Designing Your Military Transition
Thoughts on leaving the military a year later
Disclaimer: This article’s intended audience is officers who already have undergraduate degrees, it may be relevant to veterans who were enlisted, but probably less so.
Leaving the military is often confusing, exciting, terrifying, freeing, lonely, dizzying. Having spent 4 years in college wearing a uniform and then 4+ more years in the military where any choice you had was mostly limited to a few options, the prospect of getting out can be quite nerve-racking because for the last 8+ years most ‘choices’ that have been presented to you only had a few options. Infantry or Armor. Hawaii or Germany. As much as we complain about a lack of choice, it also becomes comforting over time. After all, there’s nothing better than that warm blanket of Tricare Prime. As much as we joke about the military being like being in prison, this quote from Shawshank Redemption isn’t far from the truth.
These walls are funny. First you hate ’em, then you get used to ’em. After long enough, you get so you depend on ’em. That’s ‘institutionalized.’
— Red
So what do most people do when preparing to leave the military and now have an ∞ number of choices? Well, you probably do what most people do when transitioning from a high degree of certainty to what feels like complete uncertainty — freak out.
You start haphazardly preparing for your transition two years in advance, you take every random certification under the sun, you seek out the highest paying jobs you think you can possibly get (and be miserable at), you look for jobs most approximate to what you did in the military (even though you may have complained every day about the job that you did).
You ignore what you enjoy doing, what you’re good at and what you’re passionate about because you think those need to take an immediate backseat to just surviving.
As a result, I think many veterans often end up being miserable after they transition because they are in a job or role they don’t enjoy doing, they aren’t good at and they aren’t passionate about. There is often a fear though, that in prioritizing these three things, they won’t achieve their financial goals. Your default assumption should be that this is false and you should seek to broaden your horizon and realize there are probably many opportunities that exist where you don’t have to compromise. You’ll be amazed at what you find.
So how to find your dream lifestyle — at the intersection of all 3 circles and achieve your financial goals?
One of the best guides I’ve found for running that process is the book Designing Your Life. The book is helpful at helping you uncover lifestyles that are both meaningful and fulfilling.
One of my favorite takeaways from the book is the idea of creating lifestyle experiments. Below are some suggested types of lifestyle experiments. Think of lifestyle experiments as conducting a reconnaissance of the world outside of the military.
- Conversations with people doing something you might like to do (a Life Design Interview)
- Shadowing professionals, you’d like to emulate
- A one-week unpaid exploratory project that you create
- A three-month internship
- A scaled-down version of the career you envision (for example, catering instead of opening a restaurant)
What I like about the lifestyle experiments is that it was so easy when I was transitioning to come up with ideas about what I thought I would enjoy or what my resume suggested I would be ‘good’ at. But in reality, they were just ideas and often wrong because I didn’t know much about the world outside the military. By getting out into the real world I was able to learn a lot and experience firsthand what it would be like to live those lifestyles. I didn’t read Designing Your Life until later in the transition but realized most of what I had been doing was what it described in the book.
The number one variable you should optimize for in your military transition is the speed at which you can run lifestyle experiments. More cups of coffee, more lunches, more visiting workplaces.
For most lifestyles, before you start doing lifestyle experiments, it’s a good idea to get your resume and especially your LinkedIn looking good as you’ll be reaching out to many new people. The team at Shift has put together a nice article on how to do both.
A great approach is to ask people you’ll meet if they would be willing to take a look at your resume and provide feedback. This works well because 1. Everyone loves to help veterans transitioning out of the military, 2. It is very easy to do and something just about anyone can do, and 3. In the process of discussing your resume they will learn a lot about you and be able to make better introductions.
Of course, your resume will also be much better afterward too. I would note as well each industry seems to have its own flavor for resumes, so focus on getting resume feedback from people in the industry you’re interested in.
Decide which lifestyle experiments to run
In trying to figure out which lifestyles you’re considering, I’d highly recommend going to the Beyond The Uniform website and find interviews that you find interesting. Beyond The Uniform is a podcast that interviews veterans who’ve successfully transitioned out of the military and are doing just about everything under the sun.
I would also reflect on what experiences in the military gave you the most energy, talk to friends outside of the military who you enjoy spending time with and what side projects or hobbies were while in the military. The Designing Your Life book goes into great detail on helping narrow down which lifestyle experiments you should run, but those are some ideas.
Especially when you’re leaving a very strong culture like the military, you should strongly consider which values and personality traits are truly yours and which ones you’ve just absorbed from the military. Traits absorbed from the military aren’t necessarily good or bad, you just want to be honest with yourself about who you really are and what traits you absorbed to perform in the military, but don’t necessarily want to hold on to in the long-run.
