Shawn Jenkins Blog

Be your own boss_ Shawn Jenkins

Are You a Good Boss to Yourself?

When I watch the house hunting shows, I always smile when someone says they’re looking for their “forever home.” I suppose we are all searching on some level for a calm, peaceful (and tastefully designed) physical place to live, rest, and enjoy life. 

But that’s a lot of pressure to put on a building. Do we ask the same thing of our company and our boss?

Are we searching for the perfect manager who has just the right amount of high standards combined with a kind and understanding disposition?

Seeking an ideal work environment and group of people you respect is a worthy goal. Yet putting pressure on any company to be your perfect “forever company” is even more of a stretch than finding a forever home. 

Perhaps a better place to start is with your true, forever boss: Your internal voice. 

What sort of boss are you to yourself? 

Remember when as kids someone would try to tell us what to do and we’d say, “You’re not the boss of me!”?

As an adult, who tells you when to wake up, what to eat, what to wear, where to live, how to spend your money?

Boss may not be the best word to describe the you that manages you. In all honesty, I never liked that word: boss. But let’s run with it and consider the relationship of our inner boss to our work. 

We get frustrated, sometimes even angry, with our job, our company, and our boss. We can feel overtasked, overworked, worn out from not having enough time off. We can feel under appreciated and taken advantage of. 

When we spend thousands of hours at the same place with the same people over the course of a few years, it’s understandable that there will inevitably be some tension.

I wonder if our jobs sometimes act like mirrors, reflecting back to us our inner condition. 

What sort of boss are you to yourself?

You are the one telling yourself what to eat, when to sleep, what to focus on. How is that going? How is that relationship between you and, well, you?

Are you a compassionate and loving manager to yourself? Are you a harsh taskmaster? Do you excuse things easily? Do you set high standards? Do you move the goalposts often?

You can change your current work situation relatively easily. You can find another job, turn in your notice, and find yourself behind another laptop and at another email address within a few weeks or months. But you cannot move away from your internal boss. Your “forever boss” so to speak.

I’ve found that keeping focused and motivated is a hefty part of managing myself. Here are four exercises that I’ve found helpful in developing a healthy relationship between me and my forever boss.

Make a “Good List”

Stand at a whiteboard with your favorite color dry-erase marker or hold a freshly sharpened pencil against a clean sheet of paper and just start listing things that are good in your life. Sometimes I do big macro things like my family, home, education. Sometimes I do a list of things that have gone well in the past few months or year, like achieving some small goal, losing a few pounds, launching a product, fixing a problem, or winning a customer.

Our internal managers can get hyper focused on problems; we need to remind them of our steady progress. We also need to routinely step back and look at the broader landscape of our lives and identify things that are good. 

I find this eases the tone of that inner voice and makes me more amenable to doing the things it’s asking me to do.


I’ve found writing is an effective way to listen more objectively to my inner manager. I write when I’m stressed. I write when I’m making progress. I write when things don’t go well on a project. I write down aspirations as they cross my mind. Often they contradict other goals but it’s helpful to see how my mind generates many alternative narratives of my future. 

That inner voice has good days and bad days. It’s helpful to give it a format to share its wisdom with you and to see that wisdom over time.

It helps to stand back and get a wider perspective of what you are thinking by reading your notes over the course of a few months. 

Books as Friends

I go to the bookstore just about every week. Books have become my friends. Often when I’m slogging through some mental riddle, or trying to develop a new plan, I’ll want to work out some of my thoughts by loosening the task oriented part of my inner boss. I will wander aimlessly around the store leafing through random books and magazines. Often I will discover  a story that touches on some of the themes I’m wrestling with. 

Reading a few pages or a few chapters of how someone crossed some chasm in their life, to experience their challenges and witness alternative ways of thinking, helps me view my own situation from different angles and see around the corners in my own life. It exercises the part of my mind that I need to effectively set new goals and work toward achieving them. 

Friends as Friends

It’s remarkable how a breakthrough can be just a coffee chat with a friend away. Merely giving voice to our thoughts, hearing ourselves say them, is incredibly therapeutic. We can get a sense of what that inner voice is telling us, or perhaps have a friend course-correct us when that inner voice is totally wrong about something.

Although I get recharged through solitude—I love me some quiet time—I’ve found that a steady diet of friendly interaction with people I respect is super helpful in keeping my inner boss aligned with my longer term aspirations.

Be a good boss to yourself

You’re going to work for yourself for a long time. Develop a good relationship with your inner voice. Feed it lots of interesting perspectives through books; let it breath by enjoying a chat with a friend. 

And if it’s now telling you, “See, I told you that you weren’t doing enough to better yourself,” then calm it down with a list of a few good things happening in your life!

Perhaps some of your frustrations with your job actually stem from how you are managing yourself. The good news is that you can evolve your inner boss. You can develop a healthy relationship with yourself. In so doing, you will likely go farther, faster, and with more enjoyment.


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