How do you align your career path with your core values and aspirations? We asked industry experts to share an example of a time when they had to make a difficult career decision. Here are the factors they considered and how they ultimately made their choice.
- Follow Your Own Path
- Value Integrity Over Money
- Leap for Personal Growth
- Choose Impact Over Prestige
- Align Career with Personal Values
- Delegate for Strategic Growth
- Choose Growth Over Comfort
- Pursue Passion Over Stability
- Join a Team for Greater Impact
- Pursue Education for Long-Term Goals
- Specialize for Sustainable Growth
- Embrace Innovation and Risk
- Value Independence Over Stability
- Lead with Vision and Innovation
- Empower Women Through Business
- Work Hard for Long-Term Success
- Take Risks for Career Fulfillment
17 Real-Life Examples From Experts
Follow Your Own Path
Sometimes, the best career decisions don’t make sense to anyone but you. My post-grad plan after my master’s was simple: explore Asia and figure out my next steps. But when an amazing job offer landed in my lap, I changed course. For two years, I poured myself into that role, but something inside me was restless. I realized I was following someone else’s version of success. Finally, I chose a different kind of adventure: I quit, boarded a plane to Nepal, and embraced the unknown. My decision to travel instead of “settle down” gave me a new lens on life, deepened my confidence, and taught me that risks don’t derail your career—they shape it.
Denise Fowler
Founder and Career Coach, Career Happiness Coaching
Value Integrity Over Money
In 2008/2009, millions lost their jobs in the United States. Out of the over a hundred applications I submitted, I got three interviews and one job offer to be a middle school special education and emotional support teacher. About two weeks after I started, I got a phone call to interview for the position of Supervisor of Gifted and Talented in another school district, and it paid a lot more money.
I decided not to interview as I believed it would demonstrate a lack of integrity in the commitment I had already made. At that time, I didn’t know what I didn’t know about looking out for number one: ME! I can’t tell you how much I regret that decision today. It would have changed my entire career trajectory for quite some time.
Although I love what I do now, I should have chosen to explore the opportunity to interview instead of passing it by. Lesson learned to carpe diem!
Lynne Williams
Resumes & LinkedIn – Executive Director, Great Careers Network
Leap for Personal Growth
One of the most challenging career decisions I faced was leaving my stable corporate position in digital marketing to start my business. After 15 years in SEO and digital marketing, I noticed a significant gap in the market for reliable, transparent link-building services. Despite having a comfortable salary and an established career path, I knew I needed to leap.
The key factors that influenced my decision were market opportunity, personal growth potential, and the ability to solve a real industry problem. I carefully evaluated my savings to ensure I had a 12-month runway, assessed the competitive landscape, and consulted with trusted mentors.
Looking back, this decision taught me three crucial lessons:
- Always validate your business idea with potential customers before leaping. I spoke with 50+ business owners to confirm the market need.
- Have a clear financial runway. I ensured I had enough savings to sustain myself for at least a year.
- Start building your business part-time while still employed. I spent six months developing my business plan and initial client base before going full-time.
Maurizio Petrone
Founder & CEO, PressHERO
Choose Impact Over Prestige
My most pivotal career decision came when I was offered a prestigious position at a multinational consulting firm while simultaneously receiving the opportunity to lead the digital transformation of a smaller, family-owned education company. The multinational role offered significant prestige, a 40% higher salary, and a clear advancement trajectory. However, the education company presented the chance to build something from the ground up, with direct C-suite access and the ability to shape organizational strategy.
I approached this decision through what I now call my “Impact-Growth-Values” framework:
- Impact Potential: While the consulting role would expose me to diverse industries, the education company offered the opportunity to create lasting change in an industry I deeply cared about. I could see a direct line between my work and improved educational outcomes for thousands of students.
- Growth Architecture: The multinational would provide structured training and a proven career ladder. However, the education company would force me to develop a broader skill set—from strategic planning to stakeholder management—in an accelerated time frame. This “pressure learning” environment appealed to my development goals.
- Values Alignment: During my decision process, I had extensive conversations with leaders from both organizations. The education company’s leadership showed a genuine commitment to innovation and social impact, matching my personal mission of creating scalable social change through business solutions.
