Duality and The Stories We Tell by Donald Draper
Ever feel like there are 2 different versions of you living in one body at all times? This is the struggle our new client faces. Meet Donald Draper.
Donald Draper sitting in an armchair with a cigarette
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Duality and The Stories We Tell by Donald Donald Draper

Have you ever heard the phrase, “acting like a chameleon”? In short, people call others chameleons when it seems like they’re not acting like themselves. People with chameleon-like traits are those who rapidly shift personalities, dispositions and beliefs to meet the situation at hand. 

Sometimes this kind of behavior can be helpful, such as during an important business meeting, or when you’re meeting your girlfriend’s parents for the first time. Other times it can be drastically unhelpful. If you’re constantly taking on your friends’ or coworkers’ personalities just to earn some goodwill with them, they’ll quickly see through your veneer and find you disingenuous. Or maybe they won’t, but you’ll grow increasingly dissatisfied at your inability to be authentic around others. 

That’s the position our client today is in. His name’s Donald Draper, and he’s leading a dual life: on the surface, he’s a suave, no-nonsense ad man with a glamorous life and countless great stories to tell. Underneath all of that, however, is a man waiting to be understood. 

In today’s episode of Character Coaching, we’re going to help Don through this duality he’s experiencing by leading him through some hands-on coaching. To help him do this, Don’s written us some journal entries about his current situation. Let’s reflect on those now and see if we can’t help Don find some sort of peace. 

Don’s first journal entry: leading a double life 

Entry One:

Dick Whitman, meet Donald Draper. The ad man, the legend. The name comes with a mystique, a caution… a story. The man who worked his way up on Madison Avenue to become a partner at the legendary Sterling Cooper. He wakes up every day to a beautiful woman, a beautiful penthouse suite and more money than any man could handle. He can have anything he wants for breakfast, lunch and dinner. He can because of his brain. His ideas. The stories that he tells. And because of these stories that he tells, he affords this certain lifestyle and Because of this lifestyle, he can take care of his ex-wife, his kids, his past… But how can Donald Draper keep up with this life? Is it the money? The drinks? The women? No. It’s the knowledge that the more he becomes Donald Draper, the less he is Dick Whitman. A farmer’s son. A nobody. But I am somebody, although I am not at peace with that somebody. It’s strange that the one story I can’t sell is my own.” Donald Draper 

First impressions: living with an identity crisis 

What an entry to unpack! It seems Don’s got a lot going on. So much so, that he’s writing to us in the third person, and also including an alter ego — this “Dick Whitman” character — in the mix. While we don’t want to assume anything about Don going into this coaching session, I think it’s safe to say we’re dealing with a man who has some pretty big identity issues going on. 

Before we start giving any advice, let’s try to learn more about Don’s situation. When people share cryptic messages like these, it’s hard to really get the full picture of their unique challenges, so we want to get curious about what exactly it is about this lifestyle that makes Don miserable. Is it the drinking? The women? The separation from a starkly different childhood?

More than that, we want to get at the root of who Don really is, instead of who he isn’t. Almost everything in this first journal entry concerns lifestyle choices that Don feels uncomfortable or “out of place” with, rather than choices that make him happy.   

If you’re someone who’s currently experiencing an identity crisis because you feel like your chameleon-like traits are forcing you to live an inauthentic or double life, you might be able to relate just now. Once we’ve committed to behaving in inauthentic ways or engaging in lifestyles that aren’t compatible with our true desires, it can be tough to come back to your emotional and spiritual center. But that’s what coaching is for!

So, to start helping Don (and anyone out there grappling with a bit of an identity crisis), we’re going to start homing in on questions that get at the root of his character. Who is Dick Whitman, and what would a more authentic lifestyle look like to him?

Let’s ask those questions and see what happens. 

Next: moving toward one’s true purpose  


What is it about your current lifestyle that you really like? What stresses you out about this rat race? What does not being at peace feel like? What would feeling at peace look like? 


“That moment where you breathe and don’t feel like the past is holding your feet down while you try to run away. But maybe that tells me something. Maybe there is something to Dick Whitman. Being someone who can just be.”


What’s interesting about this journal reply is that the first entry was very long, rich and descriptive. Now that we’ve moved onto the next phase, the follow-up entry is terse and to the point. There might be something to that — it might be that Don’s been away from his other half, “Dick,” for so long, that he doesn’t have all the words or feelings to conceptualize what that other part of himself wants just yet. 

Before we go too far down that rabbit hole, let’s latch onto another thing that this reply tells us. There’s an old saying that goes, “you can’t run away from yourself, because wherever you go, that’s where you are.” I think we’re learning that that’s increasingly true of Don. More than just a chameleon, he’s using his alter ego to escape a person, or life, he had before. And there’s very little healing to be done when one of your major roadblocks is your past itself. 

From what we’ve learned so far, I don’t think it’s necessary for Don and Dick to exist separately from one another. I think what’s more important is that the man who embodies both of these people is able to reconcile each part of himself, and bring his identities together. 

Rather than think about all his many dichotomies, what if we just asked Don what it would feel like for him to just “be?” If he could just be without thinking so much about who he’s trying to be, what might that look like? What would his schedule look like? Let’s get really granular about it. What would his breakfast, lunch and dinner be like, and what would he do every day? 

Sometimes taking people out of their heads and helping them think about more day-to-day decisions can help with identity crises, so let’s explore those options and see where they take us. 

Follow-up Questions:

What would it look like for you to ‘just be’? What would you do in the morning, afternoon, evening? Where would you live? Would you live by yourself? Would you live as Donald Draper or Dick Whitman?

The check-in: finding peace on a beach

Alright, we’ve given Don and Dick a few weeks to respond. Let’s see what they’ve come up with. Here’s their final journal entry: 

Closing Journal:

“I would be on a beach. The sky would be as endless as the sea and even though they are parallel, it would look like they are touching. That’s how blue the sky and the water are. I would hang up my suit and wear something comfortable. Because I want to be comfortable. I would swim every single day and just think. That’s what my peace would be. That is what I want more than anything.”

Final Thoughts:

This is a fantastic closing journal, and it tells us a lot about where Don’s head is at. First of all, you’ll notice he’s not even using either one of his egos to describe his perfect reality — he’s not calling himself Don or Dick, because in his true state of peace, he’s not thinking about the identities in his head. Instead, he’s simply having a relaxing, tranquil experience. 

What’s interesting is that, when it comes to experiences like these, people often think that tranquility is a place or destination. The truth, though, is that more than anything, peace is a mindset. When we overcome the challenges and difficulties of our own minds, we’re able to have peace in our everyday lives, and not just while we’re at a beach, or on a vacation. 

So, if I were to continue coaching Don, what I’d move to next are questions like: how can you get some of that “beach” feeling where you’re at right now? And how can you establish a sense of peace even if you’re working as an ad man in New York? 

That goes for anyone grappling with their own identity crisis. What does peace look like to you, and how can you have a little bit of that in your own life right now? What would it feel like to let go of all the identities you’re holding in your head, and just “be” for a little bit? I’m curious to know!

Alright — we’re running out of time here, but if you want a more in-depth conversation on identity, duality, personality and peace, you should scroll up and listen to our full podcast conversation about Don’s dilemma. If you like what you hear, you might want to mosey on over to our blog to get some of your own personal coaching!