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.

My Top 3 Irrational Beliefs

The real B.S. I used to tell myself—and believed for longer than I care to admit.

As a cognitive behavioral psychotherapist, I spend a lot of time helping people identify irrational beliefs.

Very often the stories we tell ourselves and the assumptions we make are flawed or self limiting. We reach conclusions and fill in gaps without much evidence.

We subjectively create rules for ourselves that, at some point, we stop questioning.

Unfortunately for me, being a psychotherapist does not make me immune to any of this.

I have my own irrational beliefs. Some which I’ve stubbornly held onto for years. And the tricky thing about an irrational belief is that when you believe it, it usually doesn’t sound irrational.

It sounds completely reasonable to us at the time.

So in an effort at transparency and vulnerability, here are three of mine.

Irrational Belief #1: “I’m a psychotherapist. I shouldn’t be in great physical shape.”

For a long time, I had this strange belief about being physically fit. I told myself I didn’t need to be in great shape because I was a psychotherapist. Part of that was probably just a convenient excuse to do bare minimums.

But there was something else underneath it.

I thought being too physically fit might actually make me less relatable. Maybe people would look at me and wonder what I was trying to prove. Maybe they’d think I was hiding something.

Maybe a client struggling with their own health, motivation, confidence, or body image would look at me and think:

He doesn’t get it.

So somehow I turned not taking care of myself into something that felt almost professionally responsible.

That was my own B.S.

The reframe was much simpler:

I can care about my physical health and appearance because I care about me.

It doesn’t have to have anything to do with other people:

A) I can exercise because I like feeling strong.

B.). I can care about how I look because it makes me feel more confident.

C.) By challenging myself physically it reminds me I can do difficult things.

And none of those things make me less capable of understanding someone else’s struggle. If anything, what actually happens is the exact opposite of what I feared. I’m more confident and speak with more conviction in my approach. Theres more heart. I genuinely feel better.

My behavior is more congruent with a lot of the things I encourage in therapy.

And I think my clients benefit from that.

Irrational Belief #2: “If my clients find out I’m divorced, they’ll see it as negative.”

For years, I was extremely cautious about self-disclosure.

I’m a therapist. The session isn’t about me. I need to have strong boundaries. And these are good reasons to have boundaries around what and how much we share with clients. But somewhere along the way, healthy boundaries turned into boxed in walls. Based on fear or my own anxiety.

I worried that if clients knew too much about me, eventually something could be used against me.

Divorce was a big one.

He got divorced.

His marriage failed.

What does he know about successful relationships?

So I kept parts of myself hidden for far too long. Not necessarily because keeping them private made me a better therapist, but because keeping them private made me feel safer.

Eventually, I had to dispute that self serving by self limiting comfort zone.

I can have appropriate boundaries without being afraid of being known.

I can be proud of choosing divorce even if someone else sees it as failure.

I survived something difficult.

I made a decision that was healthier for me and gave me more opportunity to be the father I wanted to be.

And none of that disqualifies me from helping someone else navigate their relationships.

What actually happened?

I became more comfortable acknowledging my failures.

I became more intentional with self-disclosure instead of simply being afraid of it. (Also, no one used my divorce against me. It actually is more of a gateway into understanding people)

More importantly, I stopped believing that being a good therapist required presenting some carefully protected version of myself.

I can have boundaries.

I can keep parts of my life private.

But I don’t have to hide myself out of fear.

Irrational Belief #3: “Posting on social media to get clients is for therapists who need clients.”

This one is probably the most humbling to admit because I didn’t just avoid social media.

I judged other therapists for doing it.

I thought it was cringey.

There was this part of me that believed:

Just be good at your craft.

If you’re a good therapist, people will find you.

You shouldn’t have to shamelessly promote yourself.

And if you’re constantly posting online trying to get clients, maybe that says something about your ability as a therapist.

Then eventually I had to confront something uncomfortable.

I wasn’t avoiding social media because I had some deeply held professional principle.

I was boxing myself in because I cared too much about other people’s opinions.

What if another therapist thinks I’m cringey?

What if someone thinks I’m desperate for clients?

What if people I know see one of my videos and make fun of me?

I was allowing hypothetical opinions from hypothetical people to dictate what I was willing to try.

That isn’t freedom. It’s confinement.

The reframe became:

I don’t need to do this to still do it and enjoy it.

In fact, maybe it’s better to start doing something before you need it.

And what actually happened?

It’s fun.

I enjoy writing.

I enjoy making videos.

I enjoy trying to communicate psychological ideas in ways that people might actually want to read or watch.

I’ve realized that actively creating on social media feels a lot better to me than lurking as a passive recipient of overstimulation.

I’ve connected with people I otherwise wouldn’t have.

I’ve created more.

I’ve written more.

