Wednesday, 18 June 2025 Issue#036

Transition Smarter. Tech-Driven Guidance for What’s Next

Transition’s a beast, but you don’t have to wrestle it alone.

This week, we’re diving into how smart tech is quietly transforming the veteran experience. From mental health apps, to free tech training programs that’ll have you ready to that next step.

Oh—and mentorship just got an AI upgrade too. Yes, really.

Weekly Spotlight

Tool of the Week: Wysa​

AI Chatbots & Virtual Therapists — Your New Mental Health Wingman

Opening up isn’t easy, especially when you’re taught to tough it out. For many veterans, the emotional weight of transition, anxiety, stress, even PTSD, can feel like something they just have to carry. But what if help came in the form of a 24/7 chatbot that doesn’t judge, isn't cost prohibitive, and never sleeps?

That’s exactly what’s happening as tools like Wysa, and even newer AI-powered therapy platforms like Dartmouth’s “Therabot” gain traction. Think of them as Siri meets your therapist, only these bots are trained in cognitive behavioral therapy (CBT), motivational interviewing, and crisis de-escalation. Finally a CBT that's worthwhile.

And the results? Surprisingly legit.

Earlier this year, Dartmouth released results from the first clinical trial of a generative AI therapist. Users reported a clear reduction in depressive symptoms and, more interestingly, many said they felt a “bond” with the bot that mimicked real human connection. “It was like talking to someone who actually cared, but didn’t talk back in a judgy way,” one participant said.

Users echo the same. One former Marine posted, “Been using Woebot for two weeks. Feels weirdly good. I like that it doesn’t just tell me to ‘cheer up’, it actually helps reframe stuff.”

*Note: Woebot will be discontinued 30 June 2025

So what’s the magic?

These apps use a combo of language processing, behavioral science, and consistent check-ins. If you log in regularly, you’re met with messages like: “What’s been on your mind lately?” or “Let’s walk through a thought that’s been bothering you.” It’s guided introspection, backed by real science.

Are they perfect? No. Wysa isn’t going to unpack a lifetime of trauma, and most experts agree these tools aren’t replacements for long-term therapy. But as a first step, or even a supplement, they’re powerful, private, and relatively inexpensive to even free.

If you’re in a dark place, stuck in a rut, or just need to talk something out and don’t know where to start, these tools could be a useful first step. Especially since the wait for a mental health appointment could be more than 50 days.

What We Are Tracking

From Camo to Cloud: Free Tech Training That Actually Gets Results

For veterans looking to break into tech without dropping $40K on bootcamps or going back to school full-time, there’s an alternative way.

Enter free, accelerated tech training programs designed specifically for service members and vets. These aren’t fly-by-night unvetted "courses". We’re talking about Microsoft Software & Systems Academy (MSSA), SkillStorm, NPower, and Onward to Opportunity - training pipelines that offer CompTIA, AWS, CISSP, and more. All at zero cost.

On Reddit’s r/AirForceTransition, one user shared: “I just wrapped up MSSA and already have 3 interviews lined up for cloud engineer roles. Didn’t spend a dime. Used SkillBridge for the final 17 weeks.”

What makes this trend especially powerful now is the growing demand for cleared tech professionals. SkillStorm, for instance, works with military bases to train in-demand skills like Java, cloud dev, and cybersecurity; with guaranteed employer connections on the other end. Microsoft even guarantees interviews for all MSSA grads.

Timing is everything. These programs are often eligible for DoD SkillBridge, meaning you can complete them while still drawing military pay and benefits.

And this isn’t about starting from scratch. Most of these courses translate military skills into resume language, pair you with a career coach, and connect you with a civilian mentor. If you can handle a deployment, you can definitely handle the cloud.

Bonus Feature

The hardest part of a networking event isn’t showing up, it’s knowing who to talk to. That’s where new AI-powered veteran platforms are flipping the script.

Platforms like RallyPoint, which once felt like LinkedIn Lite for service members, are now integrating AI to match vets with mentors, suggest career pathways, and even flag mental health risks based on user behavior. Think of it like having an algorithm that actually knows what your military job translates to in civilian terms...and who’s hiring.

RallyPoint’s recent expansion includes mental health AI models, developed in partnership with MIT and Harvard researchers, to spot early signs of distress and proactively offer help. One user commented, “I got a DM through RallyPoint after not posting for weeks. Just a bot saying ‘Hey, you good?’ - but it hit hard. I replied, and it got me to reach out for real help.”

It’s not just about wellness. Networking AI tools are making mentorship feel less like forced speed dating and more like real guidance. One nonprofit-backed pilot program, Vet Mentor AI, pairs transitioning veterans with certified career coaches in PM, tech, and trades—based on military experience, geographic location, and current job openings.

Instead of blind coffee chats or awkward Zoom intros, you get targeted, relevant matches. No fluff, just people who’ve been where you are.

The goal here isn’t to replace human connection—it’s to enhance it. The AI doesn’t network for you. But it clears out the noise and sends you the right signals.

For a generation used to GPS, this kind of guided networking feels long overdue. No one said transition would be easy—but tools like this can make it feel more palatable and productive.

Productivity Spotlight

Tools that help you stay, or get, productive

✅ Speechly - Speak your thoughts and get them turned into a professional, polished email.

✅ Polite Post - Rewriting your emails with AI to be professional, courteous or polite.

✅ Notion - Notion AI organizes your notes and automates tedious tasks.

Check us Out

Help us create a new community where we can exchange and share military transition related stories and best practices.

​Join Our New Exclusive Facebook Group!