How To Avoid Repeating Past Career Mistakes

By Gerald Walsh ©

We all make mistakes. We forget to call someone. We miss an appointment. We say stupid things in job interviews. 

When mistakes occur, two things should happen. First, you have to suffer the consequences of the mistake. Second, you should look for ways to make sure you don’t repeat the mistake. 

When it comes to careers, the same rules apply. We sometimes take jobs with optimism and excitement only to learn later the job wasn’t what we thought it was going to be – and we suffer the consequences of that choice.

How do you avoid repeating career mistakes?

One simple yet useful tool you can use is to look at all your past jobs to identify the aspects of those jobs that 1) you enjoyed, and 2) did not enjoy.

If this is done well, you will discover there are common threads among your various jobs. What you liked about one job tended to be the same through all your jobs. Similarly, what you disliked will likely be the same through all your jobs.

Take Craig, for example, who came from a family of bankers. From a young age, Craig was groomed to go into banking. In university all his work terms were with banks. And his family was gently pushing him toward banking which they thought would be “good, stable employment” especially since “they” hoped he would have a family someday. So Craig did what many people do. He lived up to his family’s expectations and when he graduated, he joined a bank. 

Unfortunately, after a few months on the job, he began to regret his choice. “Just give it more time,” he told himself, thinking he would eventually get used to it. But that never happened. 

When he began to examine his job seriously, he learned that he detested the formal structure of the bank and, on top of that, he didn’t like the actual work, which involved a lot of numbers and details. 

What he did learn about himself was that he liked dealing with people – more the HR side than the numbers – and in particular he loved watching them grow and succeed as a result of his coaching.

That led him to quit the bank and return to school to complete his MBA in human resources. Today, he is a senior human resources manager with a large NGO. 

We can all learn from Craig’s experience. Here’s an exercise that will help you isolate the things you liked and didn’t like about past jobs. 

On a sheet of paper, list all the significant jobs you’ve held starting with the oldest. Include all jobs whether summer or seasonal, part-time, contract, or full-time. You should also include all significant volunteer opportunities as these roles can also give you a good sense of what it’s like to work in those organizations. 

Then, apply the following rating system to each job:

1 – I absolutely hated this job
2 – I generally did not like going to work
3 – I was happy some days; not so happy other days
4 – I enjoyed going to work most days
5 – I absolutely loved this job

Once you have completed that task, take a detailed look at each job and write down:

1) what you enjoyed, and 
2) what you did not enjoy

In doing this task, think about:

Physical location
Size of company
People you worked with
Status and title
Growth opportunities
Type of work
Work culture
Hours of work
Job security

… and anything else that might have impacted your job satisfaction levels. 

If you take your time and do this assignment thoughtfully, you will find that what you liked about one job tended to be the same through all your jobs. Similarly, what you disliked will probably be the same through all your jobs. With this evidence in hand, you can more informed career choices in the years ahead.

Question: What are the common threads in your past jobs? When have you enjoyed your work the most? When have you enjoyed your work the least?


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Gerald Walsh is an executive recruiter, career coach, public speaker and writer. During a 25+ year career, he has interviewed more than 10,000 job candidates, completed hundreds of successful searches for a range of organizations and guided many individuals – from young professionals to senior executives – to successful career change. He is the author of “PINNACLE: How to Land the Right Job and Find Fulfillment in Your Career.” You can follow Gerry on Twitter @@Gerald_Walsh and LinkedIn.