Strategy
Career Planning
Reverse-engineer the life you want, then map the titles, skills, and relationships that get you there.
Think like an operator
Ask: What lifestyle do I want in 5–10 years? What mission or industry do I care about? What comp/flexibility do I need? Do I want to be a specialist, generalist, or builder? Work backwards from that end state.
Pick trajectories, not titles
| Role | Potential Trajectory |
|---|---|
| Project Manager | Program Director → VP Operations |
| Data Analyst | Data Scientist → Head of Analytics |
| Technical PM | Product Manager → Head of Product |
| Consultant (MBB/Big 4) | Corporate Strategy, PE Ops, C-Suite |
| Account Executive | Enterprise Sales → CRO |
| Supply Chain Planner | Ops Manager → COO |
Always ask: what does this role lead to?
Three-year career map
Next 12 months: skills to gain, people to learn from, resume bullets to add.
24 months: promotion/pivot/comp goals; certs, degrees, internal moves that unlock them.
Year 3+: should you be leading a team, jumping industries, or prepping for the next big move? Adjust the plan as you learn, but keep a framework.
Veterans: leverage service as fuel
- Translate your experience into market language.
- Target industries that pay for operational excellence.
- Define what “promotion velocity” looks like outside the military and how you’ll accelerate it.
Compound career capital
Every decision should give you at least one of:
- Credibility (brand name, elite school, clear promotion)
- Cash (higher salary, equity, bonus)
- Capability (new skills, certifications, cross-functional reps)
- Connections (mentors, alumni, hiring managers)
If a job gives you none of these, it’s a dead end.
Avoid drift
- Don’t stay loyal to companies that won’t grow you.
- One cert won’t magically fix direction.
- Planning only around comfort keeps you stuck.
- “I’ll figure it out later” is career drift.
Need a roadmap?
We’ll help you reverse-engineer your path, pressure-test your next move, or decide if an MBA fits the plan.
Plan with us
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