My Biggest Career Regret I Wish I Could Go Back and Change

We all make bad career choices at one time or another. However, some choices are more serious than others and can have a far-reaching impact. If you have some career regrets, you’re not alone.
Roughly 41% of employees who didn’t combine their personal passions with their work regretted their career paths, according to a survey conducted by Philips North America. On the other hand, just 23% of workers who were able to do so regretted their paths. Another study from found a whopping 77% of workers have made career choices they regret.
The Cheat Sheet asked a few professionals to tell us about the biggest regrets they’ve had. Here are some career regrets folks wished they could go back and change. Do you have any of the same regrets?

My biggest regret: I let my boss bully me

Angry Birds
Is your boss an angry bird? Don’t get pushed around. | Rovio

When I was a teacher, my boss was a micromanager who hated independent thought and tried to push me out of a job. After five years, she succeeded. My biggest regret is I put up with her bullying for five years. No one should have to spend eight hours a day in a toxic, miserable environment.

My advice

I would advise all employees to keep their dignity and stand up to bullying bosses. At the very least, look for another job. Life is too short to spend eight or more hours a day stressed and miserable. If more people refused to put up with workplace bullying, it would stop.
Jonathan Bennett, founder, The Popular Man

My biggest regret: I accepted the first job offer

woman having job interview
Don’t jump at the first offer. |

My biggest regret is moving from a human resources management position to a regional human resources manager role from one company to another on a lateral salary move. Breaking down the salary from the human resources manager job plus bonus and the flat salary of the regional position, it was a no gain in incentive, with additional work and travel. At that time in my career I wanted a new job so badly that I accepted the first offer they made without negotiating anything.

My advice

Looking back, I would have considered all options prior to accepting the position and had a solid understanding about the requirements. I would have spent more time preparing for salary negotiations and walking away from the role if I did not feel comfortable. Always have a plan B, and walk away if you feel uncomfortable with the situation. Do not get desperate and accept the first offer.
Matthew Burr, human resources consultant, Burr Consulting, LLC

My biggest regret: I dated a co-worker

couple smiling
If you start a relationship with a co-worker, learn how to separate your work and personal lives. |

I took a job as a district supervisor in a nationwide retail organization.  At first, I worked crazy-long hours, spending my days in the field and doing paperwork in the evening at our regional office. Most evenings, a fellow female supervisor and I were the only ones in the office, and we often stopped at a nearby fast-food place for something to eat before heading to our homes.
One such night we were talking about movies, and she mentioned a new movie she wanted to see, but none of her friends would go with her. I volunteered to go with her. That movie led to multiple dates and a budding romantic relationship. We didn’t know what our boss would think, so we kept things very quiet. At some point, her old long-time boyfriend got back into the picture, and our relationship eventually ended.

My advice

After our breakup, working around the office became difficult for both of us. I was quite happy when I received a promotion that moved me to another city 130 miles away. Although the episode involved some pain, I learned an important lesson: Dating co-workers is almost always a bad idea. I never did it again.
Timothy Wiedman, associate professor of management and human resources (retired), Doane University

My biggest regret: I got a degree I wasn’t interested in

person holding graduation cap and degree
Don’t get a degree just because everyone says it’s the right thing to do. |

My biggest regret was getting my master’s degree in finance. I took it only because of a large scholarship and it being a nine-month commitment. Our startup was taking off, but I still decided to pursue the degree even though I wasn’t interested in the field.

My advice

Don’t let schooling interfere with your education. I should have dropped out of the program one month in. Our company was growing very rapidly in terms of employees and revenue, and I wished I had more time per week to dedicate toward it. Drop out of school if it makes sense. The work I was doing outside of class was my dream job. I couldn’t wait to get out of class and bike over to the office. I was learning so much on a day-to-day basis at work that it rendered my classroom experience completely useless.
Ettore Fantin-Yusta, director of marketing at

My biggest regret: I turned down a new job opportunity to stay with an employer

job interview
If a job opportunity looks promising, go for it. |

My biggest career regret was not taking a job opportunity because my current employer created a role for me (only after I told them I was leaving). I thought after being at the company for years that I was truly “valued.” [I later found out] they only needed me for a limited period of time and then that job ended. I should have followed my gut instinct that had led me to go after another job offer.
Too often, as employees you forget when it comes down to it, sometimes you’re just a title and salary number on a ledger. Getting an opportunity and then staying where it’s comfortable typically doesn’t work out. Your employer will know you aren’t happy, and in the end the relationship changes.

