I Declare 'Expectation Bankruptcy!'

Hi, my name is Zack...and I’m a recovering perfectionist.

As an introvert you might assume I spend most of my time alone, but on the contrary I am instead trapped inside the prison of my own scattered, ADHD mind, bombarded by the incessant voices reminding me 24/7/365 that I am constantly failing to meet my own (unrealistic) expectations. Oh to be alone in silence for even a brief moment…

After over a decade of lamenting my inability to optimize every facet of my work and life, I’ve decided my self-worth should no longer be tied to the unchecked boxes in my habit tracker, the outreach emails I have yet to draft or send, the number of words I did not write today, the number of pages I did not read, or the countless times I intended to meditate, exercise, journal, forest bathe, or floss that I did not.

To prevent the permanent damage from further self-flagellation, and with the recent inspiration from Steve Kamb, the (soon-to-be-bestselling) author of How To Try Again, I’m officially declaring ‘Expectation Bankruptcy.’

Or to put it more bluntly...Fuck it.

I’m tired of failing to meet expectations in “the after times” that I set for myself in “the before times.” Both the world at large and my own life have changed drastically in the last three years, yet I’m still exhausting myself desperately swimming to the shoreline of an island that doesn’t even exist anymore. So last Wednesday I woke up, I paused, I took the first breath of the rest of my life, I accepted the reality show in which we’ve all been cast as background extras, and I reset my expectations accordingly.

If only overcoming perfectionism were that simple.

Just ask Tom Brady.

Tom Brady is the greatest quarterback in NFL history. Full stop. He was one Super Bowl win short of doubling the number of Super Bowl wins of hall of fame legend Joe Montana (Tom has won seven, Joe has won four). Yet despite already accomplishing athletic immortality, the thought that lingers for Tom more than any other—even almost twenty years later—is the 2008 Super Bowl loss to the New York Giants (the game with the infamous ‘helmet catch’).

As Tom shared in the 2024 documentary series The Dynasty:

“Losing the 2008 Super Bowl was devastating. If there’s one thing in history I’d change, it’s that game.”

Not killing Hitler before he became Hitler, not preventing the assassination of Martin Luther King Jr, not even undoing the mistakes that led to his divorce from supermodel Gisele Bündchen, but winning a football game—that’s the one thing Tom would change. And to be honest, I don’t judge the guy. I get it.

If you weren’t already aware, this wasn’t just another Super Bowl for Tom Brady; the Patriots were 18-0 going into this game; Tom had arguably the greatest statistical season ever for a quarterback; and he was unanimously voted the league MVP just days before. That game was not just another Super Bowl for Tom Brady. That game was Tom’s once-in-a-lifetime opportunity to achieve what no other quarterback (and frankly no other professional athlete) had ever accomplished:

Perfection.

While Tom Brady and I attended The University of Michigan at the same time (Go Blue!), I promise you the comparisons between us end there (although my mother might argue otherwise). But on a much more human scale, I can relate to Tom’s meteoric rise from obscurity to “overnight success.”

I was my high school’s valedictorian; I graduated with highest distinction (i.e. the top 3%) from U of M; it took me one resume and one interview to land my first job six days after college graduation; I was promoted from assistant editor to editor five months after and won a Golden Trailer Award for the very first trailer I ever edited; the first indie feature I edited was acquired by Fox Searchlight; my first television editing gig was for the #1 show on cable at the time; my first network TV gig broke decades of ratings records and was a culture phenomenon; and my first streaming show—for which I was the lead editor and associate producer—was the #1 show globally in 83 countries.

I don’t share any of this to brag but instead to bring to light the hardest lesson I learned upon deciding to make a midlife career pivot while still at the height of my Hollywood success:

It seems a universal rite of passage is the midlife transition from the “Self-Discovery” stage to the “Commitment” stage, as bestselling author Mark Manson outlines in his immensely popular (and helpful) article The Four Stages of Life. This messy, ugly, and painful period is when we realize our life is about more than ourselves and we want our work to have a lasting impact on others.

In short, we realize that our efforts require purpose.

At the height of my Hollywood success I became paralyzed by the painful realization that my entire purpose as a human was to stand on a stage holding a gold statue bestowed upon me by my professional peers, but at the cost of not being present for my family. Given this was no longer a sacrifice I was willing to make, I was faced with the prospect of either losing my family or “starting over.”

