How To Overcome Regret According To Headspace CEO Andy Puddicombe

How To Overcome Regret According To Headspace CEO Andy Puddicombe

Lifestyle | Posted by - September 13, 2017 at 12:30 am

Americans rank education, career, and romance, among some of their biggest life regrets. To help people recognize and learn from regret, Headspace, the popular digital meditation services company, recently held a Facebook Live Q&A with CEO Andy Puddicombe. YouInc rounded up relevant questions and answers on topics such as regret about wasted time, sending a text or email, and letting our minds dwell on decisions we can no longer change. 


Puddicombe shared a story about a 74-year-old woman, who held onto regret about her divorce for nearly 50 years. She built a narrative in her head about how she ‘could have’ handled the situation, and the negative effect lived on in her body and mind for years. 

The starting point is now, urges Puddicombe. We can’t go back or forwards. When we sit down and really accept the feeling and stop resisting the situation, that’s when we’ll naturally feel a peace of mind and accept what we’re feeling. It’s tempting to look back and imagine a story that would have been amazing and think, “life would be different.” 


We’ve all been there: an email arrives in our inbox, and we don’t like the tone or message. Then out of frustration or anger, we respond quickly with haste. Oops. The regret comes on fast.  

Other than using the Gmail recall button, here’s how Puddicombe says to handle this situation:

Introduce the idea of pause around social media posts, texts, and email. Always re-read before you post and then pause. If you have to count to three in your mind, be clear about what you’re doing, saying, and communicating, and then press send. Then you’re far less likely to regret the message. 


Someone asked the question, “I’m always playing ‘what if’ in my mind, on a loop, over things I’ve said and decisions I’ve made. Is this loop normal?” 

“When a thought arises in the mind that’s fine,” says Puddicombe. “It’s self-arising. It’s not intentional. It’s natural. It’s normal. You see it, you feel it, you let it go and move on. If you see that thought and then you think, ‘Hmmm, ya, what if, I wonder if this would have happened.’ If you then go down the loop of creating a story, then normally that’s not helpful. By gaining awareness through meditation, we learn to see thoughts coming and going, and then move on. That’s usually enough to cut through that loop.”  


When Puddicombe was a monk there was a rule at the monastery: you could only entertain feelings of regret for 30 seconds. After that you had to let go of the thought. So, in these types of situations, here’s what he suggests: 

Acknowledge the regret
Don’t entertain the thought 
Learn from the thought and let go 

He adds, “Overtime the more we respond in this way, the less interested the mind becomes in it. Regret can only persist in the mind so long as there is some interest, discomfort, and resistance. Once the mind is bored, it lets the thought go. If regret is there, there’s something we haven’t resolved.” 

When we learn to see our thoughts clearly, we can learn from their messages, and let go. In turn we’ll be more kind to ourselves and others. 

How do you handle regret? Share with our community in the comments below.

Tags: confidence, entrepreneur, happiness, mental health

Kristen Marano

Kristen Marano covers women and their work for publications around the world. She has interviewed some of the most influential business leaders in Canada and the most passionate change makers in towns and cities as isolated as Perth, Western Australia. Most recently she interviewed Canadian businesswoman Zita Cobb about reinvigorating the economy in Newfoundland through the arts. Kristen's work encourages women to share honest and open perspectives about the emotional challenges of their journeys.

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