Recently, a member of our Playing Big course asked me a poignant question. She shared,
I’m in a new place in my life, and I have room and the desire to Play Big in new ways. But I can’t help but think about all the time I spent playing small. How do I deal with the regret, so I can move forward?
Today, I want to talk about this important matter: regret. Regret about the times we didn’t find our voice, or the years we spent hiding or playing small.
I’m reminded of another woman I coached, Cathy*. Cathy had long worked in a corporate marketing job, but what she really loved was design, history, old quirky things, upcycling. All of that came together for her in antiquing, thrifting, and creating amazing spaces with what she found. She’d done some powerful coaching and the journaling work to get clear about what she loved, and she’d gotten excited about creating a weekend pop-up antique store in her town.
But as she got closer to taking action to create it, her thoughts kept drifting to the past, and to her sadness and regret that she hadn’t done this very same project years ago. She kept thinking about how she “lost so much time,” how she was “late.” Grief subtly spilled into self-blame. I just wish it hadn’t taken me so long to figure it out. I wish I’d been braver sooner, like so many other people are.
Can you see how Cathy’s regret is functioning here? It’s a highly compelling distraction, one that arrives right at the moment she’s about to truly step out of her comfort zone and create something different in her life.
Feeling the exhilaration and fear that comes when we embark on an important playing big step, her psyche said: This is feeling unfamiliar, and daunting, and scary. What can we do to get out of this heightened, uncomfortable state and back into more of a familiar dead zone?
And her mind found something: what didn’t get done in the past. We can get stuck in the mud of rumination and beating ourselves up for something we now can’t change. We can focus on the past instead of on the (scary) change that’s right here available for the taking, in front of us. We can look backward at the path behind us instead of taking that step forward through the gate that’s open, in front of us.
This is what’s most dangerous about getting pulled into ruminations of regret – the sneaky, compelling distraction it gives us, pulling us away from action.
But what about the real feelings of sadness and grief? And is pushing past regret an unhealthy form of not feeling the feelings that need to be felt?
I love this one liner from 12-step recovery circles. “We look at the past, but we don’t stare at it.” In other words, the amount of time and energy spent looking backward matters. Dose matters. Yes, we look backward – to know ourselves better, to learn the lessons we can learn from the past – but then we take those learnings in our hands and heart and we return our attention to the present. We put them to work in the now.
So we can spend some time looking back, and feeling sadness and grief if it is there, asking to be felt. But one important thing about that: there’s a big difference between slowing down to actually feel the feelings fully versus getting stuck in ruminative thoughts and beating ourselves up.
We need practices that help us actually experience and metabolize our emotions of sadness or grief about the past. That could look like journaling, speaking about those feelings aloud to a support person, having the cathartic cry, making art about it, and slowing down to really breathe along with the physical sensations of the feelings and be present to them. These kinds of embodied, intentional practices are quite different than barreling through your busy life flashing on moments of feeling regret or looping in unkind thoughts to yourself.
So: feel the feelings, deliberately and in an embodied way, so you can move through them.
Look at the past, but don’t stare at it.
And most of all, watch out for the pernicious distraction of regret, the pull to beat yourself up for the past rather than walking through the gate that is before you, wide open, today. Move your gaze back to the present moment, and the possibilities it contains.
So much more than we often realize, the gate is open. It really is.
Love,
Tara
Top Photo Credit: littleny
* Name changed for confidentiality.






