Taking Calculated Risks

I've written upwards of 15 different essays over the past couple of months for different scholarships that I had applied to, and a common theme that I found myself reflecting on was the idea of taking calculated risks — it's something that I've become quite good at, and it holds a strong importance in my life.

When I was in the fourth grade, my best friend and I spent hours researching and deliberating on whether or not two $20 investments on our "Slushie Express" machines was going to have a positive return from the yearly neighborhood garage sales. Ultimately, we decided that our "trademarked" Kool-Aid slushies would help us soar through the roof, and we'd be able to pay off our machines just from these two days, easily. And we did.

That was one of the first times I had applied financial and statistical analysis to a situation to understand the underlying risks and rewards at hand. We ultimately had to make an executive decision in the end, still face quite a bit of uncertainty (what if it had rained?), and we made out well on the other side. My friend and I used the same approach for our successful handcrafted-cutting board empire made in our woodshop and sold door-to-door, and again in our first failed company together creating longboards.

I've continued to use the same approach in many segments of my life. It's an approach my executive team and I have used to successfully transition into a new frontier with the Collegiate Entrepreneurs' Organization. It's an approach I've used to determine what University I'd end up at, and it's an approach I've used to plan my future.

As I entered my freshman year (where I'd live in good ol' 205) at Grand Valley, I understood the great importance of Career Fair and securing internships from the wonderful guidance of both of my older brothers. I developed a three-tier plan to get the most out of my summer internships during my tenure as a student, and it's held up almost entirely successful until this year (for good reason). It was planned as follows:

1. After freshman year, get into a local company and learn about software development and how a small firm operates (enter, Spice Jungle).
2. After sophomore year, get into a local, large corporation and learn about software development and how a huge company operates (enter, Steelcase).
3. After junior year, leave Michigan, and enter yet another huge corporation (e.g. Google, Atlassian, Dropbox, Starbucks, Oracle, etc.) and successfully hit the valley while learning about software development from the ultra-marathoners that are Silicon Valley Engineers (enter, failure).

I failed on that third mark, I won't lie. Yet, ultimately it was a decision I made. I applied to a number of places out west as a software engineer, but I began to realize that while I do have a strong engineering background from my experience, there are a million+ way more talented engineers applying for the same roles. I'm not meant to be just a software engineer — I'm meant to be a software-entrepreneur-innovator engineer, and OST is just the place to build on that idea.

I ultimately decided to apply, interview, and join one of the best regional software firms, Open Systems Technologies. OST will provide me with a platform to continue to learn a tremendous amount about software development, consulting, and how a medium-sized firm can operate at its full potential. I'll be able to work in one of the best cultures in West Michigan, and continue to innovate both in and outside of work with some of my side-projects continuing to grow outside of my main-line of work. (The photo above is secretly from the Connectory, and not OST — sorry to disappoint).

Taking calculated risks is all about not being incredibly rash. It's okay to step back, assess a situation, and understand how to move forward based on your experience, advice, and the context of the situation. Having a tremendous circle of people around and supporting me has allowed me to successfully hit all three of those pillars, and it has allowed me to continue to look towards a bright future. Taking risks involves so much uncertainty, but learning to trust yourself and the advice you receive can make taking those leaps much more fun.