The things I wish I know when I was in military

Transitioning out of the military is one of the biggest life changes a veteran will ever experience. If I could go back and give my younger self some advice, here are the key things I wish I had known while I was still in.

1. Invest in Index Funds and Your Retirement Early (TSP C Fund Is Your Best Bet)

A lot of young service members fall into the trap of chasing high-risk investments, hoping for quick riches. I’ve seen Marines dump their money into penny stocks or speculative pharmaceutical companies, thinking they’ll hit the jackpot. But the truth is, long-term investing is the only way to reliably build wealth.

Why Index Funds and TSP Matter:

• TSP C Fund (S&P 500) is essentially a bet on the U.S. economy. Over the long term (20-30 years), historical data shows it averages 10% annual returns. I know that Many military members either don’t contribute to their Thrift Savings Plan (TSP) at all or put in the bare minimum. If that’s you, you’re leaving a massive opportunity on the table.

• Compounding growth is key—the earlier you invest, the more your money multiplies. If you invest $200 per month at age 20 with a 10% return, by age 60, you’ll have $1.1 million. If you wait until age 30 to start investing, you’ll only have $400k—less than half!

• Roth TSP is a tax-free goldmine—if you invest now, your money grows tax-free, and you won’t owe taxes when you withdraw in retirement.

If You’re Already Out or Almost Out, Don’t Panic—Start a Roth IRA Today

If you’re already out of the military and missed the TSP opportunity, don’t stress. Open a Roth IRA today and start contributing. The concept is the same—your money grows tax-free, and when you retire, you won’t owe anything in taxes. It’s never too late to start.

Lesson Learned:

Stop trying to time the market or gamble on stocks. Instead, invest early and consistently in index funds or the TSP C Fund and let time do the work. (if you want to see a detailed version of how to manage your finance, check out my finance post.

2. Start Planning for Civilian Life At Least a Year Before Your EAS

Too many service members wait until the last minute to figure out their post-military plans. The reality is, winging it is a terrible strategy. Whether you want to go to college, trade school, or straight into the workforce, you need at least a year to set yourself up for success.

What You Should Do One Year Before EAS:

✅ Decide on a career path or educational goal
✅ Research job requirements or school programs
✅ Network with people in your desired industry
✅ Attend TAP classes and take them seriously
✅ Save money—transitioning isn’t cheap

Lesson Learned:

Start planning early so that when your contract ends, you’re not left scrambling with no direction.

3. Mentally Prepare for the Transition to Civilian Life

One of the biggest challenges veterans face after getting out is adapting to civilian work culture. The way things operate outside the military is fundamentally different—and if you’re not prepared, you’ll feel frustrated, out of place, or even disrespected.

Work Ethic—Being a Hard Worker Isn’t Enough

Civilians don’t operate on “military time.” Deadlines are looser, urgency is lower, and instead of a “mission-first” mindset, people value work-life balance.

In the military, you’re expected to stay until the job is done, no matter how long it takes. In the civilian world, most people clock out at 5 PM, no matter what’s left unfinished. This can be frustrating for veterans who are used to grinding hard until the mission is accomplished.

But here’s the key: Hard work alone won’t set you apart. Employers value whether you are:
✔ A team player – How well do you collaborate with coworkers?
✔ Adaptable – Can you adjust to changes without getting frustrated?
✔ Good at office politics – Do you know how to work within the system without making unnecessary enemies?

Lesson Learned:
Your work ethic is valuable, but in the civilian world, it’s not about who grinds the hardest—it’s about who works well with others and adapts to the system.

Communication—Your Direct, No-BS Military Style Might Backfire

In the military, communication is clear, direct, and often blunt. If someone is messing up, you tell them straight to their face. There’s no sugarcoating. But in the civilian world, it’s different.

What Happens If You’re Too Blunt?

• People might see you as aggressive or rude.

• You could unintentionally create tension with coworkers.