I ultimately chose the education company, but with a twist—I negotiated a board advisor role with an ed-tech startup to maintain exposure to the broader industry. This decision proved transformative: within two years, we increased the company’s digital learning reach by 300%, and I developed expertise in organizational transformation that would have taken years to gain in a more structured environment.
The key learning wasn’t just about making the right choice, but about creating hybrid opportunities that maximize both impact and growth. This experience taught me that career decisions aren’t always binary—sometimes the best path involves creatively combining elements of different opportunities.
Shruti Parashar
Founder, GOALisB
Align Career with Personal Values
During my medical training, I faced a particularly difficult career decision about whether to pursue a residency program or leverage my MD degree in a non-clinical path. On one hand, I had a deep passion for patient care and the clinical side of medicine, but on the other, I was drawn to the flexibility and broader impact I could achieve through writing, research, and education outside of traditional practice.
I considered several factors: my long-term personal and professional goals, the lifestyle I wanted to maintain for myself and my family, and how I could best use my skills to make a meaningful contribution. I also weighed the financial implications and the demands of residency against my desire for a balanced life.
Ultimately, I chose a non-clinical path, focusing on health education, writing, and advocacy, where I could still use my medical knowledge to help others in a way that aligned with my values and priorities. It wasn’t an easy decision, but by considering both my passions and practical realities, I was able to carve out a fulfilling career path that continues to evolve.
Tansha Casarez
Founder & Lead Visionary, HER BALANCED WORLD
Delegate for Strategic Growth
One of the most challenging career decisions I faced was determining the optimal time to transition from a hands-on operational role to a more strategic leadership position. This shift required me to delegate daily tasks and trust my team to manage them effectively.
In making this decision, I considered several factors:
- Team competence: Assessing whether my team had developed the necessary skills and confidence to handle responsibilities without my direct involvement.
- Business growth: Evaluating if the company had reached a stage where strategic oversight was more beneficial than day-to-day management.
- Personal development: Reflecting on my own career aspirations and the desire to focus on areas where I could add the most value, such as business development and long-term planning.
After careful consideration, I chose to delegate operational responsibilities to trusted team members, allowing me to concentrate on strategic initiatives. This decision not only empowered my team but also facilitated the company’s growth and innovation.
For entrepreneurs facing similar decisions, it’s crucial to assess your team’s readiness and the potential impact on your business. Trusting your team and focusing on strategic leadership can lead to significant growth and success.
Steve Neher
CEO, Mail King USA
Choose Growth Over Comfort
One of the toughest career decisions I’ve ever made was taking a significant pay cut to transition into a role that promised more opportunities for growth. It felt like a leap of faith (and let’s be honest, it wasn’t easy seeing that smaller paycheck). But deep down, I knew my current role had me stuck in neutral when I wanted to reach my long-term goals.
I thought hard about this decision. First, I looked at the bigger picture—where did I want to be in five or ten years? The new role offered me the chance to gain leadership experience, tackle challenging projects, and expand my skills in ways my old job simply couldn’t. Then, I crunched the numbers. Tightening the budget was difficult, but the investment in myself and my future earning potential promised a much bigger payoff.
In the end, it was about choosing growth over comfort. Yes, it was scary, and yes, I had moments of doubt, but this decision transformed my career. I’ve gained skills, connections, and experiences that set me up for the long haul. Sometimes, you’ve got to bet on yourself, and this was one of those times.
Eva Chan
Certified Professional Resume Writer (Cprw) and Senior Content Specialist, Resume Genius
Pursue Passion Over Stability
My most challenging career decision occurred when I had to transition from the energy sector where I focused on renewable power generation, to the education field. Two key factors influenced my decision. First, a growing passion for academia and second, my perception of the potential societal impact. Having worked in business development roles within both sectors, I found immense value and satisfaction in educational partnerships as it directly impacted individual students and global education.
Ultimately, I decided to contribute to the education realm at WeUni, helping students worldwide make informed decisions about their higher education path. This shift involved a steep learning curve but my diverse background proved beneficial, allowing me to implement best practices from my previous experiences, and make a contribution that truly matters.
Andrea Pecetto
Cco- Head of Educational Partnerships, WeUni
Join a Team for Greater Impact
One of the most challenging career decisions I ever had to make was whether to stay in a secure, well-paying job or to follow my heart and take a risk on something truly meaningful. For seven years, I worked as the Office Coordinator of a union, earning a great salary with the promise of a pension, healthcare, and all the traditional markers of stability. On paper, it was the kind of job anyone would hold onto. But my heart wasn’t in it.
