must deliberately allocate them. You can’t be excellent at everything; you build on strengths while maintaining basics in other areas.
Five job health metrics (Cate Huston): A framework for evaluating whether your current role is working for you: learning, transferable skills, recruiting pride, confidence, stress.
Job health tracker: A table that records your assessment of each metric over time, making trends visible.
Knowing What You Want
Before evaluating your current role or exploring alternatives, it helps to be explicit about your priorities. The book offers a list of common values engineers prioritize:
| Priority | Description |
|---|---|
| Financial security | Stable income and benefits; baseline needs met |
| Family | Time and flexibility for relationships outside work |
| Flexibility | Control over when, where, and how you work |
| Learning | Continuously building new skills and knowledge |
| Visibility | Recognition — within your company or the industry |
| Cool things | Interesting technology, cutting-edge problems |
| Challenge | Hard problems that stretch your abilities |
| Wealth | Significant financial upside (equity, bonuses) |
| Working for self | Autonomy and ownership over your direction |
| Making a difference | Impact on something that matters beyond the company |
No single priority is right or wrong. But not knowing which ones matter to you means you can’t evaluate opportunities well. The first step is ranking these honestly — not what you think you should value, but what you actually do.
Three Career Needs
Regardless of your specific priorities, three things help sustain a long career:
1. Building Skills
Skills compound. A decision made at year 3 of your career (to specialize in X or generalize broadly) shapes what opportunities are available at year 10.
Ability points analogy: In RPGs, characters have limited points to allocate across skills. You can’t max everything. Staff engineers must make similar choices:
- What are your core strengths? (invest heavily)
- What do you need to be adequate at? (maintain)
- What can you safely outsource or avoid? (let others own)
Don’t rush past your prime hands-on technical learning years. The Charity Majors warning applies here: if you move into staff or management roles too early, you miss the deep technical experience that makes senior leadership valuable.
2. Building Network
Your network is a primary source of:
- Information about what’s happening in the industry
- Referrals and opportunities
- Peer support and learning
- Sponsorship
Networks don’t grow automatically. Invest time in:
- Industry communities (conferences, online forums, local groups)
- Staying in touch with former colleagues
- Connecting people who should know each other (which builds your reputation as a connector)
3. Building Visibility
Visibility means being known for your skills and thinking beyond your immediate team. Benefits:
- Better opportunities come to people whose work is known
- Sponsored for talks, panels, and articles
- Considered for roles that aren’t posted publicly
Ways to build visibility:
- Write publicly (blog, social media, technical articles)
- Speak at conferences or internal all-hands
- Contribute to open source or standards
- Be the person who explains things well in public channels
Evaluating Your Current Role
Cate Huston’s five job health metrics provide a diagnostic for whether your current role is serving your career:
| Metric | Healthy | Unhealthy |
|---|---|---|
| Learning | You’re developing new skills and knowledge regularly | You’ve stopped growing; the job is stagnant |
| Transferable skills | What you’re learning would be valued elsewhere | Skills are hyper-specific to one employer or context |
| Recruiting pride | You’d recommend this job to talented friends | You’d be embarrassed to tell them where you work |
| Confidence | The work builds your sense of capability | The work is destroying your confidence |
| Stress | Stress is manageable and tied to meaningful work | Stress is chronic and not proportional to the impact |
Track these metrics over time — one bad month doesn’t indicate a broken situation, but a trend matters.
Paths Forward
If your job health metrics point to a problem (or even if they’re healthy but you’re curious about options), here are the paths the chapter describes:
| Path | Description |
|---|---|
| Keep doing what you’re doing | The role is serving you; continue with more intention |
| Push for promotion | Stay at the company, increase your level |
| Work less/differently | Negotiate scope, hours, or focus to improve quality of life |
| Change teams | Different problems and people within the same company |
| Build a specialty | Deepen in an area that makes you distinctive |
| Explore | Deliberately try new areas to find what resonates |
| Take a management role | Try the engineer/manager pendulum |
| Find a niche | Combine technical skills with a domain (healthcare, fintech, climate) that resonates |
| Same job, different employer | Similar role with better conditions elsewhere |
| Change level | Explicitly step down to have more hands-on learning time |
| Startup | Trade stability for ownership and breadth |
| Go independent | Consulting, contracting, advising |
| Change careers | Step away from software engineering |
No path is inherently better. The right choice depends on your current health metrics, your priorities, and your constraints.
Prepare to Reset
When you move into a new role (whether internal or external), set realistic expectations for yourself:
- You’ll be a beginner in some dimensions again
- The context-building process takes months
- Your credibility transfers imperfectly; it must be rebuilt partly from scratch
- This is normal, not a failure
The chapter encourages treating the reset as an opportunity rather than a setback: new beginnings are also new chances to build differently.
Your Choices Matter
The book closes with a reminder that staff engineers have genuine power to shape the environments they work in. The decisions you make about what projects to take on, what culture to model, who to sponsor, how to spend your time — these are not fixed. They accumulate into an impact that extends far beyond what you personally build.
The final message: be intentional. Don’t let your career happen to you. Make deliberate choices about what you’re optimizing for and how you spend your finite time and energy. The choices matter — to you, and to the engineers whose careers you will shape.
Key Takeaways
- Career navigation needs a framework; the trail map metaphor keeps you aware of multiple possible paths.
- Know what you actually value (the priority list) before evaluating opportunities.
- Three career needs apply broadly: building skills, building network, building visibility.
- Don’t rush past prime hands-on technical years to get a fancy title.
- Cate Huston’s five metrics — learning, transferable skills, recruiting pride, confidence, stress — provide a health check for your current role.
- Many paths forward exist; the right one depends on your health metrics and priorities.
- Your choices about how to use your staff engineering influence accumulate into organizational impact beyond your direct work.
Related Resources
- ch01-what-would-you-say — Role definition and scope evaluation
- ch04-finite-time — The resources framework parallels the job health metrics
- ch08-influence-at-scale — Building others’ skills and visibility mirrors building your own