How to Be More Compassionate (And the Ways We Fail)

We’re not always good at it. But when we do it right, compassion can rewrite our lives.

“When we’re looking for compassion, we need someone who is deeply rooted, is able to bend and, most of all, embraces us for our strengths and struggles.”

— Brené Brown, The Gifts of Imperfection

Everyday Compassion Means Everyday Suffering

When we’re attempting something difficult, we’re usually wondering, “When is this going to be over?”

For example, when we’re in the middle of an intense workout and can’t go another second.

Or when we’re taking a hard test that seems to last forever.

Or when we’re out at a party, but we’re desperate to go home and curl up with a good book.

It’s easy to dread certain experiences where the human mind perceives pain.

To be alive is to experience pain.

It exists in every area of our lives, including our physical, mental, and emotional worlds.

So, what does compassion have to do with experiencing pain?

Well, the Latin root of compassion is “to suffer” and the prefix is “with”.

Having compassion for someone means we are “suffering with them”.

Compassion vs Empathy: “Suffering With” Doesn’t Mean “Feeling With”

I always thought having empathy meant I had to experience the same emotions as someone else.

Yet, I discovered that if we allow ourselves to experience negative emotions consistently, it’s harmful.

Fortunately, that’s not the only option. Researchers suggest that there are two key ways people respond to the suffering of others.

On one hand, you can respond with empathic distress, which means you feel the full weight of their pain.

The other response to suffering is empathic concern, or compassion, which involves positive and warm emotions, paired with the desire to help.

When someone experiences empathic distress, they typically want to escape. Those who consistently respond this way are prone to negative feelings, poor health, and eventual burnout. Because this type of empathy is unpleasant, it results in withdrawal or distancing in order to self-protect.

In contrast, compassion often results in a prosocial behavior instead of a non-social behavior like withdrawal. Instead of distance, compassion creates connection. It also involves action, since the person experiencing compassion wants to tangibly ease another’s suffering.

Emotional Withdrawal & the Ways We Do It

“I don’t believe that compassion is our default response. I think our first response to pain — ours or someone else’s — is to self-protect. We protect ourselves by looking for someone or something to blame. Or sometimes we shield ourselves by turning to judgment or by immediately going into fix-it mode.

— Brene Brown, The Gifts of Imperfection

Many of us don’t know what compassion looks like.

Perhaps no one ever showed us or taught us how.

Yet, it’s possible to learn how to be more compassionate.

Truthfully, when someone shares deep emotions with me, I often feel uncomfortable. I’m not always sure what to do and frequently fall into one of these default reactions:

  • Giving Advice
  • Judging
  • Comforting
  • Blaming

When we take an honest look at why we withdraw, it’s often more self-serving than we’d like to believe.

Ultimately, withdrawing protects us. That means it leaves you comfortable, even if you claim that you’re “trying to help”.

To learn how to be more compassionate, let’s talk about these methods of emotional withdrawal in more detail.

Giving Advice

When giving advice, you distance yourself from the other person.

If they’ve just shared how sad or anxious they are, you’re sidestepping their desire for empathy in relationships by jumping straight to telling them what to do.

You might intend to be helpful. You might think you know exactly what the problem is and want to solve it for them immediately.

If so, you’re like my friend who once described that his approach was like trying to lift someone out of a pit. He told me that his primary concern is about how to get them out of the pit, not on how they’re feeling in the pit.

Although this seems like a pragmatic approach, it doesn’t address that for many people, emotions are the pit that swallows them up.

Additionally, your perception of the problem may not be the actual problem.

You may think they’re upset because of what someone said at work, but it likely strikes deeper than that. Maybe it’s less about the actual words exchanged, but more about how out of control and afraid they are.

You might tell them to change their mindset or perspective, but really all they want is for someone to look them in the eye and say, “I hear you. I get it. It may not make sense to me, but I’m present and I support you.

It’s just easier sometimes to give advice. You get a sense of satisfaction, feel more competent, and in control.

By embracing the discomfort of not knowing what to do, you allow space for their pain instead of emotionally withdrawing.

To become more compassionate, learn to first listen before giving advice.

Here’s one of my favorite videos that highlights these opposing viewpoints in a light-hearted way:


When you judge, you focus on how you feel more than how they’re feeling

When they express how devastated they are, you might feel a bit relieved or smug, thinking, “At least I’m not that bad.”

You focus on labeling their experience instead of staying present.

If someone is sharing their emotions with you, they are sharing their reality.

They aren’t interested in hearing your interpretation of their reality.

For example, imagine they’re crying because they dropped ice cream on the ground.

You might laugh to yourself, wondering, “Why are they crying? It’s just ice cream.

However, they don’t have to justify why they’re sad. They just are.

For those who have weak internal boundaries, it can be particularly devastating when they’re told they “shouldn’t” feel a certain way. Other potentially harmful messages include claiming they’re overreacting, overthinking, or “blowing things out of proportion”.

Now, why exactly might it be devastating?

Because, if you’re convincing enough, they might believe you.

They might buy into your version of reality and begin feeling shame for how they’re reacting, when they never had control over their reaction to begin with.

This shame is an example of what psychologists call a “secondary emotion”. Instead of only experiencing the direct emotional pain from the event, they experience a cascade of emotions about their emotions.

Now, it’s obviously not your responsibility to know how they will process something. You might even intend to help, trying to lighten the mood by minimizing the negative emotions.

However, in learning how to be more compassionate, it’s important to practice stepping into their reality instead of doing what’s “best for them” in your own reality.

Set your opinions aside and learn to listen.


