You Can Afford To Help—but Should You? The Line Between Love, Money, and Resentment

Between Tables is where I explore the emotional, psychological, and practical sides of money, especially for women carrying a lot.

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Boundaries are hard. Period. Full stop.

Especially for those of us who didn’t grow up learning how to draw them.

I am a recovering people-pleaser and a stereotypical Italian-Catholic who has a love-hate relationship with the day-to-day chaos of being part of a boisterous family, but a plain-out hate relationship with the textbook guilt part of it. Boundaries have not come naturally to me. They are a skill I have had to acquire the hard way, which is to say: through years of not having them, feeling the full weight of what that costs, and slowly, unglamourously, building something different.

When you grow up exposed to certain patterns and thought processes, you step into them like a wardrobe. You adorn them until they are tailored specifically to your size and height, worn-in and comfortable in the way only old habits can be, and they become a well-worn path. Not just something you do, but something you are. You don’t flip a switch to change that course. It takes years, not months. It takes a shift in thought patterns you didn’t know you had, a sustained tolerance for discomfort, approximately 1,087 setbacks, and about 350 opportunities per day to test whatever change you’re in the middle of trying to make.

It’s fun. Truly.

The Money Version Is Its Own Creature

This gets particularly layered for a lot of the women I talk to, and for me personally.

When you grow up in a household where money is a source of stress, it becomes complicated when you build a life for yourself where that’s no longer the case. The relief of financial stability is real. So is the guilt that arrives alongside it.

It gets complicated when you raise children in a household where they have safety and security and want for relatively little, and then they are launched into the world to struggle and fail and flail and make their own way (as they should).

It’s complicated when the people you love are facing a hard stretch and you have the resources to help. It’s uncomfortable to sit with the question of where you step in. When you help. What you say yes to, and what you say no to. What is enough. How many times. Where the line is. Whether the line exists at all.

Just because you have the resources, does it mean you should use them?

That question keeps a lot of women up at night. “Yes, you have the money, but it’s the principle of things.” I have said this to myself. I have watched clients say it to themselves. Obligation creeps in. Then resentment follows it. Then guilt at the resentment, because how do you resent someone you love? And around it goes.

This is not a simple conversation. I am not going to pretend it is.

The Night in the Car

I want to tell you about one moment that has stayed with me since my 20s.

A group of us had gone out for a night. My girlfriends and a few people in the orbit, one of whom I wasn’t particularly close to. Heading home, this girl, unprompted, made a comment. Because I made more money than the group at the time (I was already working in the industry, had landed a solid job that I had, in fact, worked hard to get), she suggested that I should be paying for everyone. Drinks. Food. The night out.

I let her know, in no uncertain terms, that it was one hundred percent not my responsibility to pay for her or anyone. I probably added a few other choice words. I was in my 20s.

The next morning, she had gone. Taken a cab. Disappeared. We didn’t speak for years until we ran into each other one night and she apologized to me.

I drew a boundary in front of all of my friends in that car. I don’t feel responsible for other people’s expenses. It is not my job. And yet, I will absolutely buy drinks, meals, plane tickets for visits when I want to. Because those things bring me joy. Experiences with people I love light me up. I give generously. But I give on my terms. Not on someone else’s.

The distinction between giving from choice and giving from obligation is the whole ballgame.

What’s Actually Happening in Your Body

The reason most of us can’t hold that distinction easily comes down to something more fundamental than willpower.

When we try to say no (really say it, to someone whose approval matters to us), something happens physiologically. Stomach tightens. Heart rate spikes. The over-explaining starts. The lying awake at 2am running the conversation in sixteen different directions. This is not a weakness. This is a nervous system responding to perceived threat.

Psychologists call the underlying pattern sociotropy, a personality orientation in which emotional wellbeing is heavily tied to others’ approval. For highly sociotropic individuals, saying no activates the same threat response as physical danger. The body, genuinely, cannot tell the difference between I might disappoint my friend and I might not be safe. Both read as risk.

