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Leadership Regret and Self-Compassion


A man holding a heart, representing the self-compassion that everyone should provide themselves.

Over a decade ago I left the financial industry. For years I thought the regret stemmed from going from a highly-paid industry (finance) to a lower-paying one (human services/education). Maybe it’s experience, maybe it’s time or maybe it’s the combination of books I’ve been reading (Belonging – Geoffrey Cohen, The Power of Regret – Daniel Pink), but I finally figured it out.


I remember moving down to the small town of Chariton, IA for my last financial advisor job. As soon as we pulled up with the moving truck and trailer, the CEO of the bank showed up and literally physically helped move me into my house. Looking at back my second interview with the bank – all the department heads showed up. You could feel everyone was happy to be there. The leader I directly reported to the President of Financial Services was amazing. When I hit my one year, my leader invited me out to dinner to discuss my one-year performance. I assumed it was just going to be the two of us. Yet again, all the department heads showed up and it was a celebration, not a performance review. The bank felt like home.


Looking back, it wasn’t the money or the title/position that I was missing – it was the sense of belonging. Over the last few years, I’ve realized (and researched) the power of belonging at work. I regret leaving the sense of community and having people I could depend on.


I believe that as leaders we need to give ourselves some grace and forgive ourselves for the mistakes we make – as long as we learn from them. From my experience in the financial industry, I got to understand the challenges and opportunities of running a business.


Moving forward I will be quicker to give myself compassion and spend a longer time looking at the lessons.

Reflection Question - What am I holding on to that I need to let go?


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