Here’s the moment I realized I had spent my entire life chasing the wrong dream.

I naively assumed that I would choose a different career path and enjoy the exact same level of success I had up until now (but of course on a much shorter timeline!). What I was not prepared for was the years upon years of relentless failures between my former life as a Hollywood filmmaker and my new life as a creative career coach, writer, and public speaker. My expected career transition timeline? A year or two at worst. Oh sweet, naive Zack. (I’m on year eleven and still figuring it the fuck out.)

As a perfectionist my expectations were clear: I would identify the next career path for me, become awesome at my new craft, and then I would make sure the right people knew I was awesome at said craft. And just as it worked out before, it would all “magically” come together and I would have “certainty” once again. Yet over the last decade I have rebranded my company (twice), experimented with countless offer structures, courses, masterclasses, and so many different opt-in offers I can’t keep track of them (nor can my audience). I even spent over $15k on a new website nobody outside of my team has ever seen. And the vast majority of my offerings have been complete failures. But no different than venture capitalists who invest in a diverse portfolio of startups knowing 80% or more will probably fail, the 20% of offerings that have consistently worked for my clients and students have led me to building a business and life more in alignment with my values.

Unfortunately I had to experience an incredibly painful failure in order to find my new path towards success.

Back in 2017 I launched a 5-day challenge to help creatives 5x Their Productivity (yes, in 2026 terms this is what the kids might call “cringe”), and my expectation was that a single 5-day launch of a $99 product to a tiny email list would change my entire life. I spent months making sure every landing page, every newsletter, every social media post, and every lesson was perfect. I did all the things the online marketers told me to do step-by-step, and I ignored everything I was teaching my own students about prioritizing sleep, movement, exercise, reflection, and work-life balance. I worked 18 hours a day. I methodically scheduled my ‘deep work’ time blocks to optimize my flow state for efficiency, and I ruthlessly said no to everything non-essential (including, ironically, my family).

When the cart closed at the end of my 5-day challenge, I did the math. Had I spent the same amount of time working at McDonald’s those four months instead of building my first online product, I would’ve earned significantly more per hour.

Cue complete and total burnout.

Short of mindlessly pushing buttons at my editing workstation for the next seven months (surprisingly, my life did not change overnight, and I had to go back to film editing), I was otherwise absent from the world in a fugue state of depression, anxiety, and utter shame. How could I compromise my family’s future just to pursue my own dreams? I let myself down, I let my wife down, and I let my family down.

So of course my answer was more optimization (and a shitload of therapy).

I spent the next several years setting the expectation that I could avoid failure as long as I stayed consistent.

I just needed to keep getting 1% better every single day!

As I built my ‘creator business’ (you have no idea how much I HATE this term), I set the expectations of:

• Publishing a podcast every single week

• Publishing a long-form essay every single week

• Publishing daily social media posts

• Publishing weekly YouTube content

• Launching new classes every single semester

• Coaching daily

• Exercising daily

• Reading daily

• Editing daily (yup, still had the day job)

• And oh yeah...becoming an American Ninja Warrior

That last bullet isn’t a joke. After three years of training 7-10 hours per week and learning the sport from the ground up (Parkour!), I earned the opportunity to compete live on the ANW course—twice. And I failed—twice. Needless to say, I didn’t make the final cut, and I now consider myself a 2-time American Ninja Warrior failure.

^{👆 Here’s my ANW season 14 audition video (which includes my season 13 epic fail)}

Were any of these expectations sustainable? No. Did I meet all of them? God No! But I was infinitely more consistent (ugh…there’s that fucking word again) with all of the above than I am today. Which (finally) brings me to the point of today’s essay:

Despite spending the last three years watching Hollywood burn down (both figuratively and literally), watching both of my parents descend into dementia—simultaneously—and having to liquidate their entire estate to finance their medical care (and ultimately losing my father in 2024), being forced to relocate my own family unexpectedly, watching the online education industry dive bomb to the tune of a 75% enrollment drop, and creeping into my late 40’s not even being able to afford my own midlife crisis, I’m still measuring myself by yesterday’s expectations.

