The Real Reason Your Boundaries Keep Failing (And It’s Not What You Think)
The only reason your boundaries keep failing is because you haven’t set them with yourself first.
This was me after completing 75 Hard - sitting at a restaurant on the beach, sipping coffee instead of wine, and finally understanding what real freedom felt like. For the first time in years, I wasn’t carrying the weight of everyone else’s expectations about who I should be or what I should do. I had learned to set boundaries with myself first, and everything else became so much easier. That thoughtful look? I was realizing that the woman I’d become wasn’t someone I was trying to be - she was who I’d always been underneath all the pressure to please everyone else. Sometimes the most powerful boundary you can set isn’t with other people - it’s with the version of yourself that thinks you have to carry what was never yours to carry. What boundary do you need to set with yourself first?
Everyone talks about how hard it is to set boundaries with other people.
But here’s what no one tells you: The hardest boundary you’ll ever set isn’t with them. It’s with yourself.
After my rock bottom moment on August 19, 2022, I didn’t quit drinking immediately. I backed down quite a bit and made a commitment to never get drunk around my kids again. But I didn’t stop completely.
From August 2022 to March 2024, I drank very little. The drinking slowed as time went on, but every few months, I’d find myself in situations where I felt peer pressure or thought I “needed” to drink because everyone else was drinking.
And every single time, without fail, I would hate myself the next day.
Whether it was because of the way I acted, things I said, arguments with my husband, or simply because I felt like garbage physically - the regret was always there. The shame was always waiting.
But I kept doing it because I hadn’t made THE decision yet. I hadn’t set the boundary with myself.
In March 2024, I decided to attempt 75 Hard for the sixth time over several years. This time, I completed it all the way through. After going 75 full days without alcohol and actually feeling better, I asked myself: “Why should I ever drink again?”
That’s when everything changed.
During 75 Hard, when I was around people drinking, I had an external rule: “I can’t drink because that’s against the challenge.” I built up the muscle of saying no because the boundary wasn’t negotiable - it was part of the program.
But after 75 Hard ended, something beautiful happened. “I can’t drink” became “I don’t drink.”
The boundary had moved from external rule to internal identity.
During my first year of not drinking, I still got questioned. “You’re really never going to drink again?” “You sure you don’t want a drink?” “Just one won’t hurt.”
This was hardest for my husband because drinking was all he’d ever known me to do. I drank, I liked to drink, and I drank a lot. He’s a casual drinker, so he struggled with my decision. He felt like we couldn’t do certain things anymore because I’d be uncomfortable or wouldn’t have fun.
That wasn’t the case, but that’s how he felt. Over time, he realized I didn’t need to drink nor did I want to, and he had to accept that I could still go places where others were drinking and have a great time.
Here’s what I learned: When it comes to setting boundaries, people say the hard part is telling other people no. But in reality, it’s harder to tell yourself no first.
Once you’ve made the decision to tell yourself no, setting boundaries with others becomes easy.
The only reason I didn’t quit drinking sooner was because I wasn’t ready to say no to myself. I hadn’t set the boundary internally, so when peer pressure came or situational pressure arose, I broke easily because I had no real boundary established.
But once I decided - really decided - that I was done, all those external pressures lost their power over me.
This goes for ANYTHING.
Food boundaries. People boundaries. Schedule boundaries. What you will or won’t do, where you will or won’t go, how you will or won’t act.
YOU have to decide first. YOU have to choose to set the boundary for yourself before you can hold it with anyone else.
The guilt you feel when you “fail” at boundaries? It’s not because you’re weak. It’s because you’re trying to build a fence without laying the foundation first.
The boundary has to be YOURS before it can protect you from others.
Stop carrying the weight of other people’s expectations, their emotions, their dysfunction. Stop carrying guilt that belongs to them, not you.
The biggest freedom you can give yourself isn’t learning to say no to other people.
It’s learning to say no to the version of yourself that thinks you have to carry what was never yours to carry in the first place.
Set the boundary with yourself first. Everything else becomes so much easier.
You don’t have to carry their disappointment. You don’t have to carry their pressure. You don’t have to carry their expectations.
Those were never yours to carry anyway.