Why Doing the Right Thing Doesn’t Always Feel Good

Nowadays, we are seeing a ton of pop psychology and self-help advice that encourages us to prioritize ourselves by:

~Setting boundaries.

~Asserting our needs.

~Emphasizing self-care.

~Giving yourself grace.

Most of this is reasonable advice. However, for most of us, the problem isn’t a lack of information. We already know we should be setting boundaries. We know our needs matter. We know constantly sacrificing ourselves for everyone around us probably isn’t sustainable.

Knowing what to do is often the easy part.

Actually doing it can feel terrible.

When Healthy Choices Create Uncomfortable Emotions

We might assume that doing the “right” thing should feel naturally rewarding or empowering. It may not

Although setting a boundary is healthy, it’s also unfamiliar and can lead to conflict.

Although advocating for myself is appropriate, it can also be awkward and inconvenient.

Although prioritizing my own well-being is necessary, it can feel uncomfortable.

Sometimes doing the right thing for ourselves can be naturally rewarding in the moment. Yet most times doing the right thing comes with feelings of guilt, selfishness, shame, sadness, anxiety, hurt, or even pity for ourselves or the persons affected by our decision.

We might know intellectually that a boundary is reasonable while emotionally feeling like we have done something wrong.

“I know I need to assert my needs, but it’s going to create conflict.”

“I know I need to set this boundary, but what if they think I’m selfish?”

“What if I choose myself and something bad happens to them?”

“I don’t want to be a burden.”

“What if I advocate for myself and they feel hurt?”

These emotions can become powerful enough that we start using them as evidence.

I feel guilty, so maybe I did something wrong.

I feel selfish, so maybe I’m being selfish.

They’re upset, so maybe my boundary was unfair.

But emotions don’t always work that way.

Feeling Guilty Is Not the Same as Being Guilty

Our emotions are real, but that doesn’t mean every conclusion we draw from them is accurate.

You can feel guilty without being guilty.

You can feel selfish without being selfish.

You can feel anxious about conflict without the conflict being dangerous.

You can feel sad that someone is disappointed in you without being responsible for eliminating their disappointment.

That distinction matters.

Many of our emotional responses have been reinforced through years of experience. If you are accustomed to avoiding conflict, prioritizing other people, or receiving approval for being accommodating, suddenly behaving differently might feel wrong even when you consciously believe it is appropriate.

The discomfort isn’t necessarily proof that you made the wrong choice.

It may simply be the emotional experience of doing something different.

Sometimes We Have to Feel Bad

I would love to offer a strategy for setting boundaries, prioritizing yourself, and asserting your needs without experiencing any guilt, anxiety, sadness, or discomfort.

Sometimes we can reduce those emotions. We can challenge irrational beliefs, communicate more effectively, develop greater self-awareness, and make thoughtful decisions about when and how we advocate for ourselves.

But sometimes the uncomfortable emotion is still going to be there.

And sometimes the work is learning that we can tolerate it.

This doesn’t mean ignoring our emotions. It doesn’t mean deciding that we are always right or that other people’s feelings never matter. Emotional discomfort can provide valuable information, and our choices still deserve reflection.

But feeling bad does not automatically mean we behaved badly.

Sometimes we have to allow ourselves to experience guilt without immediately trying to make the guilt disappear.

Sometimes we have to tolerate someone being disappointed in us.

Sometimes we have to accept being misunderstood.

Sometimes we have to experience the anxiety of conflict rather than continually avoiding it.

And through those experiences, we can gradually learn that these emotions are uncomfortable without necessarily being intolerable.

The Goal Isn’t to Never Feel Bad

There is an important difference between trying to eliminate uncomfortable emotions and becoming more capable of experiencing them.

If we require ourselves to feel completely comfortable before setting a boundary, we may never set one.

If we need reassurance that nobody will think we are selfish before prioritizing ourselves, we may continue putting ourselves last.

If we need to know that asserting ourselves won’t create conflict, we may continue staying quiet.

Confidence rarely comes before the behavioral change. It develops because we acted despite the discomfort and discovered that we could handle what follows.

The more capable we become of experiencing these emotions without immediately abandoning our needs because of them, the more freedom we have to make decisions based on our values rather than solely on what feels most comfortable in the moment.

We can set boundaries.

We can advocate for our needs.

We can assert ourselves more confidently.

And we can give ourselves grace when doing those things is harder than we think it “should” be.

Doing the right thing for yourself doesn’t always feel good.

Sometimes the emotional discomfort isn’t evidence that you’re doing something wrong.