• Instead of getting respect, you might get labeled as “difficult to work with.”

 How to Adjust Your Communication Style:
✔ Learn to soften your approach – Instead of saying, "This report is terrible," say, "I think we can improve this by doing X."
✔ Use diplomacy – Office politics exist, and relationships matter.
✔ Read the room – Civilian workplaces have unspoken rules. Pay attention to how people talk to each other.

Lesson Learned:
Being brutally honest doesn’t always work in the civilian world. Learning how to communicate tactfully is a crucial skill.

Leadership & Respect—Rank Doesn’t Exist Anymore

In the military, rank structure dictates respect. If you outrank someone, they listen to you—end of discussion. But in the civilian world, no one cares about your rank.

Respect has to be earned in different ways:
✔ Through performance – People respect those who are competent and reliable.
✔ Through influence, not authority – You have to persuade, not command.
✔ Through relationships – Your ability to work with others determines your career growth.

Lesson Learned:
Respect isn’t automatic after the military. You have to earn it differently—by proving your value, being a team player, and adapting to the workplace culture.

4. Use School for More Than Just Academics

A lot of veterans are eager to jump straight into the workforce after separating from the military. Some do it because they’re tired of structured education, while others feel pressure to start earning money as soon as possible. However, unless you’re transitioning directly into a civilian job that matches your exact military specialty, you’re going to face an uphill battle competing with civilians who have industry experience or degrees.

This is where college or trade school becomes a game-changer. Even if you don’t see yourself as a “school person,” higher education isn’t just about getting a degree—it’s about building a network, gaining new skills, and giving yourself the best possible chance at a strong career path.

Networking – School Isn’t Just About a Degree, It’s About People

One of the biggest advantages of going to school isn’t even the education—it’s the people you meet. When you attend a college or trade school, you’re surrounded by:

✅ Professors who have industry connections and can help you land internships or jobs.
✅ Classmates who will become future professionals—some of them might be hiring managers in a few years.
✅ Alumni networks that can open doors to high-paying careers.

Most high-quality schools have career fairs, employer networking events, and industry-specific clubs that introduce you to key people who can help you find a job. If you just try to apply for jobs cold, you’re competing against hundreds of applicants. But if you build relationships in school, you have inside access to job opportunities before they’re even posted publicly.

💡 Example:
A veteran I know majored in cybersecurity. Through a professor’s recommendation, he landed a paid internship at a Fortune 500 company while still in school. After graduating, that company hired him full-time with a six-figure salary. Had he skipped college and applied straight to cybersecurity jobs, he would have struggled to get his foot in the door.

Time to Build Skills – Rebrand Yourself Into a New Career

Military experience teaches a ton of valuable skills, but in many cases, you need additional certifications or formal education to be competitive in the civilian job market.

For example:

• If you were a logistics specialist in the military, you could use school to earn a business degree with a focus on supply chain management—making you a prime candidate for corporate logistics roles.

• If you worked in communications, you could get a degree in marketing or public relations, opening up new career paths.

• If you were in combat arms, you could pivot to cybersecurity, engineering, law enforcement, or even business—school gives you the opportunity to rebrand yourself however you want.

💡 Why This Matters:
Most civilian employers don’t fully understand military experience, but they do understand degrees and certifications. Even if you’re highly skilled, if your resume doesn’t show the qualifications they recognize, you’ll struggle to get interviews.

By picking a good major or trade, you give yourself the credentials and knowledge civilian employers trust.

Internship Opportunities – Students Get Special Access to Jobs That Veterans Don't

Employers love hiring students because:
✅ They can pay them less while training them.
✅ They can evaluate them before offering full-time positions.
✅ They often receive tax incentives for hiring student interns.

Here’s the key difference:

• If you apply for a job as a regular veteran, you’re competing against experienced civilians and other candidates with direct industry experience.

• If you apply as a college student, employers expect you to be in training mode, so they’re willing to give you a chance—even if you don’t have experience yet.

