We’ve all been there at some point—that sinking feeling when you realize you’ve made a mistake in your career. Maybe you took a job that looked great on paper but turned out to be a poor fit, or your boss turned out to be a completely different person than you thought.
Or perhaps you stayed too long in a role that wasn’t fulfilling.
We know that career mistakes can have significant consequences:
Wasted time in unfulfilling roles
Missed opportunities for growth
Decreased job satisfaction and motivation
Potential financial setbacks
Increased stress and anxiety
That’s why it’s crucial to learn from your mistakes and make better choices in the future.
One simple yet powerful tool to prevent career missteps is to analyze your past jobs. This exercise helps you identify patterns in what you’ve enjoyed and disliked across different roles.
Step 1: List all the significant jobs you’ve held in the past, including:
Full-time positions
Part-time jobs
Summer or seasonal work
Contract roles
Significant volunteer experiences
Step 2: Rate each job using this 5-point scale:
- I absolutely hated this job
- I generally did not like going to work
- I was happy some days; not so happy other days
- I enjoyed going to work most days
- I absolutely loved this job
Step 3: Analyze each job.
For each job, write down what you enjoyed and did not enjoy. Think about factors such as:
Compensation and benefits
Work environment
Flexibility in work hours
Commute time to work
Industry and company size
Colleagues I enjoy working with
Job security
Culture and value system
Commitment to diversity, equity and inclusion
Learning and development opportunities
Type of work and responsibilities
Work-life balance
Company reputation
Step 4: Identify patterns
If this is done well, you will discover common threads among your various jobs. What you liked about one job tended to be the same across all your jobs. Similarly, what you disliked will likely be the same across all your jobs.
Take Craig (not his real name), 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. His family gently pushed 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 tried to live 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 bank’s formal structure and didn’t like the actual work, which involved a lot of numbers and details.
What he learned 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 due to 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, feeling much more fulfilled in his career.
Remember, your goal isn’t necessarily to find a perfect job – it’s to find a role that aligns with your strengths, interests, and values. By learning from your past, you can create a more fulfilling professional future.