English Communication Skills to Speak about Regret

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Learn how to speak about mistakes or regrets in English. When you feel strong emotions about missed opportunities and want to voice them in English, I give you the language to do so. I also teach you two frameworks for how to know when to pursue an opportunity so that you won't have any regrets about your decision.

A lot of people have regrets in life. And many of these regrets are about not pursuing certain opportunities because they were too afraid to take the risk. It boils down to a fear of failure. 
But as we know failure is an inevitable part of life and business. And failure is important because it’s an indicator that we’re growing and learning. 

For language learners, regret might include the following scenarios. Someone might regret not taking more opportunities to speak in English and try on the language, as I like to say, because they’re afraid of any negative feedback. There might be regret about rejecting a job offer that would have involved communicating or writing in English. There might be a regret about not moving to a predominantly English-speaking country to learn and speak English. And the list goes on and on.  

In this lesson, I’m going to share a few ways of talking about regrets in English.

And I will also reveal two important strategies that help you decipher between an opportunity worth pursuing and one that’s not. This way, you won’t have any regrets about not going after certain opportunities.

Let’s get into it.


First, let’s discuss a few ways of discussing regret in English. When you’re speaking with a professional contact, you might talk about business opportunities you’ve passed up and now regret. You might also talk to a friend about regretting not having taken certain risks in life.

(1) I wish I had…

You might regret not having practiced your English speaking skills. You could say: “I wish I had been braver to speak English more often.

(2) I wish I hadn’t…

So this would be another way of expressing regret. You could say something like: I wish I hadn’t been so afraid to speak English with Native Speakers. 

(3) I should have ...

And in connected speech you’ll say “should’ve” so keep that in mind. A practice sentence here is “I should have lived abroad when I got that job offer in the United States.” or “I should have studied in London when I had the chance.”

(4) If only I had… / If I had only…

If only I had made more time to read in English. I might be able to read Mark Twain by now!
If I had only spent my weekends creating a side-hustle opportunity in English I might be able to pivot into the industry I really want to be in!

(5) What if I had...

This could be said during those times of internal dialogue. You know, those moments where you might be thinking to yourself or even possibly ruminating. Ruminating is when you focus on a memory or thought and keep replaying it in your head. Usually, these thoughts are the opposite of positive. So you might say something like “What if I had joined the tennis team? Maybe I could play tennis by now, which has always been a goal of mine.” or “What if I had told my boss I wanted to transfer to the New York office, I could be living in New York right now!”

We have a great expression in English that sums up regret. This is “shoulda woulda coulda” it stands for “Should have, would have, could have.” You might also hear this in a different order. Meaning, you might hear: “woulda, coulda, shoulda.”

So what does this mean? Well, “shoulda woulda coulda” or “woulda, coulda, shoulda” expresses regret and disappointment for missed opportunities, hypothetical possibilities and roads not taken. It’s a way of showing that the person feels regret about something but there’s not much to do about it now. In a way, it’s an expression of dismissiveness as well.

So you might say. You know, I could have studied abroad when I had the chance, but oh well “shoulda woulda coulda” right?

Or a friend might share a regret with you and you might reply, yeah, we all have those shoulda woulda coulda moments. 

To assess whether an opportunity is worth pursuing I have two strategies for you.

(1) Heart method:

When you think of the opportunity you feel a sense of excitement and openness OR you feel a heaviness and cringe. If you feel excitement then that could be a sign that this opportunity is worth pursuing. If you feel heaviness in your gut, then it might mean that you wouldn't have any regrets if you didn’t pursue this venture. 

(2) 555 method:

When presented with a new opportunity or situation, you can ask yourself “will the consequences of this action matter in 5 minutes, 5 days or 5 years?” If it will matter in those time frames, especially the long-term one of 5 years then it’s a good indicator that you can pursue the opportunity or learn new skills. In the context of English, this could also be specific skill development within your language learning journey. 


Terrific work, so we discussed how to speak about regret in English if the topic should arise in conversation. And we also reviewed two ways of preventing regret by understanding our inner feelings about opportunities.


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