Many large companies ONLY hire full-time employees from their internship programs. If you’re a student, you get access to those exclusive hiring pipelines.

💡 Example:
A veteran I know wanted to work in finance. He went to school, got a summer internship at J.P. Morgan, and was offered a full-time investment banking position before he even graduated. If he had just applied directly without going through school, he never would have gotten past the first interview.

Trade Schools Are Just as Good (If Not Better) Than College for Some Veterans

If you don’t want to sit in a classroom for four years, trade schools offer a fast-track to great-paying careers. Many veterans assume college is the only path, but if you want to get into:

✔ Welding – Pays up to $100k+ with the right certifications.
✔ Electrician Work – Consistently in demand with solid pay.
✔ Plumbing, HVAC, or Auto Mechanics – Always recession-proof careers.
✔ Cybersecurity Bootcamps – Get into tech without needing a full degree.

Most of these fields only require 1-2 years of training, and many pay as much or more than traditional college careers.

💡 Lesson Learned:
Your GI Bill is a golden ticket. Use it to invest in yourself, whether it’s college, trade school, or a specialized certification program.

School Gives You a “Soft Landing” Into Civilian Life

The transition from military to civilian life can feel like being thrown into a completely different world overnight. If you go straight into the workforce, you might feel overwhelmed adjusting to civilian work culture while also trying to build a career from scratch.

Going to school gives you:
✅ Time to figure out what you want to do before jumping into a career.
✅ A structured environment that eases the transition from military life.
✅ VA benefits like housing stipends, which can help reduce financial stress.

Instead of rushing into a job you might hate, school gives you breathing room to explore different career paths, gain skills, and network without the pressure of full-time employment.

💡 Lesson Learned:
Even if you don’t care about getting a degree, school provides a smooth transition into civilian life while giving you more career options.

5. The Importance of Documenting Medical Issues and Using a VSO for Your VA Disability Claim

One of the biggest mistakes service members make is not documenting their medical issues while still in the military. Many of us have a “suck it up and drive on” mentality—we don’t go to medical unless something is completely unbearable. But here’s the harsh reality:

📌 If it’s not in your medical records, the VA won’t recognize it.

When you transition out, your injuries don’t magically disappear, and years later, they could become serious issues that affect your quality of life and ability to work. The worst part? If you didn’t document those injuries while you were still in, you’ll struggle to get VA disability compensation.

Why You Need to Document Every Medical Issue Before Your EAS

Many veterans regret not getting checked out before separating. The VA doesn’t care if you tell them you had chronic back pain or ringing in your ears for years. They need medical records as proof.

✅ Go to medical and get EVERYTHING documented—back pain, hearing loss, knee issues, PTSD symptoms, sleep apnea, etc.
✅ Even small issues matter—migraines, joint pain, tinnitus (ear ringing), and mental health conditions can worsen over time.
✅ Get a copy of your complete medical records before leaving—do not assume they’ll be easy to get later.

💡 Lesson Learned:
If you don’t document it while you’re in, you might never be able to claim it later. Don’t be that guy who realizes years later that he can’t work due to service-related injuries but has no medical records to prove it.

Never File a VA Disability Claim Alone—Get a VSO

The worst thing you can do when filing a VA disability claim is trying to do it alone. The VA claims process is complex, confusing, and full of technicalities. A Veteran Service Officer (VSO) is trained to help veterans navigate the system, ensuring your claim is filed correctly the first time.

✅ VSOs are free—they work for organizations like the VFW, DAV, American Legion, and state VA offices.
✅ They know the VA system inside and out—they can help you avoid rookie mistakes that lead to delays or denied claims.
✅ One small error can cost you months (or years) of waiting—a VSO makes sure everything is squared away properly.

💡 Lesson Learned:
Don’t be the guy who says, “I can handle it myself” and then gets stuck in a bureaucratic nightmare for years. Get a VSO—they do this for a living.

