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Starting retirement planning while deployed


Josh Hicks Colorado Springs, CO

Hi everyone, I'm Josh Hicks and I'm just getting started with my retirement planning. My planned retirement date is around summer/fall of 2023. I'm looking to find work in the cybersecurity field in Tampa, FL.

Having limited bandwidth and limited access to many websites isn't helping my cause, but I'm making the most out of what I can get to. Right now the goal is to update my resume, conduct job searches, and start making contacts in the Tampa area.

For those of you who started your retirement planning during a deployment, what did you focus on completing?

I appreciate everyone's time and feedback!

23 January 2022 7 replies Military to Civilian Transition



Dave Mayewski Aurora, OH

Hi Josh,

Having recently gone through a similar journey I would recommend connecting with a fiduciary. They specialize in helping you put a plan together and typically don’t get paid any commissions on financial investments that you make. Financial advisors can be beneficial but think of them as someone helping you at their store. They can give you a good deal on what they have but not what they don’t. Hope this makes sense. Message separately if you would prefer to talk through the difference. A good fiduciary will also help you understand what your budget and other career goals might be. Creating your new identity is really important when you step back from work.



Eddie Starr Fremont, NE

I would encourage diversification. Depending on what you're looking to do, you may want to include bringing in a SoloK or SDIRA. You'll want to make sure you have what's called "checkbook control," so that you can make the investments you want, on your call.

These tools can be very diverse, allowing you to invest in almost anything (with a few exceptions, like collectibles): Livestock, real estate, precious metals, cryptos (stable coins are those that are pegged to USD, EURO, and others, and are "safe cryptos).

if you're looking to be employed, I would look for a company that offers an HSA, FSA, or HRA. Unless it's changed, FSAs generally aren't for the self-employed. Each of these allows you to pay out of pocket medical expenses, with various tax advantages. Who all they benefit and how, depends on the policy.

Note: HRAs belong to the company, and you can only take advantage of it, while you're with the company; not a problem if you own the company. The HSA, like a 401k or similar program, is yours, and you can take it with you.

This is only a fast overview, to serve as a starting point.


Kevin Hicks Freehold, NY


Thanks for your service and (almost) welcome to the other side. I was nervous about retirement for about a day, then I looked forward to starting the next chapter. Most of the services are very welcoming when it comes to sharing information for retirement planning. Feel from to look through the Army's Retirement Services Office page: . You've accomplished the biggest step: starting early.
My personal situation was different than your s in that I was't seeking future employment, but I still had some hiccups: managing and ensuring adequate medical coverage was an initial worry. I have a service connected disability, so the VA covers my medical needs. Tricare covers my wife. Finding the right docs for her witching the Tricare network took some effort...not a lot, but it wasn't something I was used to doing. The same goes for Dental and Vision: You'll have to shop around for your own providers (unless your employer has a network).
The previous recommendations of networking are key: you can start connecting with employees of potential firms/companies you're interested in now. Do a LinkedIn search for the name of the company and "Veteran." If employees tagged themselves that way, you can connect and start asking questions. I found Vets want to help Vets. They can explain hw their onboarding process went, and share what they wished they had done differently. One story I remember was a fellow Vet explaining how happy he was that his new employer agreed to his requested salary. He thought he had bargained well and got what he deserved. Afterwards he found out he could have also bargained for additional vacation days, but agreed to the minimum offers to new hires, so had to serve a few years before he earned enough vacation days to really start enjoying his military retirement.
Good luck and keep plugging away at it. Stay excited and keep any family involved in the process.



Kevin Trosine Oviedo, FL

Congrats on nearing retirement Josh. That’s an outstanding accomplishment! The company I currently work for has a rapidly growing Cyber practice and we also have a team in Tampa. I suggest checking out some of our technology labs and artifacts on Here you’ll get a lot of info on what’s happening in the cyber field and also see how we’ve helped businesses navigate the ever changing landscape of technology.
You could also take a look at our careers page to get an idea of the types of positions we have and the desired credentials. Here’s the link



Saul Gomez Chesapeake, VA


BLUF (Bottom Line Up Front): Start connecting with people in the industry you are seeking to get into. Cyber being that, I would also think about whether there is a specific market or type of organization (medical, education, communications, etc) you would want to be working in.

It can certainly be challenging with limited connectivity, however, it's not impossible. I'm happy to continue a conversation when you have availability-message me.

There are also tons of resources - just a matter of which to leverage, based on your aspirations. One in particular is CyberWarrior...they offer a bootcamp that provides 4 globally recognized certs, as well as several others. They also have a pipeline towards job offers and paid internships.

Be safe out there - head on a swivel - talk soon.



Richard Byrne Hillsborough, NJ

I've been adding job search links to my EE web-page.

I've noticed that most federal agencies seem to use :
I found more jobs for Network Operation Manager at other cities, so I tried cybersecurity as a keyword at this location. Maybe you would like to move to Washington, DC?

This search targets state & local government

A similar private sector search yielded 75 jobs.

To answer your question, prior to getting my draft notice, I was working & attending college at night, so I returned to both after completing my service.
I expect and hope you won't have much difficulty adjusting to civilian life.


Jerry Welsh Middleville, MI

Your profile on LinkedIn does list the correct career field, believe it or not you are ahead of many in your position. I would start trying to conduct Informational Interviews, realizing time maybe an issue, but the more you are talking with people in the career field on the private sector side, the better jump you will have. Connect with Michael Quinn on LinkedIn, he has great posts everyday and also provides useful USO training sessions on how to Network.
I would really try to network in the area (geographically) you are going. The problem is that people change positions so often now days, your contacts could change jobs and then that contact may not be as valuable in the new position. I say a highly technical young man end up overseas contracting for a couple of years, he lost his network state side. You have a good solid skill set, a degree, now you need to understand what your career role does on a daily basis in the private sector. This is huge, but also gives you a leg up on networking. Given the geographical constraint, you will need to network more to cover the same number of interviews and contacts.
Watch your resume, do not make it too generic. Create a solid IT cybersecurity resume, keep much of the military out of it. Keep in mind you will compete with people who are doing the private sector position right now today, you will have some up time, the less uptime the employer sees the better it is for you. Hire Heroes USA is top notch on resume assistance and I would also reach out to ACP for a mentor. The more time you are speaking and interacting with folks in your chosen profession the better you will be to show value to an employer. That is what they want to see, a demonstrated value proposition you bring. Keep in mind leadership is a skill, not a management career-private sector do not understand the role of senior officers or NCO's in career development, that is what they have HR for. I do not mean to be rude, but they want a Cyber IT professional first, if you can get along with people great, if you understand THEIR mission even better. So research your company prior to an interview.
Hope I am not throwing too much your way, but even at your senior grade, the chance of someone in the company understanding the military is slim (unless you go for government/DOD contractor). Less than 0.5% of Americans will serve their country and the veteran community as a whole is fast approaching 5%, working under 3%. Thank you for your service and God Bless. A couple of quick reads.

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