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Are You The World’s Worst Boss?

The most important boss that each of us answers to is ourselves but sometimes we don't do a very good job. Learn 8 ways to be better!

Ashley Janssen
Ashley Janssen
6 min read
Are You The World’s Worst Boss?
Photo by 傅甬 华 on Unsplash

My boss can be a real jerk

She often doesn’t trust my judgment and questions my every decision. She makes me feel bad if I’m not as productive as she thinks I should be. She compares me to others and finds me wanting. She discourages me from trying new things. She sometimes makes me feel like an imposter who does not deserve success or acknowledgement. She says things to me that I would never say to someone else. She can be loud and, frankly, sometimes really mean to me.

Oh, wait…my boss is ME.

The most important boss that each of us answers to is ourselves

Regardless of if you are self-employed or if you work for an organization, the most important and impactful boss in your life is you. Your inner dialogue is with you always and the way you speak to yourself, the expectations you set for yourself, and the conclusions you jump to are all within your power.

  • What do you say to yourself when you make a mistake?
  • Do you beat yourself up when things go sideways?
  • How do you react when someone says something nice to you?
  • What do you do when you see others doing well?
  • Would you ever say the things you say to yourself to someone you care about?

If the answers to these make you cringe a little, it’s ok. You are not alone.

You can’t quit yourself (though there have definitely been days I wish I could), so you have to learn to train yourself to be a better boss.

Image by https://www.instagram.com/lizandmollie/

8 ways to be a better boss

Like any performance improvement plan, it takes time and effort to change. The automatic reactions you have might be deeply ingrained and well-read paths, but they can be shifted and relearned.

If your boss sounds anything like my boss, here are some things you can do to be better:

1. Daily reflection

You need to acknowledge and know when you are doing something in order to change it. A daily reflection is a powerful way to look back on each day and think about things like:

  • The way you talked to yourself or reacted when something didn't go as expected.
  • The words you use to define a “good day” versus a “bad day”
  • The things you tried
  • The things you avoided.

Over time you will start to notice patterns that give you information to help guide that change.

For example, when I was working on my annual reflection for 2021, I looked back at my daily reflection for 2020 and noticed how often a “good day” was directly connected to how productive I was at work. I have been working on trying to separate my productivity from my self-worth by specifically noting the good things that happen each day that have nothing to do with what I got done.

2. Don’t compare your insides to someone else’s outsides

I often reference this quote when talking to my consulting clients, and think of it when I find myself comparing myself to someone and feeling bad about myself.

This is a reminder that you never know what someone else is going through, what’s actually happening in their life, or what they had to go through to get to where they are. Especially when it comes to what people share online, you only are ever getting a paragraph of a story, not the whole book.

Think of it in terms of what you share. You probably don't announce on social media or in small talk that you have a parent going through significant health problems, that you are going through a divorce, or that you are worried about how you are going to pay your bills. Most other people don't either.

Being a good boss to yourself means focussing on you and how far you've come, and paying less attention to the snippets of other people's lives.

Image by https://www.instagram.com/lizandmollie/

3. Don’t compare your beginning to someone else’s middle

This is another fav. It’s similar to the above but different enough that it’s worth mentioning. It’s not fair to look at someone who is further down their career or life path and berate yourself for not being at their level. It’s like looking at the finish line before you have run the race.

The path to “success”, whatever that means to you, is a winding one and everyone’s path is different. There are a million factors that impact what you do and which direction you take. It can be valuable to learn from others’ paths, but yours is unique to you.

Being a good boss is honouring and respecting your path with its many twists and turns.

4. Create a compliments folder

I get nice messages fairly regularly but they are hard to internalize. I read them and feel momentarily good…but my internal boss will dismiss them.

Over the years, one of the ways I have quieted her is to collect overwhelming evidence that she is, in fact, incorrect in her assessment of me.

I created a praise folder to remind myself that I am doing pretty well, that I make a difference, and I am good at what I do.

Every time someone:

  • Sends me a nice comment on my blog posts
  • Responds to my newsletter
  • Sends me a complimentary email
  • Posts some particularly positive feedback on my social media

I take a screenshot or picture and put it in the folder.

5. Create a wins folder

Similar to the compliments folder, I keep a wins folder.

Every time I:

  • Land a new client
  • Get asked to do a speaking gig
  • Have a particularly good consulting session
  • Do something that surprised me
  • Do something I have been wanting to do for a long time
  • Hit a milestone

I take a screenshot or picture, put it in the folder, and revisit it when I am feeling down.

I use Day One for both my compliments and wins folders because it syncs across my iPhone and MacBook. It’s easy to use and has a nice interface. But you can just as easily set up a desktop or Google Drive folder.

6. Talk to yourself like you talk to your best friend

Work on noticing what you say to yourself. Words are powerful and are one of the key ways we interact with the world.

There is a difference between saying things like:

  • I am a mess vs I am feeling messy
  • I am so stupid vs I made a mistake
  • I am a terrible person vs I forgot to do something

Would you tell your best friend they are an idiot if they forgot something or made a mistake? Would you tell your best friend they are a bad person or useless or terrible? I’m gonna bet that’s a big NOPE. So why would you say those things to yourself?

You are allowed to not be perfect. You are allowed to have hard days.

Reframe the words you say to yourself and show yourself the same kindness and forgiveness you show to the people you care about.

Images by https://www.instagram.com/lizandmollie/

7. Strive to fail over regret

A quote I came across a while back that changed how I think about failure is from Born a Crime: Stories From a South African Childhood, by Trevor Noah. He said:

“We spend so much time being afraid of failure, afraid of rejection. But regret is the thing we should fear most.”

This struck a strong chord for me and has become a regular refrain that I tell my inner boss when she is discouraging me from trying something I can’t be sure I will be good at.

When you are afraid of failing at something, ask yourself:

Would I rather try and fail or regret not trying at all and wonder what might have happened?

And what if you succeed? 🤯

8. Prioritize self-care and recharge time

My inner boss gets worse when I am really tired or haven’t been taking good care of myself.

At its core, self-care is paying attention to sleep, diet, exercise and downtime. What each of those looks like for you might be different, but it’s a lot easier to be understanding and kind to yourself when you are not completely exhausted and drained.

Think about the things you can do every single day to prioritize your health and self-care to fortify your inner boss.


My inner boss is a lot nicer than she used to be. I have worked hard on ignoring and quieting her and also teaching her to be better. I have shifted some of those well-tread pathways and forged new ones. It is a work in progress, but I know that I am a better boss than I have ever been and it makes me better at everything I do.

How does your inner boss treat you? What will you do to help them be better?


If you think you might be the world's worst boss, I can help!

IntentionResilience
Ashley Janssen

Ashley Janssen

Productivity consultant, writer, speaker, serial entrepreneur, chaos calmer, introvert, cat-lady. Lover of books, fitness, old fashioned’s, basketball, and video games.

Follow me on Twitter, and LinkedIn.


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