What if regret—that sharp, painful feeling you’re trying to avoid—is actually the clearest signal of what you truly care about?
This week, I have been plagued by regret. But learning from regret, I’m discovering, brings stark clarity about what you actually care about. For the past two years, I’ve facilitated a workshop on meaning as part of McKinsey’s Next Generation Women Leaders program for over 300 emerging female leaders. It’s a highlight of my year. And then I made a mistake that cost me this opportunity.
I had a brain fart. That’s the only way to describe it. R and I booked a weekend away to celebrate my birthday and mark the end of my time at McKinsey. We spent a lot of money on this. And because I wasn’t looking at my work calendar, I didn’t clock that it was the same weekend as NGWL, only realising the error a few weeks later. I was horrified. How could I have made such an error? Options ran through my head – could we rebook? But the terms said no cancellations or changes. Could I just do the workshop in the middle of the day on Saturday (5 hours?) But that would completely interrupt our plans. In this state of mind, it seemed my only option was to find a replacement. So I reached out to my network and found a wonderful replacement. She is excellent. The participants will be in good hands and still have an outstanding experience – just without me.
While I felt an immediate sense of relief that R and I would not lose a large amount of money on this weekend we’d booked, I woke up the next morning feeling incredibly intense feelings of regret. I have an aspiration to become more like Oprah – I want to reach thousands (millions) of people with my voice if it can help them in some way. I want to amplify the voices of others who have amazing things to say. And yet, here I was, turning down an opportunity to work with 300 women – an opportunity that has come through the incredible reach of McKinsey, where I won’t be working for much longer. Why didn’t I just call the hotel and see if a change was possible? Or negotiate with R for time away in the middle of the day on Saturday to do this important session? I’ve been kicking myself all week.
For a few days, the only thing I could do was try and allow myself to actually feel the regret, rather than suppress it or frantically backtrack. Eventually, I was able to investigate the topic of regret in more detail. My friend Jenny (always wise – I’m lucky to have her on speed dial) said to me yesterday: “The thing with regret is, it cuts like a knife. It helps you see in very stark clarity what you actually care about, when, before you made the decision, you were probably a lot less clear.” David Whyte, in his book Consolations, writes: “Sincere regret may, in fact, be a faculty for paying attention to the future, for sensing a new tide where we missed a previous one.” Adele, in her song “Someone Like You” sings: “Regrets and mistakes, they’re memories made.”
Ultimately, I’m grateful for this experience. It’s brought a ton of clarity to what I want to prioritise in this chapter of my life – getting my voice out there more – and that I both need to look for opportunities and ask for help. My friend Debbie works with a publicist who I’ll probably have a chat with. I’m trying to get better at self-promotion without looking opportunistic. And the next time I am faced with a choice of two paths, I will ask myself “What does my heart want most?” and then look for how to make that possible, rather than focusing on what I stand to lose and how to protect that loss.
When I look at a longer time horizon, I can also see how things that are meant to be come around in their own time. For the past ten years, I’d been regretting not pursuing a career along the lines of what I learned in Harvard’s Negotiation and Mediation Clinical Program – including in a course taught by Erica Fox. Ten years later, I’m getting my wish. In May, I’ll be joining Mobius Executive Leadership, a phenomenal organization founded by Erica and her sister Amy. It’s a privilege and an honour, and a sign to me that, while we cannot erase our past, we can, as David Whyte says, pay closer attention to the choices we make in the future. So, I may not get to participate in NGWL this year, but I definitely won’t make this mistake again, and with any look, future opportunities will come my way.
This week’s poem, The Road Not Taken, by Robert Frost, has also been a great comfort to me. While most of us know it for its last two lines – taking the road less travelled by – if you read it more closely, it takes on a new meaning. When we are faced with two paths, we must choose one, as we cannot travel both. In these times, we always second guess ourselves – what if we had taken the other road? We can fill our minds with fantasies of what may have come to be had we taken that other road. But actually, each road will have its pleasures and its pains, and there is just no way to know what may have been had we taken the other one. Once we choose a path, we must own that decision, rather than constantly backtracking – that’s the only way we can actually move forward and reach new destinations in life.