6. Keeping in Touch with the People Who Actually Matter

When you’re in the military, it’s easy to take your friendships for granted. You see the same guys every day—training, deploying, hitting the gym, or just BS-ing in the barracks. But once you leave, everything changes.

People move, start careers, have families, and before you know it, you lose contact with some of the closest people you’ve ever known. What many veterans don’t realize is that staying connected with the right people can open doors down the road—both personally and professionally.

Your Military Network Is More Valuable Than You Think

Veterans often help each other out in ways you won’t find in the civilian world.

✅ Job referrals – Your old squad mate might get hired at a company and give you an inside connection when they’re hiring.
✅ Business partnerships – Many veterans start businesses together, knowing they can trust each other.
✅ Mental health support – No one understands the military experience like another veteran.

💡 Example:
I know a guy who got a six-figure cybersecurity job just because a fellow veteran remembered him from a past deployment and recommended him. One phone call changed his life.

How to Stay in Touch with the Right People

✔ Keep a list of people you genuinely got along with. It doesn’t have to be everyone—just the ones who mattered.
✔ Check in every now and then. A quick message or phone call every few months keeps connections alive.
✔ Use LinkedIn. It’s not just for “business people.” A lot of veterans are on there, and it’s an easy way to stay connected.

💡 Lesson Learned:
The military creates lifelong bonds—don’t let those connections fade away. The people you served with might re-enter your life in ways you never expected.

7. Learn How to Sell Yourself in the Civilian Job Market

In the military, your career progression is based on rank, performance evaluations, and time in service. You don’t have to "sell yourself" because your work speaks for itself. But in the civilian world, it’s completely different.

If you don’t know how to market yourself, you’ll get passed over for jobs, paid less than you deserve, or struggle to move up.

Why Veterans Struggle with Selling Themselves

• We’re trained to be humble – The military teaches us that bragging is bad.

• We assume our experience is obvious – In reality, most civilians have no clue what you did in the military.

• We don’t translate our skills well – If your resume says “Platoon Sergeant,” most employers won’t understand what that means.

How to Stand Out in the Civilian Job Market

✅ Translate your military experience into civilian terms. Instead of “Squad Leader,” say “Team Leader | Operations Manager” and highlight leadership, logistics, and problem-solving skills.
✅ Learn how to talk about your achievements. Use the STAR method (Situation, Task, Action, Result) to describe how you solved problems and led teams.
✅ Optimize your LinkedIn profile. Recruiters use LinkedIn every day to find job candidates—if your profile isn’t strong, you’re missing opportunities.

💡 Example:
A veteran I know transitioned from the infantry to a corporate security job. He didn’t just list “Infantryman” on his resume—he described risk assessment, crisis response, and training management, which made civilian employers see his value.

💡 Lesson Learned:
Your resume won’t speak for itself. You have to learn how to market yourself, communicate your value, and stand out in the job market.

8. Your Mindset Determines Your Success After the Military

At the end of the day, your success after the military depends on your mindset.

Two veterans with the same experience can have completely different post-military outcomes—one thrives, while the other struggles. The difference? How they approach the transition.

Veterans Who Succeed:

✔ Start planning before they separate.
✔ Adapt to new environments and challenges.
✔ Network and build relationships.
✔ Continue learning, improving, and setting new goals.

Veterans Who Struggle:

❌ Complain about how “civilians don’t get it.”
❌ Refuse to adapt to the new reality.
❌ Expect opportunities to be handed to them.

💡 Lesson Learned:
The military gave you discipline, resilience, and leadership—use those strengths to build your next chapter. Your transition success is in your hands.

Final Thoughts

If I could go back and give my younger self advice, it would be this: Start preparing for civilian life early, invest your money wisely, and develop the right mindset. The military teaches you discipline, leadership, and resilience—use those strengths to build a great future.

👉 What’s something YOU wish you knew before leaving the military? Drop a comment and let’s help each other out!