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This Was My Biggest Career Mistake

I wrote a pretty popular answer on Quora a while ago. The question was “What has been your biggest career mistake?”

Writing the answer helped me reflect on my 30+ years of working. It also reminded me how fortunate I feel to be Just Rolling with It now.

This post is an abbreviated version of the answer. You can find the full answer on Quora.

My biggest career mistake was believing what I did to earn an income had to make me unhappy. I’m feeling fortunate to learn that’s not the case. I’ve learned what I do to earn an income can actually contribute to my happiness. It took me 30 years of working to realize this.

I first realized I was unhappy at my first corporate job.

I told myself being unhappy at my job was normal. That’s what I became conditioned to believe. And I believed it.

This led to me being unhappy for the next 15+ years. There were some blips of happiness here and there.

I told myself the blips were exceptions to the rule, not the rule. This led to me getting pulled back to work that continued to make me unhappy. The work started to pay better over time. I remained unhappy, even as my income level continued to increase.

I started adopting unhealthy, yet socially acceptable, habits to cope with the unhappiness.

Then my coping mechanisms stopped working. I realized my way of life was making me unhappy. Because I defined myself so much through work, I realized my work was a major cause of my unhappiness.

I began experiencing immense pain. It was a scary time. I realized that being this unhappy wasn’t healthy for me or those around me. This time I decided to stop numbing myself to the pain. This time I decided to try something different.

I started Just Rolling with It to become happier for myself, those around me and others.

Just Rolling with It is working. A few years later I’m feeling much happier than ever before in my life. I’m on a path to generate income in ways that contribute to my happiness. I don’t believe what I do to generate income has to make me unhappy anymore.

How’s your career journey going? Is what you’re doing to earn an income making you happy or unhappy?