And yeah, I may have even gained a client or two.

They Were All the Same Irrational Belief

At first glance, these are three completely different beliefs.

One is about physical fitness.

One is about divorce.

One is about social media.

But when I started looking at them together, I realized they were really just different versions of the same irrational belief:

Other people’s hypothetical opinions should influence how I live my actual life.

That one had a lot more control over me than I realized.

And disputing it doesn’t mean I’ve convinced myself that nobody will judge me.

That’s just another irrational belief.

Someone might think I care too much about how I look.

Someone might think a divorced therapist has no business talking about relationships.

Someone might watch one of my videos and think I’m cringey.

Someone might read this entire blog post and think the same thing.

That’s possible.

The healthier belief isn’t:

Nobody will judge me.

It’s:

I can withstand it if and when they do.

I don’t have to organize my life around preventing negatives. I can adapt and overcome them.

Person jogging on rural road at sunrise with rolling hills and trees

Overcoming Self-Doubt: Lessons from Running

The other day I posted about a running benchmark and captioned it:

“Do impossible sh!t. Then try to beat it. Fall short and still be proud.”

I didn’t get my best distance ever, but I completed a truly hard run.

The tongue-in-cheek “do impossible shit” wasn’t meant as a flex, some form of unbridled toxic masculinity, or an unhinged run-through-a-wall mentality. What I really meant was: do something that a previous version of you couldn’t do. Then keep working on yourself and see what you can do next.

If you’ve followed me for a while, you’ve probably noticed that I’ve become a runner. Of all the stereotypical midlife crisis responses, running has been an unexpectedly healthy one.

It has helped settle my own hypervigilance and helped me regain a sense of stability and confidence through doing hard things. Not because running magically fixes your mental health, but because it has repeatedly given me opportunities to challenge myself and find out what I’m capable of. (In different ways then my career)

I have increased confidence now but only because there was a time when I had very little. I earned trust in myself slowly, by gradually challenging myself to do things I didn’t think I could do.

Here’s the thing, though:

I still very often don’t think I can do stuff.

My routine before a benchmark is now telling anyone at the gym who will listen that I don’t think I have it today. Then, almost immediately, I’ll explain my exact plan to run X speed for Y minutes and what I’m hoping to accomplish.

I plan for what I want despite initially believing I probably can’t actually do it. The self doubt is underneath but not the reality.

And then I try anyway.

The attempt comes first.The plan comes second.The belief comes last.

I think we often imagine confidence working in the opposite direction. First you believe in yourself, then you make the plan, then you confidently go do the thing.

That has not been my experience.

The belief came from repeatedly attempting things before I was convinced I could do them. Sometimes I succeeded. Sometimes I fell short. But every attempt gave me a little more evidence about what I could handle.

Running has also become a pretty good illustration of my own cognitive process and, specifically, my all-or-nothing thinking. In a matter of minutes—maybe even seconds—I can vacillate between thinking I am unstoppable and thinking I am way too out of shape for this.

I suppose neither is true.

The truth is somewhere in the healthy middle.

I am not unstoppable. I can’t do the impossible. There are things I will attempt and fail at. There are goals I won’t reach and days when I genuinely don’t have it.

But I can do hard shit.

And maybe confidence isn’t believing that you’re going to succeed every time. Maybe it’s trusting that you can attempt something without knowing how it’s going to turn out.

That trust has been earned slowly.

One run. One workout. One race. One benchmark. One uncomfortable thing at a time.

So when I say, “Do impossible shit, then try to beat it,” I’m not really talking about doing the impossible.

I’m talking about doing something that feels impossible to you right now.

Then seeing what you can do next.

Person jogging on rural road at sunrise with rolling hills and trees

What “I Have Nothing to Talk About” Can Actually Mean

There are certain phrases psychotherapists hear that immediately get our attention.

One of them is:

“I have nothing to talk about.”

Now, if I’m being honest, most therapists don’t hear that statement and simply take it at face value.

We get curious.

Is there something they are avoiding?

Is there something they’re glossing over?

Is this an opportunity to dive deeper into something?

What uncomfortable feeling are we dancing around?

After all, avoidance is one of the most common patterns people bring into therapy.

Not because they’re dishonest.

Not because they’re resistant.

Because they’re human.

Why We Avoid

Avoidance gets a bad reputation, but it exists for a reason.

If something feels painful, uncomfortable, embarrassing, uncertain, or overwhelming, our minds naturally try to move away from it.

We change the subject.

We distract ourselves.

We stay busy.

We tell ourselves we’ll deal with it later.

We convince ourselves it isn’t a big deal.

For a brief moment, avoidance works.

That’s why people do it.

The difficult conversation gets postponed.

The anxiety temporarily decreases.

The uncomfortable emotion fades into the background.

