Episode 12: Should Thinking

The Less Stressed Lawyer | Should Thinking

Do you have thoughts about other people around how they should behave? Maybe you have thoughts about yourself around what your life should look like, or perhaps you’ve noticed yourself believing that the world should be a certain way. Well, this is called ‘should thinking’, and while it can seem useful, it needs to stop.


This is one of my favorite topics because, when you really master identifying and eliminating should thinking from your life, the impact it has on how you feel is truly profound. So, how do we get clear on where should thinking is showing up in our lives? Well, that’s exactly what we’re discussing today.


Tune in this week to start identifying and ultimately eliminating unhelpful should thinking from your brain’s repertoire. I’m sharing the most common should thoughts that I’ve struggled with, where my clients generally need to do this work, and how you can take steps to eliminate shoulds from your thought process, so you can live from a more empowering energy.


If you’re interested in taking the coaching topics I discuss on the show a step further, enrollment for the Less Stressed Lawyer Mastermind is officially open. This is a six-month group coaching program where you’ll be surrounded by a community of like-minded individuals from the legal industry, pushing you to become the best possible version of yourself. We kick off with an in-person live event and you can get all the information and apply by clicking here

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What You’ll Learn from this Episode:

  • 3 different types of should thoughts that every human being has.
  • Why most of our negative thoughts are actually should thoughts, and why they tend to make us feel terrible.
  • How to see the should thoughts that are making your life more difficult than it needs to be.
  • The most common should thoughts that my clients come to me with and the associated negative emotions they experience.
  • Why there will always be a handful of helpful should thoughts you want to keep, and that’s okay.
  • How to eliminate unhelpful should thoughts from your thinking, so you can concentrate on what is, instead of what you believe should be.

Listen to the Full Episode:

Featured on the Show:

  • I would really appreciate it if you would leave a rating and review to let me know and help others find The Less Stressed Lawyer Podcast. Click here for step-by-step instructions on how to follow, rate, and review
  • If you want more information about the Less Stressed Lawyer mastermind, visit my LinkedIn, my Instagram, or email me!

Full Episode Transcript:

You’re listening to The Less Stressed Lawyer podcast, Episode 12. We’re talking all about “Should Thinking.” You ready? Let’s go.

Welcome to The Less Stressed Lawyer, the only podcast that teaches you how to manage your mind so you can live a life with less stress and far more fulfillment. If you’re a lawyer who’s over the overwhelm and tired of trying to hustle your way to happiness, you’re in the right place. Now, here’s your host, lawyer turned life coach, Olivia Vizachero.

Hello, how are we doing today? I hope you are good. I’ve been having the best week this week. It’s been really fun, a little jam packed with work. But that’s always exciting. And, I also had an alumni event to attend for the firm that I used to work at. They do an annual alumni cocktail reception once a year. So, I got to see a bunch of my former colleagues. I love that they do that, we haven’t done it since before the pandemic. It was really wonderful to see a bunch of those people and meet some other alums for the first time. Just a really fun way to spend one of my weeknights this week.

I hope you are having fun this week, as well. And, if you work in a law firm setting, and you don’t do an alum night, consider it. It’s a really good time, I had a riot. So just an idea to offer y’all.

Alright, today we’re talking about “should thinking,” and it’s one of my absolute favorite topics. Because, when you really master identifying and eliminating should thinking from your life, the impact, making that change, has on the quality of your life and the quality of how you feel on a day-to-day basis, it’s so profound. The impact is huge. So, I can’t wait to introduce you to this topic. Teach you how to identify should-thoughts and eliminate them from your thinking repertoire.

So first, I want to start by talking about the three different types of should thinking: There’s should-thoughts that you think about yourself. Should-thoughts that you think about other people. And, should-thoughts that you think about what goes on in the world. Those are the three main categories of should-thoughts.

Remember, we think 60,000 thoughts per day, on average, and a huge portion of those thoughts are negative. I also want you to know that a huge portion of your negative thoughts are likely should-thoughts, okay? And, all three types of should-thoughts tend to make us feel pretty terrible when we think them. So, if we want to feel better, we want to make sure that we identify and eliminate the should-thoughts that we think, and get rid of them from our thinking.

