Sept. 9, 2025

How to be a Healthy People-Pleaser | S2E006

How to be a Healthy People-Pleaser | S2E006

People-pleasing often gets labeled as a flaw, but it can also be a strength when you do it the right way. Join me as I unpack why so many of us fall into unhealthy patterns, how it ties back to self-worth, and what it really takes to flip the script. You’ll learn how to set boundaries in six key areas of your life; work, schedule, environment, people, things, and adventures, so you can show up for others without losing yourself. I’ll share how to protect your time, your energy, and your joy while still caring deeply for the people around you. This is about creating clarity, valuing yourself, and building the kind of balance that actually lasts.

Key Takeaways:

  • Why people pleasing is really a self-worth issue and how to flip it into empowerment
  • The “and vs. or” mindset shift that makes people pleasing healthy instead of harmful
  • Six categories to set boundaries around: work, schedule, environment, people, things, and adventures
  • How to clearly communicate boundaries without guilt or apology
  • The hardest part of boundaries and why clarity is the ultimate kindness

About Rebecca:

In 2008, I blew up my life in spectacular fashion. I left a rule-based religious group, divorced, and lost the few people I had leaned on. I thought greener grasses awaited me. I was wrong. Despite building a wildly successful digital marketing business and growing my family to four kids, I felt nothing but dread each morning.

Then came what I now call Epiphany Town. It was that electric moment when I stopped defining my life by what happened to me and began building on purpose. That phase lit me up in a way I had never felt. Now I devote every ounce of my energy to guiding others through their own version of Epiphany Town. I help them forgive their past, let go of self-sabotaging stories, and leap into a life that is meaningful and deeply fulfilling.

I believe each of us has a story to tell, a gift to offer, and a life worth waking up for. Whether your goal is to impact one person or a million, I am here to help you see your place, claim your voice, and live your life on your terms.

https://rebeccamountain.ca/ 



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Rebecca Mountain:

Hello and welcome to another episode of

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from barriers to breakthroughs. I'm your host, Rebecca mountain,

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and today we are going to talk about the importance of people

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pleasing. Now, like most people, when they look at people

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pleasing, it's a bad thing, right? Because we are making

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other people happy, usually at our expense. That's what people

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pleasers do, essentially, is they take care of others, and

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they put their own desires aside. They put their work

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aside. They put their dreams aside because they're trying to

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make everyone else happy. Unfortunately, what they usually

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discover is that that doesn't actually work. We don't actually

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know how to make other people happy. We can't predict how

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anyone is going to feel or think or what they're going to do

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based on what we feel, think or do. But people pleasers, people

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who are really struggling with how people view them, how they

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are perceived in the world, by their peers, by their family, by

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their co workers, their bosses. It's a real struggle for people

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who have that perspective, and unfortunately, it's also driven

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by a very low sense of self worth.

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Now I have super high performing clients that are people

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pleasers, and you can imagine how awesome they feel when I

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tell them, you know, you might have a bit of a self worth

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issue, because usually when we say things, say things like self

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worth issue, it goes with really negative connotations, right

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about what this person is like. You know, someone who is really

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bad self worth never leaves the house. Is really, nervous. And

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there's just, you know, we have these constructs in our minds of

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what someone with low self work looks like. And so what I want

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to challenge today is the concept that, first of all,

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people pleasing is bad. It can be bad, and in many cases, it is

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very bad, but it doesn't have to be. There is a way of being a

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healthy people pleaser. And I'd also like to dispel the myth

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that just because you're successful that does not

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necessarily mean that you don't struggle with things like self

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worth, people pleasing, in your perception of yourself in the

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world. And so let's start first with how we can be a healthy

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people pleaser. The idea, again, is the concept that we strive to

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make people happy. Now, in the traditional sense of people

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pleasing, again, it is to our detriment. We are harmed. We are

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held back. We usually feel, eventually, very resentful when

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we are always bowing to what other people want. We put

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someone comes into our office, we put down what we're doing. We

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turn and we're like, How can I help you? So the nice thing

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about the healthy way of looking at people pleasing is to turn an

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or into an and what that means is you can try and strive and

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make it an important part of you to make other people happy, but

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you can also, in the and version of this equation, make yourself

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happy too.

