First, Write Your Story — Pt I

Jumpstarting Your Creative Career

18 min readFeb 28, 2019

Foreword:

It would be selfish of me to expect that you want to read my story. But I may have had some successes you’d like to replicate.

Or even better, failures you’d like to avoid.

The vlog series Finding Your Dream Clients will document my process from landing 5-figure to 6-figure jobs.

But what if you aren’t closing 5-figure jobs yet? Or even 3 figure jobs?

Then read on. In writing, I can explain how I got here.

Season 01 Pilot — Finding Your Dream Clients

Writing Prompt:
What’s your origin story– your mental operating system? What failures could you help people avoid? What successes could you help others replicate?
Submit it at howdareyou.pro

This story is a very unconventional one– I found myself running an angel funded design agency at 22 in Austin, TX. Little did I know, that’s probably the last thing I wanted. Hopefully at least someone can learn something from my experience.

Failure Porn: The glorification or sensualization of failure.

This isn’t failure porn, I think glorifying failure is a fallacy, but I also see it as a right of passage. If you’re really pushing the envelope, you will have some failures (or what feels like failure momentarily).

First off, I better warn you that I may believe in something called simulation theory. I have this crazy concept that the fabric of our realities are infinitely malleable. If that freaks you out, this article might not be for you.

There are many paths to becoming a “professional creative”.

This was mine.

How to become an entrepreneur, filmmaker, designer, coder, consultant, or any sort of professional creative–

Chapters:

Part I

First, Write Your Story: Define Your Reality
Becoming a Minimalist: The Process of Brutal Elimination
Tough Love: Success is Harder Than you Think
The 5 Natural Emotions: How to Jumpstart a Creative Career

Chapter 1 Intro:

First, Write Your Story

If you’re like me, you hate when people talk about themselves too much, which in turn makes you afraid to talk about yourself.

But to play devil’s advocate–

There are people who I wish talked more about themselves.

Learning someone’s story, who has already stumbled along the path you intend to take, is insanely valuable. Perhaps more valuable than a $100k education on the matter.

I can tell you the trail I took, but a million different elements come into play.

I never went to college, but I’ve worked with some globally known brands, none of whom ever asked if I had a degree. In my mind, it’s an unnecessary permission slip.

Formal education will teach you subjects, not skills. Subjects are broad– more like trying to memorize a whole mountain range from a satellite image.

Skills help you get there, but you won’t know what skills you should learn until you’ve heard people’s stories and experiences.

Stories are specific, like memorizing a certain trail.

Your mileage may vary. You can save a lot of time by learning people’s stories who have specifically done what you want to do.

Seek these people as mentors. Never call them mentors officially because that’s weird. Call them your friend. Do things for them, that they might teach you their craft.

Ask lots of questions:

Questions for others:

What is some of the worst advice you’ve ever received?
What would you tell your 25 year old self?
If you could do it all over, what would you have done differently?
Were you happy in the end?
Did you get what you always wanted?

The Fundamentals:

There’s no harder lesson than that of making and losing money. In school, there’s no making money, you just lose it. Which is kind of a bad habit from the get-go. Best case scenario, you pay your own way and lose money. Worst case scenario, you accumulate massive amounts of debt at a young age and struggle to find a job. Risky business.

Best case scenario the money isn’t an issue, you can find a job, but perhaps you lost precious time.

I’m not saying it’s a bad decision to go to school, it’s just not a necessity. My argument would be that you can learn more creating your own curriculum. The curriculum is real world experience while making money.

Perhaps you’re capable of doing it faster than 4 years.

Whether you think you can, or you think you can’t — you’re right.
― Henry Ford

The Most Powerful Thing in the Universe:

A Story

There’s what happens in life,

then there’s the story you tell about it.

The story you tell about your life is subjective.

Everything in life starts with the story you tell yourself. Whether you put it on paper or not, your story is in the background programming your entire existence.

Have you ever felt like you could attract things into your life just by visualizing them?

The important concept to grasp is that– you build your story whether you choose to design it consciously, or unconsciously. Unconsciously is what most people do.

Your story is the most important thing in your life. Your story constantly plays on repeat everyday in the back of your mind. It determines how you perceive yourself and how others will perceive you. It determines whether you will succeed or not, whether you will be happy or not, or whether you will be healthy or not. It determines how long you’ll live and what you’ll live for– nothing is more powerful than your story.

Fuck DNA. Fuck genetics. Fuck privilege.

Your story isn’t just text on paper or a screen.

Your story is your entire mental operating system applied to your reality.

Your story is going to be more impactful on your life than anything. It’s time to reconsider it’s impact– or lack thereof.

Permission Slips:

Our realities operate off of permission slips.

We find success when we feel we’re worthy of it, based on personal sacrifice.

Every great entrepreneurial story starts with great sacrifice.

In my case I found myself broke and basically homeless in Austin, TX after losing my first company.

Hopefully, these kinds of things make us stronger.

I’m going to talk more about writing permission slips later on.

Chapter 2 Becoming a Minimalist:

The Process of Brutal Elimination

World Class Fuck Up

I’ve made some idiotic decisions in my life– most of which seem to pay off.

I’ve come to think fucking up can be a skill.

