Trading Army Greens for Entrepreneur Jeans: A Former Soldier Learns To Ask “Why?”

(Photo: Anna Vignet/Flickr)

(Photo: Anna Vignet/Flickr)

Leaving the business world for the military life was an adjustment to say the least. Going from middle management and entrepreneurship, making my own hours, and completing tasks in my own way using deductive reasoning became a distant memory. Even the thought of this kind of freedom seemed laughable and was quickly discarded. My biggest strength in business was always my ability to think outside the box and solve problems creatively. In the Army, there are far more guidelines that stifle creative thoughts. This caused friction between commanders and myself on several occasions, especially if I used the dreaded jaw-dropping show-stopping word “why”. (If you were ever stationed at Fort Bragg like me, this should be an exceptionally funny joke.)

As the years went on, the word “why” was slowly eliminated from my vocabulary and replaced with a reluctant “Roger”. Questioning why we were doing something was never a good idea no matter how insanely ridiculous the task was (and trust me, most of them were insanely ridiculous).

My only saving grace: Field Exercises. These varied from three days to a month. This was my escape from the office and the constant micromanagement. It was just my men and me. 25-35 Airborne Paratroopers walking through the woods, sleeping in holes we dug, and living out of our rucksacks. In these moments, I was a true leader again. I made decisions based on guidance from my Commander and used terrain analysis and enemy disposition to execute my mission. I utilized the expertise of my Sergeants, collaborated with junior leaders, surveyed the terrain, conducted reconnaissance, and used all available information on enemy behavior to construct a plan of action. It was like running a well-oiled small business. I loved it. These are the skills and life lessons I took back with me to the civilian world and will cherish forever.

So as I now transition from the military back into the business world, I have to keep reminding myself that it’s ok to ask “why” and try new things. If I fail, no one is going to get hurt or die. No one is going to call me into his office and rip me apart for not following protocol. That’s the beauty of entrepreneurship; it’s your show, so mix it up and try new things.

Times change and so should your tactics. The Army as a whole executes this poorly because it is a huge organization and to pivot based on a change in society or technology takes an extraordinary amount of time.  We don’t have this issue as entrepreneurs, so take note of change and adapt quickly. Even though the Army as an organization may take time to transition, they have instilled these skills in us as individuals. In the military, we were constantly adjusting to change in a fast paced environment. This is an essential skill in starting your own business and will serve you well as a business owner.

Perhaps the hardest challenge of leaving the military to work from home and start my own business was the drastic environmental change. I went from being surrounded by the most diverse working environment in the world to a stay-at-home dad with only a 3-year-old girl to bounce business ideas off of. Although she is surprisingly insightful, it is a very different working environment. To this day, I still get a certain level of anxiety if I am not gainfully engaged in something at all times. It’s like I still have ten bosses walking around making sure I’m staying focused and on task.  I treat this as a blessing.

The importance of self-motivation and mission accomplishment has been seared into me from my service. I am currently working on two startup companies, doing contract work to pay the bills, and using spare time to write a blog. I am also the primary caretaker of our daughter while my wife works full time. This is not to say that I’m some sort of super human; I am just used to working 18-hour days and having high expectations placed on me.

If you have ever been in the military, this should sound familiar. Use your experience and training to your advantage. Don’t get lazy and unmotivated. I still work out every morning before I start working (although now I do this at 8am instead of 6am—another blessing). Keep your motivation high from the start because it will be much harder to revert back once you’ve let the structure go.

If you are transitioning out of the military or just thinking about it, just know that these values will be a great asset to you. Only about 1% of the population has ever served in the military. This means that you have lived and operated in a heavily structured environment that 99% of your peers cannot even comprehend. Waking up at 4-5am to do Physical Training every day then working 8-12 hours, working out again in the afternoon, being on call 24 hours a day, being in the field for weeks or months at a time, or deploying for a year. These are valuable experiences that set you apart and give you appreciation for things that most people take for granted. Even though we always operated with strict guidance, we learned to get our particular job done, and done right, even in the most austere working environments.

One of the greatest lessons I learned as an Army officer was the importance of adapting. In the Army, things change every minute and you have to stop whatever you’re doing and move on. This is something I always stress to small business owners. Many owners get bogged down with daily operations and don’t take the time to step back and see what’s changing around them. Before they know it, they are so far behind the times it seems impossible to catch up. It’s not.

When I got out of the Army and back in business, it seemed like a different world. Everything had changed. I had to learn the importance of a Facebook business page and Twitter account. I read, and still read, as many articles and books as I could on the subject. I learned not to get overwhelmed and  just take a deep breath, create a Facebook and Twitter account, upload photos, build a website, start a blog, and learn as much as I could from those already succeeding in the industry. It is very important to understand how businesses communicate to customers these days. I am still learning everyday. Technology is constantly changing the way businesses operate and it is our job to learn and adapt. Conduct your reconnaissance so you can see what’s up ahead before it’s too late.

Learn to read your new terrain. Just like in the military, it will always dictate which direction people will go. People follow the path of least resistance, so position your business on that path. Funnel them into your product or into your doors. You can’t do this if you don’t know your environment. If you want more ideas on how you can do this, please email me and I’d be glad to help you out. If you found a new cheap/free way to get noticed by customers, share your ideas with the small business community. If you served in the military, thank you for your service! Share your experiences with others. If you are David, Throw the Rock! And don’t forget to ask “Why?” whenever you feel like it.

Chuck Turay is a blogger and entrepreneur who writes at His goal is to help small businesses succeed by utilizing experts in social media management and web development.

Trading Army Greens for Entrepreneur Jeans: A Former Soldier Learns To Ask “Why?”