The final boss

Or, Life will always test you when you say you want something

I wrote half of this two nights before I left LA, sitting in a camp chair in my empty apartment on a hotspot because Spectrum shut off my internet earlier than expected. I am now editing and rewriting parts of it from a couch in Austin, TX – changing the tense to present and filling it with all of the things that have hit me since leaving.

I’m realizing that I have to start publishing these essays faster. A lot happens in a week or two when you’re busy telling the truth.

My thinking about “the quest” has been altered, changed already and it’s only been ~1 week. It was easier to dream up all these dreams when they were just dreams, and harder now that I’m confronting what living them actually means. That’s just part of it, I keep telling myself.

But I promised you and me — I’d write the real shit. So that’s what I’m gonna do.

It’s been a long time since something has felt as clear to me as the need to go on this Quest.

But then two weeks ago, I got pitched to work on a dream project, and that proved just how fragile my commitment really was.

The project pitch was insane: get paid to travel the world and make mini documentaries about creators in all kinds of interesting places (like the frontlines in Ukraine and remote villages in Africa).

I began working on it and indulging the fantasy of what it’d be like to go all-in. I kept trying to convince myself: maybe this is not a distraction, just a redirection on my Quest.

All of the logical parts of me have been like: DO IT!!! Drop everything and do it, please. This could totally work. Look at it from this angle, you’ll still be traveling the world and making art and getting paid, and isn’t that the real dream?

I haven’t been writing or sleeping well since being confronted with this decision. Two signs that something is off with me. I felt myself at a crossroads. My mission became fuzzy again. I’ve been feeling confused.

But I don’t believe in being confused. I think confusion is just me avoiding what’s actually true. Confusion arises whenever my truth comes into conflict with something that I believe I have to do, should do, must do in order to be “good” and “loved.” I’m bullshitting myself, and I know it.

You can justify anything to yourself, so be careful what you justify.

On a walk a month or so ago, I wrote down these intentions in my iPhone notes for this Quest —

1. Talk to strangers.

2. Find someone to give back to in every place I go.

3. Be where my feet are. Turn off my phone for long stretches of time.

4. Meditate. A lot. Be in my own space. Be alone without any distractions.

5. Get my Spanish back to conversational.

6. Follow my intuition on where to go next.

7. See what happens.

If I read that list, it’s easy to see that taking on this project is a way to do most if not all of those 7 things.

How am I supposed to know if I am being asked to be a little flexible and rise to the mission? Or to hold strong and fast on the energy behind that list?

I think I know, but I don’t want to know.

My true intention with this whole thing was to DOWN SHIFT. To stop pushing myself so hard. To breathe deeper. To tap into a flow of life. To allow a new vision to come through me. But that stuff didn’t really make the list because those are not things that you do, those are ways that you be.

So I probably need another list.

A “to be” list for this Quest you could say.

Because more than I want a salary or a cool gig or to travel the world right now, I want to just be alone with no obligations for a while and see what inspiration strikes.

I want to see what happens when I’m not working so hard or beating myself up over not working so hard.

Writing that to you brings up all kinds of un-digested guilt in my system. Something in me asks: You want to what exactly? You want to relax in a world that’s burning, a world at war? You’re complaining about an awesome gig to go travel and make art? How dare you?

I was praying two nights ago for guidance on what to do, and heard a whisper that felt wiser than mine: “Child, there is no world to save. Humanity doesn’t need more martyrs.”

I don’t know if I believe that yet, but I’m trying.

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Maybe you’ve hit your local maximum.

A few days ago, someone much younger and wiser than me told me about this concept of “local maximums” in software engineering. It’s a super nerdy mathematical idea that you might be on the “highest point” of somewhere directly around you, but not the highest point possible.

The trick is: to get to the highest point possible, you actually have to go down first.

