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On Failing Spectacularly and Why You Should

Last week I asked the Brainstorm Road waitlist about their dreams.

Namely, why they don’t share them: What prevents you from sharing more (in public) about work that lights you up?

I hypothesized the answers would be about belonging and rejection. How you don’t want to be mocked for your idea or you feel silly. That was part of it, but far from the Real Reason.

Here is what people had to say:

  • It feels pretentious.
  • If it’s not the right group I get, “glassy eyes and eye rolls. They are not interested. at. all.”
  • People get jealous.
  • It feels petty and unimportant.
  • I feel selfish and guilty because there are so many horrible things happening in the world and I’m spending time on art.
  • Fear of being judged or misunderstood.
  • Talking about my dreams puts me on the hook.

Talking about my dreams puts me on the hook.

Nearly every respondent said a version of this: “I have to have made progress when I see that person again or admit I “failed” and/or moved on to something else. I don’t want people to think I’m flakey or have no follow-through. So it’s easier to not talk about dreams at all.”

Another person put it more bluntly: “It feels safer not to try.”

Here’s what broke my heart the most, maybe because I empathized: the sentiment was “Why bother?” Why bother trying? Why bother confirming for CERTAIN that you don’t have what it takes? Why not live in that fantasy land of what if?

Then you can have the fantasy of what could be, untainted by reality, expectations, or execution.

I hate how much I understood this. My co-founder Kristin and I have been writing up a manifesto that is quickly becoming a book (stay tuned for more on that) and I found myself uncharacteristically blocked all of a sudden. I rarely submit to blocks as I am Team “Keep Writing, Even and Especially if it Sucks,” (see my convo with Jay Acunzo about writer’s block here).

I was shocked to discover that what I was struggling with was deeply personal. I thought I’d codified my beliefs about dreams, but when the rubber met the road I realized I had a profound amount of grief.

I had grown tired of feeling disappointed. I was encumbered with the fear of disappointing my self. 

There have been an unprecedented amount of unforeseen extenuating circumstances in my life that have thrown wrenches in my plans and ability to (quite literally) sit at my computer and face the blank page. Forget the emotional road you have to traverse, simply physically getting access to uninterrupted time, a full night’s sleep, and a clear head – were privileges I did not have. 

I wondered if I was fooling myself.

I’d watched many people choose what they call “practical” paths and wondered if I was naive for (ahem) trying to make fetch happen. But what others called practical and what I believe is practical are not the same. 

Paths that demand self-abandonment are not practical. They are very very dangerous. And that we’ve normalized this choice to the point where people like me and the hundreds of people on the Brainstorm Road waitlist judge our dreams as foolish in comparison is troubling [see my plea].

If what you “have” to do to survive involves destroying or denying parts of yourself, that is not practical. That is suicide. Because when you withhold, deny, reject, or shame who you are and what you desire – it doesn’t just go away. It metastases. It hurts you and it hurts those you love.

[Read: Psychological Honesty]

How it does this is specific to each person. You may turn bitter, fixed, and rigid. You may be the guy susceptible to unprovoked bouts of anger and rage, inappropriately strewn on employees or spouses or children. You may suffer pathological levels of denial (see: Toxic Positivity which is a form of avoidance). And avoidance creates a state of perpetual running, the opposite of being ok or healthy (you are even MORE preoccupied with your pain and suffering because when you avoid it, you quite literally CENTER it).

Lying, manipulation, gaslighting, shaming, blaming, bullying, self-centeredness, victimization, and projective identification (when you identify with what others think of you instead of what you think of yourself) become the norm in this state.

You lose your locus of control (even if you become one of the people who is obsessed with power and control, that comes from a place of not having any).  

There are psychological consequences to abandoning your self

And denying you have a dream – denying you have DESIRES – is a form of self-abandonment.

Often we do this for survival reasons (as I explain here and here). But mostly, we do this to maintain a lie we’re attached to. Because sometimes our dreams are not as simple as “a screenplay” or novel. They’re a new life. An admission to ourselves that perhaps we chose wrong. We want something different. Or we are someone different. And that demands change. And to change is too hard or too dangerous, so we choose our lie instead (often the lie is, “I’m fine,” or, “This is what I want,” when you know deep down, you are not fine and this is not what you want).

I’m listening to Prince Harry’s memoir and there’s this part about his dad, who was a garbage father and human, but Harry doesn’t portray him as such. You feel sympathy for this monster of a person. He was a sensitive artsy type who wasn’t allowed to be. 

To dream, for him, would be to let go of the bravado required – demanded – of his position and lineage. So instead, he chose the cowardly route and had a longtime affair, never addressed anything head-on or emotionally difficult or honest, closed himself off from everyone in his life, and became the “funny storyteller” and distant “typical” British adult. 

Harry describes his dad as having an appreciation for Shakespeare. Let me tell you, you don’t have an appreciation for Shakespeare if you’re not a deeply feeling sensitive person (which IS strength). 

But instead of standing in that power and strength, he denies it – which is why it comes out in inappropriate, unhealthy, and sadistic ways. 

When we deny who we are and what we desire, we deny our humanity.

And when you dehumanize your SELF, imagine how you view others?

If you cannot access your own heart and humanity, how do you expect to access others?

One thing I committed myself to amidst the chaos that is my life some days is to never lose ME. No matter how hard life tries to tell me no. The inalienable right I have is to know myself. To judge myself by my own success metrics. And to define for myself what it means to matter. 

Which is how I determined the answer to the question, “Why bother?” 

And you’re going to laugh at me but here it is:

Because I can.

Generations of women before me couldn’t. Literally could not. Legally, emotionally, and physically could not (read: Book of Longings)

I bother because I can. 

So even if I fail and get proof, undeniable proof that I do not have what it takes, then I still win. Because I could and I did. And no one in the history of my family thanks to circumstance and oppression could. 

Taking a shot, a real one, and failing is my win. 

I decided that I wanted to be able to look my daughter in the eye and tell her: I went for it. Failed spectacularly. But I no longer live with “what if.” And I do not let the fear of knowing I don’t have what it takes control me.

I redefined what it takes not as a winning outcome, but as The Practice.

Did I go all in? Did I really try? Did I learn something? Am I changed because of it? Did I have a good time? Did I grow? Is life richer now? Can I say with integrity, “I did that?” Did I show up every day? Did I give what I could (even if it wasn’t “enough” because many times, it isn’t and that’s just reality)?


Then I win.

That’s why I bother.

Because I can. 

And so many people couldn’t.  




PS: If you’ve emailed me in the past 2 months and I have not replied, forgive me. I’m reading everything that comes in and sincerely LOVE hearing from you. I’m behind on email and [insert real-life things] but I assure you, I see them. I see you. And I appreciate you. 

Don’t quit on your dreams and don’t quit replying to emails you may or may not get a reply to. I love that we take chances on ourselves. Let’s not lose that.