Lead with the best version of yourself.

Don’t Fail Your Final Mission: Retirement


This is not legal or financial advice, it’s simply how we successfully transitioned

By: Jason Criss Howk

I served in uniform from 1991-2015 as an enlisted infantry paratrooper and sergeant for five years and then a combat engineer officer, and finally as a South Asia foreign area officer (with a break in active service in the Reserves and ROTC).  After marrying, we moved around A LOT, living in 14 homes in 15 years as the Army snatched us up for rapid-fill missions.  This meant a couple things—we weren’t homesteaders anywhere and never put down roots in any community.  We focused on living on a tight budget and planning for a retirement date based on when we got tired versus when I made a certain rank or year-mark.

Health issues sped everything up as I approached the 19-year active service mark. We decided to end our service and rushed through our final year. Thankfully, retirement was a smooth transition, due in large part to prior planning. Retirement could have been a stressful life event if not for steps we took years before.  Today I am an educator that teaches, writes, speaks, and even hosts a podcast.  I also volunteer with non-profits, helping military families and endangered animals.  My passion is increasing tolerance among various religious groups though education. I wear Hawaiian shirts and collect books. Again, none of this would have been possible if we didn’t prepare for it.

When planning and executing your retirement, keep this thought in your mind…because time truly is money:

“Strategy is the art of making use of Time and Space. I am less in charge of the latter than the former. Space we can recover, lost time never.” -Napolean

Get your finances in order

If you screw up the financial piece of this mission, you will pay for it for the rest of your life—you can’t replace time lost.

Be strategic with your finances.

There is a gap between your last Army paycheck and your first retirement paycheck and it will take a while to get through the VA process so plan accordingly.

  • As you ready to retire, every penny counts; save and scrimp, make sacrifices early to reduce stress after you leave the service. It’s a horribly stressful time and unnecessary money-related stress can make a tough situation worse. It can be catastrophic for your family.
  • Save 2 months’ salary in cash for back-up in case your new salary doesn’t pay the monthly bills.
  • Save a separate chunk of cash for emergency expenses (always keep some money in that account).
  • Find a savings account that gives you more than 1.5% in interest. They exist.
  • If you can, live like college kids for the last 3 years of service. Start adjusting your lifestyle to a reduced income. We learned to live on half my paycheck.
  • Get your credit score to near perfect before you retire, there is a counselor on your base to help you.
  • If you know where you’re going to plant roots, buy your house and/or pay ahead on mortgage before you retire. If not, save money to make a big dent in your mortgage when you decide where you’re going.  It’s the biggest bill in retirement so the lower you can make your monthly payments, the easier your life will be.
  • Don’t amass big debts before you separate—Pay off your credit cards before separating
  • Have an accurate monthly household budget prepared—start living by it before your paycheck gets reduced
  • Your body and mind have taken a beating, go through the VA process and file a claim so the Army can fix it later when it really goes downhill. If you earn any service connected disability rating/payments it helps you tax-wise. Start before you separate as you are doing your medical exams for your service.
  • Some states tax your retirement check—know who they are ahead of time. That’s a big chunk of your monthly income lost to taxes.
  • You should have the basics: a retirement plan outside of the Army (401K etc.), life insurance, a will etc.
  • Find college scholarships for your children. There are lots of service organizations now that offer them. These lists change often so make your own list as you find scholarships that fit your family circumstances. They are also never complete, check with your unit associations and support organizations and high schools and colleges for more. I volunteer with the Patriot Foundation and like most, we are support a specific population of service members.  Transfer your GI Bill to your family a couple years before you retire or you may lose the chance.

The transition process works, if you work

The transition process is always changing (for every service) and it isn’t perfect but if you take it seriously and do some additional research you won’t feel you wasted your time.

  • Start as soon as you can legally do so. If it starts 24 months before you retire, then go to the retirement brief at the beginning of your window.  You will need all that time to do it right.
  • The intake day of the transition process orients you to the menu of options you can take, take notes and take your spouse if you still have one at retirement.
  • Make a calendar of all the key courses and events you want to take—take as many as you can squeeze in.
  • Do every course with your spouse (if they are available)—they offer something for both of you.  And make sure you both take notes as there is a lot of critical information in each session.
  • Use the permissive TDY to visit your next community and prepare. You can take it in 1-week chunks, so spread it out.  Don’t take it all at the end before your leave begins.
  • Save up as much terminal leave as you can, those are full paycheck months.
  • Take the Army’s transition process seriously, once you are out, the Army doesn’t care about your questions—you are replaceable.
  • It’s a part time job finding your way out of the Army; don’t skip the work.
  • Some of your transition instructors don’t give you all the info you need—do your own research based on the topics they cover—some of their info might even be outdated.

Finding and starting your Career 2.0

You may end up with 6 part time gigs, that’s OK—you won’t get bored

  • Have multiple career options so if your dream job doesn’t happen, you have back-ups (Primary, Alternate, Contingency, Emergency—you’ve planned wisely before, don’t stop now).
  • Don’t get focused on looking for just one specific job, you might find a new passion, so listen to all offers.
  • In the end, you will likely need cash or experience working outside the military, so you might need to do a job you dislike for a bit.
  • You may not need to work financially, but you need a plan so you don’t get bored—you can’t fish and golf all day (or maybe you can).
  • If you don’t like the first new career you try, then respectfully tell your boss and move on. You already paid your debt to the nation, you owe nothing to a business, they will understand.  If they don’t, who really cares— its your new life and you earned a career you enjoy.
  • You will be approached by veteran related charities, only volunteer for ones that have a high external rating for actually giving out funds/services and don’t join them if they pay their CEO big money. Many are fraudulent, paying their officers 6-figure salaries and give almost nothing to the veterans and military families.  Keep an eye out for lists of some of the worst that have been exposed. Here is another place to search for transparency and efficiency.
  • Do something you love.

Final Thoughts

  • Communication with your family and friends is critical during this final mission.
  • Don’t keep secrets from those you love…help them prepare.
  • Lay out all the obstacles and changes ahead.
  • You never know who will help you during this transition, so network your butt off and learn from others—offer to help others more than you ask for help. They may return the favor, and in the end, you will have helped your teammates be successful.
  • Help the next person to retire well. Be an asset and share your lessons—for free.
  • Stay selfless and you will be happier.
  • Be confident, you have been trained to do this.
  • You only get one chance to retire, if you screw it up…you cannot do it again.

Good luck! Remember, you’ve been taught to plan your whole career.  Do what you know.

If you have already retired and have some great lessons, please share them in the comments below.

Jason Criss Howk is an educator and public speaker that focuses on Islam and Afghanistan. You can follow him on LinkedIn, his Facebook pages (author and podcast), on twitter @jason_c_howk  and at his blog. Listen to his podcast on Itunes Podcast or here.