Transitioning - where to start

ENS Kellogg,
In a lot of ways, you are in a fairly good position to hit up the civilian market now. You are about 3 years out of college, have held two jobs - both highly responsible for your age - for about a year each, with the same employer. You have management and leadership skills that will FAR outpace those of your civilian "peers."

I don't say that as a platitude. I put the word "peers" in quotes for a reason. You really are going to have a big "recent college grad, looking for a job" cohort, but very few peers. Quite simply, at your age, the average job seeker has NOT had the leadership and management training that you have. They have NOT had positions where they had a high degree of responsibility/accountability. Not because they suck, but because the civilian employment structures rarely (not never, but rarely) give junior employees that much authority. Your actual experience will make you stand out. While we make fun of 2LTs/ENS/O1's (a habit I will happily continue ;-) ), the fact is that they simply don't have civilian peers.

Ironically, the further along your military career you are, the less the above is true. As a 45 year old O4/O5, you would find yourself competing against seasoned professionals who have a 20+ year increasingly responsible career in [whatever]. There will be people in that age cohort that are aimless, but they wouldn't be your competition.... At which point, you find out that you don't have directly relevant experience and have to start again at the bottom of the food chain and work your way up again. [Not sour grapes on my part. I've always been a "traditional reservist." But it is a pattern I see and hear over and over again.] They can generally do so at lightning speed, but it's a big hit to the ego out of the gate.

Enough rambling. Here comes the constructive part:
1. Decide what you want to do and where you want to do it. Depending on your answers will drive your search strategy and expectations. If you want to do something in PR/communications/branding, you probably are in good stead. I don't think Surface Warfare or Anti-Sumarine experience will help you, unless you are looking at DA civilian/contracting gigs with the Navy. If you want to do something other that PR/related, you will have to accept the possibility that you will need to start at the ground floor, entry-level management level.
2. Read "What Color is Your Parachute?" Do what it says. No, actually do it. (No I don't get kickbacks!)
3. Resume. A few things here:
A. Civilianize (discussed in other post)
B. Customize. You will not have ONE resume. You want one that is tailored to the SPECIFIC job you want. It will really stand out. I suggest you do this by creating a "career management document". This is an infinite-length resume-like document that you update quarterly, or more frequently. It lists EVERYTHING you have ever done in the history of ever. When you decide to apply for a particular job, you read the announcement carefully and then "build" a resume via copy & paste, and add a few finishing touches. If you do the CMD right, including formatting, you can get this down to a few minutes per resume. As a hiring manager, when I get a resume where everything is directly relevant, it floats to the top of the pile. The same goes for cover letters, though 90% of those can be pure boilerplate.
C. Use a JOB TITLE - Responsibilities - Accomplishments format. Responsibilities is a 1-3 sentence prose description of what the JOB (and anyone in it!) does - it sets the level of position in the reader's mind. Accomplishments are 1-2 sentence bullets that list the spiffy things that YOU did. Accomplishments are the "so what."
D. Please, for the love of all that is holy and good, write the resume to be human readable. MOST employers do NOT use "resume scanning software." Those that DO use it, still pass the computerized matches to a HUMAN to read. If reading the resume frustrates me, if floats to the bottom of the pile, or gets moved to its own special file.
4. Be a sniper, not a machine-gunner. Research positions you want and apply for them. Research means know about the position, the employer, the market, and the team & hiring manager if possible. This makes it sound like a lot of research/work per application, and it is. But you are looking at what you will spend the majority of your waking hours doing for at least the next several years. You are worth the work.

As a hiring manager, the worst things I see are:
- Crappy resumes that I can't easily read. Formatting, spelling/grammar, specialized terminology, etc.
- Cover letters that aren't specific to my position. And are often obviously retreads of the last one - often with details of that other position still there.
- People who show to the interview that obviously aren't familiar with the POSTED job announcement/requirements/expectations or the employer.
- People that presume that they are "entitled" and the interview is just a formality.
- People who focus on what's in it for them, and not what they can bring to the organization. (I hire because I have a need, not because I'm nice.)

Don't be those people, and you'll do great.

As far as not being able to have your dream job, I can only say that there are many paths to fulfillment. Take what was good about this one road and carry it to the next.

Ma'am, I wish you the best. CPT Riley mentioned Maj. Burns thread and I thought I'd share the link. Great resources here and it continues to grow.
https://www.rallypoint.com/answers/resources-for-veterans-service-members

You posed a difficult question and there are no easy answers. Many of your answers are going to be unique to you, but from a general position you're taking the first positive steps to be proactive.
Planning ahead has it's virtues ... so keep your head up. For starters, Maj. Burns started a thread 'Resources for Veterans & Service Members' that contains a myriad of different resources to look over. This should give you at least a head start and give you some ideas to look into. When the time comes you have to make a decision one way or the other, your chain of command should have information and resources at their disposal they can point you towards.
My best advice - keep your focus and positive attitude. As your situation unfolds, look at your options - weigh them - then use your resources to make the best decision for you. You will be able to find plenty of personal support from the members here. Good luck in your endeavor.