I remembered reading a Chris Dixon article about this years back called “Climbing the wrong hill.” (worth the read). This is the image he uses to explain it —

CD applies this nerdy idea to life design. He says when we are planning a career or a life, we often make the mistake of trying to get to the highest point of whatever hill we are currently on versus taking a good look around to see if there are any other mountains we’d rather climb.

Let’s say you’ve been climbing the corporate ladder (the small hill) but want to be an entrepreneur (the big hill). Starting a company actually requires taking steps down before being able to start ascending towards the peak of the big one. This might look like — taking less money or building less status for some time, when you’re friends that stayed on the small hill are buying houses and getting married.

That period of dipping downhill feels super scary — especially when in real life — you can never be sure that the second peak is any higher or that you’re even capable of climbing it.

But that’s the risk we take in changing course in life — you gotta let go of something that seems pretty good for the chance at having something that might make your soul sing. And to do that is always gonna feel like you’re falling off a cliff.

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Every hill I’ve climbed and descended has has made me who I am (and showed me who I’m not).

Like when I was training for the LSAT and my professor told me I’d lose my creative spark if I became a lawyer so I began to climb down. I was a senior in college and for the first time in my life owning the fact that I had no idea what I want to be “when I grew up.”

Which somehow led me to this crazy gig of building a research center at my university where I got to study game design and behavioral economics for two years.

Which led me to thinking I wanted to be a teacher, so I moved to NYC to live under the poverty line and try it.

But then I decided education wasn’t for me and descended again with my sights on Corporate Hill. I moved out to L.A. and got a job at a rapidly growing mental health company on the drive out.

Which I totally hated, but taught me so much. It took me months and months to garner the courage to quit and get off Corporate Hill.

I had no clue which hill to climb next, just that I didn’t want to be on that one. That’s when I started ghostwriting, scrubbing gym floors, listening to lots of Tony Robbins, and racking up credit card debt.

If I was in a sort of free fall, then meeting Zack was my parachute. We had coffee once, and he gave me a job to come help him manage the Yes Theory boys. He offered me the chance to climb a new, taller mountain that I could have never imagined when I was standing on the last one.

In that same week, my old employer came back to me and offered me more than double my old salary (maybe four times what Zack was offering). I was super broke at the time and genuinely needed the money, but it wasn’t even a decision. I took the gig with Zack and never looked back.

Which led me to producing short films and podcasts, building live events, and doing work that I genuinely loved for the first time in my life.

Which eventually led us to meeting Eric and starting Creator Now. A company that leveraged so much of what I’d learned when I’d worked in education.

Which led us to selling Creator Now.

Which led me to all of these crazy weird and cool opportunities that have been surfacing over the last 12 months. Like building new companies or running studios or developing shows like the one in question.

Nothing in my life has been a straight line, and every time I’ve left a hill and began the trek downwards, I’ve found one better hill more suited for me. Every hill helped me refine what I believe about myself and the world and helped me offer something more true.

But no matter how many times I do it, the choice to descend is always terrifying. There’s always this moment of: “Wait, am I really doing this right now? I’m not even at the peak. I’m just a mother fucking quitter.”

I can’t even adequately define to you what bump I’m on right now. Maybe it’s Entrepreneurship Mountain or Creator Economy Hill. I honestly am not even sure.

Regardless — it’s got a pretty good view already, and I am nowhere near the top. But I’ve said no to a lot of projects, ideas, and new companies in the last year. All stuff that would have brought me closer to the peak that I have been moving towards.

That’s how I know my time on this hill has run out.

You gotta face off with the Final Boss.

There’s a local maximum story Matthew McConaughey tells in his memoir Greenlights that I find my mind kept coming back to over and over these days I’ve been trying to make a decision about this project.

By the mid-2000s, McConaughey had been type-cast as the heart throb, but was craving more serious material. One day he realized: if he really wanted to be taken seriously, he had to take himself seriously. If he kept saying yes to more Rom-Coms, then the industry execs would just keep sending him Rom-Com scripts forever and never be forced to consider him for anything else. Which meant he had to do a big, bold thing: stop saying yes.

