I’ve spent my entire adult life in the Army, but it’s coming to a close. Here are the highlights of what I got right — and what I wish I’d done better.
Prepare early and save money
Everyone says you’re supposed to start preparing early. Realistically, you need to start from Day 1 in the military. I wish we’d started our transition fund (extra money in a separate account) the first month I joined. I knew there would be unexpected expenses, but it’s even more when you don’t have an installation or unit on the other side. You are your own support center.
Find your purpose
Finding purpose outside the military is the best preparation I’ve completed. It’s so much different when you know what you’re doing next, and being genuinely excited about the next chapter makes closing this one a little easier.
Low expenses
Our second-best preparation was keeping our expenses low and saving up extra cash. Not having car payments or other long-term expenses really makes a difference. We have extra savings specifically for the transition out which gives us stability and time to find the right opportunities in the next chapter.
Set clear goals
Get clear on the big pieces of your new life first and make sure your whole family is on the same page. My wife and I have spent hours researching and discussing where we’ll live, what jobs and roles we’ll move into, and getting the financial resources in place to make it all happen.
Having clear goals allowed us to make hard choices quickly and confidently. We stayed focused, moved money around, and kept moving.
Biggest mistakes
I regret not broadcasting key events to other people in my unit and family. I didn’t plan out my retirement ceremony or share it widely enough, and I underestimated how many people wanted to come and support me. Allow others the opportunity to support you even if you don’t think they will.
Medical records
Request your medical records early! It took me six weeks to get my medical records to start preparing for my VA claim. My records were incomplete, so I’ve had to spend way more time tracking down records and getting them uploaded than I realized.
Final tip on leaving the military
My final piece of advice: don’t do it alone! I started a “DD-214 Class of 2026” at my unit, and we’ve shared so many great things. Even if you only know one or two other people leaving the military, make it a point to connect and share. It’s surprising how much you can help each other on your way out the door!
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