My advice

Don’t look for a job hoping your current employer will “wake up” and see how awesome you are.  Once you have made the decision, stick with it. If all of a sudden a raise and title change are available, you should be concerned. What was keeping them from doing something sooner? Did they just figure you would stay indefinitely and took your contributions and value for granted? Or, my personal favorite, now that they know you were looking and you took the “new” offer, they’ll seek to replace you quietly behind the scenes anyway.
Maresa Friedman, CEO, The Executive Cat Herder

My biggest regret: I didn’t pursue my passion

woman working with a laptop
Your job can also be your passion. |

I spent so much time working toward my MBA in finance and pursuing a career in finance that I put off doing what I really loved, which was helping people. I have been an EMT for years and always loved that but didn’t see it as a full-time job until an opportunity presented itself, which led to me start my own company, ParaDocs Worldwide. I won’t call it a regret, though, because the things I learned while studying finance and during my short-lived career I use today when running my business. I just wish I had been bold enough to pursue my passion sooner.

My advice

If you have a passion for something, pursue it. Your passion and your full-time position don’t have to be mutually exclusive. It’s possible to combine the two, as is evidenced by the company I started. Forge your own path. Don’t follow the one carved out for you.
Alex Pollak, CEO and founder of ParaDocs Worldwide

My biggest regret: I waited too long to start my business

women at work
Take a risk, and start your business. |

My biggest regret was waiting until I was 57 to quit the corporate world and start my own business. I worked for a Fortune 200 company. I was compensated very well and challenged daily, but I desired freedom and control over my life.

My advice

If I could do things differently, I would have developed a mentoring relationship with other entrepreneurs and listened to their advice. I would have combined my knowledge and entrepreneurial dreams and created a detailed strategic business plan. I would have started the journey. My advice to someone in a similar situation would be don’t wait to change careers. Ten years later my life has never been better.
Bob Shirilla, founder of Simply Bags

My biggest regret: I wasn’t aggressive enough with my career

Dwight in a scene from "The Office"
Don’t be passive when it comes to your career. | NBC

I regret I wasn’t more aggressive in building out my career on TV. I had the window just before and after my book was published, The Wall Street Professional’s Survival Guide, but I was not systematic in establishing traction. Quite frankly, I didn’t know enough to know that a book doesn’t sell itself. I was naive in assuming that growth would happen organically and by word of mouth.

My advice

Following the publication of my book, I was unprepared to utilize a multi-platform strategy for promotion. Although the book became a best-seller, I didn’t understand enough at the time to tap social media and the right traditional PR machine to do the heavy lifting. My advice others in a similar situation is to be bold, proactive, and willing to make an investment.
Roy Cohen, career coach and author

My biggest regret: I didn’t nurture my talent

man writing
Believe in yourself, and you’ll go far. |

All the signs were there when I was younger for me to become a writer. However, I didn’t seriously consider this field as a possible career path until much later in my life. I finally stumbled upon a writing program offered by a local university, registered for classes, and completed my studies.
Returning to school to pursue writing has proven to be one of the best decisions I have ever made in my life. Following my graduation, I have explored freelance writing (and been published in numerous newspapers, magazines, and online markets), been twice chosen as a story contributor for Chicken Soup for the Soul, and written two published books of my own.

My advice

My advice to others at any stage of their careers? Don’t toil away at a career you dislike or don’t find rewarding. Instead, work at something you love.
Rick Lauber, author of The Successful Caregiver’s Guide and Caregiver’s Guide for Canadians

Helpful resources

woman sitting on a bench holding a coffee and reading
The right career book can offer helpful advice. |

A good book can help you navigate choppy work waters. Here are three books that can offer some guidance.

Follow Sheiresa on Twitter @SheiresaNgo.