17 Stories of Career Success
We asked industry experts to share a specific instance where they took a risk in their career and it paid off — and what they learned from that experience. Discover diverse paths to professional achievement and growth that offer valuable insights into how calculated risks and innovative thinking can lead to transformative career outcomes.
- Bold Career Shift Leads to Fulfilling Path
- Embracing Risk Shapes Leadership Journey
- Ethical Stand Strengthens Brand Reputation
- Strategic Pivot Launches Space Sector Career
- Content Marketing Gamble Yields Long-Term Success
- Startup Risk Solves Real Industry Problem
- Student Entrepreneur Seizes AI Opportunity
- Cross-Country Move Opens Entrepreneurial Doors
- Process Overhaul Enhances Business Quality
- Specialization Gamble Transforms Healthcare Business
- Market Expansion Drives Significant Growth
- Cloud Integration Boosts Operational Efficiency
- Vision-Driven Leap Creates Digital Legacy
- Career Trade-Off Accelerates Professional Growth
- Stretching Limits Unlocks Leadership Potential
- Self-Employment Gamble Pays Off
- Product Focus Reveals New Business Direction
Bold Career Shift Leads to Fulfilling Path
After completing my engineering degree, my first job was far from what I had envisioned for myself. I worked repairing refrigeration systems in grocery stores, fixing cooling units, display fridges, and freezers. It was steady and honest work, but after more than six months, I knew it wasn’t where I wanted to stay. There was little chance for growth, and I didn’t feel any passion for what I was doing.
A few months before the end of my one-year contract, I began teaching myself SEO and digital marketing in my spare time. Just one month before my contract expired, I made a bold choice: I left that path behind and accepted an internship at a digital marketing agency working on English-speaking markets. The decision was risky. I had no industry experience, my salary dropped significantly, and with no financial cushion, I struggled to make ends meet. During my internship, I even delivered food for Uber Eats to cover basic expenses.
Still, that leap of faith became a turning point in my career. A few years later, I now earn three times more than I did in my first job, I’m thriving in a field I truly enjoy, and I get to channel my skills into passion projects.
The biggest lesson I learned is that growth often requires short-term sacrifice. Stepping away from comfort and stability can feel like moving backward, but sometimes that’s exactly what you need to create space for long-term progress and fulfillment. Looking back, taking that risk was absolutely worth it.
Daniel Ząbczyk
Founder, CzerwonyRower
Embracing Risk Shapes Leadership Journey
The risks have always paid off for me. That mindset shift is one I encourage anyone with a dissenting opinion to embrace. Pause for a moment and ask yourself: Could you really be who you are today without the risks?
In retrospect, I wish I had taken even more risks, leaning into discomfort when I saw possibilities others couldn’t. Risk has shaped not just my career but who I am at my core. I once chose to leave an executive role at a company I loved because we couldn’t align on a career path. It seemed as though they were as invested in me as I was in them until I outlined a vision that deviated from their design, and resistance surfaced.
I had successfully run a market that transformed the people agenda, grew volume, and elevated service metrics. Our team not only built on strong performance but consistently exceeded expectations. I was repeatedly asked to share our model with peers, explain how HR collaboration worked, and advise on strategies for their markets. Over time, I realized what I enjoyed most was transforming culture through people strategies. I saw the need to scale that work across the business and proposed moving into HR to drive people strategy execution. The answer was no.
Within weeks, I received an offer for an HR manager role at another company. It came with less pay, fewer benefits, and a lower title. But I kept two things in mind. First, I trusted my ability and knew I would grow quickly, just as I had before. I was certain I would overdeliver and use the role as a springboard to the future I envisioned. Second, I was clear that nothing mattered more than alignment. I knew the impact I could make, drawing on both my leadership background and general management expertise. At the heart of every successful organization is the ability to understand both the business and the people.
Within three years, I was promoted twice, ultimately into a director role for multiple businesses, three general managers, and a strategic priority. I not only surpassed the initial pay gap but, more importantly, I chose work I loved.
I understood why others thought it was risky, but I never forgot how capable I was. I did not allow their opinions to become limitations for me. Ultimately, I was the only one who knew my path well enough to take it. I believe that the biggest risk we take as leaders is the choice to be ourselves. I have a lifetime of stories that show it is always a risk worth taking. Always remember that your risks got you here.
