40 Ways We Self-Sabotage and How To Love Ourselves Through It

For the month of September, the theme has been “Exposed”, the definition of which is “to make something visible by uncovering it.” Over the past three weeks, Dear Wednesday has tackled the action of belief – not merely wanting to believe or saying words we don’t truly mean. As we begin to say goodbye to September and hello to all things Fall, this theme has been important because we have begun to expose the lies we believe, the truth that sets us free, and the destiny we are called to walk in with confidence. Thank you for reading and sharing the blog this month, and let’s end the Dear Wednesday letters for September with a bang.



40 ways we practice self-sabotage and how to love ourselves through it.


Ending the month’s #DearWednesday letters by addressing self-sabotage is exactly the kind of blog that’s needed right now. We have nearly 90 days left before the end of 2019, and some of us did not meet our relational, financial, professional or personal goals because our thoughts beat us out of the ring before we fought a round. As I previously wrote in an earlier blog, “we settle for the same thoughts that keep us in the same place.”

This blog is about identifying self-sabotage before it undermines your best self.


Let’s start with 40 ways we self-sabotage and end with how to love ourselves through it. After all, sabotage isn’t bigger than your ability to conquer it when you access the right tools, beliefs and strategies.


  1. Procrastination. Need I say more? When we waste our own time, we aren’t serious about producing the outcomes we dreamed and hoped for.

  2. Offense. We get and stay offended quickly and easily, which in the end destroys and hardens us so much so that we are prone to believing the worst in others.

  3. Overspending. Spending money we don’t have and going into dangerous debt to fill the hole in our gaping souls.

  4. Zero boundaries. Lack of setting and keeping boundaries in all relationships, romantic or otherwise.

  5. Busyness. Signing up for events and opportunities we do not have time or mental space for at all.

  6. Worshipping People. Putting people on pedestals and worshipping them instead of focusing on our potential for greatness. When others-focus becomes a form of worship, we lose sight of what is important.

  7. Avoidance. Avoiding courageous conversations out of fear of disagreement. At some point everyone will not agree with us or we will have to confront tough situations, and if we fold the problem will still be there.

  8. False humility. Period.

  9. Lack of vision. Going after goals that were meant for someone else.

  10. Comparison. We are running the race, yet our focus is on how others are appearing to do so much better than we are.

  11. Quitting. Giving up on things we want because we deem it too challenging or too out of our reach.

  12. Faulty love. Falling in love with potential and not reality.

  13. Bitterness. Holding on to bitterness from our past and expecting people to read our minds as to why we are mad.

  14. Blaming others for our present condition.

  15. Negative automatic thoughts. Allowing negative thoughts to reverberate through our brains repeatedly without challenge.

  16. Refusing to go to counseling to address personal issues due to stereotypes and naysayers.

  17. Believing that tomorrow will be the beginning of our new life, except tomorrow never comes.

  18. Refusing to cut ties. Making the mistake of believing our exes can truly be life-long friends (or more if we keep them around).

  19. Blaming ourselves for someone else’s flaws and shortcomings.

  20. Believing we can change him or her by being present and supportive. Burying our head in the sand when the person continues to act in a manner we don’t approve of.

  21. Disappearing when a friendship or relationship gets too difficult.

  22. Our default answer for lack of follow through is “imposter syndrome”.

  23. Self-Medicating through overeating, undereating, extensive sex, overusing prescriptions, or substance use.

  24. Finding excuses to get into arguments as a turn on or a way to keep ourselves from feeling dead inside.

  25. People pleasing, to which there is no end.

  26. Suppression of feelings, and guilt for having feelings at all.

  27. Inflicting Wounds from the seat of our pain. Hurting those closest to us because we refuse to address our own pain.

  28. Running after perfectionism.

  29. Hiding from the world because of fear of harm or dread of having to engage in social interaction.

  30. Embracing the victim mentality.

  31. Putting up appearances instead of doing the inner work to get better and stronger day-by-day.There are not enough makeup and clothes in the world to mask self-loathing or lack of self-worth.

  32. Believing the lie that we are unlovable and incapable of love.

  33. The company we keep. Aligning ourselves with people who ultimately hurt us because we believe it’s better to be connected with someone than to be alone, even if that someone hurts us repeatedly.

  34. Blaming ourselves for someone else’s dysfunction. Taking on their burdens as our own.

  35. Accepting burnout as a natural part of the human condition that we have to endure.

  36. Choosing to be isolated repeatedly, holding ourselves hostage, and calling it introversion or exhaustion.

  37. Staying stuck in who we used to be instead of embracing who we are becoming.

  38. Accepting everything and refusing to draw an opinion of our own, no matter how unpopular.

  39. Clutter and disorganization, which is a function of dysfunction.

  40. Rejecting any and all help for the appearance of full independence and adoration from the fans we made up in our head. Wanting to wow people by saying no to offers of help at any cost.