An added benefit of this approach is that you’ll start to build relationships with people at these organizations who will help be your advocate on the inside and let you know when opportunities are coming up that are a good fit. They will also help you identify skill gaps and recommend relevant training or education that would help you (thinking about training and education in this light makes it so much easier to prioritize what to do). They can also help you reframe your experiences in a way that will be more easily understood, and thus more meaningful to people in the industry you’re going into.
Below are the three lifestyles I explored while I was transitioning:
- Go to grad school
- Join a tech company
- Start a tech startup
Going to grad school
I was an International Relations major and still really enjoyed reading books and following current events. I was also interested in businesses and since getting an MBA seems to be a pretty common option after leaving the military I thought both would be good to explore. To start things off, I visited the University of Chicago and sat in on some MBA classes as well as met with faculty in the International Relations department. I left with a sense that although I was interested in International Relations, I didn’t think that I would enjoy it as a career.
I did continue down the MBA route though and arranged class visits at Stanford’s GSB, Berkley’s Haas, Harvard’s HBS, and others. The experience culminated in attending Tuck NextStep a 2-week long intro to business fundamentals at the Tuck School of Business at Dartmouth. After attending this program and talking with other folks I eventually came to the conclusion that pursuing an MBA wasn’t necessary for the direction that I wanted to go nor a good fit in the near term. Attending Stanford Ignite further confirmed this, but did help me realize that I wanted to live in Silicon Valley which is one of the most important decisions you’ll make — where to live after the military.
Joining a tech company
Several of my friends from high school went to work at early-stage tech companies and all really enjoyed what they did. Several of them had worked at more established companies, but often became frustrated with the same things I was frustrated within the military. My interest in tech companies was further confirmed by attending a Google Resume Workshop, a day-long resume program at a Google campus for veterans. It was an incredible experience as it was unlike any ‘corporate’ environment I’d ever seen. Climbing walls. Board shorts. But also an extremely competitive environment and I really liked the mentality of the people I met there.
If you can, I would recommend going through a program like Shift or Breakline which essentially helps you run really efficient lifestyle experiments at companies, but especially tech companies. Shift.org is especially good if you are still in the military because they leverage the Skillbridge program to set up internships with companies while you’re still in the military. Breakline offers short courses in Silicon Valley and other cities that help connect veterans with top companies, especially tech companies. If those aren’t an option, start reaching out to mutual connections on LinkedIn or use LinkedIn to find veterans at the companies you’re interested in. Veterans also get a free year of LinkedIn Premium, now is a good time to start using it.
Founding a tech startup
This is where I ultimately landed. The first lifestyle experiment I ran was going to a Techstars Startup Weekend, a weekend-long program where I pitched my startup idea. The team I was leading ended up winning the pitch competition. I really enjoyed the experience and was also an indicator that it was something I may be good at. I put the idea on ice for a while until my papers got approved to get out. I gradually scaled the idea up until it became what it is today. Here is the article that goes into greater detail on that process:
Another lifestyle experiment I ran was going to Patriot Boot Camp a weekend-long event for active duty, vets, and their spouses. It was experiences like these that further confirmed I really enjoyed the type of people who work on tech startups.
However, I wouldn’t recommend founding a startup right out of the military, unless all of the following are true. Note: this list probably doesn’t apply to entrepreneurs starting businesses other than high growth tech startups.
- A year plus of runway (you have enough savings to not pay yourself for a year)
- You have a co-founder (for most veterans starting a tech startup, this means someone who can write code)
- Live in Silicon Valley (not required, but strongly suggested)
- You think there is a vanishing window of opportunity to start the idea and if you were to start in two years, it would be much more difficult
There simply is a lot of, ‘you don’t know what you don’t know’ when getting out and startups only exacerbate that. If your co-founder isn’t a veteran or hasn’t been in the military for the last couple of years, that is also a great way to reduce risk. If you are interested in startups, I think joining an early-stage tech company is often a great way to go and will set you up for success to start your own because you’ll see what right looks like and meet people who may also be interested in starting a startup and complement your skillset (see the previous section on joining a tech company).
In conclusion
Transitioning out of the military is often equally exciting as it is terrifying, but you can do it. Transitioning to a job or role where you wake up every morning and enjoy what you’re doing, fits with your strengths, and is something you’re passionate about is possible. There are many roles where you can also achieve your financial goals and not have to compromise on those three circles. The Designing Your Life book is a great guide to executing your transition and running lifestyle experiments to find the intersection of those three circles. Enjoy!
