A client has come to me recently carrying a load of regret. It has risen hard to the surface because a couple of key decisions he has made recently have had negative consequences, and have triggered in him a painful awareness that he is not where he wants to be in his life, either in his career, his finances, or in his relationships.

And so he is getting caught up looking back over his life, questioning the decisions he has made for  years. Did I make the right decision? What if I had taken another path, another approach? I’m not where I wanted to be at this point in my life, so I must have made a mistake, missed an opportunity, taken a wrong turn. For example, he said, “I regret my time in my 20s (a time of extensive travel, study, and exploration) because I’m not where I could be in my career.” And that was almost two decades ago, a time he still reflects on.

Regret lies heavily on his mind these days, but not only these days. He is aware that he has long had difficulty with regret, difficulty letting go of the past. Added to that, he admits to having a particular “talent” for seeing in hindsight the path he could have taken. Or, as it sits in his mind, should have taken. A life of missed opportunities, regretted for years and years, that is taking an emotional toll on his sense of self and wellbeing. “I am not happy about the person I am today. I could be better, and I beat myself up for that.”

Coaching Regret 

I asked him what he has personally done to work with his regret. Up until we started working together, his primary approach was to distract himself. Go out on the town, have a few drinks, hang out with friends, or find something to do that would take his mind off the looping thoughts of what could have been.

How do you coach regret?

• As a deep coach, what approach might you take working with regret?
• How might you work with thoughts that have a strong grip on the mind?

Head over to the forum to share your thoughts on how you would coach this. Tools, exercises, questions, approaches?

If you hear his life story you will hear that he has actually lived an interesting and unconventional life. He followed his own drummer from an early age, and it has taken him to many places far beyond his homeland. When you hear his life story it’s easy to think, “Wow, what an interesting life. Look where it’s taken you, look at what you’ve been able to experience. It’s not been without challenge, but what’s to regret?” (At least that voice popped briefly into my head.)

But of course, coaching him to see the positives in his life is only moderately helpful in situations like this. It’s not that he can’t see the positives, he certainly can, it’s that he sees in hindsight a host of potentials missed, paths that if taken could have brought him to a better place than where he is today.

Coaching this, the first step was to reveal more of how his mind is working – his thought patterns and perceptions of himself and his life – so that he could understand why he feels the way he does, and the effect it’s having on his life.

What we learned is that his mind is gifted at seeing how “the other path could have been,” and it gets locked onto that imaginary “grass is greener” scenario. Once these thoughts come in, he is terribly challenged to let them go. His mind revisits and replays the imaginary scenario over and over, and that’s when he starts to spiral downward into regret and feeling negative about his life and the choices that got him to where he is. He then starts worrying he’s made the wrong choices, and does not see the good on the path he is on. He gets concerned he’s missing out on what could or “should” have been. It’s like his mind is stuck in a groove and he struggles to get out of it.

From this understanding, we laid out a larger framework for our work. He identified three integral pieces he believed would help him let go of regret over choices that did not turn out as desired and (perceived) missed opportunities, and become more present in his life:

1) Forgiveness

2) Gratitude

3) Faith (in self, process, past, future etc.)

Of course the story continues. All of this has come out just from our initial conversations. There is a long road ahead of further revelation as to what’s underneath. Jumping into and working with these three areas will take time, patience, practice, commitment…and since it’s all new to him, it won’t necessarily be easy.

Deep Coaching Tip

What sets the deep coaching conversation apart from a conventional conversation conversation however, is that we are always listening for an opportunity to activate these within the session itself, not just talk about them as potentials. This activation process (exemplified in Practice 1, Live Your Spiritual Values) is what makes the deep coaching session a healing space.

I’m always listening for his readiness to move beyond speaking about the value of forgiveness (or gratitude or faith) to an actual experience in the moment with me, his coach. It is not my agenda—I don’t force it; I let my client’s deeper self lead, so he must open the door—however I can activate an energy field of potential and weave that into the space.

This is a way of inviting without inviting (spiritual energy, not words), and trusting that as spiritual partners we are connecting at some level of mind and soul — he is receiving the invitation to experience himself as forgiven or grateful or living in faith.