Everyone comes to the table with baggage, experiences, and history. Some things are good, and some are more difficult or painful. Although we all experience similar baggage, it’s easy to forget that when we interact with others—especially at work or in a professional environment.

For many of us, pain and sorrow, in particular, bring us down. Society tells us to hide the pain away, and we listen. Not acknowledging and listening to that part of us can be detrimental to our lives, growth, and interactions. These hidden sorrows often cause detachment and misunderstanding for those who lead and manage others. To become better people and leaders, we must learn how to better process and embrace sorrow. Susan Cain is someone who knows a lot about this.

Susan is the bestselling author of Bittersweet: How Sorrow and Longing Make Us Whole and the world-famous Quiet: The Power of Introverts in a World That Can’t Stop Talking, and her TEDx talks have been viewed over 40 million times. She’s incredibly well-versed in everything that makes us human and has a lot to say when it comes to changing our relationship with pain and sorrow.

This essay was written based on the conversation I had with Susan on my podcast, The Learning Leader Show.

Embrace the sorrow and longing we all experience.

Toxic positivity, unrealistic cheerfulness, smiles on our faces—these are all things our culture tells us we need to do and have, but this is not all that humanity is about. As wonderful as these things are, they always come with the opposite experience of pain, sorrow, heartache, and longing.

Part of growing emotionally—both as a human and a leader—requires an acceptance of this coexistence between joy and sorrow. One doesn’t come without the other. The more we recognize these experiences come together, the more access we have to true joy and human connection.

“There’s so much beauty alongside so much tragedy in the world. Joy and sorrow come in pairs and are the only way to understand the world.”

This is not to say that sorrow and sadness aren’t painful and hard to work through. It is. But there’s empowerment in using that sadness to your benefit. Everyone, especially creative people, can use their sadness as fuel to do great work and positively impact people. I recommend that whatever pain you can’t eliminate, make it your creative offering. When you feel sad emotions most intensely, do work that requires the most heart and soul.

Susan told me on The Learning Leader Show, “I lost both my father and brother in the last couple of years. I remember feeling the deep vortex of emotion everyone feels in the wake of unexpectedly losing people you love. I would ask myself, “Do I want to write right now? Or do I want to avoid it?” I would then sit down and make myself write. I remember thinking: “What’s coming out of me right now is something I don’t think I could have written at any other time.” And it’s some of the most beautiful prose I’ve ever written.”

As a leader, when you embrace this sorrow and let it move you—instead of tucking it away and trying to forget it—you can better show compassion and connect with the people you lead. Our compassionate instinct helps us balance out the pains of life with creativity and connection.

Just like kids learn so much from their parents’ behaviors, employees learn so much from their leaders’ behaviors. Embracing the sorrowful parts of life will benefit you and those who follow you.

Show up for others and be willing to go deep.

One of the most powerful things a leader can do is believe in someone else before they believe in themselves. Remember, you never know what someone else is dealing with. When someone goes through something tough, they will remember who showed up for them in those moments for a very long time.

Susan told me, “When I met my now husband, we made a connection right away—he even told one of his friends that he knew he would marry me. After my second date with him, he sent me an email that said, “Keep writing. Drop everything. Write, woman, write.” I have that email framed in my office now, and it’s a great reminder not only of our humble beginnings but of how much he believed in me before I believed in myself. My husband opened up an honest, authentic, vulnerable line of communication between us early on that still serves us well.”

Showing up for someone doesn’t have to be extravagant. Just show them you’ll be there in whatever way they need. When you do, you’ll find talking about those deep emotions and experiences comes naturally to those comfortable in your presence.

Be authentic when you’re being vulnerable.

Vulnerability can be such an amazing tool to use as a leader and can bring you immense success. Unfortunately, society has made us feel like being vulnerable is a weakness.

Lately, vulnerability has become trendy, and this is a good thing. Vulnerability allows us to be more open with others and understand each other more deeply. However, that trendiness comes at a cost—some try to use it as a weapon and an act. The end goal of vulnerability is true expression, connection, and honesty; if you fake being vulnerable, people can sense it.

“We are so deeply designed to be reading each other’s social cues that whatever we truly feel or believe will come out ‌no matter our choice of body language or words.”

How quickly should you go deep with others? That depends on who you’re talking to. There’s beauty in offering comfort so people can cut the small talk and be their authentic selves with you. As a leader, having this relationship with your team is invaluable.

You can tell a lot about a leader—and a person—by their questions and the information they provide. Authentic vulnerability is the hallmark of a great leader and requires you to truly be in tune with your feelings.

Surround yourself with people who possess the strengths and powers you lack.

One of the best things to do as a leader is to be self-aware of your strengths and the strengths you lack and then decide to partner with or manage people accordingly. One person cannot have every single skill.

“One person doesn’t get to have all the powers; each person gets one or two. The trick in this life is to use the powers you have access to well.”

One way to find out your strengths around sensitivity and creativity is by taking my Bittersweet Quiz.  Here are some questions from the quiz:

  • Do you tear up easily at touching TV commercials?
  • Have others described you as an “old soul”?
  • Do you find comfort or inspiration in a rainy day?
  • Do you prefer poetry to sports (or maybe you find poetry in sports)?
  • When you have conversations with close friends, are you drawn to talking about their past or current troubles?

Answer these questions on a scale of 1–10, 10 being “completely” and 0 being “not at all,” and see how much you agree with them. Depending on your score, you may be more cheerfully optimistic or bittersweet. Those who are more bittersweet are often also considered “highly sensitive.” Essentially, this refers to people who feel both the good and bad deeply and intensely.

Some people come to this highly sensitive nature from birth, while others come to it from life experience. Regardless of how you got there, an intense sensitivity is one of your powers in this life. You’re likely persistent, insightful, and skilled at concentration.

If you’re a sensitive leader, surrounding yourself with those who are more sanguine, optimistic, and logic-focused may be a good idea. It’s all about finding the right balance.


Learn more from incredible leaders like Susan through The Learning Leader Show and receive direct coaching by applying to be a part of my Leadership Circle today.