Many of us have heard the phrase, ‘employees don’t leave companies, they leave bad bosses.’ Research supports this. Stories from friends and former colleagues support this. And, my own career experience supports this. Lately though, I have been wondering if this sentiment is not entirely fair to the bosses out there. How fair has it been of me to have put all (or most) of the responsibility onto my past bosses for my work satisfaction, my career progression, and my happiness? How realistic have I been with my expectations of what a boss should be?

I am one year into my transition to self-employment. One of the most surprising challenges of this transition has been figuring out how to work with my new boss, aka me.

Having professional freedom and living professional freedom are not yet the same thing. One aspect of self-employment I was most excited about was having newfound professional freedom – the freedom to do the work that I wanted to do, to set my own hours, and to put more of my personality into my work. I thought this would be an easy transition to make. After all, I’m the boss so that means that I call the shots. Of course, I theoretically have the professional freedom I was seeking. That happened the moment I left my last job. And yet, I am still held back by some of my old ways of operating, and that is getting in the way of me truly experiencing professional freedom. 

One of the hardest things for me to figure out has been how to work without guilt. This is not to say that my past bosses guilted me into doing work. But I think the guilt was always there, operating in the background. I felt guilty if I took too long to respond to an email or return a call, if I wasn’t available on-demand, if I had to decline a meeting, move a meeting, say no to a project, or miss a work event. I’ve always known this about myself and I’d like to think that I’ve made good progress in managing that guilt and setting boundaries for myself.

Sadly, that guilt resurfaced when I started working for myself. And since I no longer have a boss to report to, I have realized that my guilt is one hundred percent self-imposed. This has been most evident in how I perceive the hours that I work. I have not been able to fully enjoy the flexibility that self-employment gives me because I feel guilty when I am not working. And now that I see my working life in billable and non-billable hours, I am even more acutely aware of the hours that I put in.

Seeing this pattern of behaviour has helped me to acknowledge how I have been conditioned to operate, boss or no boss. And that it is a pattern and habit that I want to change. Part of my learning is figuring out how to measure the value of what I do, shifting to seeing value in terms of outcome and delivery instead of hours worked. And, another part of my learning is figuring out how to give myself permission to spend parts of the “working day” living my life. It’s a constant conversation with myself and I know that I will get there.

I’m re-learning how to set my own expectations. Last year was about setting the foundation for self-employment and seeing how it felt, how I worked, and if I liked it. This year will be more of the same plus the addition of a business plan (I now feel like I have some actual data to create said business plan). As I’ve started working out my vision and goals, I have realized that I have the freedom to link my personal vision with my professional vision. It feels obvious to say this aloud and kind of sad that I hadn’t thought of this sooner.

Before self-employment, I led with how I wanted my career to progress and then built my life from that. Becoming my own boss has created the opportunity for me to flip the script on that. It’s hard and I am still a work in progress, but it feels liberating to know that I can lead with how I want to live my life and to see career as one part of it. 

It’s about being kind to myself and taking responsibility. Before self-employment, I was looking for leadership externally when I should have been looking internally. At the end of the day, I am responsible for my own career and how I work. Whether I am working as an employee or self-employed, there are many aspects of working that I can and should own, like knowing and respecting my boundaries, seeking feedback and listening to that feedback, and having self-compassion. These are the things that I have control over. I have always known this, but I don’t think that I really lived it.

So now the phrase, ‘employees don’t leave companies, they leave bad bosses,’ has new meaning for me. In getting to know my new boss, I have realized that many of the expectations that I had of my past bosses were less about them and more about me. And, the best part about where I’m at is that I finally have a boss who gets me. I just need to help her to continue to trust herself and look inward before outward.

Where do your career expectations come from? How much responsibility do you put on your boss for your work satisfaction, career progression, and happiness? What is one change you could make to shift your expectations?