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And so the example I was just giving you, if someone walks

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into your office, you know, demanding your attention or

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asking, you know, got a minute, you know, you can ruin your day

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with got a minute meetings. And there's many of my top level

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clients that do in the or version of people pleasing, you

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put your stuff down and you give that person your full attention

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immediately. In the am version of the equation, the healthy

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people pleasing version, you turn to them and say, Hey, Bob,

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I really want to help you with this. I'm working on something

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right now. Check your watch. Look at your calendar. Can we

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pick this up at this time or in this way, or whatever? And you

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allow yourself to be helpful and available, but you also protect

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what's important to you. You protect the time that you'd set

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aside to do this work, or you protect the actual work itself.

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You don't want to blow a deadline just because someone

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came into your office, not a really good excuse to give as to

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why the deadline got blown. Nobody really wants to listen to

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that. And so when you look at people pleasing as an and versus

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or now you feel very empowered, because my people pleasers in

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the world get really, really upset when I say you really

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can't make other people's happiness your focus. A lot of

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people grew up like this. There could be even some trauma

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reasons as to where this come from, and so it's difficult and

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sometimes nigh on impossible, for me to tell someone who has

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built their life around making other people happy, that they

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now have to blow that up and ignore that very integral and

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what's important to them, piece of who they are. Instead, it's

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acknowledging that you can have that but you. Also need to raise

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your level of importance.

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If you are putting your work aside to take on somebody else's

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task or emergency or agenda, you are declaring yourself to be

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less valued and valuable than that person or that person's

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task or activity or emergency or whatever has come into your

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world. That's what I mean by people pleasers tend to have a

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low self worth. If you had a higher self worth even equated

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yourself as as valuable and important as anyone else, then

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that's how you can step into healthy people pleasing. That's

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when it's okay to try to make other people happy. I'm not

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saying we should go through the world and just be completely

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narcissistic. That's terrible, but the and version of that

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allows everyone to win. So let's now move into how do we make

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that happen? How do we create that, that habit, that mindset

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of being able to tell people that you want to help them, and

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it's important to you because that's who you are. But there

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are some parameters, and as you can probably imagine, they're

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called boundaries. And boundaries are incredibly

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important and really hard to protect. They're easy to say.

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How many times do we come every January, we set our New Year's

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resolutions, and we create these boundaries, we create these

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goals. This is what I'm going to do. This is the kind of person

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I'm going to be, and then they just kind of go by the wayside.

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So I'm not going to suggest that setting and protecting

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boundaries is easy, but it's essential for you to get what

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you want, and that's actually where you start when you want to

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set boundaries. The actual question that very few people

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answer, they rarely even ask themselves, because they feel

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like it's being selfish, is, what do you want? And I come

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across people all the time that when I ask them that question,

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they actually deflect and they start going about what other

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people want and what how they want to serve other people, and

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I have to stop them, and I go, I get that, and that's important,

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and we'll get there. But what do you want? Then? It's such a big

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question that I encourage you to break it down into six different

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categories.

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The first category of what do you want is, what kind of work

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do you want? What kind of work do you want to do? And it could

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be what industry you want to be in if you want to keep it at a

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high level, or it could it be down to, like, what do you want

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to do in your day to day? Like, for instance, I want to do stuff

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like this. I want to share my ideas, because if it can help

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you even a tiny little bit, then I really feel like I've added

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some really good to the world. What I don't want to do is

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paperwork. And so when you're looking at your boundaries, you

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can go this one of two ways, or you can use both. You can do the

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what do I want? And if you're not familiar with asking that

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question over yourself, you may find that really tough, because

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you're like, oh, I don't really know. I don't really know what I