Let’s talk about some examples of these should-thoughts. Here’s some common ones, that people think about themselves: “I should have done X. I shouldn’t have said Y. I should be more like so and so. Or, it should be more like this. I should be less like that.” Right? I’m being very general with this; you can fill in the blanks in each of these sentences.

But I just want to be general, to give you some examples: “I should know how to do this by now. I shouldn’t need help with this.” Here’s a really common one, that a ton of my clients think pretty frequently: “I should be further along. I should offer to help. I shouldn’t say No. I shouldn’t be so behind.” Those are all different variations of should-thoughts that we think about ourselves.

And, when we think thoughts like this, we tend to feel guilty, or ashamed, or disappointed in ourselves, or frustrated with ourselves, right? You think, “I should have done X, instead of what I did.” You’re going to feel guilty, disappointed, frustrated, ashamed, things like that. “I should be further along,” maybe you’ll feel really dissatisfied, or discouraged, or disappointed with the progress that you’ve made so far. “I shouldn’t be so behind.” You might feel guilty or ashamed there. “I shouldn’t say no,” you’ll feel guilty, and then you’ll people please in response to that.

When you think should-thoughts about yourself, you’re going to feel pretty awful in those specific feelings that I just described to you. So, you want to get in the habit of identifying these thoughts, and coming up with a different way to think about yourself. Alright?

I’m going to get into that a little bit more in a second. But the first thing that you always want to do, is gain awareness that these are the thoughts that you’re thinking. So, start to slow yourself down and pay attention when you go into should-thinking about yourself. You probably do this all throughout your day, so you just want to start to become mindful of it, so you can catch it and replace it. Okay?

When it comes to other people, we tend to be hypercritical of what they say and do, or what they don’t say and what they don’t do. Should-thoughts about other people will look like, “He shouldn’t have said that. She should have done this instead. She shouldn’t have done that. She should be more like that. He should be more like this; he should be less like this.”

Again, these are widely applicable, pretty vague sentences that I’m giving you. More specifically, should-thoughts about other people might look something like, “She shouldn’t have written that in the email. He shouldn’t have scheduled that meeting at that time. They shouldn’t make us come back into the office x-times per week. She shouldn’t have said no when I asked her to do that. He should be more accommodating.”

Maybe you’re thinking this about your employer, “They should pay me more.” Maybe you’re thinking this about a friend or a family member, “They should be more supportive. They should do this when I ask them to.” These are more specific should-thoughts that we’ll have.

And, when we think should-thoughts about other people in this way, we tend to feel disappointed, frustrated, annoyed, resentful, angry, and everyone’s favorite; I always describe this as like the dark chocolate covered caramel, delicious emotion of self-righteousness. That can be really tasty, really addictive, a go-to for a lot of people when they’re thinking should-thoughts about others. Those are some examples of should-thoughts we think about other people.

We also think should-thoughts about the world: “This shouldn’t have happened. It should have gone this way instead. I should have gotten that job. I should have gotten a bigger raise. There shouldn’t be a war in Ukraine. The Supreme Court shouldn’t have ruled on the decision this way. A judge shouldn’t have decided our case in this manner. The jury should have come back a different way. The deal should have gone differently than it did. The motion hearing should have turned out differently than it ended up.” All the things that happen in the world that we tend to argue with.

“There shouldn’t be mask mandates. There should be mask mandates. There shouldn’t be pandemics. There shouldn’t be vaccine mandates.” These are all things that people have a lot of different opinions on recently, right? They’re just should-thoughts that we think about what happens in the world.

When we think should-thoughts about what happens in the world, we tend to feel a lot of the same emotions that come up for us, when we think should-thoughts about other people: disappointed, frustrated, annoyed, resentful, angry, maybe, self-righteous. We also might feel defeated, discouraged, powerless, and maybe out of control. I want you to start recognizing some of these thought patterns that might be showing up in your daily thinking.

What should-thoughts are you thinking about yourself? What should-thoughts do you think about other people, the people that you engage with, encounter on a daily basis, at work, in your personal life? Do you think that they should do things differently than they do? Do you think they should be different than they are? Do you think things that happen in the world shouldn’t happen? Do you wish things were different in the world than they are? You want to start finding those thoughts. Okay?

