How to Deal with Regrets & Should-Haves

Let go of the “should-haves.” Try this five-step process to make peace with your past mistakes and missteps instead of beating yourself up over them.


Listener Feedback

We wanted to share some listener feedback (which we love and immediately send to each other):

Jules said that Episode 12: Triggers & How to Cope resonated with her a lot: “I never knew I had so many triggers until I had a baby and now everything seems to get to me. I really liked the idea of naming your feelings, that has helped me a lot.”

Melia talked about her goal of putting together an emergency kit back in Episode 7: Tighten Up & Lighten Up. Nicole wrote to us to share her own emergency kit tip, which unfortunately stemmed from the very real and scary experience of going through the California wildfires. Her tip is: Refresh your emergency kit monthly, rather than one and done.

Nicole said, “We were all prepped for sheltering in place, so more appropriate for an earthquake. After the fire, we knew we needed to think about it differently and we keep it as a regular (monthly) ‘chore’ to pick up the research, maybe add an item or two, check expiration dates, etc. This after a first initial push to get the kit 90% there. It’s not going to be a one time thing and then you cross if off the list… it’s kind of a practice.”

We also talked about podcast reviews quite a bit on the last episode, and we were excited to see some new reviews for Semi-Together. Thank you to everyone for your comments and reviews! As a refresher, it’s easier to leave them on iTunes desktop than Apple Podcasts; Mac users will have iTunes built in, and Windows users can download iTunes here. Search for Semi-Together, click on the cover art, click the Ratings & Reviews tab under our names, then Write a Review. ❤️️


Regrets & Should-Haves

We’ve talked about how mistakes or missteps are a big trigger for both of us. When things don’t turn out as we want them to, we’re really hard on ourselves if we think we could have done something better – or acted on an opportunity that was open to us. If you hadn’t sent that email, or if you had taken that job, everything would be perfect, right?

We can spend a lot of time dwelling on regrets — often in the middle of the night! This sums it up perfectly:

We often wonder how much time we’ve wasted beating ourselves up over regrets. And research shows that obsessing over regrets takes a big toll: it has a negative impact on our mood and sleep and can lead to impulsive behavior, binge eating or even misusing alcohol.

Gill recently made a work mistake that kept her up late, spiraling over all the ways in which she is flawed. Melia has a couple of flavors of regrets – the small and short-lived, and the huge and ongoing. Melia’s biggest regret is not using her Reschool Yourself project as a door to a career in personal development.

For those who aren’t familiar with it, this was a project she did back in 2008. After so many years following other people’s directions, she didn’t know what she wanted anymore or how to make her own decisions. So she pulled a Billy Madison and went back into her schools, elementary through college, for a do-over. But now Melia looks back on a pivotal moment in the project, wondering what would have happened if she had made a different choice.

How to Cope with Should-Haves

What can you do instead of beating yourself up over what happened in the past – and even use regrets to motivate you in a positive way?

From our research and experience, we recommend this five-step process. As with anything we recommend on the podcast, it’s something we’re practicing ourselves (and definitely not perfectly)!

Step 1: Stop the spiral.

Interrupt your obsessing and get your brain back, moving from the fight or flight center to the thought and reason center. The more you do this, the more you teach your brain more productive thought patterns than going in circles.

There are a lot of ways to do this. You can do the three-breath pause we’ve mentioned in previous episodes – three deep breaths in and out. You can also get your own attention physically by running cold water over your hands or wearing a rubber band on your wrist that you can snap. That mini-shock to the system gets you out of your head and helps train you not to ruminate (like a spray bottle for a naughty cat!).

The strategy that works best for Melia is to close your eyes, put your hands over your heart and say (in your head or out loud if you’re alone): “You are safe.”

Step 2: Put your regrets into words.

According to research, suppressing our emotions can reduce our capacity for joy and even show up as physical pain. So the most important thing is to get real with yourself about what’s bothering you, so you can stop that energy from harming you and use it as fuel to propel you forward.

When you pinpoint your regrets and voice them, whether you write them in a journal or talk about them with your partner or trusted friends, you “declaw” them, taking away their power and the shame you feel about them. Those regrets don’t usually look as scary once you bring them into the light, and then you can deal with them.

Step 3: Get compassionate.

Practice showing the compassion to yourself that you would a dear friend – which is challenging for many of us!

Practice radical self-forgiveness. 

