14 Examples of Risk Taking in Business - Pursue The Passion (2023)

What is one risk you took in business? Did it pay off? If so, how? If not, why?

To help you better understand business risks vs. rewards, we asked business professionals and leaders this question for their insights. From quitting your job to taking out business loans, there are several examples of strategic risks that other business leaders have taken.

Here are 14 examples of risks taken in business:

• Taking Calculated Risks
• Earning Extra Money Abroad
• Working With Family
• Starting a Medical Tourism Company
• Becoming a Student Entrepreneur
• Going All Organic
• Taking Out Business Loans
• Trying a Different Career Path
• Launching a Remote Business
• Scaling a Company
• Creating a Personal Brand
• Transitioning to a New Startup
• Investing in Digital Marketing
• Quitting Your Job

Taking Calculated Risks

One thing I learned in interviewing 300+ business leaders about their career paths is that everyone takes risks in business. The difference is that successful business leaders take calculated risks. As one interviewee put it, “a lot of spreadsheets have gotten me to where I am today.” When the best- and worst-case outcomes can be validated through a calculation, the risk transforms into a logical next step.

Brett Farmiloe, Markitors

Earning Extra Money Abroad

I have played tennis most of my life and worked as a tennis instructor as my side job in my home country in Poland. When I went abroad to study marketing in Germany, I decided to start my own tennis business there to earn extra money for my student expenses. It was a risky decision because of the language barrier and all the legal requirements I had to follow to be a self-employed worker in Germany.

Even though it was challenging at first, I’m very grateful for that experience. Not only did I improve my language and build meaningful relationships, but I also strengthened my self-confidence. During that time, I learned that I could do things that I had never considered before. Now, I know that most limits are only in our heads, and we can achieve things if we only give ourselves a chance to pursue our dreams and passions.

Dorota Lysienia, LiveCareer

Working With Family

Working with loved ones can be a risk, as this does not always work out. Fortunately, I have been able to work with my husband as he is the COO of my skincare clinic. I have a background as a nurse practitioner, and he is a CPA.

Due to the fact that we bring very different kinds of expertise to the business, we’ve worked out a situation where our skill sets do not overlap too much. At the same time, these skill sets are both very important for the growth of the business.

Maegan Griffin, Skin Pharm

Starting a Medical Tourism Company

I left the Army in 2019 to start my medical tourism company. It was a big risk to leave the career path offered by the military. But since I began working on the business full time in March 2020, we have built a network of 17 medical providers in three countries, and we have facilitated major surgical procedures for our first patients. Now, the company is growing, hiring, and helping people save big on their medical care.

Wesley Jacobs, Apollo Medical Travel LLC

Becoming a Student Entrepreneur

Our business was a risk in the beginning. We got started as three students with no experience, putting all our savings into our first business investment: a photo booth. Then, all earnings from the first one went into the second one, the third one, and so on.

There was no promise of success, just working day by day. Now I look back and see that our persistence and patience paid off. Today we employ around 50 talented people, and we are international leaders of passport photo processing. Starting the business was the most significant risk, but the greatest reward!

Tomek Mlodzki, PhotoAiD

Going All Organic

As a bug repellant, it can be very difficult to become 100% organic in this space. A majority of repellants use harsh chemicals to ward off insects, and organic is viewed as not as effective.

We were able to create a very effective repellent while still being organic and safe to the environment, plus help change the image that organic repellents have. It has definitely paid off, and we are working on adding more products to our line.

Michael Jankie, Natural Patch

Taking Out Business Loans

I had just started my first business and knew capital was important to build a successful team. I took out a loan before I even purchased my first home. It was risky, but I believed in my business so much without a doubt, I knew I would pay it back within two years.

That is what I did exactly. I sit here today 25 years later with the same business still profitable and recognize the value of a business loan and make sure to get one for each new business I start.

Galit Ventura-Rozen, Empowering U

Trying a Different Career Path

My degree was in industrial design. Before founding my company, I had never worked in the mental health space. However, I had a passion for providing accessible therapy to others, which stemmed from personal challenges with this issue. My drive to provide a better experience with mental health services for others paid off, and I’m now able to provide online talk therapy to people who are struggling.

Mike Clare, Mood Health

Launching a Remote Business

I started my business and made it remote even before the rest of the world did. It has definitely paid off to start my fun-loving custom pet goods brand. It has been very well-received. We are dedicated to helping pet owners express their love, adoration, and sometimes even their obsessiveness with their beloved pets. I’m also happy to see the rest of the world moving to more remote work even though it took a pandemic to force it on us.

Adam Reed, Crown & Paw

Scaling a Company

One risk we took in business was scaling our company. Scaling our business required a huge upfront investment to hire more employees, develop our product, and produce our product at scale. This was a huge risk, and fortunately, so far, it has paid off.

We see a huge demand for our product, and it is propelling our business to grow very rapidly. At the time, we were worried we were trying to grow our business too quickly, but I think this concern helped us scale our resources to the perfect amount to scale at a rate that was meeting demand.

John Wu, Gryphon Connect

Creating a Personal Brand

As a CBD hemp oil extract business, I initially created my company because my mother had a difficult and tumultuous bout with cancer. As I processed and worked through my own emotions with her diagnosis, the prospect of creating a business dedicated to decreasing the pain of individuals everywhere became an obsession. Such an obsession is why the business exists today.

With that being said, creating a business that is so intrinsically tied to a personal issue is extremely risky. It blurs the line between work and life, creates a subjective perspective that is difficult to separate from, and initiates difficult boundaries that are at times difficult to navigate.

However, I am very happy that I chose my path. My company has helped countless individuals and continues to inspire others to find organic and natural ways to deal with their own health concerns.

Inesa Ponomariovaite, Nesa’s Hemp

Transitioning to a New Startup

After two years of salary stagnation, I left my comfortable, stable job with a 60-year-old company. I became a director at a two-month-old startup, and to my surprise, every startup stereotype was true. Did the switch pay off financially? Yes. But I missed having a predictable workday. And I really missed having a large, comfortable, private office.

Karen Zachary, Anchor Virtual Assistants

Investing in Digital Marketing

When I arrived at my company, I immediately proposed investing heavily in digital marketing. All home services have been slow to adapt in this way and still are. The reason is that all home services, including ourselves, have always relied on word-of-mouth as the foundation for bringing in new business.

Our digital marketing was slow going at first, but our digital ROI continues to increase each year, and we continue to acquire business that would have been missed without taking the leap.

Charles Leduc, Mold Busters

Quitting Your Job

Without any backup plan in place, I left a very comfortable salary and my employer’s health insurance plan. The global death toll was approaching 2 million, and over 10 million Americans were jobless, trying to survive under record-breaking unemployment rates economically.

My family thought I was crazy, but it became abundantly clear that time is precious, possessions are temporary, and I could no longer spend another second enslaved to a job that consumed my entire life.

I took a bet on myself, sight set on the passions that spark my fire. Shortly after saying “Sayonara!” I landed on my feet and significantly advanced my career in a company that actually cares about me as a person, performing meaningful work I enjoy and excel at.

Kaelee Nelson, Pawlicy Advisor

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