I’m supposed to be at this place in my life by now.

I should be earning this much income.

If Steve Kamb has this many Nerd Fitness members, why don’t I?

If Tim Ferris has this many podcast downloads, why don’t I?

It should NOT be this goddamn hard anymore.

Well guess what? It is this goddamn hard. Nothing worthwhile is easy. And I’m tired of living by unrealistic expectations that no longer serve me.

As Steve Kamb writes in How to Try Again (which could just as easily be titled “Atomic Habits For Mortals” if it not for fear of the lawsuits from both James Clear and Oliver Burkeman):

“Rather than starting with how life used to be and all the ways we’re coming up short, let’s preserve our sanity and start at zero.”

Steve further proposes using a strategy called “zero-based budgeting.” This is where rather than building a budget based on previous expectations and benchmarks you instead start with a clean slate.

I’m building my own zero-based budget on the following core assumptions:

• I have ADHD. Consistently sticking with just about anything is FUCKING. IMPOSSIBLE. I crave systems and structure. And the moment I build systems and structure that finally work, I need to change everything and start over. It’s demoralizing, embarrassing, and exhausting. And I’ve come to accept that it’s also just me.

• I’m closer to fifty than forty. My ability to recover from intense exercise is far different than in my thirties when I was training for ANW. My hormonal makeup has changed significantly, and it’s harder to achieve the physical gains and body composition I once did. And once again, it’s time to accept my reality rather than fight it.

• I’m ready to not be ready. No matter the goal, I’m no longer interested in waiting for things to be perfect before beginning at the expense of making progress. I have to be okay with sucking at something before I’m good at it. And then doing it anyways.

All of which brings me to the biggest public declaration I’ve made since writing about my aspirations to become an American Ninja Warrior way back in 2018:

Yeah, that’s right. As of Wednesday, May 27th I’ve transitioned from the future tense mindset of “I’m going to write a book someday when all of the conditions are perfect and I have all of my ducks in a row and I’m ready and prepared” to the present tense of actually writing the fucking book despite not being ready and not having the time.

Among the other countless insights Steve pointed me to in How to Try Again was a reminder of the following quote from bestselling author and artist Austin Kleon:

“If you want to be the noun, first do the verb.”

If I want to be a writer, I need to be writing. Not waiting to write. Not preparing to write. FUCKING. WRITING.

Given this will most likely be the most difficult professional undertaking of my entire career, and having recently declared expectation bankruptcy, these are my new zero-based expectations:

• I’ll do my best to release a couple of long-form podcast interviews per month. I might hit this goal. I might not. But the book comes first.

• I’ll do my best to write a couple of long form Substack essays per month. I might hit this goal. I might not. But the book comes first.

• I will continue to work with clients and students in The Arnold Academy both privately and in small groups, but I will protect my calendar such that there is always time to write. Because the book comes first.

• In order to avoid burnout during what will undoubtedly be an ultra-marathon rather than a sprint, I need to move consistently every single day. Some days I might exercise. Some days I’m going to skip it. Some Sundays I’ll absolutely kick my ass, Spartan-style. Other Sundays I will rest. But as long as I’m walking 15 minutes a day more often than I’m not, the rest is gravy. Because the book deserves it.

• Sleep will continue to be non-negotiable. Without sleep, it all falls apart. Because the book deserves it.

• In work, the book now comes first. But in life, family will always come first. Even if the book suffers because of it. Because my family deserves it.

On that note, I’ve got some writing to do...

Join us in The Arnold Academy as we read Steve Kamb’s How to Try Again in our monthly book club and turn knowledge into action!

Here’s how it works:

• All active members of The Arnold Academy are eligible to join

  • Not a member yet? → Click here to subscribe with The Community Pass

• You will need to purchase the book here by Monday, June 22nd

• There will be a live kickoff Zoom call on Tuesday, June 23rd at 8:30am PT

• There will be weekly reading assignments beginning Tuesday, June 23rd

• There will be weekly community posts (in our learning platform Circle) to encourage discussions, further your learning, and keep you accountable

• There will be a closing kickoff Zoom call on Thursday, July 23rd at 8:30am PT WITH STEVE KAMB DOING A LIVE Q&A!!!!!

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