Top Career Regrets You Might Want To Avoid

There are always going to be decisions you make and things that you do, which you regret later on.

Learning from past mistakes is just one way that we grow, but learning from what others believe to be their biggest career regrets, can allow you to hopefully skip some of the trouble.

Daniel Gulati, an author and venture investor, interviewed a diverse mix of people, in order to learn about their top career regrets. He spoke with people from various age groups and occupations, such CEOs, photographers, rich entrepreneurs and an investment banking MD.

Here’s the regrets that appeared most often.


Not Quitting Earlier

Most of the people that are dissatisfied with their career/employer/industry wait a very long time before they finally quit, to pursue something they are more passionate about.

In many cases, it boils down to the person staying in a job that they don’t like, and not quitting at all.

They usually stay in their current employment due to rat race conditioning, variable reinforcement and fear of public failure, among other things.


Picking a Job Solely for Monetary Reasons

Many people have the career regret of choosing their job based solely on monetary reasons, and later find out that this was not enough to motivate them to want to do their jobs day in and day out.

They wish they considered other factors as well, and/or made compromises somewhere along the road, so that they could take lower paying but more satisfying jobs.


Not Having More Confidence To Start Out Independently

People can often regret not having more confidence in themselves to start their own venture.

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Many want to own their own business and be their own boss, but do not have the confidence to take that first big step.

So, they remain with their employer and regret not trying to have a go at starting their own company.


Not Maximizing Schooling

Another common regret involves not maximizing time at school and merely getting a degree.

Some may have rushed getting through school to land that first job. They may find that they want to go back to school to either learn something new or get more familiar with something they glossed over the first time around.


Not Following Gut Feelings

The final regret that many people face is not following their own intuitions - that “gut feeling” that tells them that they should jump into an opportunity, or take some risk.

This could for example, come in the form of being offered a position in a new/untapped/unfamiliar market.

These moments of change may make a person hesitate when deciding whether or not the reward is going to be worth the risk, and some may underestimate the reward or overestimate the risk, due to which they decide not to go ahead.


As they say, “Hindsight is 20/20.” Therefore, it can be hard to be sure if any decision that is made today will lead to a regret tomorrow, but learning from others may help you to prevent some regrets in your own career.

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Written By:
Nigel Nolan - Senior Consultant, Sandbox Advisors

Nigel has vast experience in Training & Development, Facilitation, Lecturing, General Management and Operations. In addition to an educational background in philosophy, psychology, theology and communications, he has advanced qualifications in business, adult education and coaching.