I also want to clue you in here on subtle should-thoughts. Because every once in a while, I’ll talk to a client and I will tell them, “Here’s what I want you to do this week. I want you to go into your week, and pay attention to all of the should-thoughts that you’re thinking throughout the week, so you can start to gain awareness as to why you’re feeling a lot of the negative emotions that you’re feeling: why you’re feeling guilty, ashamed, frustrated, resentful, discouraged, disappointed, resentful, angry, self-righteous, all of those emotions.

And, they’ll come back the next week, and I’ll say, “How did it go? What did you see? What did you realize? What did you notice, as far as your should-thinking goes?” They’ll come back and say, “You know, I couldn’t really find any should-thoughts.” But based on the emotions that they told me that they experienced pretty regularly, I know that the should-thinking is there.

And, when we start to dig a little bit deeper, we’ll uncover some subtle should-thoughts that sound like this instead, they don’t actually use the word should, but they’re a variant of a should-thought. So, it would sound like, “I can’t believe they did X. What they did was so rude or disrespectful. How dare they do that? I would have never said that. He or she isn’t being “blank” enough: Isn’t being supportive enough, isn’t being respectful enough, isn’t being kind enough, isn’t being supportive enough, productive enough,” any words like that, right?

“This wasn’t supposed to happen. You can’t do it this way. You can’t run a business like this. You can’t operate in this manner.” Or, another really common variant of a should-thoughts is: “A good ‘blank’ would do this, instead. A good friend would come to your kid’s, second year old birthday party. A good spouse would plan romantic date nights, once a week. A good colleague would help me when I’m really behind on something, and I asked them for help. A good friend would pick me up from the airport. A good associate, who works underneath me, would handle this on their own, and not ask me any questions, and figure it out and be resourceful.”

So, any variant of, “A good ‘blank’ would do it this way,” is also a variant of a should-thought. These are just different ways of thinking, that people should behave differently than they have behaved. So, even though they’re not using the word “should” in the sentence, they’re still thoughts that are rooted in should-thinking. Because you’re arguing with what someone has done with their behavior, what they chose to do, what they chose to not do, and you’re thinking that it should be different than it is, okay? So, it’s still a should-thought.

Now, why is should-thinking so problematic? Well, first of all, it makes you feel terrible, as I’ve gone through with each of these three categories: should-thoughts you think about yourself, should-thoughts you think about other people, and should-thoughts that you think about the world and what takes place in it.

You end up feeling awful when you think should-thoughts. But moreover, when you think should-thoughts, what you’re really doing is you’re arguing with reality. You’re thinking about something that’s already occurred, actions someone has already taken, or you’re thinking back on something that people didn’t do, but it’s focused on the past, right?

And, you’re arguing with what’s already taken place. So that’s always going to be a pointless endeavor, completely futile. When we argue with reality, with what’s already happened, we lose 100% of the time.

Now, you’re taking issue, like I said, with something that’s already happened. And, the reason that’s so problematic: A. It’s just unnecessary frustration. But B. It’s also really disempowering.

Instead of arguing with reality, you have two better options to choose from: You can accept what’s happened, or you can learn from it. Or, you can actually do a combination of those two things.

All of that is what I recommend, I don’t recommend just arguing with reality, and sitting in the frustration of it. So, instead of being judgmental with your should-thinking, get curious. Ask yourself: Why? Why did you do X, Y, and Z? Why did you not do X, Y, and Z? Why did they do something, or not do it? Why did they say something, or not say it? Why did this or that happen? Get really curious, and see if you can get yourself to a place of understanding.

I’ve taught you the model now. You know that circumstances are neutral, and that thoughts cause feelings. Feelings drive actions, and actions produce results.

So, if you’re looking at your own actions: Why you did or didn’t do something, why you said or didn’t say something, why something happened a particular way, why someone else did something or didn’t do something, all of that is going to go in A-line of someone’s model. Either your model or their model.

And, you can work it backwards. If it’s a negative action, it’s likely because you were resisting, avoiding, or reacting to a negative emotion. Ask yourself, “What was that feeling?” Gain that awareness.

From there, ask yourself what thoughts caused you to feel that feeling? Or, what thoughts might they be thinking that caused them to feel that feeling? If it’s something that’s going on in the world, work it backwards, “How did we get there?” Maybe it makes sense. It probably does, when you dissect it, when you pull it apart.

