14 Risks That Are Worth Taking


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What’s one risk that you’ve taken that looking back, was kinda worth taking in life? 

To help you become more comfortable taking risks in your life, we asked HR experts and business leaders this question for their best advice. From leaving a comfortable job to follow an entrepreneurial passion to investing until it hurts, there are several risks on this list that you may be interested in taking in the future!

Here are fourteen risks, worth taking:

  • Leaving A Six-Figure Job For Entrepreneurship
  • Follow Your Passion
  • Short-Term Financial Success Or Long Term Fulfillment
  • Hiring Your First Employee
  • Moving Away From My Hometown
  • Spend Money I Couldn’t Afford
  • Moving To A New Country
  • Don’t Be Afraid To Be The Young One
  • Pushing Past Societal Norms
  • Quitting My Job Without A Backup Plan
  • Risk The Office
  • Invest Until It Hurts
  • Taking An Initial Pay Cut To Gain Experience
  • Career Transformation

Leaving A Six-Figure Job For Entrepreneurship

Just over two years ago, I left a six-figure job with the intention of joining an early-stage start-up. But, unfortunately, that business failed before I could even join the team. Now left having no job or steady income but some savings, I decided to try and build my own business. Thinking about it rationally, I realized that there was no better time to give this a shot but now. I wasn’t married, and I didn’t have much going on in terms of responsibilities. It was clear that unless I tried this now, I’d likely find an excuse not to do it later. While it’s been super tough, and there’s been a fair share of pivots, I’m happy to look back and enjoy the flexibility I now have in my life as a remote company business owner. All I know is If you don’t take calculated risks, you’re never going to move mountains. Maybe you won’t even move an inch, so keep pushing!

Ahmed Mir, Sip Coffee House

Follow Your Passion

Too often we follow our mind and weigh the cost and benefits of a decision. I have found that following my heart, even though the mind’s cost/benefit sheet was heavy on the cost side, always brought me the most life benefits. I once left a job environment I loved for a start-up company that was unpredictable. It took a couple of years, however, in the end, my new job and environment far outweighed the benefits of my old job.

Sonja Talley, CORE HR Solutions, LLC

Short-Term Financial Success Or Long Term Fulfillment

I spent the first 5 years of my career in the financial services field. I was climbing the corporate ladder and making a very respectable amount of money. However, I would come home night after night and feel an overwhelming sense of dissatisfaction with how I was spending my days. While I wasn’t able to put it into words at that time, the gift of hindsight has led me to the conclusion that I wasn’t living my purpose. So, with the support of my wife, I decided to re-boot my career and start over in a new field. It’s been 21 years since that decision and it was the single best career decision I’ve made. I feel like I am in constant alignment with who I am and what I do and that is worth its weight in gold over the long-term.

Brian Mohr, anthym

Hiring Your First Employee

Going from freelancer to business owner is quite a transition, and mustering up the courage to send your first offer letter to your first employee feels like a huge leap. It’s scary to change your lifestyle, pursue a vision of success, and have someone else financially dependent on the success of your business. But like any carefully calculated risk, hiring people is often a risk worth taking. Great employees help you do more than you could ever do on your own. Looking back, I’m happy that I decided to get out of my comfort zone as a freelance and start building a team that could make a positive impact on small businesses. 

Brett Farmiloe, Markitors

Moving Away From My Hometown

After growing up in Pittsburgh, PA, I left on January 20, 2002, to venture out west. I wanted to challenge my comfort zone and take on a new adventure. I loved my family and friends and left the known for the unknown. Moving from the East coast to the West coast mentally, I found it took me about 6 months to hit my stride at business, with friends and the new experiences in my new hometown. As a car guy, I enjoyed seeing all the modified cars and enjoyed waking up to the sun, virtually every day; a big change from the 300 days of clouds I was used to. The easy path, or the more challenging path…it’s our choice. While the easy path is much more comfortable, the challenging path is filled with adventure and amazing insights about ourselves.

Mark Jamnik, Enjoy Life Daily

Spend Money I Couldn’t Afford

I started AtticSalt seven years ago with barely any money. What I lacked in budget, tried to make up in work ethic, and marketing. We invested more into the quality of our work than the client was willing to pay for at the time. We underpromised and over delivered every single time. The payoff was extraordinary. Our clients were so satisfied that they referred their friends and family to us. Our portfolio also looked like it was from a much bigger firm, and that attracted bigger clients. Once I saw that our work was converting for us, I decided to spend money I couldn’t really afford to drive more traffic to it. I was so confident that if more prospective clients saw what we were doing they would want to work with us. I was right. Even though our clients are spending far more these days, we still strive to overdeliver on everything. We also still spend more money on marketing than agencies double our size.

