Shoulda, Woulda, Coulda: Overcoming Guilt and Regret

By Steve Backlund


Success is not a goal to be obtained; it is a state of being. If we need something outward to validate us as a success, we are not successful. Consider Joseph from the Old Testament. “The Lord was with Joseph, and he was a successful man” (Genesis 39:2). Joseph’s success was not the result of a position he held or possessions he had, but it resulted from who he was because God was “with Joseph”. He was successful as a slave in Potiphar’s house, in prison, as second in command in Egypt, or any other place you put him. 


When we consider Joseph’s story, we realize he could have lived in guilt and regret because of what should  have happened, what could  have happened, and what he should have done:

  • “I should not have told my brothers about my dream of ruling over them.”
  • “I could have used greater wisdom in staying away from Potiphar’s wife.”
  • “I would be out of prison now if the chief butler had remembered how I interpreted his dream and told someone.”


Those who live confidently realize the importance of overcoming what is called “woulda, shoulda, and coulda”. These words represent the regret and guilt we feel for missed opportunities, mistakes, unjust happenings, and failures in meeting our own expectations or the expectations of others. They cause various levels of shame and unworthiness which limit our ability to attach faith to what we are doing now. 


The “woulda, shoulda, coulda” mindset can certainly be the result of major wrong choices or happenings in our past, but it is most damaging to us in seeming smaller areas of life where we remain in low-grade guilt because we have not decided in faith what to do. 


Let’s get practical here. We are all bombarded with many opportunities and things that we could and should do. I have battled guilt feelings in areas like the following: not sending Christmas cards to people who send me Christmas cards, not connecting with people who want to connect with me, not giving to a certain cause or project that is presented to me, not having my yard as great as I think it should be, etc. I have wavered between two opinions regarding these and have lived in doubt that I am doing the right thing. 


Each of these things is an opportunity to go higher in our decision-making because great decision-makers know what they are called to do and what they are not called to do. We can strengthen our decision-making muscle in matters like these by clarifying our priorities for the season we are in and then deciding (attaching faith to) how we are going to think about particular matters. 


Let’s go deeper in this. We may be driving a non-successful car or our physical appearance may not be as successful as we want it to be. We cannot allow ourselves to have low-grade, negative beliefs about these things. A better attitude would be to say, “I need to drive my non-successful car in faith because I know this is the season that I'm in, and this is what I'm supposed to be driving at this time.” God makes people successful on the inside when they don't look successful on the outside. And one of the ways to be successful on the inside is to attach faith to what you're doing or what you have now.


So “I shoulda, woulda, coulda. I should be better at this. I should be farther along in this season of my life. I wish I had a college degree.” or something else. Whatever it is, as we take inventory of things in our lives that create shame, inferiority, or guilt that we are letting people down or disappointing others, we can address each one and then become fully convinced about how we are going to think about them. We can do this by believing, like Joseph, that God is really with us now in our current situations and we can become successful on the inside through faith in God and attaching faith to what we are doing or not doing. This is a powerful key to becoming fully convinced. 


About Us

STEVE BACKLUND

Steve Backlund is a prolific encourager, catalytic author, joy activator, and revivalist teacher. He brings transformational levels of hope to churches and organizations around the world. He is uniquely gifted to release hope, joy, and healthy leadership everywhere he goes.

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