As legend has it, he and his family downsized their life from a beach house in Malibu to a ranch in Austin, and he made peace with the fact that he might never do another acting gig again. Then, he directed his agents say no to all Rom-Com Scripts and to put out the message that he was looking for more serious material. Rom-Com scripts kept coming, and his agents did as directed.

Then one day, a huge offer came through. Like $7M or something, and they felt it’d be irresponsible to not pass it along to Matthew for consideration. He said no. Then, the studio upped it and upped it all the way until the deal sat at $14.5M. After some serious contemplation, he still said no.

Word got around to all of the studios in town. Nothing comes in for months. At this point, he’s been dry on projects and income for almost two years. But he doesn’t panic or beg his way back into the studio’s good graces. Instead, he just waits it out. And he eventually lands Dallas Buyers Club and the rest is history.

I think we underestimate how hard it is to say “no” to opportunities and money. Much harder when you’re saying no to $14.5M and having your face plastered all over Sunset Boulevard than when it’s your old boss coming back with a bigger paycheck.

But underneath, we all deal with the same fears: if I say no to this, am I ever going to get another gig? Am I being totally ridiculous and irresponsible? What good could I do with all that money? What if I’m not even good at this other thing that I think I want to do? What if there is no other hill?

We can always justify to ourselves that gigs in front of us are “good enough.” That we should be so fucking lucky to even have the opportunity. Sometimes we even have to — because we need to put food on the table or pay the rent. I’ve been there, and you probably have too.

The highest point on Rom-Com Mountain was saying yes to that check. McConaughey’s life probably would have turned out alright, alright, alright if he took it (ugh, I can’t believe I did that).

But, I think he was being tested. With what you might call “The Final Boss” (you know, like being forced to beat Bowser in the final level of every Mario game). Or what Joseph Campbell of "Hero’s Journey” fame might call “The Ordeal.”

It’s like God / The Universe is saying to you: “You want something, prove it. Risk something that’s near and dear to you. Show me that you’re willing to say no to all of the things that society has trained to believe will make you happy and good. Show me that you’re willing to stick it out and not panic. Show me that you’re willing to walk down this hill and give up the view. Don’t just tell me. Show me.”

The thing is: McConaughey didn’t know for sure when he started saying no to all those gigs that there was more out there for him. He didn’t know that Mud or Interstellar or Wolf of Wall Street was right around the corner.

He didn’t know what the other hill would entail or if the view would be any better. But he had to do it anyways. That’s the conviction the universe requires when you’re switching paths.

There’s always one more big test that offers you an easy way out.

Or you can free fall a little longer.

Risk death.

And see what parachute pops up.

I don’t know whether God is trying to redirect or test me.

Some part of me wants to believe this latest project is a railway ticket to another mountain. But if I’m honest with myself, it is part of the same climb. And saying yes would be indulging the part of me that believes that I gotta keep ascending right here, when my soul just wants to go down and see what else is out there.

I don’t know why I’m like this.

So dramatic with my words and neurotic in my thoughts.

But this is my process of discovering myself and what life is about, and hell, as you just read I’ve been beyond blessed so far.

Only time will tell if this was the right decision — whether it’s just like that time I said yes to Zack when my old boss was offering me 4x the money. Or whether it’ll open up new trails to mountains I don’t even know exist. Maybe I’ll regret it at some level — and realize it was THE project of a lifetime and that I was insane to turn it down.

That’s the thing about making decisions.

We can never really know where the paths will lead.

But for whatever reason, I gotta say no this time.

And channel all of my energy towards what’s in front of me, not behind me.

I gotta trust that there’s a new path out there that I can’t yet see, and that this new path is better suited for me at this moment in my life.

I gotta bet on my compass to find it and not panic a second too soon.

And in that process say Yes to staying on this mother fucking Quest once and for all.

Maybe I’m wrong, but I think this was my Final Boss.