Leaving Service: One Irregular’s Transition Lessons (May 2025)
Bill Christian, a member of our IrregularChat community just retired this past April 2025 after a long career as a Master Sergeant. He generously shared his real-world lessons, pitfalls, and tools from navigating the transition from Fort Bragg to the Washington State tech industry — with a spouse, a child, and big career goals ahead.
This post is meant to complement our community wiki resource:
IrregularPedia: Leaving Service Guide
Background Snapshot
- Retired April 2025, Master Sergeant
- Final duty station: FBNC
- Relocating to: Washington State
- Family: Married, 1 child
- Education: MBA (2024)
- Target Roles: Program / Project Management in tech
- Salary Range Target: $90K – $180K
- Post-military Prep: 50+ informational interviews with veterans in tech (Fortune 100)
Key Lessons + Tips
1. Start Way Earlier Than You Think
“I assumed 90 days was enough. Some applications have been ‘under review’ for 5+ months.”
- Start applying 6–9 months out.
- Timelines are wildly different than DOD PCS orders.
2. Don’t Go “Big or Bust”
“I aimed for Oracle, Microsoft, and Amazon. My aperture was too small.”
- Broaden your search to less flashy but stable companies and state jobs.
- Springboards matter more than dream brands.
3. Certs > Experience (Frustrating but True)
“I ran five programs of record, but without a PMP or Scrum cert, it didn’t matter.”
- Get certified ASAP: CALL, Onward to Opportunity, SkillBridge, etc.
- Spouses are often eligible for certification support too!
4. People Want to Help
“95% of my cold LinkedIn DMs led to real convos.”
- Cold DM veterans in your target industry.
- Be clear, respectful, and don’t ask junior folks about exec-level decisions.
5. Study Company 10-Ks
“Use a 10-K to ask informed questions or tailor a killer cover letter.”
- Publicly traded? Read their SEC 10-K before writing or interviewing.
- Use it to match your experience to their strategic goals.
6. Brace for Cost of Living
“You can’t survive in Seattle on $120K. You’ll need $200K+ to own a home.”
- Consider Olympia, Tacoma, or state jobs as stepping stones.
- WFH can buy you time and breathing room.
7. Springboard Roles Are Smart
“I stopped ruling out jobs just because they weren’t my dream job.”
- Look for entry roles at companies in your target industry.
- Focus on getting inside the industry, not landing the perfect fit right away.
8. Hire Our Heroes is Gold
“Most Fortune 100 vets I talked to came in through HoH internships.”
- Internships are undervalued but powerful.
- Use them to prove value and convert to full-time.
9. WFH Gives You Flexibility
“I can WFH while I move my family and finish my transition.”
- Always ask if roles can start remote or hybrid — many can.
10. Start Low (On Purpose)
“Start in a job you’re overqualified for. Learn the industry first.”
- Civilian lexicon, org structure, and workflow are different.
- Overqualification lets you learn fast and promote quickly.
11. Don’t Self-Select Out
“Let them say no. I ruled out jobs for no good reason.”
- Apply broadly — you’re not the best judge of your own eligibility.
- Consider GS jobs, contractor roles, or defense tech to gain experience.
12. Cover Letters Matter… Sometimes
“Only write one if the application asks for it.”
- Use it to explain what you bring and any missing credentials.
13. Accuracy by Volume
“Referrals are great, but don’t overextend your network.”
- Apply often.
- Save referrals for the most aligned roles.
14. Learn Company FY Cycles
“Some fire during hiring freezes. Others hire like crazy after Oct 1.”
- Each company has its own fiscal calendar — time your applications accordingly.
15. SOF Soft Skills Shine
“The ability to operate in chaos, adapt quickly, and manage ambiguity is huge.”
- Emphasize this in interviews.
- It won’t get you the job — but it might win the offer.
16. Don’t Count on Your Service Alone
“Experience > rank. Translate your work and ditch the ego.”
- Most hiring managers don’t understand the military.
- Your value is in results, not ribbons.
