How To Remain Confident When Things Don't Go As Planned


Have you ever crafted the perfect plan only to experience the crush of disappointment when things don’t go as spectacularly as you hoped? Both in my entrepreneurial journey and in my Corporate America days, I know about the roller coaster of dreaming up a big plan and fantasizing about its perfect execution with quick results.

But instead, there were times that I was crushed because it felt like results weren't coming fast enough. People weren't getting on board with an idea. Or, what I thought was the perfect product or program simply flopped. Many times, my confidence tanked alongside these disappointing outcomes. I was frustrated that my reality wasn't matching my ideal goals.


Our inner critic loves this opportunity to remind us that we never should have tried this, we are not qualified, and we've failed because results should come faster than this. It's tempting to feel like a fraud and rationalize quitting altogether. 

Try this thought on for size. What if our stress doesn't come from our results, but From our expectations of “perfect” results.

How do you remain confident when things don’t go as planned? Counterintuitively, it begins with a dose of compassion, a willingness to get curious, and even a bit playful. 


I liken this to a time when I was a little girl and I loved coloring interchangeable fashion plates. You’d lay plates together to create an outfit, place paper over it, and use your crayons to color it to bring the outfits to life. I would sit at the table for what seemed like hours and interchange plate after plate, creating some pretty high-fashion looks for 1987! If I didn’t like one of my designs, I would just put the paper aside, change the plates and start a new one. I wouldn’t get critical with myself (like I do today), with thoughts that I wasn’t creative, I couldn’t draw, or that I was unqualified. I would simply change the plates and keep playing. This is a mentality that is of our most childlike essential self. It’s a place that is higher than our ego can reach.


Freedom From the Inner Critic

How do we access that today? When I’m having doubtful thoughts, I draw a line down a piece of paper. On the left side, I write down all of the thoughts that my inner persecutor or critic says. Often its judgments such as: You’re not moving fast enough. Who do you think you are? You’re unqualified. You’re going to mess up. You need to wait until this is perfect. You need to be pushing. On the right side, I tap back into my inner child, the one that loves to play, and write down what my childlike self would love to have. For me and many of the leaders that I coach, it’s outcomes such as: I want to collaborate. I want great team to work with. I want to have fun. I want to feel relaxed. I want to feel connected.


Moving forward in freedom begins with having compassion for the two selves inside us. How do I have compassion for my inner critic? I can ask, “How is it just trying to help me?” I don’t listen to it, I just notice it’s chatter. I can also have compassion for your inner child by understanding what it’s trying to help me accomplish, and to also just notice it? The trick is not to 100% agree with or become connected to either one.


The answer is a both-and. My inner critic could be there to help me notice some helpful rules. My inner child could be trying to bring out the fun side of me so I’m more approachable. So, a question I can reflect on is: How can I work within some rules at work AND be collaborative, have fun and relax?


Turning Disappointments Into Future Results

Reflective journaling is an excellent way to silence our inner critic and turn disappointments into learning moments. As you’re thinking about moving through the perils in your “big idea” journey, you can ask:

  • Why are big results so urgent?

  • What could this disappointment be teaching me?

  • What could I be learning from it?

  • What’s another time in my life that I launched something and it didn’t go exactly as planned? What skills did I use to learn inside of that? What am I learning about myself

  • How could knowing myself, your skills and my strengths at this time be more helpful to me longer term rather than trying to get it perfect the very first time?

It can be helpful to remember to take on the mindset, even at work, that you are just playing. You are just interchanging plates as you learn more about what works for you and what doesn’t. Our stress isn’t coming from our results, but from the expectations we place on perfect results.


As you take away insights from your journaling to apply them to future efforts, here is a a confidence-building meditation:

Disappointments are a gift. If I never feel the sting of disappointment, I’ll never feel the urge to seek wisdom. From wisdom, future success. How freeing to appreciate life’s disappointments as the birthplace of building a joyful life. Kelli Thompson

Learn more about my 2020 Rise Confidently Leadership Masterclass program: kelliraethompson.com/leadermasterclass


Download the Journal Prompts + Meditation!



This post was originally featured on Thrive Global.

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© 2020 by Kelli Thompson