Designing Your Military Transition

Thoughts on leaving the military a year later

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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 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.

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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.

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Source: Designing Your Life
  1. Shadowing professionals, you’d like to emulate
  2. A one-week unpaid exploratory project that you create
  3. A three-month internship
  4. A scaled-down version of the career you envision (for example, catering instead of opening a restaurant)

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.

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.

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  1. Join a tech company
  2. 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.

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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.

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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:

  • 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
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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!

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Notes from a founder trying to make an idea a reality.

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