Career planning: where you are, where you want to be, how to get there

Career planning is engineering

Most infrastructure professionals treat career planning as something that happens to them (“I got promoted”). The strongest careers are engineered — planned, tracked, and adjusted.

This lesson covers how to assess yourself, set targets, and build a plan that delivers.

flowchart LR
  A[Step 1<br/>Assess<br/>self-evaluate against ladder] --> B[Step 2<br/>Define target<br/>role, level, comp]
  B --> C[Step 3<br/>Gap list<br/>what's missing]
  C --> D[Step 4<br/>12-month plan<br/>activities, outputs, dates]
  D --> E[Step 5<br/>Execute &amp; track<br/>weekly, monthly, quarterly]
  E --> F[Promotion<br/>or pivot]
  F -.->|12 months later| A

Step 1: Assess where you are

Most companies have engineering levels (e.g., L3 → L4 → L5 → L6). For each level, there’s an expectation document. Find yours and read it.

If there’s no formal ladder, use a public one as a reference:

• Dropbox engineering career ladder
• Square engineering levels

For each level, the expectations are usually described in terms of:

• Technical scope: how big are the systems you work on?
• Independence: how much direction do you need?
• Influence: who else are you affecting through your work?
• Leadership: are you growing others, or just yourself?

Self-assessment

For each level expectation, rate yourself 1-5:

Total up and find your current level. Be honest; this is for you, not your manager.

Step 2: Define where you want to be

Career targets are not just titles. They’re a combination of:

• Role: IC vs manager vs architect vs specialist
• Level: within that role
• Domain: what you work on (infrastructure, security, ML, etc.)
• Environment: startup, mid-size, big tech, public sector
• Compensation: where you want to be (be realistic)

A good target answer looks like:

“In 3 years, I want to be a Staff Infrastructure Engineer at a mid-size company, working on hybrid cloud and on-prem, with a compensation band of $X-Y, and mentoring 3-5 engineers.”

A bad target:

“I want to be a senior engineer.”

The first is specific enough to plan against. The second is too vague.

Step 3: Build the gap list

Compare where you are to where you want to be. The gap is your development plan.

Each gap becomes a development activity. Estimate the time and effort.

Step 4: Build the 12-month plan

For each gap, define:

• Activity: what you’ll do
• Outcome: what success looks like
• Timeline: when
• Resources: books, courses, mentors, projects

A 12-month plan in template form:

# Career plan: 2026-2027

## Target
Staff Infrastructure Engineer at a mid-size company, by end of 2027.

## Top 3 gaps to close
1. Lead architecture reviews
2. Mentor 2-3 juniors
3. Speak publicly (1 talk)

## Activities
1. Architecture reviews
   - Lead 3 reviews in Q1 (1/month)
   - Outcome: each review produces a decision doc
   - Mentor: Alice (will shadow her next review)
2. Mentoring
   - Take on 2 mentees in Q2
   - Outcome: each mentee writes a 12-month growth plan
   - Mentor: Bob (will pair-mente with him)
3. Public speaking
   - Submit a talk to <conference> by March
   - Outcome: talk accepted, given, recording posted
   - Mentor: no specific; join a local Toastmasters

## Quarterly check-in
End of each quarter, review: did I do the activities? What blocked me? Adjust.

## What I'm NOT doing this year
- Switching to management (focus on IC path)
- Pursuing additional certifications (already have core ones)
- Job search (focus on growth at current role)

Step 5: Execute and track

A plan without tracking is a wish. Track:

• Weekly: review your plan in your weekly review; what did I do this week toward the plan?
• Monthly: 30-minute check-in with yourself; any blockers?
• Quarterly: major review; adjust the plan if needed

Tools:

• A simple doc in your private notes
• A spreadsheet with activities and dates
• A todo list with a “career” tag
• A mentor you check in with monthly

Pick whatever you’ll actually use.

The artefact portfolio

One of the most powerful career-building techniques is the artefact portfolio: a collection of public outputs that demonstrate your skills. Examples:

• Blog posts explaining technical decisions
• Conference talks
• Open-source contributions
• Architecture diagrams and design docs (sanitised)
• Internal documentation that became team standard
• Training material you wrote
• Post-mortems (with appropriate redaction)

Why artefacts matter:

• They outlast your memory (“I worked on Ceph” → “Here’s my blog post on Ceph tuning”)
• They demonstrate writing and teaching skills, not just technical
• They’re easier to talk about in interviews than projects you can’t describe
• They compound — 10 small artefacts are more impressive than 1 big one

For a 12-month plan, aim for:

• 1-2 blog posts per quarter
• 1 conference talk per year
• Active contribution to 1 open-source project
• Internal docs that get linked from team onboarding

Common career-planning mistakes

“I’ll wait for my manager to tell me what to do”

Your manager has 5-10 other reports. They don’t have time to develop your plan. You need to bring the plan to them.

“I need to switch jobs to grow”

Sometimes true, often not. Most growth happens in the role you’re in, if you’re deliberate about it. Switch jobs when the current one genuinely can’t offer what you need, not as a default.

“I’ll just get more certifications”

Certifications are inputs, not outputs. They’re useful for structured learning but don’t substitute for artefacts and outcomes.

“I want to be a senior engineer” (vague)

Too vague to plan against. Define what “senior engineer” means at your target company. What does the person do day-to-day?

“I’ll do it eventually”

Without a date, “eventually” is “never”. Put dates on the activities.

“I need to learn Kubernetes / Rust / AI / etc.” (technology-driven)

Don’t chase technologies. Chase skills: design, communication, leadership, judgement. Technologies come and go; skills compound.

When to revise the plan

Revisit your plan when:

• You get promoted (the goal shifts)
• You change companies (new ladder, new gaps)
• The industry shifts (new technologies matter)
• Every 12 months, regardless

Don’t revise it just because it’s hard. Most plans need 12-18 months to show results; quitting at 6 months is a common mistake.

Key takeaways

• Career planning is engineering — assess, target, gap, plan, track
• Your manager is not your career planner; you are
• Be specific about targets; vague targets lead to vague plans
• Build an artefact portfolio; outputs > inputs
• Track weekly, review monthly, adjust quarterly
• Don’t switch jobs by default; switch when the current role can’t offer what you need

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