Resources
More Community Guidance:
→ Leaving Service - Irregularpedia
Certifications:
- Onward to Opportunity (Syracuse)
- Army CALL Program (for certs on active duty)
- PMP, Scrum, Agile – Popular PM certs
Internship Pipelines:
- Hiring Our Heroes
- SkillBridge / Career Skills Programs
Cost of Living Reality Check:
- Zillow + Rent.com for relocation insights
- Compare mortgage qualification using the 25% of income rule
Join the Thread
If you’ve recently left or are thinking about it — share your tips, frustrations, or resources below.
Let’s build the transition playbook together.
RAW Lessons Learned:
Lessons learned:
Application timelines are far longer than you may think. I assumed I would be safe applying for jobs about 90 days out from retirement. That was grossly underestimated. I have applications in for 5 months that are still under review with Oracle (as opposed to denied, which they have done for a few other roles so far).
Overly ambitious. I set my goal at Oracle, then Microsoft, and then Amazon. I’m not a native of WA and not sure of who is available there. My aperture was far too small and this greatly limited my options. In the words of one of the guys I talked to, “You are competing against the best of the best for these companies.”
Knowledge is trumped by certifications. This is related to the above. Having done something, such as manage five programs of record for the past few years, means nothing if you don’t have some sort of certification stating you are certified to manage those programs. It is pedantic, but it is the reality. You may have 10 years of PM experience, and so does the person at Google looking for a change. They have 10 years as well, plus they’re a certified scrum master and have their PMP. You don’t stand a chance against that. DOD positions do not translate that well so that is an additional hurdle that must be overcome, and having the certifications to back it up is essential. Take advantage of CALL if it is still a thing to get certifications in fields you’re interested in. Use Syracure University’s Onward to Opportunity program to get 1x major certification paid for once you get out (spouses eligible too).
People genuinely want to help. I probably have a 95% success rate cold-messaging people on LinkedIn that are in roles I’m interested in. The other 5% either didn’t check their LinkedIn, or wanted me to buy their book first (a REFRAD 18A. I did buy his book too so I could support his effort to help the next guy). Keep your questions appropriate for the position the person you’re talking to holds. Case in point, I was talking with a PM at Honeywell about their looming schism to split their business units up. They didn’t want to say it directly, but that was far above their paygrade.
SEC 10-Ks are your friend. If the company you’re interested in is publicly traded, check out their latest 10-K to get an idea of how the company is performing and where they’re headed. This helps to generate valuable questions, demonstrates a level of analysis if you make it to the interview stage, and can be useful when writing a cover letter. Case in point, I did a cover letter for an Oracle PM role I was well qualified for. The job listing was ambiguous, so I looked at their 10-K, saw they had three SBUs, and stated that I was not sure which SBU the role was for, but my experience demonstrates I am versatile and successful in a variety of roles.
If going private sector for a fortune 100, expect a MASSIVE cost of living adjustment. The fortune 100s are not located in Fayettevilles. They are in San Francisco, Austin, NYC, Seattle, Chicago, etc. For comparison, I budgeted a $120,000 as my minimum salary to afford a mortgage in the greater Seattle area. This is on top of my pension and disability, putting my pre-tax earnings around $200-250,000 a year (still pending disability rating). Following the 25% mortgage rule, I would not qualify for any SFHs near Seattle. When talking to a very senior executive at Blue Origin, he said it bluntly, “Why are you focusing on Seattle? Any job you get here requires a $1,000,000 mortgage or a 1.5-hour commute one way.”
Find springboards. This is related to above. Finding a position that you’re qualified for in a less-known company that provides the necessary experience and knowledge in the field you want is paramount. For my situation, I’m looking at positions within the state (Olympia) and positions around Tacoma in the private sector. The cost of housing is more reasonable, and it allows me to get the exact industry experience I’m lacking.
Hiring our Heroes is the golden ticket. Of the ~50 interviews I’ve had, nearly every single person was hired at Oracle/Microsoft/Amazon after being an intern with HoH. Survivorship bias is in play here, of course. I did not even think about being an intern for Oracle/Microsoft/Amazon because I was still in NC.