My partner, Mark Schulze, was in the early stages of building our business. I could see the passion and vision he had for shaping it into something extraordinary—a company dedicated to storytelling through video production. It was infectious. The thought of contributing to something we could build together, something that reflected our creativity and values, became harder to ignore.
The decision wasn’t easy. I had to consider the risks—leaving the security of a stable job for the uncertainty of a small business in an industry that was just beginning to blossom. I thought about what mattered most to me: Was it financial security, or was it the chance to create something meaningful with the person I loved?
Ultimately, I chose to leave the union job and dive into the business with Mark. It was a leap of faith, but I’ve never regretted it. Over the years, we’ve grown the company into San Diego’s longest-standing video production company, winning awards and working with incredible clients. More importantly, it allowed us to live a life that aligns with our values, doing work that brings us joy and helps tell important stories. Looking back, I know I made the right choice—not just for my career, but for my heart.
Patty Mooney
Producer, Editor, Content Creator, Crystal Pyramid Productions
Pursue Education for Long-Term Goals
One of the hardest career decisions I made was stepping away from full-time freelance writing to join my current company as their Managing Editor. For years, I built my career as a solopreneur, enjoying the flexibility and independence that came with running my own business. But as much as I loved freelancing, I found myself wanting to be part of something bigger—collaborating with a team, shaping content strategy at a higher level, and helping other writers succeed.
The decision wasn’t easy. Giving up the control and variety of freelancing meant trading one kind of freedom for another—more stability, but also new responsibilities. I weighed factors like long-term growth, the impact I wanted to have, and whether the role aligned with what I loved most about content marketing. In the end, I knew it was the right fit. It gave me the chance to not just create content, but to build something meaningful with a team that shared my passion. Looking back, it was the best move I could have made.
Jenn Greenleaf
Managing Editor, nDash
Specialize for Sustainable Growth
One of the most difficult career decisions I had to make was a few years ago when I decided to forgo a promising future as a software engineer, earmarked for roles in technology leadership, at a massive multinational financial institution to attend graduate school in a foreign country.
I started my tech career at JP Morgan Chase in Mumbai, India. I really liked my job, and the people who I worked with. And I was also very good at it, landing successive promotions to rise to the post of Senior Associate in the investment banking business of JP Morgan. I could’ve easily stayed on course, and climbed the ladder of corporate leadership at one of the biggest banks in the world.
However, I knew that I had to be true to myself, I still had a lot more to learn and experience and that I needed to pursue further educational opportunities—preferably at a top graduate school program in the US. Fortunately, I got accepted to the University of Arizona’s Technology Leadership Program, which allowed me to pursue master’s degrees in Management Information Systems in addition to an MBA.
Though the journey post making the switch has not been easy—including attending grad school and working multiple jobs as a grad assistant during the pandemic—with hindsight I can say that it was the best decision I have ever made.
Studying and working in the US has brought many challenges, but even more satisfaction. I find myself again working at a company where I can pursue great things, work with incredibly talented people, and learn a lot along the way.
Things that helped me make a decision were my focus on my long-term goals, careful consideration of the risk involved vs. the potential and magnitude of the payoff, but most importantly, a gut feeling. Being true to how I imagined myself helped me deal with the consequences of my decision—the good and the bad ones.
Anuj Mulik
Software Engineer, Featured
Embrace Innovation and Risk
One of the most significant career decisions I faced involved the strategic direction of my law firm. When I first started, we handled a broad range of personal injury cases. While this provided a solid foundation, I recognized the need for a more focused approach to achieve sustainable growth.
I carefully considered several factors in making this decision. I thoroughly researched the legal landscape in different regions, identifying areas with high demand and favorable legal environments. This led me to relocate my practice to New Mexico, where the legal climate was more conducive to pursuing complex cases. I also analyzed the specific needs of clients in my target market, recognizing a significant gap in representation for individuals facing medical malpractice claims. Finally, I sought to differentiate my firm by specializing in medical malpractice cases, positioning us as experts in this complex and challenging area of law.
Making this shift required significant investment and involved considerable risk. However, I ultimately decided to proceed based on my conviction that this strategic direction would better serve my clients and position the firm for long-term success.