Bonus: We self-sabotage every time we feel guilty for saying what we want, every time we shrink back from demanding respect, every time we allow the narcissist to take advantage of us physically and manipulate us mentally, every time we are afraid to say no, every time we are afraid to say yes to things that have the capacity to lift us up, every time we decide to believe the lie instead of walking free in truth, every time we deny who we are just to fit in… we self-sabotage. I’m sure you can think of more than what I just named.


What numbers above resonate with you most? Which self-sabotaging behaviors are you operating in currently?



How to love yourself through it.

Self-sabotage does not come with an overnight fix label. To undo the damage done, we must choose to acknowledge that we engage in self-sabotaging and self-defeating behaviors. We must choose to derail our own patterns for the sake of developing new ones. We must ask for help frequently and look in the mirror into our own eyes and begin to get honest. We must be willing to expose the ugly so that we can finally heal. We must stop lying to ourselves about ourselves. Also, we must clean up the mess we made when we chose to honor everyone and everything and left nothing but piles of scraps for ourselves.

Joyfully revisiting the questions I asked you at the beginning of the month, several blogs ago, I am ending the September blogs with questions for reflection. I purposefully made some changes so that you can adequately expose the areas in which you currently self-sabotage:

  • What would your life look like if you dealt with the you that you’ve been hiding? If you confronted self-sabotage? Describe it.

  • What are some specific ways you currently self-sabotage and why? How did you get there?

  • What is a lie you need to expose right now that may be holding you back from the greatness within you?

  • What is a strength that you have that you’ve never told anyone? What held you back from exposing the strength you have identified.

  • Name some specific ways you are making progress in your life right now. Talk about what you’re doing now, not what you want to do in the future.

  • How will you know you’ve made progress? How would your life look differently? What specific areas would change to let you know you’ve changed?


I hope that you take the time to dig in and defy the doubting, naysaying part of yourself who says this really isn’t important right now.


Oh, but it is.


It is important today, tomorrow, and years from now. The more you expose, the more of life you can compose.


The more you do the inner work, the more beautiful and joyful you will be not just to others, but especially to yourself.

That’s a me I can live with. What say you?


With love,


Dr. Joy Well


P.S. As I wrote before, “Be sure that you don’t get caught in the question of “why is this happening” as much as you situate yourself in the belief that in all things you can and will overcome.”


Until next time, Be good to yourself and others!

Evaluate your relationships!

Check your thought life!

And, invest in opportunities that increase your quality of life.


DWL Lifestyle Strategists Weekly Favs

  • Who doesn’t love Surf N Turf?? We’ll in the spirit of land and sea, Ashley’s favorite this week is Nantucket Restaurant in Chapel Hill. The steak is seasoned and cooked perfectly. The seafood is prepared fresh, and the service is wonderful. You even receive a greeting from the towering cakes displayed in the bakery shelf when you walk in. It is truly a gem in this Tar Heel city! Visit the website here for more

  • One of Joy’s favorites is the website thehealthyapple.com, which includes recipes, detoxes and articles for those struggling to find healthy, delicious recipes to help improve circulation and inflammation, as well as overall health. As she was perusing The Healthy Apple, she happened upon an article entitled “How to Soften Yourself: A Key Step for Healing". Read it here.

  • Patrice struggles with staying hydrated and can’t stand to carry around a bunch of bottles of water just to enjoy the filtered taste. A daily addition to her bag is the Brita 36387 Premium Water Filter Bottle. Now she can enjoy clean tasting water by filling her reusable bottle at any faucet. The bottle is leak proof and sturdy, which has been tested by the many times she has dropped it while getting out of her car. You will definitely want one of these!



  • Follow us at @challenge.courage on FB and Instagram.

  • Email us at Challengeyoself@gmail.com.

  • Join the premier University for women who are ready to define their lives for themselves - Joy University."I'm a Hot Mess: Now What"

  • The Premier Signature Masterclass is out now and if you aren't enrolled yet, reply and let's get you in now - Let me check it out!


Brought to you by Ashley, Joy and Patrice, your DWL Lifestyle Strategists


This Dear Wednesday Letter was hand-crafted by Dr. Joy. Dr. Joy Well, mental health clinician, confidence catalyst, professor, and avid researcher is one of the quintessential experts on the connection between the mind, body, and immune system. Her doctoral work explored the experiences of women of color living with autoimmune diseases and how they function and experience the medical community and beyond. Once a shy, small-town girl with big dreams, Joy has found peace and purpose working with women of all ages to develop a fierce, faith-filled identity, personally and professionally. She is a clinician and entrepreneur in mental health private practice, seeing all ages, backgrounds, and genders. In her spare time, she enjoys music, movies and getting into mischief with friends. You can find Dr. Joy on social media @captivatingjoy.


Dr. Joy Well (@captivatingJoy)

#selfsabotage #selflove #confidence #loveyourself #blog #dearwednesday

©2019 by Dear Wednesday Life. Proudly created with Wix.com