Do You Second Guess Yourself to Death?

Is second guessing robbing you of peace and contentment? Hard to admit, but being an idealistic, second guessing fanatic has stolen my joy one too many times.  Deep inside, I desire to make perfect choices 100% of the time.  Though history proves that it’s impossible, I continue to wage war to make that perfect decision. And those perfect decisions aren’t reached quickly.  They require strategic thought, advice, pros & cons lists, and much prayer.

Add Fear to Idealism and Second Guessing is Inevitable 

Don’t forget fearfulness… add fear to idealism and you have a recipe for a second guessing every time. I am so afraid of making the wrong decision.  What if this or that…what if I made a mistake and on and on.  I must drive the people around me crazy. Especially those like my husband who are decision makers by nature. In him, I don’t see fear or idealism.  I see a person moving forward with good decisions and navigating the way if it doesn’t go as planned.

Do You See Yourself In My Second Guessing Story?

Recently we bought a new house.  My husband and I knew the town we wanted to live in and the builder we wanted to buy from.  After touring the model homes we spent time discussing needs vs desires.  Then, compared that to the price we wanted to pay.  We thought about the future and how this house would serve our shrinking family. Together we sought wisdom. Coincidentally, we happened to be reading a book called Ask It by Andy Stanley.  Andy encourages readers to have the courage to ask themselves one question before making any decision:  “What is the wise thing to do?”  Simple, yet a complex question that helped us decide to buy the smaller, less expensive home with a slightly bigger backyard.

Decision Made…Second Guessing Mind War Begins

We put the down payment on the home, sold our current home and began making plans for moving day.  This was a move across town to another city about 25 miles away.  During the packing process I began to experience doubt and fear.  Did we make the right decision?  I started asking myself questions. Why are we leaving our current home…this is a great house?  The new home is smaller…will there be enough cabinet space and storage? Suddenly all the reasons we wanted to move faded and I was second guessing why we were leaving in the first place.  My anxiety levels went through the roof.  However, we already signed the paperwork.  This was a done deal.  I kept telling myself to stop looking back and focus on moving forward.  My husband and I made a wise decision.  We wanted something better for ourselves and our family and this move would provide just that.

The First 90 Days

By the grace of God, I made it to moving day. We settled in, unpacked and made the home ours. I was sure we made the right decision.  I loved the new city, the shorter commute, and the neighborhood.   Oh, and the cabinet and storage worked out just fine in the new home.  My worries were for nothing.  All seemed to be well.
After getting settled, I started looking around at all the homes being built. Once again, I began to doubt the home we bought.  Should we have gotten a bigger home with one more bedroom? Thoughts like, “If I just had one more room I could….or if we had a larger backyard we could….”  or “Why didn’t we get the other floor plan…yes that would have been better.”  I would drive by the other house we almost bought and wonder what our life would be like in that house.  Logically, I remembered that we made a wise, thoughtful decision, but my idealistic tendencies wouldn’t rest.

Then, a Big Light Bulb Turned On….

There is an ongoing pattern in my life.  I struggle to make a decision… then once I do, I second guess the decision to death.  As an idealist, decisions don’t come easy.  What does come easy is fantasy and imaginary reality. That dreamy state where you believe your ultimate bliss lies and all negative things cease to exist.  That place where life is perfect but all the while, forgetting there is no such thing this side of heaven!  Wake up!  Just wake up!

How Can I Reconcile the Inner Conflict

Always looking back, second guessing, and believing that I would be happier on the other side of my decision is foolish.  It’s as if I have decision amnesia and I forget all the reasons why I needed/wanted to make a change. Then, suffering selective memory, I only remember the good about what I just left. This is insanity…it stealing my peace, contentment, and ability to be present in the moment. What then is the answer to this insanity?  How can I reclaim my peace and contentment and release the desire to second guess myself to death?

Steps to Reclaiming Peace:

Here are a few steps I have taken to reclaim my peace.  This list isn’t comprehensive so please add to it by commenting.

  1. Remember why you made the decision in the first place.  Big decisions require big reasons.
  2. Post your reasons on your desk, on the bathroom mirror or other places where you will easily read them.
  3. Talk with friends who know your reasons so they can remind you.
  4. If you journal, go back and read the journal entries during the time you were making the decision.
  5. Accept the decision is already made and that you must move forward.
  6. Discipline your mind to be content and do not allow your thoughts to wander.
  7. Don’t compare yourself to others.
  8. If you an idealist like me, RADICALLY ACCEPT that life isn’t perfect.
  9. Count your blessings and be thankful always.
  10. Pray for God’s peace.


Sometimes Chickening IN is about embracing your life and resisting the temptation to second guess, compare yourself, and/or try to create the perfect life.  Do you struggle with similar issues?  If yes, let’s walk this Chickening IN life together, radically owning our decisions and reclaiming our peace.   

Please share anything that has helped you when second-guessing strikes.


For more on Andy Stanely’s book Ask: