I was talking to an old friend just the other day. What made the conversation truly special is that we had not seen or spoken to each other in almost 30 years since our high school days.

The amazing part of the conversation was our instant reconnection over the phone. Our tone and familiarity as we spoke was as if though we had only seen each other last week.  As we shared stories about high school we laughed about the good times we had and could now laugh at the bad times as well.

We started to compare notes on who we had seen since our high school graduation and what was the latest news on our closes friends: Do they still live in Chicago? Are they married? What was their profession? Who passed away? 

After getting passed what our friends were doing, we started to talk about our own lives and what we had done over the last 30 years. I shared with my friend all the things I had been up to; including some down times but many more good times. I told him that on the whole, if I were to die tomorrow, I would count this lifetime of mine as being a blessed one. 

Here’s the fascinating part of this story.  I then asked him to get me caught up on his life and what he had been up to in the last 30 years. It became apparent after a few moments of talking that his 30 years were filled with many tales of poor missteps and mishaps both personally and professionally.  He went on to tell me about his trials and tribulations; it wasn’t pretty in some cases. Like any one of us, he made his fair share of mistakes. But unlike some of us, the mistakes carried with them a high price both financially and emotionally. 

Now before I go any further, let me be clear in saying that I am not judging my friend. In my lifetime I’ve learned not to judge others. There’s a saying about never judging a man unless you’ve walked a mile in his shoes.  The only person in a position to judge is the individual going through the struggle. 

As I listened empathetically to my friend I wasn’t impacted so much by the stories of his misfortunes, but more so by the tone in his voice which, consciously or unconsciously, transmitted the muffled pain of many years of regret. In his voice I could sense him tabulating the mounting debt of lost time and missed opportunities. Like many us he made poor choices along the way. 

In high school he, in my opinion, was a gifted musician who I thought would one day for sure be atop the music business somewhere, somehow. I asked what had happened. He again went on to describe poor decisions he had made; many regrettable ones.  He then revealed something that shocked me. One of the things that held him back from pursuing his music career, aside from personal family matters, was his lack of confidence in his own abilities. You would be shocked too if you saw this guy play a guitar at the age of 17.  He was a virtuoso back then on the guitar.  I can only imagine what he could’ve done if he had pursued his passion.  

Yet, somewhere along the line he lost confidence in himself.  I could tell that his biggest regrets were those linked to his inability to take action and follow through on doing the things “he” wanted to do.   As I listened to his story I was reminded of the story of “The Parable of Talents” where a servant buries his talent instead of investing it for growth.

As the conversation wore on I told him that he had to stop reliving the “would’ve, could’ve, should’ve” in his life and that it was time to look forward and make some new decisions based on where he is at today and what he wanted for himself in the next 10 years. He agreed with me but I noticed that his conversation kept referring back to the past decisions in his life.  I finally said something along the lines of, “You can’t change the past.  Some people keep living in the past and never learn to erase the board. You have to learn to erase the board and start fresh.”  I couldn’t see his face since we were on the phone, but I could sense his reaction to the phrase, “erase the board”.  So I continued, “I’d like you to imagine that in front of you have a whiteboard or chalk board if you prefer. Written upon it are all the bad decisions you’ve ever made and all the plans you never followed through on. Now mentally take an eraser and erase everything on the board and start mapping out what your next 10 years are going to be like.

The problem most people have is that they can’t erase their own board. They use it as an excuse or a crutch for not moving forward. They can’t let go of what they can’t change. Erase your board and start, again, now. Today!”  Maybe it was the slight pause in his response, but I could tell that my words were having some type of impact on him.

For some people starting over can be very difficult.  How does one make that type of commitment without resorting to self-pity given the things that have happened in the past?

Erasing the board is a metaphor I use for giving ourselves the permission to start new without the mental handicaps of the past.  If you think about it, the act of erasing the board is not about erasing what we’ve learned from our mistakes, it is about the power to forgive ourselves for past mistakes. 

What is often ironic is how we are more apt to grant forgiveness to others for their trespasses, but we are reluctant to confer upon ourselves the same courtesy. For some egoistic reason we hold ourselves up to a higher standard and we are thereby less forgiving when it comes to our own human actions. 

We all, sooner rather than later have to forgive ourselves.  This can only happen when we stop criticizing ourselves for past mistakes or missteps. The author Rob Reese in his book, The Wisdom of Imperfection has a statement that I found profound enough to commit to memory. 

“There is humility, honest and compassion in the capacity to allow our fallibility and frailty as human, sentient beings. To try to be otherwise can be seen as embracing a kind of false self that is in denial of our fallibility. This compassion allows us to be who we are without destructive judgment and self-criticism.”

We have to accept who we are and how we are built; can’t change that. We are all perfectly imperfect.  What we can change is our mindset and begin to let go of the past along with all the mental anchors that have been holding us down is the only way anyone can move forward. 

My old friend who finds himself unable to move, feeling constricted by the past.  Unless he can learn to erase the board cluttered with all his mistakes, failures, missteps, mishaps and regrets, he will never move forward.   He’ll always be held back by the “would’ve, could’ve and should’ves” in his life.

I believe my friend’s biggest regret was his lack of confidence in his own God given abilities. We talked about his musical talent and how it wasn’t too late to salvage his dream if that is what he indeed wanted to do. I asked him to give it some serious thought and really think about what he wanted to do for the next 10 years.  In his case, the worst thing would be to wake up another 10 years later in the same situation. That would be a human travesty! 

We’ve all made mistakes.  We’ve all made choices we now know in hindsight weren’t the wisest.  We’ve all missed opportunities to take advantage of opportune moments or situations.  We’ve all said yes when we should’ve said no and vice versa.  We’ve all hesitated to ask that one question that would’ve saved us from heartache and failure.  We’ve all trusted and been betrayed only to repeat the same mistake again. 

And as the economy continues to struggle to recover and the financial pressures build, the tendency to blame and dwell on regret becomes all too tempting.  Regret is fertile ground for negativity and pessimism to set in which only begets more regret.

Yes, it’s true, you are perfectly imperfect; you are human.  You’ve made mistakes, who hasn’t?  The question going forward from here on out is, “Will you forgive yourself and allow yourself to move on?”  I’m going to ask you to GIFT YOURSELF the greatest gift any human being can give themselves… permission to erase the board! 

Please share this with someone who needs to hear this message.

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