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want. I've never really asked myself that question. But

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there's a guaranteed question you've have have asked yourself,

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and that is, what do you not want to do? What work drives you

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absolutely insane, that makes you just want to stab yourself

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in the eyeballs or just run away and hide your head. Never have

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to do it again. For me, that's paperwork. Anything related to

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paperwork, anything related to tedious work, detailed work, my

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brain goes on a vacation as soon as I have to do something that

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is kind of minute in nature or finicky or requires me to pay

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attention. I'm a creative mind, and that does not lend itself

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well to detailed work. I've actually been fired for it when

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I worked in corporate Canada. True story. So what work do you

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want to do? And again, if you find that too difficult, what

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work don't you want to do? And based on those two categories,

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you come up with a plan. Okay, if I don't want to do this by

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process of elimination, that means I'm left with this work.

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If you want to be brave and say, No, this is what I want, and you

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want to make that declaration again, now you have much more

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clarity on what work makes you happy is totally in line with

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how your brain is wired. Is something that you could do all

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day and never really get tired of doing. Okay, so that's work.

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What work do you want to do?

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The second category is schedule. When I went and well, quite

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frankly, I got fired enough times that I decided to go out

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on my own. I wanted to be sure that I created a schedule that I

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could work with. I was a single mom. I had two small kids. They

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were three and five at the time, and I needed my schedule to be

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flexible in case something happened. And when I was with my

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little one, something always happened. When I had the my

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phone would ring and it said, school. I'm like, Oh, now you

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never knew what it was, box of chocolates and so. My schedule.

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I wanted to be flexible. I wanted to make sure that I could

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go on vacation and have it such that I had someone else on my

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team that could look after my email so I didn't have to look

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at it. I wanted my schedule to be only Monday to Friday. I

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wanted to start at nine. I wanted it to end at five when I

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worked in corporate Canada, and for many years, when I ran my

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own agency, I would work 8090, hour weeks, and I did not like

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that. So again, sometimes we come into like, what kind of

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days drive you, but in is what kind of days drag drain you and

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drag on? And is there a way that you could, if you could wave a

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magic wand and create the best schedule for yourself. What

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would that look like? And I want to challenge you to be creative.

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I have a client who gets everything done by two o'clock

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and at two o'clock onward, She does whatever she wants. She

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makes exactly the money she wants to make based on that

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schedule. She attends to all of her client needs. She gets

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absolutely every single piece of whatever needs to be done, done

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by two o'clock. She is an absolute machine between 830 and

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two because that extra time afterwards is so important to

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her. Sometimes she'll have meetings in the evening, but

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most often she doesn't, and she doesn't like to work weekends.

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And so when you're looking at your schedule, what often

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happens is just like, well, I have to work weekends. No, you

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don't, because if something is important enough to you, like

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not working weekends. And I'm speaking of someone who works in

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real estate, so working weekends is kind of part of the draw. But

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because she's like, Ah, I really don't want to work weekends.

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Then she brought a junior realtor into her team that

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wanted to they actually want the they want the experience. They

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want the ability to practice what it is that they're

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learning. They want that extra time. There are people out there

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that want to do what you don't want to do, and so when you have

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that mentality of whatever you create, there's a path to make

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that happen. It will make your boundary creating much, much

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easier, particularly when it comes to work and schedule.

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Those are the two that people struggle with the most in terms

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of creating boundaries because they think they can't do it, or

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they think that it's going to be too hard, or it's going to cost

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too much, enter all the excuses for now I want you to just

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release yourself from the bondage of your excuses and

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things that you think might not work and just suspend it for a

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second and believe that it is it is possible to have the work and

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the schedule and All the next four things we're going to talk

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about. To talk about to create the boundaries for the greatest

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life of all time, for you and just for you, everyone's going

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to have a different set of boundaries. Boundaries are not

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made to make other feel other people feel comfortable. They're

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made to feel you feel comfortable. So let's go to the