Anika Apple
Founder & CEO, Remarkably Me Enterprises
Ethical Stand Strengthens Brand Reputation
I once risked alienating a major client by refusing to execute an unethical campaign. They wanted aggressive tactics that would have delivered quick results but dangerously eroded our brand’s integrity. Choosing values over revenue felt daunting, especially because we were still growing and financially vulnerable. Yet drawing that line gave my team confidence that our principles weren’t negotiable, even under pressure. That moral clarity turned into a compass, guiding every tough decision we’ve faced since then.
The payoff was greater trust from future clients who valued integrity as much as results. Over time, that reputation attracted exactly the kind of brands we wanted to serve. The experience taught me that saying “no” can sometimes be the most profitable risk taken. Other entrepreneurs can replicate this by defining boundaries early and communicating them with confident consistency. Integrity rarely feels easy, but it always strengthens your brand long after the conversation ends.
Marc Bishop
Director, Wytlabs
Strategic Pivot Launches Space Sector Career
Three years ago, after two years as a Tech Project Manager, I recognized the transferable value of my accumulated skills and felt ready for a bigger challenge. My research into tech future projections revealed that the Space sector would grow exponentially, demonstrating massive potential for jobs, GDP growth, and technological advancement. Despite having no formal space industry background, I took the calculated risk of pivoting into the Space sector — driven by both personal fascination and this compelling market opportunity.
Rather than making a dramatic leap, I approached this transition strategically with small, achievable milestones. I began actively attending space industry seminars and conferences, immersing myself in the community and learning the landscape. I subscribed to industry newsletters and news outlets to stay current with trends and developments. Simultaneously, I invested in targeted professional upskilling, focusing on areas where my existing project management expertise could translate into space-related applications, technologies, and capabilities. I also strategically grew my LinkedIn network and community, connecting with space industry professionals to learn from those who had advanced in their careers by studying their backgrounds and career paths to understand how they reached their current positions.
This methodical approach paid off when I successfully landed a role at a global Tech company, in their Space capability unit. The risk taught me several valuable lessons: First, that curiosity and genuine interest can be powerful career drivers when backed by strategic action. Second, that skills are often more transferable than we initially realize, as my project management foundation proved invaluable in navigating intricate space-related projects and initiatives.
Most importantly, I learned that calculated risks with proper preparation often yield the best outcomes. Rather than abandoning my existing expertise, I leveraged it as a bridge into an entirely new industry. This experience reinforced my confidence in taking on challenges outside my immediate comfort zone, knowing that thorough preparation and genuine passion can overcome apparent industry barriers.
The transition ultimately launched my career to new heights while aligning my daily work with something truly meaningful by being part of the industry that’s expanding human presence beyond our planet, but also safeguarding our citizens.
Geraldine Olea
Thought Leadership Contributor On Tech, Career Strategy & Dei | Founder & Owner, Academy Olea
Content Marketing Gamble Yields Long-Term Success
Early in our journey, I invested heavily in content marketing while peers focused on advertising. At that time, content seemed slower, harder to measure, and less glamorous externally. Yet I believed in the compound effect of consistent storytelling and evergreen educational content creation. It was risky because results weren’t immediate, and cash flow felt dangerously fragile during campaigns. But within two years, those articles became our best salespeople, consistently generating inbound opportunities.
The payoff went far beyond leads; it gave us authority, credibility, and organic sustainability in the long term. Today, we attract clients who have followed our content for months before reaching out. That risk taught me the importance of betting on foundations rather than fleeting marketing hacks. Small business owners can replicate this by investing early in content that compounds over years. It’s patience disguised as strategy, and it becomes your most loyal growth engine over time.
Jason Hennessey
CEO, Hennessey Digital
Startup Risk Solves Real Industry Problem
When I left the laundry business after building and expanding 2ULaundry, I chose to start Franzy instead of taking another safe leadership role. It was a risk; I went from running a proven, profitable company to building a new franchise platform from scratch in a space where long-standing competitors had decades of head start. It paid off because we believed franchise owners deserved better technology. I learned that risk works when it’s tied to a real problem worth solving, and that moving fast, listening to owners, and iterating in real time beats hiding away trying to build some “perfect” product no one’s even used yet.