This decision has had a profound impact on my career. By specializing in medical malpractice, we are able to provide highly specialized and effective representation to clients who have suffered significant harm. This focus allows us to make a meaningful difference in the lives of those we serve and has ultimately led to greater professional fulfillment.
James Wood
Law Firm Founder and Medical Malpractice Attorney, James Wood Law
Value Independence Over Stability
I recall being offered a more traditional marketing leadership position at a well-established company that promised a comfortable salary and excellent organizational stability. At the same time, I had the opportunity to join a rapidly growing DTC brand that aligned more closely with my passion for data-driven innovation despite the inherent risks of a smaller, more agile environment.
I weighed several factors:
- Long-Term Growth Potential: Could I implement the advanced analytics and iterative testing I’d become known for?
- Cultural Fit: Did the company’s mission reflect my drive to build more customer-centric and experimental marketing teams?
- Risk Tolerance: How would I handle a leaner budget and a more volatile growth path compared to a well-funded corporation?
Ultimately, I chose the DTC brand because I believed my track record of scaling e-commerce strategies and fostering cross-functional collaboration would flourish in an environment where I could innovate. Although it meant embracing more uncertainty, the decision allowed me to transform an emerging brand into a serious market contender. It validated that my core skill set—data-informed strategy and customer-focused execution—was truly valuable in a high-growth context.
Windy Pierre
Founder, eCommerce Manager dot co
Lead with Vision and Innovation
As a self-employed individual, one of the most challenging decisions I faced was whether to continue running my own business or to take on a more stable, full-time role with a company. I weighed factors like financial security, growth potential, and personal satisfaction. On one hand, self-employment offered flexibility and the opportunity to work on projects I’m passionate about.
On the other hand, a full-time job promised a steady income and less risk. After considering the long-term goals of my business, my desire for independence, and the satisfaction I find in building something from the ground up, I chose to stay self-employed. The decision ultimately came down to valuing the freedom to create and manage my own path, even if it meant facing the uncertainty that comes with it.
Rahul Shrivastava
Founder & Pastry Chef, World of Cookies
Empower Women Through Business
Stepping into the role of CEO at Invensis Technologies marked a transformative moment in my career. It was a decision to embrace not only leadership but also the responsibility of driving innovation and growth for a 5000+ strong organization. Three factors influenced the choice: alignment with long-term goals, the potential to make a global impact, and the ability to steer the organization toward next-gen solutions like RPA, AI, and Analytics.
The chance to position the company among the “Top 10 Most Promising BPOs in India” reinforced the belief that calculated risks often lead to significant rewards. Ultimately, it was about embracing challenges with a clear vision and commitment to creating world-class teams and solutions. This decision has shaped a journey defined by resilience, innovation, and a passion for transformative leadership.
Anupa Rongala
CEO, Invensis Technologies
Work Hard for Long-Term Success
Partnering as a co-founder of a faith-driven, women-owned business was a deeply personal and faith-led decision. I wanted my work to reflect my passion for empowering women and busy moms, reminding them that they are deserving of self-care and love.
This company’s mission aligned perfectly with my values. Each piece is named after an “I Am” affirmation, inspired by the belief that we are created with purpose and strength. When women step into these pieces, they are reminded that they deserve to be loved and nurtured aside from all the roles they play.
Choosing this path was more than a career move; it was an act of faith and purpose. I saw the opportunity to serve women in a way that uplift their spirits and encouraged them to embrace their best selves, all while being part of a community grounded in shared values.
Mandi StGermaine
Co-Founder, MBS | The Woman Beyond the Cape
Take Risks for Career Fulfillment
I always laugh when people ask me how I became an overnight sensation, I smile and respond that I have worked my butt off for 35+ years! There is no shortcut to success—no manual or playbook either. I have all the war wounds and scars from years of stumbling, falling, getting up, and trying again until I make it work.
I commuted 56 miles each way to work for more than 3 years, worked thousands of miles away from my husband for a big job for almost a year, I worked 80+ hours per week on Wall Street in the 80s and at 3 successful startups in the 90s and early 2000s. By commuting for jobs that gave me great work experience and working long hours at a young age, I knew I was creating long-term career opportunities, more options and flexibility down the road which is a tradeoff I was willing to make to set me up for long term success.
Paige Arnof-Fenn
Founder & CEO, Mavens & Moguls