So, work on getting yourself to a place of understanding. Intellectual understanding where you’re like, “Oh, I get exactly how that happened the way that it did.” Or, “I get why that happened.” Not from judgment, but just from curiosity. Work towards understanding.

Now, understanding does not mean condoning. It also doesn’t mean that you’re operating from a place of compassion. That is so, so important to understand. You don’t have to love what you did. You don’t have to love what someone else did. You don’t have to love what happened in the world. But if you can get yourself to a place where you intellectually understand why it happened, or didn’t happen, exactly the way that it did, you’re going to give yourself so much emotional freedom, with that understanding.

I’d be like, “Oh, of course, that happened that way. Of course, it unfolded that way, because of X, Y and Z. Because they were thinking this way, and feeling this way, and then they responded, in kind.” You know, “I did that thing, because I was thinking this thought, I was feeling this feeling. And then, I avoided it by doing this, instead.” Or sequentially, “This thing took place in the world because this was in place first. And then, this happened after this. And then, that thing happened. And, it all makes perfect, logical sense. I don’t have to like it. But I do understand how we got to where we are now.”

Again, if you can get yourself to a place where you understand why what happened, happened the way that it did, you’ll open yourself up to feeling much more accepting and understanding of whatever circumstances you’re encountering.

You can also use this as an opportunity to learn about yourself. If you’re making judgments about yourself or other people, or what’s going on in the world, you can ask yourself, “Why do I think it should be different? Why do I believe that? What is that should-thought based upon? What values or beliefs do I have that are serving as a foundation for this should-thought scaffolding, so to speak? Does it serve me to keep choosing to think this way? Do I want to think about this differently?” Those are great questions to ask yourself when you catch yourself in a should-thought cycle.

Now, the biggest pushback that I get from people, when I talk about eliminating should-thinking from your thought process, they typically say to me, “So, Olivia, what are you saying? I’m just supposed to not have standards? I just shouldn’t have expectations? Should I just be a doormat and let people walk all over me?”

No, that’s not what I’m saying here. Here’s what I am saying, you get to have expectations and standards for yourself, and for other people, and for what goes on in the world. Alright?

Here’s the kicker, though. You get to have all the expectations and standards that you want to, you just have to take the disappointment and frustration that comes with them when people, or the world, or yourself fail to meet those expectations. Okay?

These circumstances, other people’s behavior, their actions, that’s not what’s causing your disappointment or your frustration. It’s your expectations that cause those negative feelings. If you didn’t have those expectations in the first place, you wouldn’t feel badly if they went unmet.

So, you get to have expectations and standards, but you have to take the disappointment and frustration that comes with them, when people invariably fail to meet those expectations.

Now, I’ve talked about this before; sometimes we want to have expectations, and choose to feel negative emotions when people don’t meet them. You may want to think that someone shouldn’t have done something because it doesn’t align with your values. You may want to choose to feel disappointed as a result, that’s fine, you get to make that choice. You just don’t get to blame that other person for how you feel.

You feel that negative feeling, that frustration, or disappointment because of how you’re choosing to think about that person’s actions. And again, you get to do this, it’s totally fine. There’s plenty that goes on in the world, or there are plenty of things that other people might say or do, and I want to choose to think a should-thought about that, and then feel a negative emotion as a result. Alright?

My suggestion here, is to be very discerning with the should-thoughts that you choose to think. Be picky when it comes to your should-thoughts. Don’t think a ton of them, be selective. Pick the ones that really matter.

Here are a few examples of should-thoughts that I really value, that I want to keep: So, people shouldn’t physically hurt one another. I want to think that that behavior is unacceptable. And when it takes place in the world, I want to be upset about it. People shouldn’t use racial slurs or derogatory comments. That’s a value that I consider really important.

I did criminal defense work. I’ve talked about that before on the podcast. So, I think police shouldn’t plant evidence. And, they shouldn’t ignore someone’s request for an attorney; I’ve seen that on a couple cases. So, that’s a should-thought that I’m going to hold on to. I think you should pay your employees on time if you’re an employer. I also think people shouldn’t offer their opinion unless someone asked for it. I think it’s impolite. And, I want to choose to feel a little offended when people offer an uninvited opinion.