It might even be evidence that you’re finally doing something different—and doing the right thing for yourself.

Parenting by Example: How Confidence is Modeled, Not Taught

At this stage of my career, I primarily work with young adults and adults navigating anxiety, depression, and self-esteem. But not that long ago, I was the young, cool therapist—the one parents wanted their ADHD or ODD sons to connect with.

I still love child development. I still enjoy working with kids and adolescents.

But nothing grounds you quite like having an 11-year-old daughter and a 13-year-old stepdaughter.

I am no longer the young, cool therapist. And almost certainly not the cool guy at home. (The eye rolls out number the laughs nowadays)

And honestly? That’s probably for the best.

When Being “Cool” Stops Being the Goal

Not that I’m trying to be cool to middle schoolers. Insert generic dad joke about not having rizz. (Listen, I’m cool enough to know not to even attempt it.)

A man wearing a red cap and skateboard, dressed in casual attire, greets a group of young people with the phrase 'How do you do, fellow kids?'

What’s shifted isn’t my sense of humor—it’s my focus. Somewhere in the second decade of parenting, the question quietly changes. It’s no longer about telling them they’re awesome little achievers that can do anything they put their little minds to.

It becomes about showing them what it looks like to be proud of yourself in life.

Am I someone I’d want to become?

Am I leading by example?

The First Decade: Building Their Confidence and life. 

During the first decade of parenting, I spent a lot of energy cultivating my daughter’s self-esteem. I encouraged her and celebrated her achievements. I made sure she knew she was capable and worthy.

Lately?

She gives significantly fewer shits about what I think.

She rolls her eyes and sarcastically asks “is this another life lesson?!” She complains when I encourage her to be proud of herself. I get it. It’s dorky now. It’s parent stuff.

The Second Decade: Modeling Living a confident enjoyable life. 

What actually needs my attention now isn’t coaching her confidence—but modeling it.

That means being proud of myself.

Not “cool” (that ship sailed when I started making comments worthy of Progressive Insurance commercials).

But grounded. Intentional. Honest.

Sometimes I catch myself wondering:

Would my daughter want to live a life like mine?

Two individuals running on treadmills in a gym with large windows showing a view of the outdoors.

Leading by Example Isn’t About Control—It’s About Consistency

I hope my daughter continues to be her own independent, creative self. (Though, good or bad, she has many of my idiosyncrasies.)

My role now feels less about directing her growth and more about living in a way that demonstrates self-respect.

One of the best things we can do for the people we love is take care of ourselves. We are not do it performatively, not perfectly, but consistently.

Good parenting isn’t just being present and attentive.

It’s being able to stand behind the life you’re living.

That includes being proud of your own:

  1. Daily habits
  2. Physical health and movement
  3. Mental health and emotional regulation
  4. Relationships
  5. Interests, hobbies, and passions

Kids notice what we do far more than what we say.

A framed sign with the text 'SELF CARE ISN'T SELFISH' displayed against a pink background, accompanied by a shadow from a plant.

Modeling Matters More Than Motivating

Recently, our girls did wall sits for an absurd amount of time—because I was doing a wall-sit challenge at my gym.

No lecture required.

No motivational speech.

Just modeling.

My daughter has also been leaning into humor lately. (I like to think we’ve made her life just stressful enough to have good material, yet comfortable enough to feel secure being silly.)

She told me a story from school that stuck with me.

She wanted to leave school early. She Googled me, pulled up my website, and showed her friends my profile—where my session fees are listed.

She announced:

“Guys, I have to come up with at least a hundred dollars for my dad to come get me.”

I was proud—not because she was “flexing,” but because she was playful, confident, and comfortable sharing this tibdit with her classmates ( and now with me). She proceeded to ask her classmates if she looked like me. (She did not need confirmation—unfortunately- poor girl looks exactly like her dad.)

What that moment told me was this:

She wasn’t embarrassed by me.

She wasn’t hiding me.

She was proud.

A man in sunglasses stands with a water bottle and a towel over his shoulder, watching two children play soccer in a sunny park.

Being Someone Your Kids Can Be Proud Of Starts With You

I know 11 is still young. The next decade will likely involve plenty of eye-rolling, boundary-testing, and days where I unequivocally take the L.

But I want to give myself the best chance possible—not by being perfect, but by being someone I respect.

Because when I’m proud of how I live,

when I show up for myself,

when I take care of my mental and physical health—

I’m not just teaching her confidence.

I’m showing her what it looks like.

And hopefully, one day, she’ll be damn proud of herself too.