Alex Smereczniak
Co-Founder & CEO, Franzy
Student Entrepreneur Seizes AI Opportunity
Starting my business was a risk! I actually started my business while I was still an undergraduate student. I had been researching AI models and realized that as generative AI became more available to the public, the need for AI detection was going to be huge, so I developed AI detection software. I experienced practically overnight success and started my business while still in school. Doing this took a major leap of faith, and even though I was fully confident in my knowledge and technology, I still had worries about my age and being taken seriously. However, I surrounded myself with great people who helped me see that I was making a great move. I learned that having a great support system is everything.
Edward Tian
CEO, GPTZero
Cross-Country Move Opens Entrepreneurial Doors
Yes! I took a risk when I was in my early 30s living in Maryland. I quit my cushy Regional Account Manager job for a large Auto Glass Company. I had a company car, company credit card, and the job involved lots of traveling. I left that position to take a job that paid less and had fewer benefits in a more expensive area: San Diego!
Why did I do that? Because I wanted to live in San Diego more than anything and was not willing to sit around and wait years for an opportunity to come with that company! I absolutely love it. It did not pay off immediately, but eventually, I found my true calling out here, which was to be an entrepreneur. I am now the owner of a fast-growing small local moving business in San Diego, and I really enjoy living here and working for myself! Without taking that huge risk of moving across the country on my own, with no real family or community, I would not be in as good a place as I am today. I’m in a place where I love where I live and what I do for a living.
What I learned is that if you really want something badly enough and are willing to take a risk to get it, it can pay off even more than you ever dreamed.
Steven Soucoup
Owner/Operator, Soco Moves LLC
Process Overhaul Enhances Business Quality
I took a business risk by stopping new client work for one quarter to create an entirely new process that prioritized accessibility and performance. The time I dedicated to creating a reusable design system, development standards, and a client-accessible checklist led to better client matches and reduced revision needs. The decision to pause operations seemed dangerous at first, but it brought better clarity to my proposals, made pricing easier, and the final results demonstrated exceptional quality. The outcome delivered clients who matched better with our services and required fewer modifications to their work. The practice of denying certain opportunities enables you to find your most suitable business opportunities. Establish your core competencies through documentation before you present them to others and establish protective measures.
Darryl Stevens
CEO & Founder, Digitech Web Design
Specialization Gamble Transforms Healthcare Business
The military taught me to obey, while healthcare leadership often demanded going against common sense. The majority of home care agencies are not willing to accept dementia patients due to the increased number of emergency calls and family complaints. I went against industry trends by choosing to focus on dementia care at a time when our rivals were turning these patients away.
The financial risk appeared significant since clients with dementia require four times more staff training and triple the number of after-hours calls. We paid more, approximately $18,000 more a year in insurance and another $12,000 to purchase special equipment.
This specialization transformed our business in less than 18 months. Families with dementia patients are charged 25% more since not many companies provide quality specialized care. We increased our client retention rate to 89% because once families trust our experience, it becomes difficult to switch providers. We now have a waiting list of 6 months, while competitors are struggling to fill basic slots.
Instead of competing on the standard services that everybody provides, healthcare markets reward specialization in areas that other providers do not serve.
Stephen Huber
President and Founder, Home Care Providers
Market Expansion Drives Significant Growth
One of my personal experiences about taking a risk that turned out to be rewarding happened a few years ago when I decided to invest considerable time and resources into expanding our company’s services into a new market segment despite initial concerns about the market’s stability. Trusting my instincts despite the uncertainty, I moved forward with the expansion. The risk ultimately paid off, opening a valuable new revenue stream and driving significant growth for the company. From this experience, I learned the importance of calculated risk-taking, trusting my intuition, and being adaptable in the face of challenges. It taught me that sometimes stepping out of your comfort zone can lead to great opportunities and growth, both personally and professionally.
Jack Nguyen
CEO, InCorp Vietnam
Cloud Integration Boosts Operational Efficiency
Taking calculated risks can drive transformative growth, but thoughtful planning and adaptability are essential.
A few years ago, we faced a decision that could shape our future. We had a reliable data management system, but I saw the potential of integrating cloud technology and AI. The risk was significant — moving away from what worked and investing in new, untested technology.
