The Road Not Taken: 15 Greatest Career Regrets Revealed

Have you ever regretted not asking for a pay rise or staying in a job too long? You’re not alone, and to show you, we’ve compiled a list of the biggest career regrets.

We all want to pursue our dream career, one that fulfills us and pays well. The challenge is that we change over time. What once gave us a sense of purpose can become a job we dislike. Most of the time, career regrets occur through a lack of confidence. Whatever stage you are in your career, it’s crucial to eliminate potential regrets by getting ahead of them with self-reflection and honest feedback.

We’re revealing this list of 15 greatest career regrets based on our work experience and mistakes.

1. Staying At a Job Too Long

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Sometimes, we stay at a job too long because it seems safe and familiar. We know the job and get too comfortable, and the prospect of change seems overwhelming. Other times, we may enjoy working for a company but dislike the job. Working for the same company may look good on your resume, but if you genuinely want more, begin exploring your career options.

2. Not Negotiating Salary For a New Job

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Are you worried about negotiating a better salary in the excitement of a job offer? If so, you are not alone. After starting a new job, asking for a pay rise immediately is not good etiquette, so asking for more before accepting the job offer is good practice.

Provide a rationale for your request to the hiring manager, such as your experience or qualifications that justify the increase.

3. Not Getting a College Degree

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There’s an assumption that having a college degree means a higher salary, but that isn’t necessarily the case. In some careers, a college degree matters, but primarily, an employee’s skills, aptitude, and ability to work with a team is more important than a degree. However, many organizations require applicants to have a degree, making it challenging to pass the resume screening process.

4. Not Prioritizing Work-Life Balance

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At some point in your career, you may reach a tipping point where you realize that your career is not everything. The problem arises when employers continually reward employees who sacrifice their time off. Coworkers fear they will miss out on promotion if they don’t go above and beyond, and this behavior becomes a constant loop.

5. Not Speaking Up In a Meeting

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One of the biggest regrets for employees is not speaking up in meetings. Depending on the meeting leader, most employees fear management singling them out as troublemakers if they disagree with the status quo by speaking up. However, change cannot happen unless there is some disruption. It’s worth being brave because you could have ideas that could significantly impact the organization’s growth.

6. Making Career Decisions Based on Money

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We spend a considerable amount of time working, so chasing a career for money can backfire. Money does not make you happy in the long term, and if you’re in a job you dislike, it won’t make up for your feeling miserable. The experts say to follow your passion, and the money will take care of itself, so decide what career would fulfill you and explore your options.

7. Not Asking For a Pay Increase

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In Western society, we have an antipathy for discussing money, so asking for a pay raise seems like a big deal. If your company has regular appraisals, that is the best time to ask for a pay increase, especially if your review is positive. The most effective strategy is to prepare documented evidence of your excellent work to justify your request.

8. Not Asking For A Promotion

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Occasionally, if you are exceptional at your job, management is reluctant to offer a promotion. For you, that’s unacceptable. From the offset, clarify to the organization that you want to pursue promotion. Ask for their advice for a strategy to progress your career and set progress goals. If the company resists your requests, it could be time to move on.

9. Being In Your Chosen Career

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When you leave college, you have no work experience and unwittingly believe a career is more rewarding than it is. For example, many students pursue a law degree and then switch careers some years later, feeling disillusioned by their chosen path.

Before choosing a career, talk to people doing your job and ask for honest feedback on the drawbacks. That way, you can make a better-informed decision.

10. Not Getting Professional Qualifications

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Professional qualifications can set you apart from other candidates. Gaining certification often gets overlooked or delayed. Employees may regret not taking action earlier, especially if the job market enters a downward spiral. It’s never too late to gain additional qualifications, especially as most courses are available online. Follow the trends in your industry and get ahead with some snazzy qualifications.

11. Being A Remote Worker

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Working from home seems like a dream come true, but it doesn’t come without challenges. There are multiple distractions to overcome, such as a neighbor popping around for a coffee if they see you are home, or your children or pets may make noise while you’re on video calls. Remote working can be lonely, and employees may miss interacting with colleagues.

12. Not Making a Full Career Change

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It’s easy to get stuck in one career and then think it’s too late to make a change. This is particularly challenging if you have followed a family career pattern, such as working as a doctor or lawyer. The good news is that it’s never too late to start a new career. These days, you can study for a degree or other certification online.

13. Not Pursuing Career Hunches

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Have you ever had a hunch that a specific career would make you happy but then failed to follow that hunch? Perhaps you were influenced by friends or family and talked out of making the change. If that’s the case, does that hunch still seem reasonable? If so, take the steps now to explore a career change.

14. Working Long Hours

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We are physically and mentally capable of working long hours up to a point. Still, that doesn’t make it right. Eventually, extended periods of working long hours can lead to burnout, which leaves you feeling physically and mentally exhausted and can result in serious illness if not addressed. We’re not robots. The mind and body need rest.

15. Putting A Career Ahead of Family

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Delaying starting a family ahead of a career is a big regret, especially among women. A successful career can become addictive, especially when you love what you do. Still, a family needs time together to make it work. Over-committing to a career can result in relationship breakdowns like divorce.

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