The problem is that while avoidance often provides short-term relief, it tends to create long-term suffering.

The conversation still needs to happen.

The decision still needs to be made.

The grief still needs to be felt.

The fear still waits for us.

One of the primary goals of therapy is helping people gradually build the ability to approach the things that they would rather avoid.

Not because it’s pleasant.

Because it’s often necessary for change.

The Therapist’s Suspicion

This is why therapists become suspicious when someone says they have nothing to talk about.

We’ve heard it before.

Sometimes “nothing to talk about” means:

“I don’t want to discuss the fight I had with my spouse.”

Sometimes it means:

“I don’t want to admit how anxious I’ve been.”

Sometimes it means:

“I know exactly what I need to talk about, and I’m hoping we can spend the session discussing the weather instead.”

Years of experience teach us that there is often something sitting beneath the surface.

Which is exactly why a recent session stuck with me.

Sometimes There Really Is Nothing To Talk About

About fifteen minutes into a session, a client told me they didn’t really have anything to discuss.

My therapist brain immediately started searching.

Work?

Family?

Goals?

Stressors?

Future plans?

I explored a few areas.

And what I found surprised me.

There wasn’t a hidden crisis.

There wasn’t a conflict being avoided.

There wasn’t some painful topic hiding behind the curtain.

Things were simply okay.

Not perfect.

Just okay.

And that’s different.

There was still some anticipatory anxiety about the future. There always is. Life doesn’t stop being uncertain simply because things are going well.

But in this particular moment, this person had achieved many of the goals they had worked toward.

They had made significant changes in their career.

They felt more secure in themselves.

They were handling challenges effectively.

They had done the work.

Peace Can Feel Unfamiliar

What struck me was how unusual this moment felt.

Not because peace is rare.

Because we often don’t know what to do with it.

Many people become so accustomed to solving problems that they struggle to recognize when there isn’t one.

We become scanners.

Always looking for the next issue.

The next challenge.

The next thing to fix.

The next source of stress.

Sometimes this mindset is useful.

Sometimes it helps us grow.

But sometimes it prevents us from appreciating where we currently stand.

It’s difficult to enjoy a view when you’re constantly looking for the next mountain to climb.

Celebrating Progress

So instead of searching harder for a hidden problem, we spent time acknowledging something important:

How they got to this moment of quiet peace.

We talked about the work they had done.

The changes they had made.

The growth they had achieved.

The discomfort they had tolerated.

The risks they had taken.

The person they had become.

Therapy often focuses on what’s wrong.

Naturally so. People usually come to therapy because something isn’t working.

But growth deserves attention too.

Progress deserves attention too.

The absence of suffering isn’t always avoidance.

Sometimes it’s evidence.

Evidence that the hard work is paying off.

A Final Thought

Not every therapy session is challenging because life is difficult.

Sometimes the challenge is learning to be at peace when life isn’t difficult.

Sometimes the work is allowing yourself to stop searching for a problem and simply acknowledge:

“I’m okay right now.”

That may not sound like much.

But for someone who spent years anxious, overwhelmed, self-critical, or stuck in survival mode, that moment can be one of the greatest achievements of all.

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.

“Nothing” Can Make Us Happy

Today I realized something important: nothing is going to make me happy.

For so long, I believed happiness was something to strive for—an outcome that would arrive once I achieved enough, earned enough, or became enough. But if happiness depends on something, then that very thing—or the absence of it—also has the power to make me unhappy. That’s not freedom; that’s dependency.

The truth is, if I need something to make me happy, I’ve already placed my peace of mind outside myself. I’ve made it conditional, fragile, and fleeting.

So what if nothing could make me happy?

Happiness Without Conditions

Imagine existing with a default happiness—one that doesn’t require circumstances, achievements, or approval.

We don’t need more money or professional success.

We don’t need a lower number on the scale.

We don’t need to hit the gym a certain number of times.

We don’t need the luxury vacation or the dream house.

We don’t need likes, followers, or recognition.

We don’t even need family or friends to validate our worth.

Of course, these things can bring comfort, joy, and connection. They can enrich our lives. But they are not prerequisites for happiness. Happiness itself has no requirements.

Detachment as Freedom

Contrary to societal norms our peace of mind does not come from adding, but from subtracting. That is reducing expectations and demands. When we detach from the belief that happiness must be earned or supplied by outside factors, we step into true freedom.

Detachment doesn’t mean giving up on goals or relationships. It means we can enjoy them without being controlled by them. We can love fully, strive fully, and live fully—while knowing that our happiness exists independent of outcomes.

Choosing Happiness in Nothing

So today, I invite you to join me in this radical experiment: be happy with nothing. Not because life is empty, but because happiness doesn’t need to be filled.

When nothing makes us happy, everything else becomes a bonus. Choose happiness and look for at least one bonus every day.