Coaching Corner
Life Coach Tal Fagin Provides Guidance to Your Quandaries
Tal Fagin

Riddled with Regret

Life coaching expert Tal Fagin responds to a reader who feels they are wallowing in the past. Tal suggests devising a plan to fill what needs filling, to shed what needs shedding.

Dear Coach,
Everyone is talking about mindfulness and the beauty of the present moment, but I seem to be stuck in the past. It’s as if my brain has a broken rewind button, and wherever I am, whatever I am doing, mentally I am rehashing some old event. It could be something small (like when I wake up in the morning regretting my late night snack), or something more significant (like an ancient conversation with my father I wish I had handled differently). It’s like a cough that won’t go away, a persistent case of “if only I had known then what I know now…”

I know we all make mistakes, but what I can’t quite figure out is how to move past them. I don’t want to spend my whole life looking backwards, wallowing in the past. Any advice for how I can move forward?

Riddled with Regret 

Dear Riddled with Regret,
Regrets are a fact of life, a byproduct of being human. We all make poor choices sometimes, then lie awake at night wondering what might have been. From the investment we shouldn’t have made to the love we foolishly pushed away—fully lived lives necessarily include decisions we might later live to regret.

When we get bogged down in regret, we are comparing our actual lives to some ideal “if only” life, a perfect fantasy of what our lives might be like if only we had opted otherwise. The problem with this tendency, of course, is its futility. There are no sliding doors through which to slip one minute earlier, no magical cars to ride back to high school so you can punch out the bully. You simply can not return to those crucial moments of decision armed with the knowledge of how it will all turn out, then edit your choices accordingly.

So what can you do?

Make Meaning. Every instance of woe-is-me can teach us powerful lessons about designing the life we truly crave. Mistakes can be valuable opportunities for learning, just as disappointment can be a catalyst for change—but only if you embrace them as such.

Whatever it is, whatever you’ve done in the past that continues to hurt, what lessons can you derive? What might you learn? What might others learn from you?

Whether your wounds have been self-inflicted or imposed upon you, you can not undo them. You can, however, use them as a spring board from which to grow and inspire others.

Make new meaning of your old story and turn your sad tale into an inspiring saga—starring you as the wise, resilient and reformed hero.

And while you are at it…

Try a Little Tenderness. Most of us are far harder on ourselves than we would ever be with another. This is part of our survival instinct, and comes from a belief that the more we smack the whip against our own rump, the faster we will run.

Why not try a little tenderness, instead?

When my earnest, well-meaning children screw up—whether it’s a tumble they’ve taken because they were rushing, or a test they’ve botched because they didn’t study quite enough—what do I do? Do I berate them for their carelessness? Do I insult them for their laziness?

Heck, NO!

I give them a hug, I wipe their tears, I whisper sweet nothings into their soft heads. I remind them that everyone makes mistakes, and that this is how people learn. I encourage them to remember this moment—the pain or sorrow or disappointment of it—and to use it as motivation to be more careful, to work a bit harder, to do better next time.

Might you be willing to try this approach with yourself? Can you afford yourself the same compassion, understanding and TLC you might use with a small child or beloved friend?

Feel the Pain: Some of our greatest regrets involve permanent loss. Loved ones die. Careless mistakes and tragic accidents alter the lives we expected to live. These gut-wrenching twists are not insurmountable, but before you can learn from your mistakes, you might have to spend some time grieving what you have lost.

I would not advise lingering in this place too long, but since you can’t seem to escape the call, heed it. If it is too painful to do alone, consider enlisting support from a friend, therapist or coach. Whatever it is that you have lost or wish were somehow different, name it, sit with it, allow it to be there without resistance or judgment.

Denying your pain is as futile as wishing it away, and will only cause it to fester and persist. Instead, just be with it. Allow it to move through you, so you can move on.

Embrace the Ripples. Just as we all have things in our lives we regret, we all have things we appreciate, as well. The part we tend to forget is how inter-connected these various aspects of our past, present and future are. Every experience has a ripple effect. Each move we make has an influence on every other aspect of our lives, impacts we can never fully calculate or even be fully aware of.

I personally know at least four people who met their spouses in connection with one of the worse events of their lives. Alex might wish he hadn’t gotten slammed by that car and landed in the hospital, but he is forever grateful that he met Jen while in physical therapy. Embrace the ripples of your life. If there is something you simply can’t get over, try to connect the dots toward something positive. Remind yourself, “If I hadn’t ___, I might not have ___ .”

And last but definitely not least, my favorite, most productive approach to regret…

Plug the Holes. When you catch yourself lost in the past, wondering what might have been, pause. Take a deep breath, then ask yourself one simple question.


Why has your mind wandered back in time to the interview you botched or that phone call you never made? Why, all these years later, are you bemoaning this or that decision, or wondering what it cost you? Why is it still causing you pain or remorse?

Ultimately, this series of “why” questions will lead to a place of yearning. There is something you are missing in this moment, something you are wishing was different in your current life that feels inextricably linked to the moment you want to redo.

What is it?

Once you identify the holes that need to be plugged—or the excess baggage that is weighing you down—you can get proactive. You can devise a plan to fill what needs filling, to shed what needs shedding. You can take decisive action right now to cure what ails you.

I would encourage you, Riddled with Regret, to move beyond the woulda, coulda, shouldas. Delve beneath the surface of your regrets to the deeper waters of what you crave. This is your opportunity to get creative, to assert some control, to DO SOMETHING!

Every instance of sorrow is a treasure-chest of information, a personalized map guiding you toward the life you really want.  I suggest you follow it.

Try any or all of the above, alone or in combination. It may be uncomfortable at times, it may be scary, unpleasant or even painful. I assure you, however, there is lots to learn and much to gain.

I will leave you with some encouraging words from my favorite morning meditation (which, of course, I highly recommend you try):

Each day is a new beginning, a new opportunity to be how you want to be, to be your best self, to make the most out of every situation.    

Good luck!