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third one. So we have work, we have schedule, and now we have

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environment. Where do you do your best work? So right now I'm

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recording this in my office. This is where I do my office

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type work. I do my client meetings in here. I do these

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kind of recordings in here, and that kind of stuff all happens

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here in my office. But when I'm writing my book, I have to go to

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Starbucks, I have to go to a cottage, I have to go to a

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beach, and I have to be as far away from my office as humanly

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possible, because I need to do my super creative work. Now,

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some people are like, wow, you know what? I do this kind of

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work really well at home, but I do this work really well at an

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office. You can have two different locations. You can

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have three, you can have five, whatever works for you. But what

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environments do you need to create for yourself to be the

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most productive? Do you need to be around people? Do you need to

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hear some low level noise, like, you know, the like in a cafe, or

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something like that? Again, when I do my creative work, I need

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that little rumble going on in the background, because it just

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feeds my ADD brain, just enough so that I can focus on the big

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thing at hand. So what environment, or environments are

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ideal for you to be? You're either your most productive or

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your most creative or your most insert term here that you need

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to be to be at your best.

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Okay, so what environment? So we have work, we have schedule,

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environment, and we're going to now come to people. What kind of

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people do you need to surround yourself with? And this is kind

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of a multi parter here, because people can come in different

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forms. You have your personal relationships. What do those

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people need to be like, and this one can be really tough, because

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there could be people in your life, and you really need to

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question whether they should be there or not. And it's not like

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you have to remove them, because I've, I've done this analysis

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for myself, and I'm like, You know what? I'm not gaining

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anything from this. They make me mad all the time, but I. Can't

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cut them out. And so what I do instead is I create distance,

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and I control how much time that I put into that I might even

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control my car like I might be okay. I'm only going to meet

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this person if I drive there, which means I can peace out

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whenever I need to. So people is also on your front, as much on

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your personal side as it is on the professional and

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professional also goes in a couple different directions. Who

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on your team or in your office do you want to surround yourself

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with? Do you like being in sort of an open concept, or do you

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like it being closed off so that you can engage with people? But

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again, you have that door. You're like, peace, I'm out. And

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do you need those people to also respect that door? Do you need

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them to make sure that when they see that door is closed, that

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they don't knock on it, or maybe put a sign, don't knock, you

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know, don't disturb if the person because I'm working on

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something I'm doing my focus work. What kind of people in the

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office or in your work environment do you want to

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surround yourself with. And if you run your own business, what

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kind of clients do you want to have? And the more you can

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really detail out who those people are, like really describe

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them in detail. You activate the reticular activation system in

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your brain, and you're going to see more of those people, and

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you're going to open up more opportunity to engage with them

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in a deeper way so the people part of boundary settings is

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also incredibly important.

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So now we're going to go to the last two often. I started those

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four, but I've added two more over the years, because I think

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they're important. And the fifth one in our list is things, and

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it's not that we want to put our value into things, right? So if

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you have a really fancy car, if you if that's part of your

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identity, that's a problem, because if that car gets

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squished or something happens and again, you don't have it

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anymore. You don't want your identity and all the things that

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you hold dear about yourself and how you think about yourself to

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be driving away on the back of a tow truck, or you having to walk

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away from it for whatever reason. But things still can

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make us feel joyful. So for instance, I have little things

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that I've collected from my children over the years, and

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those things are really important to me. I have cards

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that someone sent to me. There's my old babysitter, as she died

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when she was 100 before, but she took care of us for years, and

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she was so lovely that there are things that I hold onto that

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have personal meaning, or they may have spiritual meaning or

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emotional meaning. And so when it comes to things, things you

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want to surround yourself with, things you want to have around

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you that can trigger certain memories, certain emotions,

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things that make you feel good, you don't have things around you

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that make you feel bad. But if you have little things, whether

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it's knickknacks or photographs or cars or homes, whatever it

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is, as long as the emotion is joy and not something that is

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more cloying, more something that you feel like if you didn't

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have it, you wouldn't be who you are. That, again, dives right

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back into self worth. Self worth is at the bottom of a lot of

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what's challenging us these days. And so when you have

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things and you understand I have these things because they bring

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me joy, then those are what I would encourage you to bring

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into your life and have all over the place. And it doesn't matter

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what the price tag is. It matters that it means something

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to you.