Despite pushback, I decided to take the leap and partnered with a cloud services provider. We focused on thorough training and constant testing to ensure a smooth transition. Within six months, our new system improved operational efficiency by 40%, reduced data errors by 25%, and led to a 15% increase in customer satisfaction and 20% higher client retention. We also saw a 30% boost in revenue as new clients were attracted by our innovative approach.
Calculated risks, if planned well, can transform a business. If you’re considering a risk, research thoroughly, listen to your team, and stay flexible. Stepping out of your comfort zone can pay off, but it requires preparation and commitment.
Riken Shah
Founder & CEO, OSP Labs
Vision-Driven Leap Creates Digital Legacy
One of the biggest risks I ever took was leaving a business I had built from the ground up — a safe, steady path — to start Evaheld. I walked away from stability because I believed deeply in a bigger vision: creating the future of digital legacy preservation and helping people leave less unsaid with those they love. It was scary, and for a long time there were no guarantees things would work out. But that leap has been worth it. Evaheld is now growing with incredible partners and users, and I’ve learned that when you lead with conviction and purpose, the risk becomes the reward.
Michelle Gomes
Cofounder & CEO, Evaheld
Career Trade-Off Accelerates Professional Growth
I once left a secure job with a good income and joined a smaller company that had no established systems in place but offered much room for decision-making. It was a shock because my income decreased by almost one-third, but it placed me at the round table where client strategies were being developed. The projects I worked on involved ten or twenty clients at a time in a given year, which gave me exposure that I could not have gotten in a larger, more organized setup.
That move taught me that risk is not defined by uncertainty but by the trade-off between safety and accelerated growth. I was able to practice my decision-making skills under pressure, as I used to build tax models and coach small teams in complex filings late at night. Those experiences gave me a sense of judgment that is gaining value with every challenge.
J.R. Faris
President & CEO, Accountalent
Stretching Limits Unlocks Leadership Potential
Early in my career, I took a risk that felt both exhilarating and terrifying. Until that point, I had been cruising along in a steady job, but I saw an opportunity to take on a new project outside of my standard work responsibilities. It was a cross-department initiative that no one else in our organization wanted to lead. The project had high visibility, and the risk of failure would have been apparent, but I felt that gaining this experience and involvement would greatly accelerate my growth and demonstrate my abilities to others.
I dove into the project, unafraid to spend extra time learning details about it and working with partners I had never had the opportunity to collaborate with before. There were definitely times of uncertainty, along with some mistakes I made along the way. However, because I stayed flexible, constantly asked for feedback, and was able to learn in real time, the project was a success! In fact, it exceeded our expectations and provided me with opportunities to move into new leadership roles and responsibilities that I had previously thought were no longer available to me.
The most significant lesson I’ve taken away is that taking risks doesn’t necessarily equate to making a big leap; it can be as simple as stretching your limits in a manageable way, taking action, and being willing to potentially fail forward. It solidified the idea that growth primarily comes through risk and uncertainty, trusting your intuition, and leaning into uncertainties rather than away from them. This mindset has greatly impacted how I seek opportunities since then and has made me more confident in dealing with complexity and striving towards meaningful forward movement.
Sergio Oliveira
Director of Development, DesignRush
Self-Employment Gamble Pays Off
I would say that starting a business and working for myself was one of the biggest risks I’ve taken in my career. This can be daunting for just about anyone. I have found it to really pay off, though, as I enjoy high-level leadership and the responsibility that comes with it. Mostly, I learned from this experience that sometimes the things that are hard and scary are the most worthwhile risks to take.
Soumya Mahapatra
CEO, Essenvia
Product Focus Reveals New Business Direction
The biggest risk I ever took was leaving our agency’s comfort zone to create Zaturn. I chose to abandon steady client contracts to work on a product that had no revenue and many uncertainties. The first week without client phone calls made me wonder if we had lost our minds. Our first paying customer joined us, followed by ten more users, and then a hundred.
The most frightening transition revealed our most concentrated direction. Our work with clients required constant reaction to their needs. Through Zaturn, we created our own forward-thinking solution, which represented our prediction of marketing industry developments.
Vincent Carrié
CEO, Purple Media
