2.14 What to Expect When Having Expectations with Benjamin Winter

Season #2

We’re joined by Benjamin Winter, a team building expert and the author of What to Expect When Having Expectations, whose biggest message is that a lot of people have expectations backwards, or at least a misconception of them. Ben shares how compassion helps us to see toxic people from a different angle and how he started his own personal growth journey. He also discusses if being upset is okay. Finally, we also get to know the impactful ripple effects of communication in our relationships with others and the reason we need to start focusing on objective truths. Join our very relatable discussion on this week’s episode.

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Episode Highlights

0:19 Episode introduction

2:51 Ben shares his biggest message

3:44 Why being upset is okay

4:50 Is it wrong to have expectations?

“It's not wrong, and it's impossible not to have expectations. My perspective on expectations is that expectations aren't good or bad, positive or negative; they are simply a thing. Most of the time, when an expectation is being met, we don't think about it as an expectation; we don't give it a second thought in general.”

7:01 The importance of awareness training

“It's all about awareness training, because if you become aware that you have this process when you get upset, and that you had an expectation, the faster you are at recognizing the expectation before it goes unmet.”

9:37 How Ben’s way of personal growth is different

12:41 Ben’s view on the phrase “toxic people”

“If we come from a place of compassion, we're going to understand that there's a lot of stuff going on behind the scenes, that they are scared, and frightened, and in pain That's where compassion comes in; we have to understand that they're lashing out because they don't know how else to deal with it.”

15:55 Communication creates compassion creates understanding.

“You have got to come together and talk and listen and communicate with one another. Because if you can communicate with one another, that creates that compassion we were talking about that creates understanding. You're able to come to a common ground and negotiate, and maybe both expectations can fully be realized, without missing anything with one another.”

21:09 Our subconscious actions and projected hypothesis

“This is our subconscious saying this is how the world works. So that if you come across anything that contradicts your subconscious, there is now an internal fight within your brain that says, ‘This isn't okay - something's wrong.’”

27:44 Ben’s own personal growth journey

31:34 Harry and Ben discuss expanded awareness, subjective and object truths.

“And that is, I think, one of our biggest issues with society today. Let's stop fighting about subjective truths. Let's start focusing on objective truths, get on the same field, figure out the same goal and then decide if it's true or not…”

36:56 Where to find Ben

40:39 Harry’s key takeaway


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