A monthly newsletter on mastery and creativity Subscribe


How to Coach a Friend Through Pain and Adversity


When I think about how my long-lasting friendships have developed over time, I realize that our biggest leaps of growth didn’t happen in moments of happiness, but in moments of pain.

These were moments when a friend dropped his or her guard and was completely vulnerable. The moments when all of the insecurities and invisible facets of their personality were being revealed for the first time. The moments when we connected on a raw, honest level and could see — and accept — each other for who we truly are, and we both knew it.

It doesn’t always work out well. Like a teacher who scolds a student for drawing outside of the lines, a lack of trust can turn you away from exploring and playing. When a friend drops his or her mask and their vulnerability is met with shame, it amplifies their pain and creates a memory that causes them to withdraw from that kind of connection in the future.

Here are four things to keep in mind when helping out a friend.

  1. Don’t walk with dying friends

Author Anne Lamott said in Small Victories, “The worst possible thing you can do when you’re down in the dumps, tweaking, vaporous with victimized self-righteousness, or bored, is to take a walk with dying friends. They will ruin everything for you.”

I understand that passage like this: Let’s say you get laid off. You’re fuming, hot around the neck, and ready to vent all of that stress out of your pores. It turns out, the same thing happened to your friend. What may happen is a conversation that is self-serving, entitled and unhelpful. There will be gossip, ranting and loads of self-justification because the chaotic event now needs some kind of meaning (“I hated that place anyway.”).

But a friend who wasn’t laid off can listen to you objectively because they aren’t emotionally attached to the event. They can empathize with you, sure, but their body isn’t going through the same emotional storm that you’re in; they’re at best imagining and summoning those feelings, but nowhere near the degree that you’re feeling it. They can provide feedback, even guidance, on what to do next and how to move forward, rather than spend hours/days/weeks entertaining your ego.

Grief is a part of the healing process, but you cannot live there. Let the pain singe your skin, but as soon as you internalize the lesson, get out.

  1. Reveal possibilities

Anger and sadness are blinders to our perception. They narrow and fog the lens through which we view the world. The less light that comes in, the darker our lives become. Especially in heartbreak, one of the default stories we tell ourselves is that we’ll never be loved again. Dating is tiring and seemingly fruitless, and heartbreak just hurts too much, so we start seeing the ruin around us as home.

Good friends wake up your senses and inspire you to flip this adversity into an advantage by revealing what life can become, not what life is.

As the philosopher Søren Kierkegaard said,

If I were to wish for anything I should not wish for wealth and power, but for the passionate sense of what can be, for the eye, which, ever young and ardent, sees the possible. Pleasure disappoints, possibility never. And what wine is so sparkling, what so fragrant, what so intoxicating as possibility?

Part of our nature is that we’re all risk and loss averse — some more than others depending on personality. We view losses more strongly than gains, i.e., the one F on your report card gets more attention than the long string of A+s.

For the friend in need, it’s not helpful to remind them of how bad their ex-partner was or how toxic their workplace was. You’re reinforcing and replaying the memory — and for what, exactly? Instead, help them imagine all of the things that they now can do — what life can become now that they’re free from something that was causing suffering.  

  1. Remove your sense of certainty, Dr. Love

If you’re a pro at the game of love, your heart proudly adorned with battle scars and bruises, your overconfidence in having all of the right answers is actually unhelpful.

When a friend is telling their story and you interject because you think you know the right answer, you’re undermining the space in which your friend can be vulnerable, where they can articulate their pain, and where they can discover life lessons for themselves.

To believe that you’ve suffered it all, that love always begins and ends in the same way, is a kind of arrogance that doesn’t help anyone but yourself. At the end of the conversation, who listened more?

Removing this sense of certainty requires you to realize that your journey is not the same as your friend’s, and above all, that this illusion of control makes you feel good about yourself. Instead, listen wholeheartedly, ask questions, and approach your friend’s pain with curiosity and compassion rather than an absolute certainty that you have the panacea for their pain.

  1. What you’re feeling is what everybody feels, and it’s okay

In a rant to my friend, I remember saying something childish like, “I just don’t get it — I know that I have to move on, I know what not to do, but why do I still feel this pain? Why won’t it just go away, especially now that I know better?”

He laughed and reminded me of a wonderful quote by brain researcher and TED speaker Jill Bolt Taylor. One morning a blood vessel in her brain exploded, and she watched herself have a stroke. She spent eight years recovering her abilities in walking, thinking and talking, and she soon became the spokesperson for stroke recovery. She brilliantly said, “Although many of us may think of ourselves as thinking creatures that feel, biologically we are feeling creatures that think.”

This wisdom is a perfect reflection of an essay where I explored why we can’t rationally think our way out of heartbreak. Like the elephant (emotions) versus the rider (rationality), emotions are far more powerful than logic. The part of the brain that regulates emotions (like fear) isn’t responsible for language.

So before your friend goes on about feeling like a coward, a fraud or worthless, remind them that what they’re feeling is what all of us feel. That’s the hefty price you pay for trying to love and be loved, but damn, when it works, it’s totally worth it.