WFH is still a thing and opens opportunities. Related to above. I’ve talked with numerous people that said to just apply for any role you’re interested in, whether it is WFH or physically at the office. You can negotiate WFH at the interview stage if you make it there. For my specific situation, I could WFH for a couple months while I finish up my affairs in NC, and then relocate to WA and start working either hybrid or FT at the office (looking at you, Amazon).
Screw the Air Force, aim low. There are numerous jobs that you may be qualified for. However, you’re competing against a civilian that has the connections, lexicon, and knowledge of that exact industry. Multiple people have told me it is far better to start off with a job you are overqualified for. There is a massive learning curve to understanding the industry, terminology, corporate structure, etc. Being overly-qualified helps to level that out. Once you’ve gained sufficient exposure and experience in that industry, then you can branch out to more ideal jobs.
Don’t self-select. Let a recruiter tell you you’re not qualified. Just apply. The worst case is you are denied. The best case, you get a message asking for an interview. I screwed this up in the beginning by saying I’ll never work for or with the federal government again. Even after DOGE, there are MANY GS positions I am very well qualified for that pay well and keep me from being homeless. I ruled them out on principle, but they could very well provide the necessary industry experience I need to pivot towards my desired companies. I’ve also worked back my stance on defense tech for the same reasons. I may not like Northrop-Grumman, but doing the role I want to do for them for a couple years so I can pivot away is far more realistic, and you have a much greater chance of landing a defense tech role being prior military.
Cover letters. I was told by an executive recruiter this rule: If the job requires it or has it optional, use a cover letter. If it is not required, do not provide one. Don’t regurgitate your resume, but use it as an opportunity to explain how you are uniquely qualified and also how you’re addressing any limitations (e.g. currently enrolled in PMP).
Accuracy by volume. Referrals are preferred, but you must balance it with their schedule. If it is a job you are 100% into and absolutely love it, definitely reach out to a contact and get a referral. If it is a job you’re qualified for and simply using as a springboard, just apply as you will have far more of these opportunities and don’t want to overextend their hospitality. I’ve been told it takes 100 job applications to land 1 job.
Potentially only for Microsoft, but CTJ in the job descriptions equates to TS/SCI. For MSFT job boards and potentially others, searching for CTJ is a way to only find roles that require clearance.
Focus on business units that are future-proof. For the tech behemoths, this is their cloud infrastructure. OCI, Azure, AWS, etc. all have strong future potential growth, and therefore are more resilient to market uncertainties and consequently layoffs.
Actually, the Air Force was right, aim high. If you find a role you are super interested in, don’t be afraid to cold-message executive leadership on LinkedIn. This level of boldness is not common. In the words of another person I interviewed, “Kick in the door, don’t knock.” I initially thought that this level of brashness would be perceived as arrogant, but it has a lot of potential. It shows you are willing to go far above and beyond to get results. It shows you are confident in your ability. It shows you are not shy talking to executives. The worst-case scenario is they ignore you or say they are not interested. Best case, you either get to talk with the executive, or they direct you to the recruiter and say to talk with them, which comes with a lofty endorsement.
No one cares about your service. Do not bank on your service to help you land a job. Your experience and how you portray it is far more valuable. Many companies, especially larger ones, have Employee Resource Groups (ERGs) that include a veteran’s group. This is a good indicator that a company is veteran friendly.
DEI is currently dead. This is not political. A veteran hire is by definition a DEI hire. Recognize that being a veteran may not provide any benefit on a job application.
SOF soft skills are where we shine. Anyone can create a POAM. Anyone can take a product to market and make it successful. What sets SOF apart from the rest is the soft skills developed over years. The ability to effectively operate under ambiguous guidance. The ability to find solutions where none are readily present. The ability to react to unexpected changes. The list goes on. Your soft skills won’t get you the interview, but during the interview, they are a critical distinguishing factor against the competition.
FYs vary by company. Military assume a FY is OCT to SEP. Private companies can have any FY they want. Early in the FY equates to a hiring increase, and towards the end of a FY is more likely for letting employees go.