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The last thing, which I personally love and have been

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very much setting boundaries around this is adventures. So

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this could be travel, and most often it's travel, but you can

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have local adventures. You can have little mini adventures. I

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remember I used to have many adventures with my boys when

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they were small. And we go off into the forest and we try to

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find stuff and it I hold on to those memories because they're

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beautiful. And I also went on adventure, my 10 year

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anniversary with my husband to the Maldives. And that was an

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adventures, an adventure getting there, and his adventure when we

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got there, swimming with manta rays and dolphins and sharks and

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turtles and squid and, oh, it was just so beautiful sitting on

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the back deck of our over water bungalow, watching the dolphins

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go across the horizon and the manta rays. It was ridiculous,

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it was incredible, and it was an adventure that I remembered, and

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I have so much joy thinking about that particular trip that

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I made, but I also have joy with those tiny little adventures I

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have with my kids. I'm an empty nester now. They're all off at

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school and working, and so I don't have those let's go into

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the woods. Moments with the kids doesn't quite happen the same

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anymore. Also, that sounds slightly threatening, but you

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know what I mean? When they were. Little though those are

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the times where I would just look at them and feel so much

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joy, like I feel it right now. And you want to surround

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yourself as much as possible with those adventures. And when

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you finish this work, which is not small work, by the way, so

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when you finish the work of setting the boundaries of what

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you want, or doing the process of elimination, using what do

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you not want, and you come up with a set of parameters, and

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those become your boundaries. This is what you want, and I

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want you to take a look at that. And if you have any tendency to

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be a people pleaser in the negative way, in the unhealthy

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way of taking what you want and going it's just not as important

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as everybody else. I want you to hold it in front of you like the

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most precious thing in the world, and look at it as an

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something that you will never, ever compromise away.

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There is no amount of compromise or settling that will make you

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happy. Eventually it makes you resentful. And I've seen lots of

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people pleasers that at the end of many, many, many, many years,

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even decades of doing it, have nothing but bitterness because

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they gave so much but they never felt they got anything back, and

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that's typically because they a, never asked for it, but B, they

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never knew what they wanted, and they never communicated it,

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which is the next step of boundary making. So you set the

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boundaries, and you don't put it down. You set it in front of

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you, and that stays there forever. Write it on the wall,

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write it on your arm, whatever you got to do, but this is now

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what you want, and what is going to make you feel happy and safe

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and secure and fulfilled, right? All of these things are so

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incredibly important now you need to communicate it.

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Communicating boundaries is tricky, especially if you've

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never done it before, and especially if people have come

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to look at you as someone who will always drop what you're

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doing to take care of everybody else. It sounds magnanimous.

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It's actually horrible, and we really need to stop idolizing

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that as a culture. What we need to do instead is to value the

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whole art of everybody gets what they want. We just need to

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sometimes be a little bit creative. So when you need to

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communicate these wonderful boundaries to other people, it

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might take a few ghosts. They may be they might be confused.

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They might be wondering, like, this is different. This makes me

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feel weird and squidgy, because they're not used to you

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communicating it, but it's using kindness. And kindness is not

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being nice. Kindness is being firm and clear. Being nice is

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taking everything you want and stuffing it under the rug again.

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Oh, it's okay, you know, I know it makes you feel uncomfortable,

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so like we'll, we'll do it later. Nope, you're kind to

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yourself and to others by saying, Well, you know what?

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This is really what I would I would love, but I love it when

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people give me my personal space.

