How Working for a Startup Changed My Life

If life were a high school, then startups would be the cool kid table right now. Everyone’s talking about them, trying to work for them, or thinking of starting their own. But it wasn’t always that way. Just a few short years ago, startups were deemed to be risky at best, immature and pointless at worst.

Those were the days when I entered into the world of startups.

It all started when I began the third year of a job I hated. I only took the job in the first place because it paid better than a part-time job and it guaranteed that I’d be home by 6:30pm every day, thus allowing me enough time to work on what I really wanted to do: write.

So for three years I kept the job and worked diligently on my writing on the side. The main downside was that I was writing novels, which meant it could be years or even decades before my writing would be successful enough to be my full-time job (if ever). And as year three began, I realized I couldn’t do it anymore. I couldn’t continue to pay rent for life by working a job I hated, all while hoping that my writing would someday maybe eventually come to fruition and have an impact.

This desire to have an impact through my work is what ultimately got me thinking about startups. Startups have always had a reputation of beginning with small teams and moving fast. It seemed like a way to really do something instead of feeling like I was pushing paper just to make someone else money. So I packed my bags and moved to San Francisco…and what happened in the years following is something I could never have predicted.

Transitioning from Corporate America to Startups (Or, Learning to Live without the Rules)

It only took a few weeks to land what would eventually become the job of my dreams. But that doesn’t mean it was easy to transition from the structured world I was working in to a startup. As much as I hated it, I became used to being tasked out with assignments. I was great at executing, but I didn’t know how to create.

To go from a job where I was being told what to do all day long to a job where I was told to “build a customer service system and a digital marketing platform” was a transition I completely underestimated. On the one hand, I was thrilled to finally be challenged and to see what I could do. I pinched myself daily just to make sure it was real! But on the other hand, I went home at night feeling like I would be buried under the pressure. Why would they think I can do this? What is “this” anyway? I didn’t have any experience – how could I build these platforms from scratch?

Luckily most of the self-doubt I felt came on after work, so I was able to learn a lot and get a lot done during the day. But I was working for a company whose mission I truly believed in – helping people pay off debt – and I wanted to succeed so they could succeed. For the first time in my life, my work was personal. I had to pour everything into this company because I knew this company needed to exist. Over the three years I worked there, it became a core part of my being.

But back to the transition. The first six months of the job were wonderful and terrifying at the same time. And there is one – and only one – reason I was ultimately able to succeed and grow my career (and life) to what it is today:

The environment I worked in fostered creation above perfection. Failure was perfectly fine as long as you learned from it, improved, and kept going.

It was the first place where I learned that, to build something, you must first create, measure your results, and iterate like crazy until you get it right.

Here’s the thing: I’ve been a perfectionist for my entire life. I had to have perfect grades, I had to be the perfect daughter/friend/girlfriend, and I had to always be on perfect behavior. While this perfectionism certainly helped me in school, it did nothing but hold me back in life. Instead of having a willingness to try and fail, I wouldn’t actually do anything until it was perfectly planned and foolproof. Experimentation was out of the question – calculation was the only way.

I put myself in a box of perfectionism. It stunted my growth and kept me firmly rooted in fear. Working at a startup where the main goal was to move forward forced me out of that box. There was no time to be perfect! If I waited for something to be perfect, nothing would get done. I never left work with my to-do list crossed off (in fact, the whole team made jokes about how our to-do lists seemed to grow exponentially every day). I never felt like I did anything exactly right. But you know what? I executed like crazy. I tried and failed and tried again. I learned a ton. I launched initiatives and ideas I didn’t even know my brain could come up with. Releasing the need to be perfect opened the floodgates of creativity. And, finally, beautifully, I got comfortable with being uncomfortable.

The Ultimate Freedom and Growth

Getting uncomfortable with being uncomfortable was the best thing that ever happened to me. Instead of stopping at the proverbial red light and waiting for green, I kept moving forward all the time. And if something didn’t work? I learned from it and tried again, but with a better strategy thanks to the knowledge I gained through the failure. Suddenly I could move faster than ever, learn more than ever, and find in myself a creativity and confidence I didn’t think I could ever have.

It was only a matter of time before this philosophy seeped into the rest of my life, and I’m so glad it did! Since I landed in that wonderful place (let’s call it my comfortably uncomfortable seat), I’ve been able to grow my career, move across the country a few times, and enjoy a whole new outlook on life.

Releasing the chains of perfectionism helped me see how full of possibilities the world could be. Instead of obstacles, I saw opportunities. Instead of saying “no” or “I can’t”, I would say “why not?” or “let’s find out!” I went from being a girl bundled in fear to an adventurous spirit. And I’m grateful every day for the amazing things I’ve been able to learn and do ever since.

Even after a great transition, it’s not always easy to retain the new you and not fall back into old habits. I’ll always want to be perfect. I’ll always have fear in the back of my mind. The difference is, this transition has taught me how to deal with it. I can laugh in the face of perfectionism and I can tell fear to get the hell out of my way, even when it lurks in the corner of my brain. Some days are certainly easier than others, but I am far too changed, far too different of a person, to ever go back.

Image Credit: Morgan Sessions


One Comment

  1. Congrats on your new blog. Love the article. Stepping outside the box and your comfort zone opened so many doors. Good for you. My favorite line of the article is ” I got comfortable with being uncomfortable”

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