Attachment research makes it more specific. People with secure attachment styles are generally able to assert their needs without excessive guilt. Those with anxious attachment are more likely to surrender their needs entirely to preserve connection. Which means the struggle is about what felt safe when you were first learning how to be loved, and whether that definition of safety has been updated since.

For many of us (especially those who grew up in households where love and performance were tangled together, where being the helpful one was the same as being the good one), it hasn’t been updated. Not automatically. That update is the work.

The Three Modes (Two of Them Are Costing You)

Nedra Glover Tawwab, a licensed therapist and the author of Set Boundaries, Find Peace, names three types of boundary styles worth sitting with:

Porous boundaries are weak, ill-defined, and often invisible to the person who has them. Signs: you can’t say no, you over-explain when you do, you feel responsible for everyone’s feelings, you’re chronically overextended, and you’re carrying a low-grade resentment you can’t quite name. Porous limits don’t just drain you. Research links them to significantly elevated rates of anxiety, depression, and burnout. When I read Tawwab’s book a few years ago, I finally had a name for what I’d been doing for most of my adult life. I have since likened my boundaries during that period to swiss cheese. Everything just flows right through.

Rigid boundaries are the overcorrection, walls built so high that almost nothing gets through. These usually form after years of having soft limits violated: a self-protective measure that becomes its own kind of prison. Distance that looks like coldness. Self-sufficiency so extreme it forecloses intimacy. Not asking for help even when you desperately need it.

Healthy boundaries live in between. Clear enough to protect you. Flexible enough to allow real connection. Not applied as armor, but calibrated, relationship by relationship, based on what you actually need.

Most of us oscillate between porous and rigid. We give and give until we hit a wall, then shut down. Feel guilty for shutting down. Go soft again. The cycle is exhausting. It doesn’t resolve on its own. And it costs more than most of us are tracking.

At almost 42, I Am Still Very Much a Work in Progress

I want to be honest about this.

I continue to struggle. Not every day, but enough. Past me over-commits future me with remarkable regularity, and present me has thoughts about that. I backtrack on things I said yes to when I should have said no. I beat myself up for wanting to back out. I spiral about letting people down. I know the pattern intimately. I know it doesn’t serve me. I do it anyway, and then I do the work of unwinding it, and then I do it again.

This is what actual progress looks like. Not a clean arc from people-pleaser to self-possessed. A messy, recursive loop with a gradually improving average over time.

Where This Hits Women in Their 40s and 50s Hardest

By the time most of us reach our 40s, we’ve spent decades functioning as the emotional infrastructure of every room we walk into. We are the ones who remember. We are the ones who smooth things over. We are the ones who hold the plan, manage the logistics, absorb the fallout, and quietly add every uncompleted task back to our own list when someone else drops it.

Therapists observe that by their 40s, many women have spent years overcommitting, people-pleasing, and filling their calendars with obligations that didn’t serve them. What changes at midlife isn’t that the demands get smaller. It’s that the body starts sending louder signals. The resentment is harder to suppress. The bandwidth genuinely runs out. And the gap between who you are and who you’ve been performing becomes harder to live inside.

This shows up in everyday life as the committee meeting you stay in past the point you’d decided to leave. The group text you answer because the silence is unbearable. The favor that multiplies. The friend who vents for two hours every week while you hold all of it and say nothing.

And it shows up financially in ways that almost never get named.

The adult child who needs help, and then needs more help, and you keep saying yes because you have the resources and they are struggling and you know what it felt like to struggle. But you are not adjusting your own retirement contributions to account for the ongoing outflow. You are funding two lives on your savings plan for one.

The family member you’re supporting out of love that has become obligation that has become resentment that you are not allowed to say out loud, because what kind of person resents someone they love?

The salary negotiation you didn’t have because asking for more felt presumptuous. The colleague who asked and got it. Economists Linda Babcock and Sara Laschever found that two people offered the same starting salary, one of whom negotiates a modest increase, can end up more than $1.5 million apart in lifetime earnings over the course of a career. From one ask.