If you’re aware and uncomfortable with someone’s pain, you might instead react with willful optimism.

People who do this go straight to, “You’ll get through this!” and throw out Hallmark statements like, “It’s always darkest before the dawn.

There’s a reason that grieving people respond poorly to cliches, even though these “comforters” are well-intentioned.

For example, the author in this article describes a time when her father was dying of cancer. Her friends responded to her by focusing on the positive and ignoring how much she was struggling.

She writes, “Both of them love me and my family, and they just wanted to be happy for us for the first time in a while. But I felt like I hadn’t been heard and that I couldn’t be fully honest with them.

Many of us are guilty of responding this way, especially because we’re afraid to say something to worsen their situation.

For instance, just a few days ago, I had trouble trying to find the “right” words to say to my grieving uncle who is now a widower. I sat in front of my keyboard for at least 30 minutes, trying to resist the urge to say anything overused and disingenuous, like “She’s in a better place now”.

It doesn’t have to be complicated. Often, grieving individuals just want someone to listen.


If you’re feeling tense toward someone, it’s easier to slip into blaming.

However, if you’re really committed to being compassionate, that doesn’t change just because of the emotions you happen to be feeling.

Often, when you’re seeing red, it’s one of the most important times to choose compassion, and this is why:

When we see ourselves as a victim, we’re perceiving the world through a distorted lens. Compassion shifts our perspective back to reality.

The reality is this: No matter what someone has done, they are still a human being worthy of respect and compassion.

It becomes a slippery slope as soon as you put conditions on that statement.

No, they only deserve respect if they…

No, they only deserve compassion if they…

It goes both ways.

Are you only worthy of respect, compassion, and love if you’re “good” all the time? If you never mess up? If you never hurt someone’s feelings?

Of course not.

Blaming someone else allows us to discharge our emotional tension on someone or something else.

However, that prevents us from staying open and having compassion for that person.

You might also blame others if you’re afraid others will take advantage of you. In that case, it makes sense why you’d be concerned about being “too compassionate”.

Yet, being compassionate doesn’t mean being a pushover.

In fact, it’s the opposite.

How to Be More Compassionate with Better Boundaries

Brene Brown, a researcher whose TED talks have been viewed millions of times, states, “One of the greatest barriers to compassion practice is the fear of setting boundaries and holding people accountable… Setting boundaries and holding people accountable is a lot more work than shaming and blaming.”

How does setting boundaries look in practice?

It starts off by knowing what you are and aren’t okay with.

Once you know those things, you’re responsible for expressing those boundaries to others..

Not only that, but you need to state the consequences of someone violating your boundaries.

Then, if someone crosses your boundaries, you must follow through; you do what you say you will.

It might sound harsh.

However, Brown’s research shows that compassionate people are boundaried people.

“The heart of compassion is really acceptance. The better we are at accepting ourselves and others, the more compassionate we become. Well, it’s difficult to accept people when they are hurting us or taking advantage of us or walking all over us.

When we don’t:

  • Express our boundaries, or
  • Follow up with consequences

It’s easy for resentment, judgment, and anger to build up inside of us.

Before I started working on developing healthy boundaries, “no” wasn’t an option when someone was asking me for help.

I didn’t even hesitate before responding, “Sure, no problem!

I didn’t want to offend anyone or make anyone upset.

On the surface, I seemed like a nice person, when in fact, I was a coward.

I was afraid of what people would think of me, because I didn’t know what I thought of myself.

I had gotten used to allowing others to dictate my boundaries; I didn’t know what I was okay with or what I liked.

Because of this uncertain, self-effacing approach, Brown would’ve described me as “sweeter — judgmental, resentful, and angry on the inside — but sweeter on the outside.

How to Be Compassionate to Yourself

“When we practice generating compassion, we can expect to experience the fear of our pain. Compassion practice is daring. It involves learning to relax and allow ourselves to move gently toward what scares us.” — Pema Chodron, “The Places That Scare You”

Biology has hard-wired us to escape pain.

Because of our impulse to survive, it makes sense for us to avoid this pain.

However, I’ll be honest.

When I consider the ways I’ve failed to give compassion in the past, shame and judgement washes over me.

Memories flash in my mind, a play-by-play of the ways I’ve messed up.

Could’ve done better there.

Probably shouldn’t have said that.

Whoops, made a mistake there.

  • I recall how my best friend in college showed signs of depression. Because of my discomfort, I often avoided her so I wouldn’t have to acknowledge how much she was hurting.
  • There’s also the time I offered detached advice to someone who was genuinely afraid that his mother would take her own life.
  • And then there’s the time I cut someone out of my life for giving in to their alcoholism after months of successful sobriety.

The shame tells me, “I walked out when they needed me most. I wasn’t strong enough.

If we’re not careful, shame can overwhelm us. If that happens, it’s another way we withdraw from others.

Perhaps there are similar memories that come up for you.

When you think of them, notice any emotions that come up. Acknowledge those emotions and place them gently to the side.

You were protecting yourself.

The way you responded makes sense.

You did the best you could, given what you had.

You didn’t show compassion then. And that’s okay.

In learning how to be more compassionate to others, we need to first practice showing compassion to ourselves.

Because if we’re used to withdrawing from our own suffering, we’ll do the same with others.

Only when we truly acknowledge our pain can we be fully present to the pain of others.

Whoo hoo! You made it to the end!

Want to be a compassionate and productive human? Get STOKED, my weekly newsletter for down-to-earth dreamers and visionaries that want to take consistent action without burning out 🔥

empowerment coach. encourager. relentlessly curious. Get STOKED

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store