Rani Sweis, AtticSalt

Moving To A New Country

I took the risk to leave my home country and embark on a new adventure where I had better opportunities to grow. It’s very easy to get stuck in your comfort zone, a place where you are not happy, where you feel stuck, you don’t see many opportunities to grow, and you’re only surviving at this point. Getting out of our comfort zone is scary, and many people talk themselves out of it because we are afraid of the uncertainty. Though it was hard for me to leave my country and family, I learned a lot from moving to a new country and challenging myself to make it on my own. This experience not only helped me personally, but it made a huge difference in my professional life as I learned to push myself to give my very best. It also made me a quick learner and a lot more responsible. I learned to believe in myself and my abilities and to embrace change.

Jessica Ulloa, MyPerfectResume

Don’t Be Afraid To Be The Young One

Don’t be afraid to be the young one. This was something when I was 21, I remember being an intern in a meeting and I spoke up and was nervous because I was in a room of people that have been working 5, 10, 15 or even 20 years. They ended up listening to what I had to say and actually implemented a new initiative within the organization. I was worried they would think, “Who is this college girl like offering her two cents?”, but age doesn’t necessarily mean wisdom in the sense that you can’t feel slighted or that can’t contribute just because you lack years under your belt from a career perspective. I think everybody always has good advice and insight to offer. So never hold back, especially when you’re in the infancy of your career. When you speak up and you have your voice heard, you put yourself in a better position and it leads to a greater sense of respect and self-confidence for yourself.

Stephanie Hayman, Global Payments Integrated

Pushing Past Societal Norms

There is always some risk when setting out to create a product and kickstart a business venture. The risk, however, varies upon your industry. For me, I set out to create a delicious and diverse chili sauce to represent my Sichuanese background and bring recognition to my culture’s delicacies. In this, there was a good amount of risk. Food from my home is not widely accepted as high-end. People expect cheap. So, getting notoriety was initially a challenge. I had many critics of my business telling me that people would not pay the price for my sauces. Despite this, my company has prevailed. I would encourage all women, especially minorities setting out to create something they love, to take the risk.

Jing Gao, Fly by Jing

Quitting My Job Without A Backup Plan

Although I would never recommend this normally, I chose to resign from a position in an incredibly toxic work environment without having another job lined up. I was lucky enough that I had established a strong network and built relationships personally and professionally to immediately pivot into HR Consulting. But, the most valuable lesson was that it’s important to know your value, go where you’re valued, and take control of your professional future. No one should allow their mental health to suffer to the extent that they dread going to work every day. I wouldn’t change a thing about that choice in retrospect, as scary as it was.

Eric Mochnacz, Red Clover

Risk The Office

The one risk I took that was worth taking in life was getting an office back when we scaled the business. We had no profit – but I needed a place to work outside of my home where I could focus. I looked at a co-working space that was about $450 a month and it changed our business. It allowed me to focus, appear bigger than what I was to consumers and have a place to network.

Trevor Rappleye, CorporateFilming.com

Invest Until It Hurts

I was investing in a new business venture that I was going to be a part of running. A mentor told me to “invest until it hurts.” I cashed in everything I had to invest in the company. We sold the company three years later, and I quadrupled my investment. The risk of investing everything in myself and my business partners set me up financially to pursue other opportunities.

Kimberly Bogues, Flourish Business Services, LLC

Taking An Initial Pay Cut To Gain Experience

Taking an initial pay cut to gain new experience as an agency marketer was absolutely a risk worth taking. At the time, I was an in-house marketer at a finance firm. Internal marketing positions are known for paying very well and having other “cushy” perks when compared to agency marketing, such as being less stressful. That said, I had hit a wall with what I was going to learn, and frankly, I was bored. To widen my knowledge and work with other industries and their unique challenges, I needed to be in the fast-paced, “sink or swim” environment of an agency. Looking back, it was hands down the best career move I could have made. I ultimately surpassed my income, working now as both an agency marketer at an incredible agency, as well as a freelancing. I have zero boring days (seriously!) and learn more new and exciting things about marketing every single day.

Jessica Mason, Digital Marketing Strategist

Career Transformation

Career transitions are one risk that pays off – as long as you are moving toward a goal, rather than merely trying to escape where you are now. As a resume writer, I facilitate hundreds of transitions per year, from bank branch manager to corporate trainer, from accountant to marketing director, from retail manager to HR exec. Since I transformed from HR exec/recruiter to professional resume writer and small business owner 12 years ago, I can confidently report that it’s worthwhile!

Joni Holderman, Thrive! Resumes

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