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Key Lessons in Risk-Taking for a Happier Life and Career

Risky decisions come in all shapes and sizes. Some come with minimal consequences and some can be life-changing. The gnawing fear of uncertainty keeps many people from stepping into the unknown. Career decisions are particularly daunting, but they’re necessary to get from where we are to where we want to be. After all, wishful thinking — that things will sort themselves out eventually — will only take you so far. That’s why professionals must inspire each other to make empowered decisions to enjoy the careers they want. With this top of mind, here are four key things I learned from taking risks:

I Learned How to Take Action Up until the age of 24, the biggest risk I had taken in my short life was downloading Tinder. Otherwise, across all facets of life, I almost always took the safe route. Career-wise, this meant enrolling in a graduate program at my alma mater in North Carolina with hopes of becoming a social psychologist. My professional experience spanned taking exams and bagging groceries, and with great fear of getting left behind while my peers had already launched their careers, grad school seemed like a wise choice. I started my journey in the Fall of 2015.

Three months and $7,000 later, I quickly realized this was not the right move. In my mind, I was not only a loser but a complete failure who wasted everything I worked hard for. Writing became my coping mechanism for dealing with failure and major depression. I always knew I could write well, but a writing career never seemed feasible — it was just a long-lost passion from my high school days. With my future weighing on my conscience, I could either stay the course or adopt George Costanza’s “opposite” strategy. Staying in school seemed safe, but then I would never see or be the change I envisioned for myself. So, for the first time in my life, I took a risk and dropped out of grad school. Even though I would return home to live with my parents, I had made a critical decision with my career, happiness, and well-being top of mind.

Key Takeaway: If you don’t take action, don’t expect change. Actions big and small are important catalysts for living the life you want to live — both personally and professionally.

I Learned the Value of Breaking the Mould Post dropout, I worked the same grocery job I had in high school during the day, built my writing portfolio at night, and submitted job applications for writing positions whenever I could. After 100 or so applications, I never scored a single interview — just robotic email rejections, if anything at all.

With an admittedly lackluster resume, I had to do something to help me stand out. I stumbled upon an article about a college graduate who penned a brutally honest cover letter to a Wall Street firm asking for an internship. It was a big gamble, but he scored numerous interviews anyway and inspired me to do something similar. After all, I risked my future dropping out of grad school, so what’s one more risk?

I drafted a humorous, brutally honest cover letter and included it in all my applications moving forward. My heart beat furiously thinking I ruined my career before it even got started. Then, just a few weeks later, an executive at a festival startup in Austin, Texas, emailed me back regarding an open Copywriter and Content Creator position. My ridiculous cover letter not only caught their attention but it got me an interview. They then hired me a few more weeks later. It was only a part-time contract position to start, but it jump-started the writing career I wanted. If I had followed any generic cover template devoid of meaning and personality, it’s likely they would have ignored me entirely.

Key Takeaway: The world is constantly changing and rules — whether written or unwritten — are meant to be broken. Dare to be different and try something new.

I Learned How to Build Confidence Two major risks deep, a year later the festival startup secured Series A funding and asked me to move to Austin for a full-time position. I had lived with my family my entire life up to this point, and moving to another city—let alone in another state—made me sick to my stomach. But I knew life had grown stagnant. I saw no growth, happiness, or any reason to stay in North Carolina other than my family. After all, taking two major risks and reaping positive rewards made me feel like I could do no wrong, so I decided to take my biggest risk yet and move to Austin despite never having visited or known anyone.

Being in a new place where everything and everyone around you seems alien forces you to take all kinds of risks to make friends, connect with your colleagues, grow in your career, and ultimately build your confidence. Joining Meetups, going to festivals with coworkers, attending networking events, and working in a startup environment—things I was too afraid to try before—helped me to solidify my place in a new world.

Key Takeaway: Doing things that scare you will solidify the confidence you need to be your best self.

I Learned How to Embrace Failure and Build Resilience After three wonderful years with the festival startup, I, unfortunately, got laid off the week before Thanksgiving in 2018 and began what I thought would be a brutal, long-lasting job search. I took what I learned from past risks and applied to work for a renowned content marketing agency in Austin. I landed a job as a Content Marketing Specialist just a month later — my Christmas was made. I had never worked for an agency before, but I was convinced I was making the right career move that would get me closer to my end goals.

Unfortunately, all that glitters is not necessarily gold. I learned during my first day on the job that I was a terrible fit both culture and skill-wise. They were a great company and lived their values to the fullest, but the environment was simply too fast-paced for my liking and I could never meet deadlines. They let me go just a month and some change later, and I found myself feeling like a failure yet again. I hopped on the phone with my father, a few colleagues, and a former boss over the next few weeks for guidance, clarity, and direction. They all told me some variation of the same thing: “You gave it a shot and did your best. For that alone, you should be proud.

Failure is essential to building resilience and now it’s time to move forward. Take what you’ve learned, try something new, and bounce back.” Within two months, I had taken my newfound resilience and found a job with an artificial intelligence company where I thrived for two years before moving to Scottsdale to work in behavioral health.

Key Takeaway: Sometimes, things not working out is a blessing in disguise. Be thankful for your disappointment, take what you learn, and apply it to the next situation for a better outcome.

The journey to success is almost never a straight line, but if you’re willing to try something new and step into the unknown, you’ll find yourself that much closer to what you want out of your career, and ultimately your life. If you’re wondering whether that career risk will pay off, I challenge you to take that leap with confidence in the outcome. Even if it doesn’t work out, you’re still one step closer to where you want to be.


ABOUT THE AUTHOR: Evan is a passionate and creative individual with over five years of content marketing, social media, and communications experience. Possessing a unique background that spans social experimental psychology, entertainment, artificial intelligence, and now mental health, Evan serves as Senior Marketing & Communications Specialist at

evolvedMD, a leading behavioral health integration company based in Scottsdale. In

his free time, he enjoys hiking, writing short stories, and exploring the local music

and craft beer scene.



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