Startup Culture Shock: The Joys of Leaving Corporate America

If someone walked up to me when I was 18-years-old and said I would one day work at a startup that was founded within the last year, with less than 5 employees, and that I would love every moment of it, I probably would have said something immature or rude, and mocked them for obviously knowing nothing about what drives or motivates me.

I’m happy to say I was absolutely wrong, and that I finally found the right career fit for me. For the last six months, I have worked in the opposite environment than the one I sought my entire life, and I feel more confident about my future than I did working in any corporate or traditional job markets.

Startup life isn’t for everyone - like any career, it has its ups and downs. It's secure in some ways and less in others. Overall, though, it has improved almost every aspect of my life.

Adjusting to Military Culture

Like so many children of immigrants, I was raised with the same false narrative we all were;  work hard, go to college, and you will be successful in life. Unfortunately, college did not seem to provide the financial security I needed to feel comfortable with taking that next step into adulthood, so I joined the Marines instead and was immediately thrust into an environment where the expectation was excellence at all times.

Culture lessons I learned from the military were that my appearance must be flawless and professional at all times, and that I had to monitor and edit every word before I spoke to ensure the highest degree of propriety was observed. Mistakes were . . . frowned upon.

The military’s approach is one Darwin and Nietzsche would approve of. A zero tolerance policy meant mistakes or stumbles were swiftly corrected with immediate consequences. Those able to live up to this impossible standard remain in the military, are promoted, and prosper.

I loved military culture. Imagine being surrounded every day by people who are dedicated to being the best version of themselves, and that anything less was completely unacceptable. I honestly would have remained in the military and spent my life working within that unforgiving system if not for the physical wear and tear of military service.

The other end of this survival of the fittest policy meant living in an environment where you are not allowed to make mistakes, weakness of any sort isn’t tolerated, and individual growth takes a backseat to competitive dog-eat-dog attitudes.

So, if I couldn’t do the thing I loved, why not get rich, instead? That’s why I spent the next year working in marketing and sales - there I was, at the age of 26, entering the corporate world for the first time, and It made me absolutely miserable.

Similarities Between Corporate Business & the Military

Corporate America and military culture are similar in many ways: You are given a dress code and expected to be at work on time. In regards to perfection, the corporate world can be just as demanding, coupled with zero tolerance policies designed to weed out those who “don’t belong”. But everyone was out for themselves and standards were never enforced.

During my six months doing sales and lead generation at a marketing agency, I witnessed coworkers stealing sales without any repercussions even when improprieties were reported. The culture of backstabbery was simply unacceptable to me, so I left marketing and tried my hand at selling insurance.

In the Marines, every tiny aspect of my uniform and the customs I observed had some meaning, which I was taught and expected to know by heart. We yelled “ooh-rah” and had a rule for pretty much every behavior you could think of. In a similar yet much less meaningful way, my account manager position required I memorize silly songs, shout slogans, and teach them to coworkers. I was also expected to stomp out any negative speech about having a bad sales day. I was even instructed by the owner to chastise my team when they thought about leaving the business.

While the culture at my second sales job was much friendlier, the pattern of corporate conditioning had finally dawned on me. These traditional jobs may have started as family friendly and people-oriented businesses, but at some point they simply grew too large to maintain that grassroots family feeling. Instead, they create doctrines, rules, regulations, corporate retreats, and motivational speeches, and teach managers to treat their employees like automatons so they can program them to worship at the altar of the corporate culture. It works amazingly if the bottom line is a company’s only concern.

I was able to handle military culture because despite the difficulty and anxiety of that always-on-point lifestyle, the Marine Corps lives up to its values. When someone broke the rules, the punishment was swift and the message was always loud and clear: Be the best version of yourself . . . or else. In contrast, my experience with corporate culture was that corruption was rampant and no one was held accountable for their bad behavior. Abuses would go unreported, and whatever pride I felt for doing a job well done was quickly eroded by this toxic culture.

It left me craving a disciplined, well-organized career with a clear track to success, yet almost every career I could think of, to achieve that goal, followed the traditional/corporate mentality of profit first, people last.

Positive Aspects of Startup Life

Depressed and disillusioned by life as a civilian, I decided to go to college to officially figure out what I wanted to be when I grew up!

After completing my master’s I moved to Portland, Ore., without any career prospects, in a last ditch effort to find something stimulating and meaningful. And definitely where no one would ever ask me to shout a stupid corporate slogan at the end of a morning meeting, or expect me to completely change my personality to fit in.

That’s when I met Kasey Jones and took my first job at a startup. I was terrified. Startups are new, unproven, they fail all the time, there is no job security, and for the first time in my life, I could not imagine where I would be, or what I would be doing, in ten - or even five! - years.

I thought job security was what I needed, when really it was freedom. The freedom to make my own schedule, work from home, take a sick day without worrying about eating up my annual allotment. It was as if the weight of the world had been lifted off my shoulders.

For me, freedom is the biggest selling point of working at a startup. If I wanted to take a trip halfway across the world for a week, I don’t even need to take time off, because I can do 100 percent of my job from a laptop, wherever I may be.

But that’s crazy! How does my employer know that I am working 8 hours a day and not slacking off?

She doesn’t. But she trusts me to get the work done.

Startups are not multi-thousand employee machines. I know my co-worker's names, their significant others, and way more about their personal lives than would ever be deemed appropriate in a stuffy corporate job. Knowing people that well is what engenders trust and that is the foundation of the culture at any successful startup. You have to trust the people you work with to get the job done because if one cog stops spinning, the whole train comes off the tracks.

That can be a very stressful thought for a lot of folks. It was my primary concern coming into this field, but with that trust also comes a desire to do right by the people you work with. It’s the reason we can burn the candle at both ends for weeks to organize an event for our clients and never once complain or feel overworked because at the end of the day you are helping people who have become your family.

Startup Freedom

As the social media manager for A Better Jones, I don’t just manage clients accounts, I also get to manage a system I created from scratch and fine tune it for performance, every day. I’m not just a piece of the machine that does what he is told, and on other people’s schedules. Rather I am a valued member of a team where I am allowed to innovate, research, and work when I want, how I want, and my ideas are always heard.

The most important lesson I’ve learned with startups is that 18-year-old me got it all wrong. Job security is an illusion. Real job security comes with adapting to the changing job market and pouring blood, sweat, and tears into helping make the people around you better, instead of focusing on nothing but your own career.