How to Go from Fear to Freedom: Bookending Your Way to Healthy Boundaries

Issue 115. March 14, 2025 ✨ Higher Power Coaching & Consulting ✨

How to Go from Fear to Freedom: Bookending Your Way to Healthy Boundaries

Bookending is a concept I learned in recovery that I found extremely helpful when setting difficult boundaries or having really tough conversations. If you’ve ever had an accountability partner for something, then you’ve been exposed to the concept of bookending. The idea is that you “bookend” your commitments with another person by connecting with them before and after you do the thing you’ve committed to.

Leveraging codependency powers for good.

For example, if you’re having a hard time going to the gym, you might text a friend and say, “I’m going to the gym today come hell or high water. I’ll text you when I’m leaving the gym.” I think of this as leveraging my codependent powers for good.

What I mean by “leveraging my codependent powers for good” is this: I have codependent tendencies and I’m probably always going to have them. That means (among other things) that I want people to think well of me. Therefore, if I tell someone I’m going to do something, I am so much more likely to follow through than if I didn’t tell anybody.

I’ve been using my codependent powers for the benefit of other people my entire life. I’m now learning to use them (or leverage them) in such a way that they finally benefit me. I more easily get myself to follow through on things when I involve other people.

This works for me to this day. I have two accountability partners for meditation and one for yoga. I meditate twice a day and that second meditation is sometimes difficult for me.  I wouldn’t meditate that second time daily as consistently as I do if it weren’t for my accountability partners.

The basic and complex models of bookending.

At its most basic, the idea of bookending is that you have someone be your accountability partner before and after doing something you’ve committed to doing. There’s a much more complex way to employ this same technique in much more difficult circumstances, which is the main topic of this essay. 

It’s very powerful when you’re doing something that extremely difficult, like setting a particularly important boundary with someone you’re close to or afraid of. If there’s a boundary you’re really nervous about setting, this more complex form of bookending can be a Godsend!

For difficult situations, choose a supportive and emotionally mature “boundary partner.”

This could be a trusted friend, a sponsor, a clergy person, a coach or a therapist. Ideally, it’s someone who’s not emotionally involved in your situation.

You start by asking for their support with the situation. Once you get their consent to support you, run your thoughts by them about what you want to say to the person you’re setting a boundary with (the target of your boundary). Remember, this is your boundary and you get to make the final call on what to say, when, and the setting you’ll say it in. But it’s a good idea to get feedback from someone not involved. That person can help you think through whether it makes sense for you to use those particular words, do it at that particular time, and in that particular setting. For example, they might say, “Are you sure you want to do that in person? Perhaps doing it on the phone or zoom will make it easier for you.”

Once you’ve made your decision about what to say, when and where, let your boundary partner know, “This is the day and time I’m going to do it. I want check in with you that day before I do it and after it’s over so I can bookend my boundary setting with you.”

The power of a boundary partner.

On the day of your boundary setting, connect with your partner. This serves two crucial purposes: accountability and emotional support. They can affirm your decision, reminding you that you deserve to set healthy boundaries. Moreover, you can process any pre-boundary anxieties or fears, reducing the likelihood of projecting those emotions onto the other person.

When we were growing up, many of us didn’t have supportive others to help us manage our difficult feelings. That’s why they can be so overpowering. The feelings of guilt and shame that arise when setting boundaries (or even thinking of setting boundaries) are what frequently stop people from setting boundaries, or cave once they set them. Having someone to process those feelings with you reduces the burden of those feelings. 

You don’t want to launch those emotions at the target of your boundary because that makes it much more likely to be a confrontational experience rather than just a simple conversation about “this is how things are going to be from now on.”

Navigating difficult emotions.

At the beginning of learning to set boundaries and have difficult conversation, I’d feel like I was going to die. I’m not exaggerating! It felt like my life was under threat! It wasn’t really setting a boundary that made me feel like I was going to die, it was the emotions associated with setting the boundary. I didn’t know how to handle them, so having another person to process those feelings with changed everything! Just the idea of not responding to an email from ex-boyfriend caused my nervous system to go way out of whack. And that was an ex-boyfriend!!

You don’t want to process those feelings with the target of your boundary, which is a major reason why you’re bookending with your supportive boundary partner. When you go into the situation with the target of your boundary and tell them what you want to tell them, you’ll know that someone else 

• knows where you are
• knows what you’re doing
• knows what you’re going through
• and is waiting to reconnect with you afterwards

Then, once you’ve set the boundary, you reconnect with your boundary partner (the other end of the bookend process). Once again, you get reassurance and affirmation from them (you did the right thing, you showed up for yourself, you stood your ground, you’re so brave). You also get to process any difficult emotions with them again. Even if things turned out fantastically, you may still have difficult emotions to process and you don’t have to carry those alone. You get to share them with others. 

That is, you get to be connected to others. Remember – we’re protected when we’re connected. Here’s why this is important: most people with unhealthy boundaries have no experience with healthy connection to others. We’ve typically experienced enmeshment or abandonment, or both. That means when we set a boundary, it feels like abandonment. That is, we know it’s not enmeshment, and the only other thing we know is abandonment. 

But, if we’re connected to our boundary partner through their love and their support, we know we’re not abandoned.

From enmeshment to healthy connection.

If you’ve only experienced enmeshment or abandonment, you have no concept of what healthy connection is. That’s why setting boundaries can feel like abandonment rather than creating a healthy connection with others. 

Here’s the thing about abandonment: it doesn’t matter who initiates it, it still feels like abandonment. For example, if you break up with a someone, you could still feel abandone. It’s doesn’t matter if you initiated the breakup because they were there and then they’re not. If you have a history of abandonment, it feels like just another instance of being abandoned.

Setting boundaries means coming out of enmeshment. You’re delineating the boundaries of who you are, differentiating yourself as your own distinct person with your own distinct identity and preferences. That can feel like abandonment because you’re no longer enmeshed with others.

Bookending with your boundary partner lets you know on an experiential level “I’m not abandoned – I’m still connected to this other person.”

If you need to set a difficult boundary or have a very tough conversation, getting support from someone else can be absolute magic!y family pattern of indirect communication, and why I did it – because I wanted to blame other people for my problems. If you recognize any of these patterns in your own life, know that change is possible. Start by paying attention to your conversations and asking yourself: ‘Is this my business?'”