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.

Home for the Holidays: Handling Family Stress

The holidays have a funny way of amplifying everything—joy, nostalgia, expectations, and yes… family stress. Old roles resurface, familiar buttons get pushed (often expertly), and suddenly you’re reacting like you’re 14 again instead of the well-adjusted adult you worked so hard to be.

The goal isn’t to eliminate stress or conflict entirely (good luck with that!). It’s to manage it in a way that protects your energy, your values, and your sanity—while still allowing for connection, meaning, and maybe even a little fun.

Here are a few grounded (and realistic) ways to get through it:

1. Set boundaries for yourself

Have a game plan for how you want things to go. Boundaries aren’t about controlling other people. They’re about deciding what you will participate in.

This can look like:

  • Having a firm plan for how long you’ll stay somewhere
  • Deciding in advance, “If things escalate or get draining, I’m leaving”
  • Giving yourself permission to step away without over-explaining

Instead of trying to convince others to behave differently, you’re setting parameters for your own behavior. This shifts boundaries from confrontational to self-protective—and that’s usually far more effective.

2. Some conflict is okay (even during the holidays)

The holidays aren’t a conflict-free zone, and they don’t need to be.

People need feedback. If someone is pressuring you, ignoring your limits, or resorting to guilt, it’s reasonable to name what’s happening. You don’t have to shut down, explode, or silently endure it.

Sometimes the most regulated response sounds like:

  • “I’m not going to participate in this conversation.”
  • “That feels like guilt, and I’m opting out.”
  • “I’m open to talking, but not like this.”

Not everyone realizes their behavior is rude—or manipulative—or crossing a line. And even if they do, you’re allowed to acknowledge it in real time. I’m not a big believer in pretending things aren’t happening. You can “let them” do what they’re going to do and still name it.

3. Look for what you like. (Focus on the Fun)

When stress rises, attention narrows. We fixate on what’s annoying, uncomfortable, or disappointing. Focus less on who deserves coal and more on who deserves your presence 😉 

Intentionally look for:

  • People you genuinely enjoy talking to
  • Small moments of calm 
  • Opportunities for humor
  • Environmental pleasures (quiet snow, lights, a warm drink, the family pet)

This isn’t denial—it’s balance. You can acknowledge what’s hard and still orient toward what’s pleasant. Don’t just focus on the problem; focus on the fun, however small or fleeting it may be.

4. Keep nurturing your needs daily

Sacrifice is part of relationships. Losing yourself entirely is not.

Continue doing things that regulate you:

  • Reading
  • Exercising
  • Writing
  • Listening to music…that’s not Mariah Carey (unless that’s your thing—no judgment)

The holidays don’t require you to pause your identity or abandon the habits that keep you grounded. Protecting your energy isn’t selfish—it’s preventative care.

5. Lower the expectation bar (just a little or..)

Many people arrive at holiday gatherings with an unspoken script: This should be meaningful, memorable, peaceful, and deeply connecting.

That’s a lot of pressure.

Sometimes success looks like:

  • No major blowups
  • A few decent conversations
  • Leaving with your nervous system mostly intact
  • Advocating for yourself 

Connection doesn’t have to be profound to be real. Let “good enough” count.

6. Remember: you don’t have to process everything in the moment.

Just because you notice something doesn’t mean it needs to be resolved over mashed potatoes.

Some insights are best saved for:

  • Later reflection
  • Therapy
  • A journal
  • A walk the next day

You’re allowed to observe without immediately engaging. Not every realization needs an audience.

Final Thought

The holidays don’t magically change family dynamics—they just put them under brighter lights. The aim isn’t perfection or total harmony. It’s showing up in a way that aligns with your values, protects your well-being, and leaves room for moments of connection where they naturally exist.

And if all else fails? You can always step outside, take a deep breath, and remind yourself: This is temporary.