12 Examples of Making Difficult Career Decisions

In this article, we delve into the challenging decisions that professionals have to make in their careers. We have gathered twelve insightful responses from leaders across various fields, including CEOs and Founders. From choosing family over extended tenure to downshifting your career for work-life balance, these leaders share their experiences and the processes they used to navigate difficult decisions.

  • Choosing Family Over Extended Tenure
  • Shifting From Corporate to Academia
  • Leaving a Full-Time Job to Start a Business
  • Sticking to a Commitment Despite Better Opportunities
  • Focusing on Happiness Over High Pay
  • Transitioning From Physician to Entrepreneur
  • Prioritizing Passion Over a High-Paying Job
  • Withdrawing From a Small Company for Personal Growth
  • Picking a Strategic Partnership Over Market Expansion
  • Accepting Limitations and Seeking Fresh Opportunities
  • Walking Away From Success to Reunite With a Mentor
  • Downshifting Your Career for Work-Life Balance

Choosing Family Over Extended Tenure

The most difficult decision I’ve made was to not extend my three-year tenure as the Chief Economic Adviser to the Government of India in 2021, despite the Honorable Prime Minister being keen that I continue.

Clarity of objectives helps me make tough decisions. My aim has been to balance my career and family responsibilities, especially my kids’ education. In 2021, as my son started Class XI, the next two years were critical; they would determine the path his life takes. So, being there for him during his critical two years was consistent with my objective.

As CEA, I felt I had contributed to conceptualizing and advocating the policy responses that India needed to overcome the Covid pandemic and the preceding economic slowdown. I had witnessed that these ideas had gained traction at the highest levels, especially with the Honorable PM. So, I was confident that these ideas would be carried forward even after I left.

Between enjoying being CEA and fulfilling my family responsibilities, I’m glad I chose the latter.

Krishnamurthy V Subramanian, Executive Director, International Monetary Fund and 17th Chief Economic Adviser (2018-21), Govt. of India

Shifting From Corporate to Academia

I spent the first decade of my life as an actuary in the corporate world. Then, at age 31, I was unexpectedly given a unique opportunity to move into a completely new career as an academic. The proposition presented itself not merely as a career choice, but as a life-altering decision where I had to carefully consider both personal and professional dimensions. 

I used a cost-benefit analysis to help me make the right decision. This involved taking a systematic approach to carefully examining and assessing the advantages and disadvantages of moving into academia. 

After weighing things such as future earnings, long-term career trajectory, legacy, impact, and lifestyle implications (especially important for three young children), I eventually jumped into the academic world and haven’t looked back!

Dr. Mark Farrell (FIA), Actuary and CEO, ProActuary Jobs

Leaving a Full-Time Job to Start a Business

After six years at a well-established firm, during which I had two pregnancies, I craved more meaningful challenges. Leaving the security of my full-time job to start a business was one of the toughest career decisions I’ve made, especially with a family to support. But I felt that I’d peaked in my role and couldn’t envision myself in the same job for another six years.

I spent months reflecting on my readiness, asking myself: Could I make it? Would I succeed? How long could my family go without a stable income stream?

To make the leap, I relied on a set of guiding principles. First, I had to believe in myself and my capabilities. I took calculated risks, carefully evaluating my comfort level with each one. Setting realistic goals and mentally preparing myself for potential setbacks were also crucial.

Starting my company has been both challenging and incredibly rewarding. I am now in control of my destiny and lead a passionate team that empowers clients to achieve long-term success.

Katie Tu, Managing Director, Kepler Search

Sticking to Commitment Despite Better Opportunities

After applying to several jobs in 2007, I accepted a long-term substitute-teaching job at a school district to be a special education teacher. After I accepted the job, I was offered an opportunity to apply for a Director of Gifted and Talented role in another district that paid more money. 

Even though the salary would have been significantly more, I turned down the opportunity because I had integrity and did not want to back down on the commitment I made. In retrospect, it was an idiotic decision, and I never should have turned down the chance to interview. 

The first district could have found another special-ed teacher, and I could have made more money and had more responsibility. Don’t limit your options and turn down potential opportunities that you may regret. Keep your mind open and explore possibilities!

Lynne Williams, Executive Director of Resumes and LinkedIn, Great Careers Groups

Focusing on Happiness Over High Pay

In my career, one of the most challenging decisions I faced was choosing between a high-paying job in a city I didn’t particularly like, and a lower-paying job in a city I loved. To make my decision, I started by listing the pros and cons of each option. I also reached out to mentors and peers for their advice, hoping their insights could offer a fresh perspective. 

Last, I took a moment to reflect on my long-term goals and values. I ultimately chose the lower-paying job because I realized that my happiness and well-being outside of work were crucial for my overall life satisfaction. While the financial sacrifice was significant, the benefits to my mental health and personal growth made it worth it.

Ryan Hawker, Founder, H3 Home Buyers

Transitioning From Physician to Entrepreneur

My first wave of difficult decisions in my medical career began in 1996 when, as a newly graduated physician, I moved to America as a first-generation immigrant. Once I became a physician, it was difficult to shift to entrepreneurship and professional speaking to balance clinical work and not give up my credentials as an oncologist. 

