In this episode, Kathleen and Rachel chat with Air Force veteran Jacki Davenport, a 20+ year intelligence and special operations professional who refused to take no for an answer from the very beginning. Jacki shares her journey from recruiter office moments to tight-knit special missions units, cyber operations, and eventually, the private sector. Along the way, she gets honest about the cost of high-tempo deployments, the identity whiplash of going reservist, and the power of a network that believes “we can all win.” Her story is a reminder not to self-select out, and to use your non-negotiables to steer your next chapter instead of settling for whatever comes first.

Chapters

02:18 – Jacki’s Path to the Military
04:05 – Saying Yes to the Unknown
09:14 – Humanity Catching Up & Choosing the Reserve Path
10:35 – Redefining Identity and Impact
11:40 – Standing Up an Offensive Cyber Unit
13:25 – From Intel Targeting Officer to Chief & Mama Bear
15:01 – “We Can All Win”: How Jacki’s Network Carried Her Transition
16:33 – Starting at the Bottom Again: New Acronyms, New Language, Same Grit
19:35 – Building Intelligent Systems in the Private Sector
22:24 – Don’t Self‑Select Out & Know Your Non‑Negotiables
23:40 – It’s Okay to Ask for Help: Using Your Network Without Shame

Key Takeaways

Prepare for Identity Whiplash: Going from a fast‑paced, small special mission unit to the reserves was Jacki’s first real separation struggle. Recognizing and naming identity shifts early can help you avoid making rushed decisions to return to what’s comfortable.
Don’t Self‑Select Out of Opportunities: If you can say yes, say yes. You can always course-correct later, but you can’t win if you never step up to the plate.
Your Network Really Can Be the Difference: The right people can open doors you didn’t even know existed when it’s time to transition. Jacki reminds us: you are not burdening your network by asking for help; you are finally using it for what it was built for.
Let Your Non‑Negotiables Guide Your Next Role: Go into your civilian job search (and interviews) clear on what you will and won’t accept. Those guardrails will help you quickly rule out misaligned roles.
Be Humble Enough to Start at the Bottom Again: By the time Jacki retired, she was at the top of the food chain in uniform—but in the private sector, she had to be the person writing down acronyms and Googling them after meetings. Her advice: accept that your rank and past titles don’t automatically transfer. What does transfer is how you bring value, learn fast, ask questions, and build credibility all over again.
Impact Can Shift from Mission to People—and That’s Okay: In uniform, impact meant operational results and mission success. As a chief and later in industry, Jacki’s impact became about developing people, protecting her team’s mental health, and reducing human cost through better systems. Accepting that your definition of service can evolve is key to feeling fulfilled after the military.

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We Can All Win: Don’t Self-Select Out of Your Next Mission