Those are some examples of ones that I still carry with me. I choose to think them, and I’m fine feeling the negative feelings that come from having those should-expectations, when those expectations go unmet.

Now, here are some should-thoughts that I have gotten rid of over the course of learning about coaching, and learning about the model, and learning that my thoughts are what cause my feelings. I realized that I just didn’t want to be upset about certain things anymore.

I’m a big planner. I spend a lot of time planning nights out for people, planning what restaurant we might go to, comparing a bunch of different menus. I do this when I travel with friends, as well. And, I used to get really upset that people weren’t being appreciative, or wouldn’t default to my expertise, because I spent so much time and invested so much energy in curating the perfect plan. And, I would think the thought, “People should appreciate all of the hard work that I put in.”

But here’s the thing; no one asked me to do that. I was doing it because it makes me happy to do that. So, I’ve totally given up that people should appreciate the hard work that I put in. Now, I just appreciate my own hard work, and I let it go. Regardless of whether someone else appreciates it or doesn’t, it’s totally irrelevant. I don’t cause my own frustration or disappointment by thinking that should-thought.

I also used to be a little bit of a pusher. So, if I wanted to go do something, and I would ask a friend to join me and go attend an event, or go out to dinner, or go out to do X, Y or Z, and people would say no, I would get really frustrated, and kind of try and convince them to come with me. It was based on me having this belief that people should say yes, if I asked them to go to something with me, that a good friend would do it if I asked them to.

I caused so much of my own frustration from that line of thinking. So, I gave it up. Now, I trust people to know what’s best for them, to know what they can accomplish or accommodate, as far as their schedule is concerned. I let other people be the best judge of what they should or shouldn’t do, what they should or shouldn’t say yes to. So, I don’t think that anymore.

I also, for a while, thought that people should be supportive of my career decisions. Now, that was a really painful thought that I chose to think for a while. There were a whole host of reasons why people, in my life, weren’t supportive of some of my career decisions, especially some of the bigger transitions that I’ve made in recent years.

Mostly, they were just worried for me. It makes total sense to me, why they would be worried. They knew a lot less about the industry that I went into, they had their own beliefs about what was responsible, or secure, or reasonable, or practical, right? They just have different belief systems and values than me.

But me thinking that they should be supportive, and then when they weren’t supportive, that was really painful. It caused me a lot of strife and negative emotion. So, I’ve given that up. Now, I’m like, “Of course, they feel the way that they do. Of course, they think the way that they think. Of course, they’re not supportive, that makes total sense. I don’t need to make it a problem. I can just accept it, and not be disappointed as a result.”

I’ve also given up the thought that people should follow through on their commitments. I see this as a big one with my clients, too. They think, “Oh, if someone said that they were going to do something, they should do it.” But here’s the thing; people get to not follow through, that’s just a reality in the world. People get to say one thing, and then do another. They get to say yes, and then they can say no. They can not follow through, for a whole host of different reasons.

So, if you want to feel disappointed when people don’t follow through, you can choose to think the thought, “People should follow through on their commitments.” But invariably, they won’t. And, you will feel disappointed, as a result.

I like to, again, think that people are best positioned to make the decisions that are right for them. I don’t always have all of the information; I don’t always know what they’re dealing, with what’s going on, so I’m going to trust other people to make the best decision that’s available to them, at that time.

And, maybe the best decision for them, in any given moment, is to not follow through with a commitment. That doesn’t mean I have to love what they choose to do, but it means that I’m not going to think a should-thought and cause my own disappointment, as a result.

My dad and I actually had a conversation about how he thinks should-thoughts, about certain things related to his business, or the world. And, he upsets himself as a result. He always looks at me, and he’s like, “How are you not upset? How do you just let things roll off your shoulders and not take it personally, or not get super frustrated by something?” And, I explained to my dad, “You know, I just think about it differently than you. I think that it should happen because it does happen in the world. And you think that it shouldn’t. I think, ‘Of course, that happened.’ And, you think, ‘It shouldn’t happen,’”

I had a ding on one of my car doors, and he got super frustrated about it. Now, he owns a collision shop, so he’s gonna be the one to fix the ding in my car door. But he has a belief that cars shouldn’t get damaged. That’s not a thought that I’m going to choose to think, because cars do get damaged, they get damaged every day. That’s why my dad runs a successful collision shop. Right?