As I shared my expertise about pancreatic and colorectal cancer, more people started being interested and asking for my personal story. This led me to create an Organic Bravery™ framework: 

1. Embracing Uncertainty: being willing to take calculated risks and being comfortable with uncertainty. This involves encouraging innovative thinking, pursuing new opportunities, and learning from successes and failures. 

2. Developing Emotional Resilience: fostering an environment where challenges are opportunities for growth, and failures are viewed as learning experiences rather than setbacks.

Liudmila Schafer, CEO, Founder, Physician, and Medical Oncologist, The Doctor Connect, LLC

Prioritizing Passion Over a High-Paying Job

In my career, one of the most challenging decisions I faced was choosing between a high-paying job with a reputable company and a start-up position that aligned more with my passion but came with risks. To make my decision, I first listed out the pros and cons of each option. 

Then, I consulted mentors and peers for their insights, considering the long-term growth and potential in each role. Finally, I reflected on what I truly wanted in my career: fulfillment or security. Ultimately, I chose the start-up, prioritizing passion and potential growth over immediate monetary gain.

Olivia Kepner, Founder, Coolwood Wildlife Park

Withdrawing From a Small Company for Personal Growth

After dedicating over five years of my professional journey to a smaller company that I deeply cherished and cared about, I left my position and took a new job opportunity at a larger, well-known corporation. 

My decision-making process was rooted in self-reflection, pursuing personal growth, and countless deep conversations with my closest peers and support network. Leaving a familiar place where I had invested so much heart and soul in developing the department and culture weighed heavily on my mind. 

Ultimately, my hunger for new challenges, personal growth, and belief that I could make a difference in a new setting inspired me to take the leap of faith to embrace changes and the unknown.

Tarren Khoury, HR Manager

Picking a Strategic Partnership Over Market Expansion

One of the most challenging decisions in my career was when we had to choose between two potential growth opportunities for our business. The first option was to expand our product line, 101 Karaoke, into a new market, while the second involved entering a strategic partnership with a complementary company. 

To make this decision, we started a thorough decision-making process. We conducted market research, analyzed potential risks and rewards, and sought advice from industry experts. We also held team discussions to weigh the pros and cons of each option. 

After extensive deliberation, we opted for the strategic partnership, as it aligned better with our long-term goals and allowed us to leverage the strengths of both companies. It was a hard decision, but it has ultimately proven to be the right one for our business’s growth and success.

Michael Chien, Small Business Owner, 101 Karaoke

Accepting Limitations and Seeking Fresh Opportunities

There comes a time in everyone’s career when you have to confront the brutal facts. I’d achieved a measure of success, but for several years, I seemed to languish in a series of second-tier positions. There is nothing wrong with being the guy behind the guy. That’s an art unto its own. But it stings when you want more and cannot grasp it.

My turning point decision involved acceptance. After a few near misses and second-place runs, I accepted that the powers that be in this organization simply didn’t see me in the top spot. I also learned what I could from that assessment and then forcefully cast it aside.

One danger with staying too long is that sometimes otherwise exceptional people continue to see you as who you were instead of who you’ve become. I left and was instantly seen with fresh eyes. The experience made me a better leader and a talented developer.

Tim Toterhi, CHRO, Plotline Leadership

Walking Away From Success to Reunite With a Mentor

One difficult career decision that I had to make was in my mid-career, working for a company that had tremendous ongoing media coverage and online viral activity. 

I was the Director of Marketing at the company and worked only with the CEO, who quickly became a true mentor. During COVID, we could pivot from our traditional business and provide solutions for creating temporary hospitals, converting convention centers into COVID relief and recovery centers, and working with government officials and agencies across the U.S. Around that time, the company was sold, and I continued running the Marketing Division. 

My former CEO started a new business venture and asked if I would like to take this new journey with him. While I enjoyed all the success surrounding the former brand, I left the company to work alongside my mentor once again. It was a hard choice because it was a new market for me, but it was the best decision to work with him once again.

Joshua Brownfeld, Director of Marketing, Garrison Flood Control Systems, LLC.

Downshifting Your Career for Work-Life Balance

A few weeks after I turned 38, I quit my full-time corporate America job. It was a hard decision. Looking from the outside in, you would think I was nuts. After all, I was the breadwinner in my family of five. I earned a six-figure income and enjoyed flexibility in my fully remote role.

I received significant financial incentives through equity and had the occasional fun, work-related travel. Last, I took pride in my achievements, as I built a marketing practice from scratch into a highly profitable division of the business. 

But deep down, I felt unfulfilled and exhausted as a full-time working mom. I was constantly spinning on a hamster wheel at full speed, juggling my responsibilities as an agency director by day and switching to being a mom to three boys by night. 

Given my kids are in school, I still wanted to keep my toes in my industry part-time. I found a consulting job for fifteen hours a week. It’s been almost a year since my career downshift, and I’m in a much better place!

Ann Hand, Affiliate Marketing Consultant, The Full Hand