As people approach the golden years of their career, the focus often shifts from money to fulfillment and satisfaction. However, the wrong job choice can lead to regret, stress, and dissatisfaction. Understanding the jobs people often regret taking in their 50s and 60s can help you make informed career decisions as you age.
This list is based on real-world trends, data, and expert interviews, rather than anecdotal experiences or conjecture. We aim to provide you with a comprehensive understanding of the jobs that often lead to regret in later life. Expect a detailed exploration of each job, why people take them, and why they end up regretting their decision.

High-Stress Corporate Jobs
High-stress corporate jobs often come with significant paychecks, making them attractive for many individuals. However, people in their 50s and 60s often regret taking these jobs due to the high pressure and long working hours, which can negatively impact their health and personal life.
Today, with the increased focus on work-life balance and holistic wellness, more individuals are realizing the negative impact these jobs can have on their wellbeing. According to American Psychological Association, chronic work stress is linked to health issues such as insomnia, depression, and obesity.
Physically Demanding Jobs
Physically demanding jobs such as construction, landscaping, and truck driving may seem appealing due to their active nature and independence. However, people in their 50s and 60s often regret these jobs due to the substantial wear and tear on their bodies.
With the trend of ageing populations worldwide, it’s essential to consider the long-term physical toll of these jobs. According to the Centers for Disease Control and Prevention, older workers are more likely to suffer severe injuries and illnesses when engaged in physically demanding jobs.
Low-Paying Retail Jobs
Low-paying retail jobs offer flexibility, social interaction, and a break from the corporate world. However, many individuals in their 50s and 60s regret taking these jobs due to the low pay, lack of benefits, and limited career progression.
Given the current economic uncertainty and increasing cost of living, it’s crucial to consider the financial implications of low-paying jobs. A report by Economic Policy Institute highlights that low-wage workers often struggle to meet their basic needs, particularly in their later years.
Start-Up Jobs
Start-up jobs offer an exciting environment, potential high rewards, and the chance to be part of something new. However, people in their 50s and 60s often regret these jobs due to the high risk, instability, and long working hours.
With the current economic climate, the risks associated with start-ups are even more significant. According to a recent study by Brookings Institution, start-ups face a higher risk of failure in today’s uncertain times, making them a risky career move for older individuals.
Travel-Intensive Jobs
Jobs involving extensive travel, such as consulting or sales roles, can seem glamorous and exciting. However, people in their 50s and 60s often regret these jobs due to the impact on their personal life, health, and work-life balance.
In today’s world, where remote work and digital communication are becoming the norm, travel-intensive jobs are increasingly seen as unnecessary and burdensome. A report by Psychology Today discusses how frequent business travel can lead to chronic stress and health problems.
As a mom of three busy boys, I know how chaotic life can get — but I’ve learned that it’s possible to create a beautiful, cozy home even with kids running around. That’s why I started Cultivated Comfort — to share practical tips, simple systems, and a little encouragement for parents like me who want to make their home feel warm, inviting, and effortlessly stylish. Whether it’s managing toy chaos, streamlining everyday routines, or finding little moments of calm, I’m here to help you simplify your space and create a sense of comfort.
But home is just part of the story. I’m also passionate about seeing the world and creating beautiful meals to share with the people I love. Through Cultivated Comfort, I share my journey of balancing motherhood with building a home that feels rich and peaceful — and finding joy in exploring new places and flavors along the way.


