Try Monthly Check-Ins to Build Self-Esteem

September 7, 2020 Jessica Kaley

I started doing monthly check-ins a couple of years ago when I first recognized that I had a self-esteem issue. Poor self-esteem often keeps us stuck in the past with regrets or pinned to the future with hopes and dreams. My monthly check-ins keep me grounded in the present and give me a realistic view of my accomplishments and productivity level, which keeps my self-esteem healthy. Before I started doing monthly check-ins, I lived with a never-ending to-do list which made me feel like a failure and less than enough.

Self-Esteem Grows Each Month

Each month I take a fresh look at which parts of my life are least satisfying and would benefit most from my attention at that moment. Then I plan a few activities for the month ahead to address them. Instead of working a list that rarely changed because I never finished anything, I focus on making one or two things just a little more satisfying than they are.

When I started using this system, it was usually the same items that were bumming me out each month, but after a couple of years working on baby steps in the worst areas, I feel more balanced than I was and now I enjoy the surprise each check-in brings me. After identifying the areas I want to work on, I choose a few baby steps to commit to for the month ahead. Then I can celebrate next month when I check them off as done and recognize my progress.

I found that monthly check-ins were my sweet spot. It stopped me from getting overly anxious by thinking about my progress on the big items every day, plus it made me spend some time thinking about the areas that I am satisfied with, which gives me a more positive, holistic and realistic view of my life.

Baby Steps Make Monthly Check-in Progress More Visible

Baby steps combined with regular check-ins make it easy for me to see the progress I've made in different areas of my life. My self-esteem feels strong when I complete each baby step and celebrate success. 

After you watch the video, tell us how you keep track of your progress toward your goals. Does your self-esteem suffer from over- or under-thinking about some areas in your life? How do you think a monthly check-in would change your self-esteem? I look forward to reading the stories you share as we work together to build healthy self-esteem.

APA Reference
Kaley, J. (2020, September 7). Try Monthly Check-Ins to Build Self-Esteem, HealthyPlace. Retrieved on 2024, June 20 from

Author: Jessica Kaley

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Lizanne Corbit
September, 8 2020 at 9:26 pm

I absolutely love this idea! I think the combination of baby steps and regular check-ins is such a powerful combination for working with anything, particularly something like self-esteem. I think it is such an important thing to look at in terms of practice and habits (this is so true for so many things). Thank you for sharing this so others may benefit from this as well.

September, 9 2020 at 3:20 pm

Thanks, Lizanne. For most of my career, I was a Project Manager, and I learned the value of regular check-ins combined with breaking down tasks to the smallest component as the best way to ensure things got done without stressing. After my studies in Life Coaching, I was able to apply this methodology to improving my life and helping others do the same. I love to share the skills I learned on the job that can be applied to building self-esteem after proving to myself they work on me.

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