The Veteran (Semi) Professional: Networking Above Your Pay Grade

In the military, your rank sets a ceiling and a floor. Outside it, nobody is holding either one in place. I sat down with Mark Delaney on The Veteran (Semi) Professional to walk through my own exit: Naval Academy, surface warfare, a lateral transfer into Naval Special Warfare, just under eight years as a SEAL officer, and then out in July 2020 into an executive MBA and a finance career several people told me I was not eligible for yet. We covered cold outreach that actually lands, why enlisted guys build better businesses than officers do, and why "thank you for your service" buys you nothing on your first day.

In this article is a summary of what we covered on the show. Keep reading below for more.

Listen To The Episode

Listen to the full conversation on Apple Podcasts, or watch it on YouTube.

Specificity Is The Whole Game

Most of us leave with the same elevator pitch. I led small elite teams in austere, resource constrained environments. I managed assets and worked across cross functional lines.

Buzzword soup. Someone nods politely and asks what you actually want to do, and the honest answer is usually "I like solving hard problems." That answer helps nobody.

Think of it as a doctor's appointment. You do not know what is wrong, so you hand over every symptom you have and let them work backward. Once I started giving people real symptoms, the guidance got sharp. I wanted somewhere without much bureaucracy. Somewhere fast enough that I could learn and perform at the same time. A company going from sixty people to two hundred, where I would touch most of the business. I stopped treating the first job as a performance test and started treating it as a training opportunity. I wrote more about that stretch in Transitioning From Military to Civilian Life.

Sharing Requires Vulnerability

The military trains the sharing instinct out of you. You never want to be the last person in the room to learn something.

That habit works against you the moment you leave. This is a bigger question than a job search. You spent years inside an identity you were fully inculcated into, and now you are starting fresh, largely on your own. Nobody can step in and help until you have said out loud what you want, usually before you are sure of it.

Officers And Enlisted Build Differently

A friend of mine spent years hiring veterans into one of the largest private equity firms in the US. To get better at it, he went and studied the recruiting and screening pipeline inside a special operations unit. What he found there reframed the whole thing for me.

Officers are not specialists. We manage specialists. The job is context switching: take a commander's intent, distill it, hand it to your senior enlisted leader, who hands it to the people actually turning wrenches.

Enlisted guys spend those same years without the template. No endless funding behind them, no support structure waiting to catch the fall. Make the most of what you have. That is why so many of them go zero to one so much faster on the outside. Look at the security companies that came out of my old community. I can think of one that an officer built. The rest came from the enlisted side.

There is a reps argument underneath this. A major league hitter would rather see a thousand at bats than five hundred. Delegation is the right call in uniform. It also means somebody else gets the reps, and you do not find out what that cost you until you are on the outside trying to solve something with nobody under you.

The Risk Anchor

Mark put the sharpest version of this on the table and I could not agree with him more.

Officers carry a safety net. The academy, a good business school, the O-3 line on the resume. You can always fall back on it, and that is exactly what turns it into an anchor. When your downside is soft, you spend your energy protecting it instead of going after the upside. An E-5 without those credentials on paper has to fight for the thing, and when it finally lands, it lands because they made it land.

Networking Above Your Pay Grade

At some point in the military I noticed I had caught up to my mentors. So I went looking for people I could not surpass in the next twenty years, with a lifetime of experience across industries I had never touched.

Then I made it as easy as possible for them to answer me. A few pieces to that:

• Lead with no ask. Do the homework first. The lockdowns had just hit and I could see one guy's family was deep into fitness, so I sent over a PDF of twenty at-home workouts before I ever asked him for anything.
• Report back. I read the article, I tried it in my own life, here is where it worked and here is exactly where it did not. Real professionals want feedback on the advice they hand out.
• Pre-package the problem. Never open with "I have a problem." Open with the issue, how you characterized it, the three ways you are thinking about solving it, and a line of context on each.
• Expect curt. Some of these people have been served their entire lives by full staffs. I asked one about a compensation package that felt light. The answer was "ask for more, you already know what you want." That is a complete response.
• Some want shotgun. Others will ask what deal you have coming up, tell you to hold on while they dig into the person across the table from you, and then want to know what time the call is.

One caution. Nobody is a whole role model. You will meet extraordinary operators with wrecked home lives, and extraordinary family men who are poor leaders. Pick the parts you actually want.

The Failure Rate Is Supposed To Be High

A 20% failure rate in the military is unacceptable. In cold outreach, an 80% hit rate would put you in a rounding error of the human population.

Mark framed the downside correctly. The realistic worst case is silence, which costs you thirty seconds of typing, or half an hour if you did the diligence first. Throw the shot.

Upper And Lower Bounds

Rank hands you a ceiling and a floor. You will not make decisions below your level, and you will not make them above it either. You get asked for your analysis and your perspective, and then it moves up the chain without you.

On the outside you own the whole stack. Everything before it reaches the customer, everything up to what the CEO reviews. A lot of people will pass your work along without ever touching it. That is a much wider band than most of us are used to operating in.

Start Eighteen Months Out

Picture telling someone a year before you met: in twelve months I am going to want to date you, so tell me now what I should get better at.

Absurd in a relationship. Completely normal in a career, and almost nobody does it. I started engaging two firms about eighteen months before I got out. One told me flatly that it does not work that way, that I needed a stop in between before venture. Fine. So I asked what I should be learning instead and who I should be talking to. Recruiting high quality people is genuinely hard, and people fall back in their chairs when someone shows up early like that.

Tell Them About Themselves

My favorite move in an informational interview is to stop the person right before the company overview.

Let me tell you what I think you do, and you tell me where I have it wrong. Then push it one step further. Here is a line in the National Defense Authorization Act that might touch the area you are expanding into. One firm forwarded that straight to their capture team.

You get graded on a curve here, so being roughly right is enough. They already know you can execute a task you were handed. What they have no evidence of yet is whether you are proactive.

The Flip Side Of Empowerment

Nobody knows you. Thank you for your service, now go deliver something.

Someone introduced me in my second week as having been in the Air Force. That is roughly the amount of credit your record carries into a new building. You will be an individual contributor on day one, and you have to prove yourself competent before anyone lets you prove yourself responsible.

Two practical notes. Do not call yourself Chief of Operations when you were an executive officer, and do not call yourself an operations manager when you were a platoon commander. Say the real thing, then translate it. And nobody is reading a four or five page resume covering six or seven years of service. Tell your story. Do not make them assemble it.

Age is the part nobody wants to say out loud. I once saw someone answer a captain who was weighing whether to stay in for command and retire at twenty: I have no idea what a lieutenant colonel is, but I do know I do not hire 45 year olds. It is not supposed to be a factor. It is very much a factor.

Learn To Set Boundaries

The skill I have had to unlearn is being a yes man.

In uniform you take the tasking and you figure it out, because the alternative usually costs somebody something real. On the outside almost nothing carries that weight, so it costs you nothing to say yes, and you end up agreeing to work that pulls against everything else you are building. Someone remembers a thing they forgot at noon on a Saturday. If it is an emergency it is really important, and if it is important it is really an emergency. Most of it is neither.

Conclusion

It is a whole different life you are leading now. Try to recreate the one you had and you will end up disappointed, frustrated, and confused.

So reach out. To the friends still in uniform and the ones already out. Be open about the headwinds you are hitting and about what you actually want out of your life, because the people around you have been looking for a way to help and you have finally given them one. If you are working through a transition and want to talk it through, contact me today.