So, I’m going to think, “Of course, my car’s gonna get damaged.” I don’t park in Timbuktu to avoid door dings, or people hitting your car with a grocery cart when you go grocery shopping, or anything like that. I don’t park far away because I prefer the convenience of parking a little bit closer. So yeah, there’s gonna be greater traffic in those areas. The likelihood that my car door gets dinged, probably pretty high. So again, when it happens, I don’t get frustrated, because I don’t think that it shouldn’t happen. I think, “Yeah, that makes sense.”

I feel the same way, this is a pretty unpopular opinion, but I feel the same way about cheating. So many people go through the world and think, “People shouldn’t cheat.” Or, “People shouldn’t lie.” Right? Now, if you choose to think that there’s nothing wrong with it, you’re just going to be really frustrated or disappointed when people invariably do those things, because they happen all the time in the world.

Instead of thinking that people shouldn’t do it, I think, “Yeah, of course, they do. That’s something that people do every single day.” Again, I don’t have to like it. Like, I’m not jazzed that my car door is damaged, but I don’t think that it shouldn’t have happened, because it is something that can happen in the world.

Same thing… Like our cars can get broken into. Or, a person can miss a deadline, when they promised us to have a work product by a certain time. Like, it happens, they’re going to miss it. If you think that they shouldn’t, you’re going to feel a lot of frustration when invariably they do. That’s something that gets to happen.

If you think people should message you when it’s your birthday, and wish you a happy birthday, and they don’t; they get to not, and you’re going to cause your own upset by thinking that they should, if they don’t, okay?

So, start to think about this for yourself. Where do you think should-thoughts? Go on a hunt for them. Find them. What should-thoughts are you thinking about yourself? See how they make you feel. What should-thoughts do you think about other people, what other people say and do, what they don’t do and what they don’t say? How do those should-thoughts make you feel? What should-thoughts do you think about the world, and what goes on in it? How do you feel when you think those?

Now, once you gain that awareness and you start to see these emotional patterns come from this should-thinking, you get to decide which should-thoughts you want to eliminate entirely.

One of the ways that I do this, eliminate should-thoughts, is I just accept that it is what happened. This is very circular, but why should it have happened this way? Because it did. Why shouldn’t it have happened differently? Because it didn’t. It should have happened the way that it happened because that’s how it happened. I know that sounds very circular. But if you switch to that thought process, it will get you to stop arguing with reality, which again, when we argue with reality, we lose 100% of the time.

So, go on a hunt for your should-thoughts, decide if you want to keep thinking them, and work to get yourself to a place of acceptance and understanding. You can do that by thinking, “It should have happened the way that it did, because that’s how it happened.”

Or, you can walk through that why process that I explained to you a little bit earlier. Why did this happen? Look for the thoughts and feelings that would have driven your actions. Look for the thoughts and feelings that would have driven someone else’s actions. Look for the logical sequence of steps that led to something occurring in the world. Work to make sense of it and gain that intellectual understanding.

Then ask yourself; can you replace the should-thought with a more productive thought? You might go somewhere along the lines of, “Well, of course, this happened this way.” That’s a thought that I love to think, instead of, “It should have happened differently than it did.”

“Of course, this happened. This happens sometimes. People get to do this. People have free-will.” All of these lines of thinking are going to be more productive than a should-thought. “I understand why this happened,” will be more productive than a should-thought.

And, last but not least, if you get to a place where you’re like, “Nope, I can’t get to a more productive thought here. I want to keep my should-thought.” You get to choose it on purpose. And then, you get to make the empowered decision to feel a negative emotion as a result, on purpose too. And, that’s okay. You just don’t want to slip into blame, where you’re blaming other people, your own actions, or what occurs in the world, any of those circumstances, for how you feel.

How you feel is always a result of these should-thoughts that you’re choosing to think, and choosing to think them is optional. All right? Hope this helps. Have fun hunting for those should-thoughts and eliminating them, as many as you can so you can feel better. All right? Have a beautiful week. I will talk to you in the next episode.

Thanks for listening to The Less Stressed Lawyer podcast. If you want more info about Olivia Vizachero or the show’s notes and resources from today’s episode, visit www.TheLessStressedLawyer.com.

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