The financial decisions deferred to a partner not because you don’t care (you care) but because pushing back requires a willingness to create friction in a relationship you’ve been managing, carefully, to feel frictionless. That deference has a cost that compounds and shows up when it matters most.

Financial limits are real limits. The inability to draw them carries real costs.

The Honest Tradeoffs

I want to give you both sides of this, because I think the conversation usually only goes one direction.

The case for solid boundaries is well-documented: lower anxiety, less depression, stronger relationships over time, better emotional regulation, significantly reduced risk of burnout. People who protect their limits show up better for the commitments they do make. They give more meaningfully because they give from choice. They tend to know what they want and be able to ask for it, including at work and financially.

What doesn’t get said as often: drawing clear lines costs something too. People will be disappointed. Some will push back, hard. Some will be angry. If you’ve built relationships (including family relationships) on a foundation of unlimited access and availability, changing those terms feels like a rupture, even when it’s really just a renegotiation. That discomfort is real, and it lasts longer than the motivational content implies.

Porous limits carry their own appeal. Short-term peace. Approval. The feeling of being needed, which is real and not nothing. For many of us, being the person who always shows up, who always has more to give, is tied in complicated ways to our sense of worth. Dismantling it isn’t just uncomfortable. It can feel like losing a self.

The actual cost of not drawing the line is burnout, resentment, anxiety, and the kind of chronic depletion that becomes so normalized you forget it isn’t how everyone feels. Financial decisions made from guilt or obligation rather than choice. The slow erosion of knowing what you actually want, because you’ve been tracking everyone else’s needs for so long that your own signal has gone quiet.

A Framework for Starting

This is not a “five steps to better boundaries by Friday” situation. But here is where I’d suggest beginning.

Notice the resentment before you try to change anything. Where do you feel it? After which conversations, which requests, which commitments? What does your body do when someone asks something of you that you don’t want to give?

Understand what the guilt is actually doing. Guilt in boundary-setting is a nervous system response to something unfamiliar registering as threat. The discomfort means you changed a pattern that’s been in place for a long time. It is supposed to feel uncomfortable. You will feel guilty. The question is whether you’ll act on that guilt or let it pass.

Get specific about what you’re actually being asked to give. Time. Energy. Money. Emotional labor. In each case: Is this coming from a place of genuine choice, or from obligation? From love or from fear of what happens if you say no?

Start smaller than you think you need to. Start with something low-stakes. Decline a request you’d normally absorb reflexively. Let a question sit unanswered in a group chat. Skip one obligation and watch carefully what actually happens. Most of the time, the answer is: less than you feared. Survive it. Build from there.

Prepare for the push. People who have benefited from your swiss cheese limits will often test them when they change. This is not evidence that you were wrong to change them. It is evidence that the change is being registered. Your job is not to manage their reaction. Your job is to hold the line. This part is hard. Do it anyway.

The Permission Isn’t Coming From Outside

At almost 42 years old, I have worked hard enough on this to say with some confidence: the women who struggle most are not the ones who don’t know what they need. They are the ones who know exactly what they need and are still waiting for someone to tell them they’re allowed to have it.

You’re allowed.

The limits you are afraid to draw are not going to destroy the people you love. They are going to ask those people to meet you differently. The financial lines you are afraid to name are not going to make you selfish. They are going to make you solvent and present. The no you have been swallowing is not going to break anyone. It might, eventually, save you.

Tawwab writes that a boundary is the distance at which I can love you and myself at the same time.

I have found that to be true. The distance I’ve learned to hold, imperfectly, inconsistently, still very much in progress, is not distance from the people I love. It’s what makes showing up for them actually sustainable. It’s what allows me to give generously, from a place of genuine choice, rather than giving from an account I’ve been slowly draining for years while calling it love.

I give on my terms. Not on someone else’s.

That is the line. And it has taken me the better part of two decades to find it, name it, and learn how to hold it on most days.

You don’t have to wait that long.