On trouble with the boss, and ambition.

Tim Parkins
3 min readJun 5, 2022

This article explores ways to navigate the uncomfortable situation where you are simply not connecting with your boss. There is a saying that people don’t quit bad jobs, they quit bad bosses. There is truth to that.

However, someone that some people might consider a “bad boss” might be exactly what someone else needs. We are all different. We come with differing needs, differing expectations, and a variety of experiences that have shaped how we respond to people.

The article focuses in on understanding “personality traits”. This resonated with me, as I leverage personality tests as part of my coaching practice. Some people dismiss personality tests. I view them, particularly the OCEAN model (which has been rigorously validated scientifically) to be a useful tool to help understand yourself and others.

What I liked about the approach suggested in the article was to reflect on you and your boss’s personality differences, and to engage in an open dialogue. Experience has shown me that time invested in reflecting and honest communication tends to lead to amazing results.

This article challenged me. I did not understand the concept of how “having too much ambition” could be detrimental; that there is a “healthy” level of ambition did not sit right with me at first. I was definitely more in the camp of “the more ambition, the better”.

After having read the article and reflected on the idea that being overly ambitious can, in fact, be detrimental, I have to admit that I was probably wrong. That is why I felt it was important to share this article; it challenged a belief that I previously held and to help me form a new opinion. That is valuable.

As part of my reflection, I came to realize that there were instances in my career where I had been overly ambitious — and it had a negative impact on the project. By setting the bar so high, people got discouraged and disconnected from the project. If people can’t believe that they can deliver an excellent result that they can be proud of, they will not engage.

Like most things in life, there is a balance. We need ambition to force us to stretch and grow. But too much ambition can lead to disengagement and fear — which is obviously not healthy either.

A great lesson that we need to be very conscious about how much we are encouraging people and teams to strive for.

Quote that I have been reflecting on

This quote from the brilliant James Clear does a great job of summarizing my entire philosophy around work. Decide what you want out of life and learn what your strengths are. Then experiment with ways to leverage those strengths to be of service to others. If you do enough of that, work will become fun again.

“It’s only work if you would rather be doing something else. Find a way to carve a career out of what you already want to do.” — James Clear

Journal Prompt

I firmly believe that one of the best uses of time is to journal. Writing forces you to think. And getting clear in your thinking leads to deeper insights, understanding, and better results.

This week’s journal prompt asks you a challenging question.

Are you living your life avoiding fear? Or seeking adventure? And which of those options do you think is more likely to get you to where your heart longs to be? “

Spend some time thinking deeply about that. Your life will be better for it.

If you want to make sure that you get my latest thoughts, straight to your inbox — subscribe to get my weekly newsletter.

And if you are not happy with where your career is at, I can help. I work with people just like you to redefine your relationship with work. Check it out!

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Tim Parkins

Career Coach & Work Architect. I help successful but unhappy professionals craft a working life that works for them. https://timparkins.com