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So one of the things I like to do in communicating boundaries

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is not to say to people, don't do that, don't do this, don't do

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that. Is to say, You know what makes me really happy. You know,

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what makes me feel really awesome is when people do this

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and you use the positive behavior that you're looking

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for. First of all, that's what people's brains hear anyway, and

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that's what you want to push so that's how you be kind in the

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communication, right? You may go to your boss, you may go to your

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team, and you talk about the work that you're doing. You

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know, it'd be really great. You know, open up so much for me and

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make me feel so much joy. Is if we can figure out how to Redis,

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redistribute the work, give this work to someone else, whatever

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the case may be, and you just go through each one of those six

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layers of boundaries, and you communicate each one when it is

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necessary. If you're the kind of person who kind of has done this

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a little bit, you're not a super people pleaser that hasn't been

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your personality. You may find this easier than someone who has

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had years and years of just bowing to other people's

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emergencies and agendas, be it as it may, communicating what

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you want is going to be important. And the final step,

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and this is the hardest step, which you thought maybe like, oh

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yeah, setting the boundaries was hard. Ooh, communicating sounds

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hard. Nope. The hardest part is actually protecting them. And

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what's going to happen, especially if you haven't set

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boundaries before, is people are going to try to mow them down.

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Take a deep breath. You put the barricades back up, and you're

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like, Nope, this is actually how things are going to go. And be

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adamant and firm and kind. You don't have to have a freak out,

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and you don't have to wonder. Why are people violating your

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boundaries? Well, maybe you never set them, maybe never

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communicated them. Maybe they're, you know, a little bit

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of an asshole kind of going on in there. Who knows? Doesn't

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matter. What matters is you re communicate that boundary you

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like, Hey, did saw that. You know, I asked for this. You did

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the absolute opposite, or you keep coming into my office, even

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though my door is closed, there's a sign that says doing

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my focus work, and you might need to kind of work out what's

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causing them to do that. And most often, it's because your

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boundaries make them realize they don't have boundaries, and

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it makes them feel weird. So if they can make you, you know,

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throw your boundaries out the window, then they don't have to

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go through what feels like the hard process of creating and

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communicating and protecting their own so that's why I always

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encourage kindness in these kind of situations. Because most

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often, especially when people are really giving you the gears,

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it's driven by a fear of some kind that either you're

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progressing without them, or you're growing they're not, and

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that reflects badly on them, and they're just maybe not

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emotionally capable of processing that themselves. And

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when people aren't emotionally capable of processing their

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emotions, which is most of humanity, they're going to take

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it out on you, because it's easier to spew the poison than

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to process it. It takes a lot more work, and so just continue

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that kindness, continue that direction of saying, Okay, what

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do I want? How do I communicate it? How do I protect it? And you

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might have to take a lot of deep breaths, and you might need to

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adjust things over time.

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Boundaries are meant to adjust over time. But when you can say,

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Okay, this is clearly what I want, and you adopt the healthy

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people pleasing attitude of an and versus an or everybody can

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get what they want, and you spread more of that message into

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your sphere of influence, so more people set their boundaries

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and create that wonderful expectation that everyone has

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boundaries and all are to be respected, communicated and

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protected. Everyone around you and everything around you

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becomes so much easier any kind of game playing and mind reading

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goes away, because clarity is now in the room, and clarity

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above anything else is kindness. And so if you have been a

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healthy people pleaser or an unhealthy people pleaser, maybe

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you've done a little bit of boundary work. Maybe you've

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never even tried. I want you to be able to take some time right

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now, set those boundaries, understand how you're going to

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communicate and protect it. Really look at those as the most

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important and meaningful thing that you can have in your life,

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and then adopt the overarching attitude of and I can be this

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happy, fulfilled, successful, respected person, because these

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are the parameters that will allow me to feel that way and

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continue to do whatever and however much help you want to

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provide to other people, because it's important and meaningful to

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you.

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So go out there be the healthy people pleasers you know you can

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be and enjoy setting, communicating and protecting the

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boundaries that are going to give you the life, work and love

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that you really want you.