Intro: Questions to Ask Yourself Before Breaking Into Tech
Getting a job in tech is hard. Even with a strong technical military background, great advice, and advocates inside companies — it is still hard. You can have good outcomes (product manager, solid compensation, cool company), but recognize that it requires effort, some luck, and may be a multi-hop journey rather than a linear path.
You likely will not land your dream job immediately. You will make compromises — on pay, location, brand, or work-life balance. Think about what matters most to you and what is negotiable. Plenty of senior engineers didn't get their ideal first (or second) job.
Be kind to yourself. Job searching is stressful and overwhelming, especially when you've never done it before and your end of active duty is looming. Don't get stuck in decision paralysis — make a plan, aim at a target role, and start working toward it. Take care of yourself along the way.
Questions You Should Ask Yourself Early
- What problem in the world do I want to work on solving? This defines your industry (healthcare, defense, finance, consumer, etc.)
- What is the best way to solve that? A big corporation, an existing startup, or something else?
- What are my goals in 5 years if everything goes perfectly?
- Am I competitive for the roles I want right now? If not, can I upskill before I transition? If not, can I get into a position that makes me more competitive for that eventual dream job?
- What are my financial goals? Note that taking a lower-compensation role with the right fit, team, and company may have a higher ROI in the long term.
- What am I seeking? Fast pace? Structure? Learning? Autonomy or collaboration? Growth opportunities? Financial security?
- What type of company do I want to work in? Public vs. private? Large vs. small?
- How do I feel about working with the government?
- In defense-focused companies (e.g., Anduril, Shield AI)
- In a government role within a commercial company (e.g., AWS GovCloud)
- Is government-adjacent work a dealbreaker?
- Do I put more emphasis on the work I do or the company I work at? Do I want a specific vertical (e.g., health-tech, defense-tech)?
- Is location important to me? Is remote work important to me?
- How long can I wait before needing a job? How much decompression time do I need?
- Strong recommendation: Take at least a month off between roles to recharge
Location Considerations
- Don't put your location on your resume if you're willing to relocate. A San Francisco company may see "Fort Bragg" and screen you out before reading further.
- Major tech hubs: San Francisco/Silicon Valley and Seattle are the largest. New York and Austin are sizable. Smaller hubs include Raleigh-Durham, Pittsburgh, Denver, and Salt Lake City.
- Larger hub = more career stability (more jobs in the region), but also higher cost of living and lifestyle creep.
- Remote is less available than it was in 2021. Expect to be in the office 3+ days per week unless the posting explicitly says otherwise.
- Cleared roles: Washington DC has many federal engineering positions, often requiring TS/SCI with full scope polygraph. Companies like Microsoft (look for "CTJ" in job titles) and Amazon offer clearance bonuses — typically around $15K.
- This may be your best chance to geographically reset. If you've always wanted to live somewhere new, apply for roles there.
Timing Your Transition
- Start preparing early. At least 6 months out, ideally 12+ months. There is a lot to learn that your military career never covered.
- For software engineers 12+ months out: Build a serious coding side project. It becomes a strong talking point in interviews.
- For software engineers under 6 months out: Focus on LeetCode and learn the question patterns until you can recognize them quickly.
- For non-engineering roles (PM, TPM, etc.): Focus on frameworks (STAR method, product sense, technical communication) and network aggressively with people already in those roles.
The Tech Career Guide
This article is part of a larger series on breaking into tech:
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