An Open Letter to Millennials

Dear Millennials,

You’re amazing. You shine with a light humanity has not seen before. Your energy is boundless, your passion inspiring, and your sense of freedom and possibility may very well be what saves humanity from its own shadow. 

But you’ve got a shadow, too, and I’m concerned. I’ve coached many of you and seen what you’re capable of. I could write for pages about what’s great about you, but you already know about that. I want to tell you how the millennial shadow looks to me. I want to help you be the best you can possibly be, and you can’t do that without addressing your weaknesses. 

I think I know a bit about what it’s like to be you. I’m part of Generation X, but my parents gave me very few boundaries, so my shadow was essentially the millennial one until I matured through many hard lessons in my twenties and thirties. I still work hard every day to grow up, and I write this letter to myself as much as you.

Not all of you have the millennial shadow, but a lot of you do. You’ve read  articles that describe the shadow as entitled, arrogant, ungrounded, and distracted. I don’t think these labels help you, so I’m going to talk about it in a way you haven’t heard before. 

There is some truth to those adjectives, but the bigger issue is in context. That is, you have a profound difficulty looking at yourself when it’s emotionally uncomfortable, so much so that you don’t even notice the difficulty. This is the essence of the millennial shadow blind spot: the entitlement of being happy and comfortable. Often when something threatens that, you argue, lip-service, tantrum, spin, or ghost. I know you don’t mean to do this, but it’s what happens. Many people in a position to help, like me, give up trying to get through to you because of the effort and stress. But I care too much about you to give up. I think you’re worth the effort.

The light side of your grip on feeling good is your powerful positivity and boundless enthusiasm. I love those qualities in you. You feel like you can do anything! You question limits. I love that. But strengths and weaknesses are two sides of the same coin, and what those who came before you know is that freedom is always within boundaries, not without them. Until you get this, you’re living in a childish illusion, chasing something that does not exist.

Because of its misunderstanding of what real freedom is, the millennial shadow avoids accountability like the plague. I know  it’s hard. When you make a mistake, it doesn’t feel good at all. It’s like walls are closing in on you. But interestingly the social science shows that embarrassment actually helps create change. Not only is it normal, it’s vital. But you’re so afraid of feeling bad for even a moment. And even when you do admit you’re wrong, you don’t really feel it. You’re energetically disconnected from the impact you have. And this stops you from learning the lesson, meaning you’ll inevitably repeat the mistake. 

But somehow that boundless sense of possibility makes you feel so powerful that you can’t bear the moments and places where you’re weak, where you’re limited, because you don’t want to believe in limits. We all have those places, and in order to be truly powerful we must learn to love our deepest weaknesses. This is difficult for everyone, but for you it seems sometimes impossible.

When I work with you, I feel like I’m walking a tightrope. If I’m too hard on you, you get upset or you bullshit me with lip-service. But if I don’t hold you accountable enough, nothing will ever change. You want so badly to think you have everything together, and this means you don’t take in feedback. You think you listen, but your actions prove otherwise when you don’t keep agreements or follow through. You tell yourself you’re going with the flow or doing it your own way, but the truth is you’re lost and can’t bear the shame of asking for help. You don’t even know that you don’t know how to vulnerably ask for help. It’s completely off your radar. You may have never done it.

Because significant change of any kind requires turning toward emotional discomfort, you resist change without realizing it. You think you embrace change because of your sense of possibility and your passion, but when it comes down to actually doing difficult things, you avoid everything uncomfortable and stagnate. But you mostly can not see the stagnation because you have this incredible optimism that everything is great and things are only going to get better. 

When this isn’t true, it cripples your ability to operate effectively in reality because you’re not in it. Meanwhile things get worse and worse, so you have to deny it even more because the pain of looking at it squarely in the face would be so great. You would have to look at how you’ve been avoiding the uncomfortable truth for so long, and take responsibility for letting it get this bad. This is called hitting bottom, and it hurts tremendously, I know. But it’s where you learn the most and become the most powerful version of yourself. That’s true for everyone.

The millennial shadow looks to me like an amphetamine addict, convinced that forever charging forward with positivity and energy is somehow sustainable, even desirable. This is simply not reality. Happiness and joy have no meaning without their opposites, the same way we cannot appreciate the summer without the winter. Sorrow, pain, sobriety, embarrassment, despair—these feelings make us who we are as much as the pleasurable ones. When you distance yourself from the “bad” ones, you distance yourself from your own humanity. This is why you often appear so ungrounded, like a picture of yourself taken from far away. 

I want to make you a deal. There’s so much we can learn from millennials, and I really want us to. But the millennial shadow makes it very difficult for us to do so. We can’t trust you when your shadow is running the show because it erodes your responsibility, your realism, and your trustworthiness. I know you want us to listen, but we can’t do that if you don’t listen. And I know it may not seem this way to you but your shadow only hears what’s comfortable. 

I want to invite you to become hungry and curious to know your shadow. I know it’s hard to trust the older generations that made the world you were born into such a mess. There’s a lot we have to learn. Much of that we can learn from you. But your part includes the willingness to look at your shadow, or else none of us can take you seriously, and all of the gifts that you have will be lost.

In the larger scheme of things, it seems to me that a great deal depends on your ability to look at yourselves and bear discomfort. I have met dozens of grounded, sober, responsible, self-aware, and introspective millennials. They’re some of the most powerful people I have ever known, but they are the extreme minority in your generation. I very much wish to help that change, and I’m at your service. 

You may think you’re already one of those millennials. That is either true, or you have the very problem I’m talking about. How could you know for sure? I challenge you to show this letter to three people in older generations who know you well. Ask them to be brutally honest with you and see what happens. This is asking for help. This is being curious about your shadow. This is humility. This is one step to freeing you from the millennial shadow. The only reason you’ll likely come up with to not accept this challenge is because it would be uncomfortable. Prove to yourself you’re bigger than that. 

It’s my experience that Life doesn’t support people who escape reality for very long. When any of us lives in some kind of illusion, eventually Life takes steps to wake us up, bursting the bubble. Please do what you can to awaken from your illusion. As difficult as it might be, it will be easier than if you wait for Life to do it for you.


Thank you for reading,


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