When do boundaries get easier?

My knowledge of boundaries used to be just that – intellectual understanding about what they were. Period. End of story. 

They were things I knew I needed and had no delusion that I could express them or exercise them or do whatever you were supposed to do with them. 

I sort of “stated” them when I was angry enough to feel powerful and justified in having them. Mostly that was when I was sick or going to be out of town or was simply burned out by giving too much in the first place.

When I “stated” them, I fumbled a lot. More like MUMBLED a lot. 

Even when I mumbled a boundary, this awful flimsy feeling would usually take over afterwards because I knew myself and I knew in my gut that there was no chance in hell I would keep them or ‘defend’ them once set. 

So, I developed a love/hate relationship with boundaries. 

I loved the IDEA of them. 

I hated the ACTUAL expression of them. 

And I hated MYSELF for being so scared of saying what I wanted. 

Nonetheless, due to algorithms, I kept hearing about them. 

In books. 

In podcasts. 

On Instagram.

Once I wanted to kick an Instagrammer in the face because she had this cute reel about “Just say it! Just freaking say No!” and told me WHY I should say “no” more than “yes”, but she didn’t tell me how or even address how freaking hard it would be IF I tried it. 

C’mon people! Don’t make it look easy because IT’S NOT!!!!!

Aside from my on-again-off-again relationship with boundaries, I still tried to let them slip out once in a while and I started to get some practice. I do understand a little more about them now that I have gone through the fire. 

I don’t want to be like that Instagrammer so I am gonna tell you how it really is –

I can’t make boundaries easy for you. 

I can’t rescue you from the intensity of getting the words out and then sweating while you stand up for yourself and keep them. 

It’s not easy. 

I still have to contemplate for a while IF it’s okay for me to ask for what I need. Or simply say “no”. 

But that is okay. Changing a well-worn pattern is going to be a long game. It’s not like driving a speed boat where you can shift direction in an instant. This is like driving an ocean liner. Slow micro movements. 

But let me tell you something you have over other people. 

Lots of people aren’t even aware of their patterns of pleasing. They are on autopilot. 

The fact that you asked this question, okay I know, I am the one that asked it, but still, the fact that we are asking when it gets easier is an indication that we are on the road to recovery from pleasing. 

One thing that helps me is to cut back on comparing myself to non-people pleasers. They just don’t struggle with boundaries like I do. I do watch them and silently curse them for the ease by which “no” comes out of their mouths, but I also know that Jerry Garcia was right, 


“There is a road…no simple highway…between the dawn and the dark of night and if you go…no one may follow…that path is for…your steps alone.” 

Consistency, repetition, and compassion will be our guiding lights on this path. 

One strategy I discovered was learning and exploring what my personal “no” felt like, like felt like in my body. 

I realized if I knew what was and wasn’t right for me then I would feel more solid or centered in my “no”. 

So here is a video where I offer a simple exercise that you can do in real life to learn what your boundaries are from the inside out. 

I’d love to hear what you think!

Be well fellow pleasers!


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