Writer Glennon Doyle recently posted about this, saying that her secret to moving on from her past mistakes is forgiving herself relentlessly, because shame takes away our energy and power and leaves us useless to others and the world.

Write a letter of self-compassion.

The Science of Happiness podcast recommends writing a letter to yourself. Write down what you regret and how it makes you feel. Then, as if a trusted friend or mentor were replying, write back with understanding and acceptance.

Recognize the good in your actions.

Sometimes missteps come out of good intentions gone awry, and sometimes you beat yourself up over not doing more when you’ve done plenty! For example, when Melia takes a step back and looks at the Reschool Yourself project, even if nothing else comes of it, it was pretty awesome for what it was! And most importantly, she came out of it happier and more whole, which was the real point.

Step 4: Look for opportunities.

Instead of dwelling on everything you missed out on, look for open doors and silver linings.

Recognize that you don’t know anything for sure. 

What looks like a setback can often be an opportunity. Our listener Jena said that the trigger of mistakes and regrets from Episode 12 reminded her of the Zen parable about the farmer and his horse, which is one of our favorites, too. The moral is that sometimes what we think of as mistakes and misfortunes end up leading to things that benefit us – and we just don’t know.

A kids’ book called “Fortunately” that tells a version of this story:

Fortunately, Ned was invited to a surprise party.
Unfortunately, the party was a thousand miles away.
Fortunately, a friend loaned Ned an airplane.
Unfortunately, the motor exploded.
Fortunately, there was a parachute in the airplane.
Unfortunately, there was a hole in the parachute.

Think of the regret as an opportunity to learn and grow.

Should-haves keep you stuck in the past, criticizing and blaming yourself for the actions you didn’t take or the words you didn’t say. Instead, try to break out of this cycle and ask, “What can I learn from this?”

This process often relates to what we talked about in Episode 9: Change Your Environment to Change Your Habits. Instead of asking, “How can I change myself to fix this problem?” ask, “How can I change this situation to fix this problem?”

Look for silver linings and open doors.

Ask the question that Michael Hyatt suggests: “What does this make possible?” Even though some doors may have closed, others will have opened — often because of the very event that you regret. Start ignoring the closed doors and paying attention to the open ones.

For the Reschool Yourself project, Melia is thinking about silver linings of not publishing the book right after the experience. She has had time to figure out what the experience was really about: finding her own inner compass again instead of following the path laid out for her, and helping other people do the same thing.

Another benefit of the time passing is that it’s opened up possibilities in format for memoir. It used to be that you “wrote your memoirs” as an autobiography at the end of your life, but now people zoom in on a particular experience and write multiple memoirs, like the author Dani Shapiro. Melia is thinking about putting together a memoir that’s a book of themed essays, like the one that actor Andrew Rannells has coming out.

Step 5: Take action starting now.

On the Happier in Hollywood podcast, they shared the tip, “Action is the antidote to anxiety.” We’ve both found this really helpful when we’re spinning our wheels.

Another helpful mantra is a Chinese proverb: “The best time to plant a tree was 20 years ago. The second best time is now.”

If your regret involves a relationship with someone, you can try to clear the air and make amends. If you’ve done something that you feel hurt someone, talk to them about it. Schedule a time to talk, or write a letter. Even an instant message or text chat can work, depending on your relationship.

Often, people will either not even remember what you’re talking about – or they forgave you a long time ago. When Melia did this recently, a friend told her, “One great thing about getting older is that I don’t dwell on the past, because I can’t even remember it!”


Listener Takeaways

Here’s a recap of the five-step process for identifying and coping with your regrets:

  1. Stop the spiral.
  2. Put your regrets into words.
  3. Get compassionate.
  4. Look for opportunities.
  5. Take action starting now.


Get It Together / Got It Together

We each share something that’s going well for us at the moment, and something else that we’d like to work on.

Melia Get It Together: Blowing a gasket while buying plane tickets

Melia Got It Together: Focusing on a realistic to-do list, accepting help and resisting distractions at work

Gill’s Get It Together: Taking on too much and then getting burned out

Gill’s Got It Together: Getting out in nature and taking advantage of beautiful spring weather


Get In Touch

Tell us about the regrets that keep you up at night, and which strategies you’re using to cope. Just putting them into words will help take away their power.

Email us at podcast[at]semitogether.com, or record a voice memo on your phone and email it. You can also leave a comment on Facebook or Instagram. We’d love it it if you’d subscribe, rate and review this podcast on Apple Podcasts or wherever you listen.