How Do I Avoid Career Regret?

The sheer volume of professionals who look back on their working lives and wish they had done things differently is startling. Some data suggests that as many as 66% of workers admit to having career regrets, while other observations indicate that a significant 90% of people regret rushing their initial career choice. ^[4] These feelings often surface not because the chosen field was inherently wrong, but because the decision process itself was flawed—driven by external pressure, incomplete information, or the pursuit of something other than personal alignment. ^[4][5] Avoiding this future dissatisfaction requires a proactive approach centered on self-awareness, strategic risk assessment, and adopting a long-term perspective that embraces inevitable change.

# Hasty Choices

The initial decision point in a career, often made when one is 18 or in their early twenties, is frequently made under significant pressure and with a very narrow view of the professional landscape. ^[4] Many people regret rushing this choice because they lacked adequate research into what truly suited them as individuals, often listening instead to the expectations of others. ^[4] The problem is exacerbated by a fundamental lack of context; when leaving school, people often only know about the jobs they see frequently—those on television, those requiring uniforms, or those their parents’ friends held. ^[4] If you don't have access to guidance or mentors within various fields, you might mistakenly believe your options are limited to a few traditional roles, like teacher or reporter, overlooking countless specialized paths that have emerged more recently. ^[4]

This is why some professionals find themselves in careers where their innate interests do not align with the daily tasks. For example, someone who struggles with or dislikes high-level math may have been steered toward engineering without truly understanding the profession’s nature. ^[4] Instead of trying to lock down the perfect career from the outset—an impossible task given how much the world and you yourself will change over decades—the focus should shift toward selecting a path that keeps you learning and growing right now, making pivots as necessary. ^[4]

# Financial Pressures

A consistent source of professional dissatisfaction centers on compensation and job longevity. It is common for people to regret taking a job primarily for the salary, only to discover that the role offers no fulfillment or aligns poorly with their values, leading to burnout. This regret is often compounded by two related financial actions—or inactions: failing to negotiate starting salary and failing to advocate for raises later on. Nearly 60% of professionals regret not negotiating their starting salary, and an equal percentage regret not asking for a pay increase later.

The fear surrounding salary negotiation is potent; many worry about appearing greedy or ungrateful. However, the cost of not asking is tangible and accumulates over time. If you consistently deliver results, you are entitled to fair pay, and avoiding that conversation means accepting a discounted rate for your contributions year after year. It’s important to weigh the immediate discomfort of advocating for yourself against the long-term financial and job satisfaction deficit created by accepting less than your value warrants. Furthermore, staying in a job too long—even one that pays well but starves the spirit—is a common pitfall, with about 58% of workers expressing regret over not moving on sooner.

How to get over career regret?

# Adopting The Infinite View

To counteract the impulse to make static, fear-based decisions, it helps to conceptualize your career not as a finite game, like winning a championship, but as an infinite game that is constantly evolving. ^[5] In a finite game, the goal is to "win" a specific role; in an infinite mindset, the career is seen as an adaptive experience designed to continue indefinitely, regardless of setbacks like economic shifts or unexpected changes. ^[5]

This perspective demands a commitment to continuous capability building. The single most important skill you can cultivate is the ability to learn. ^[5] This "learning agility" must encompass more than just technical competencies; it includes resilience—how quickly you recharge after a challenge—and digital fluency, given how automation is reshaping work. ^[5] When you embrace learning as the core element of your professional life, you are far less likely to regret decisions because you are equipped to adapt to whatever external forces or internal shifts arise in the labor market. ^[5]

# Questioning Your Guides

When making big career decisions, the loudest voices often belong to parents, peers, and mentors, but their advice requires sharp scrutiny. ^[5] Parents often give counsel based on their own career experiences, which might reflect an economic reality that no longer exists for today’s job seeker. ^[5] If a well-meaning supporter is telling you what to do rather than asking probing questions about your interests, you should approach their input cautiously. ^[5] For example, peers might share the same limited information you possess, while teachers might be trained for a different era of career counseling. ^[4][5]

A proactive strategy involves actively interrogating the basis for their advice. Questions such as, "What market data supports that role as stable?" or "What biases might be coloring this recommendation?" can help peel back the layers of outdated assumptions. ^[5] When you realize you were guided toward practicality or security over genuine interest—a common source of regret—it highlights the necessity of looking inward and seeking advice from those who can speak to the current landscape, perhaps through experts or practitioners familiar with contemporary trends. ^[5]

How Do I Avoid Career Burnout?

# The Cost of Playing It Safe

Regret is not only tied to the decisions made but also, often more acutely, to the calculated risks not taken. While stability feels safe, avoiding bold moves frequently leads to later remorse. ^[5] One key risk to consider is applying for a job when you only meet about 60% or 70% of the listed qualifications. Hiring managers often outline an ideal candidate, and if you wait until you check every box, you may miss opportunities where your potential and ability to learn are valued far more highly.

Equally important is the risk associated with declining an offer out of fear. If you are job-hunting for a long time, the temptation to accept the first offer, even if the culture feels off or the role doesn't match your strengths, is strong. This often results in taking a job that feels wrong, leading to frustration, burnout, and eventually quitting quickly, which creates red flags on a resume far more damaging than simply waiting for the right fit. A related bold move is relocating for a better opportunity; while moving is complex, the experience can refresh energy, lead to faster promotions, and broaden your mindset, offering value even if you eventually return to your original location.

It is insightful to see the relationship between the fear of taking a risk and the regret of inaction. The fear of moving or asking for more money is temporary and focused on an immediate outcome (rejection or a difficult conversation). The regret of not moving or not asking, however, manifests as a lingering dissatisfaction that lasts for years, often eroding personal fulfillment because you prioritized short-term comfort over long-term growth alignment. ^[5]

# Self Alignment and Intuition

At the foundation of a regret-free career lies the ability to listen to your internal compass. Professionals often look back and wish they had trusted their gut instinct regarding job offers or difficult professional relationships. Cultivating this trust means valuing your internal cues as legitimate guidance, not just irrational feelings. This internal alignment is closely connected to honoring your personal life. A significant regret cited by many is not prioritizing family and personal needs due to career demands, leading to strained relationships.

To combat this, setting clear boundaries between work and personal life must be a deliberate, conscious effort reflected in career decisions. Furthermore, you must define what success means to you, separate from external markers like salary size. If you are constantly thinking about doing something different, or if your job no longer reflects who you are, that persistent feeling is your intuition signaling a misalignment that requires attention, even if it means taking a pay cut or starting at a lower level in a new field.

Ultimately, avoiding regret is an exercise in continuous, intentional management rather than a one-time perfect choice. It involves engaging with career professionals or coaches who can facilitate self-discovery while supplying accurate labor market data. ^[5] By defining clear goals, committing to learning new skills constantly, and having the courage to interrogate the advice you receive and the risks you avoid, you can build a career that serves your evolving self rather than one that leaves you wishing you had lived a life truer to your own expectations. ^[5]