I’ve learned that fucking up is key. The “break things faster” kind of approach. Most people won’t get past this point because they’re scared of what people will think of them when they do fuck up. Fucking up is not to be confused with failure. They’re related, but not exclusive. Fucking up is a right of passage, failure is not.

All failure is, is quitting.

How to Become a Professional at Anything

When I was 21 I quit my cozy corporate job, and moved into my parents basement to become a full-time wantrepreneur.

The easiest way to become a professional is Minimalism. It almost comes down to a simple math formula.
In my opinion, being a professional simply means two things:
• You make your living off of it
• You do it every day
So if you can get your living expense down below a couple hundred dollars a month, it’s practically cheating.

I got rid of everything I owned that was a distraction– my phone, my new SUV, my xbox, my ocean-view apartment– and moved into my parent’s basement in rural Utah.

Welcome to Utah

This picture perfectly describes how cold and discomforted I felt when I got home. There was a road ahead of me that was so long, all I could do was stare an inch ahead.

instagram.com

I set out to simulate the equivalent of a design/business degree.

No one person is more responsible for my outlook on lifestyle-design than Tim Ferriss. I first read The Four Hour Workweek when I was 18 (2009)– then I instantly flushed out everything I knew and built a new mental model from scratch using Tim’s model. For an 18 year old Canadian farm-boy, raised Mormon, I had a plenty of unproductive thinking patterns to reprogram.

I can tell you one thing I don’t agree with Tim on:
I’ve heard him say multiple times that you shouldn’t jump ship, quit your job, and jump straight into entrepreneurship.
I don’t agree, because that’s exactly what I did. Given, I had a support system to fall back on if I failed.
I think he’s just to afraid to give you advice which will certainly ruin your life in some ways.

But from my personal experience, burning your ship is the only option if you intend to succeed.

Burning Your Ships:

Ship burning is the act of taking away all safety nets. It comes from the story of the Spanish Captain Cortés. Same concept that was used in Batman in The Dark Knight Rises, how the only way he could succeed at climbing out of the cave was without a rope.

It may be Hollywood romance, but it’s not beyond reality.

Just look at Alex Honnold and Elon Musk. Two living examples of people who burn their ships daily.

Alex Honnold
The world’s top free solo climber, climbs some of the largest rock faces in the world without a safety rope.
When I first wrote this, 3 years ago, Alex wasn’t as well known. That all changed when he recently became an Oscar winner for his documentary Free Solo.

Elon Musk
When I first wrote this 3 years ago, Elon also wasn’t as well known. Since then he’s secured his spot in the tabloids. All drama aside, perhaps something not everyone knows about him.
He sold Paypal, to Ebay– and made enough money to sustain him and his family comfortably for generations.
Instead of comfort, he decided to invest every dime back into new ventures– Space X, Tesla, and Solar City. Even when things were looking like they’d go under, he went all in.
He put everything on the line long after he was financially comfortable, and almost went completely broke over it.

What have I taken from these two humans?

Insanity is key.

When I made the jump, I already had a good idea of something specific I wanted to do. Don’t get me wrong– I’m kind of a generalist. But I knew there were specific skills that if prioritized, would make all my other goals easier to accomplish, or irrelevant.

That’s how prioritization works:

Which option gives me the most options?

The curriculum I came up with was simple: eat, breathe, and dream pure design until I’m making a living off of it. Go full throttle, even– no, especially– if everyone around you thinks you’ve lost your sanity.

One of my good friends had already made the jump and was making his entire income writing copy on his laptop. I had directly seen it work, I knew it was possible, so I doubled down on it. I wanted the freedom of a remote lifestyle.

In my mind, design is entrepreneurship. Simply because he/she who most understands design will win.

We might be close to seeing the first trillion dollar company, and somehow I know it’s going to be a company which is fundamentally rooted in design.
— Also written back in 2016

There are many forms of design, and I wanted to learn it across the spectrum.

You should have seen the look on my mother’s face when I told my parents I was going to start sleeping 6 times a day for 20 minute intervals.

I’m a firm believer in permission slips.

A permission slip is something you use to allow yourself to do something you’re afraid of. It has a lot to do with discipline, confidence, and frame of mind. That in turn opens the door to completing a task or learning a skill you never thought possible.

Suppose you wanted to become the best entrepreneur that ever lived. You might shave your head and go study spirituality in India, like young Steve Jobs did.

I can promise you this–

If you don’t show that kind of dedication, you’ll probably never impact the world the same way Steve Jobs did.

In my case, I came up with my own permission slip. I used Matt Mullenweg’s method, the creator of Wordpress– polyphasic sleeping.

You might not believe in permission slips now, but you’ll see that it’s easier to convince people you’re good at something when you only sleep 2 hours a day, and spend the other 20 hours a day at your craft.

Put enough obsessive work in, and that snowballs into your peers actually believing in you.

Which in turn boosts your confidence. Which in turn should boost dedication. It’s a big feedback loop.

If you’re one of those people saying “I do work hard! But my peers still don’t believe in me!”. It’s obvious that you either overestimate how hard you work, or you need new peers. Peers that have interests in your goals. Peers that want to learn from you and teach you. Surround yourself by people who truly want to see you succeed.

Don’t under-estimate the permission slips. External validation is only a cherry on top. Never, ever rely on it. Be sure of what you will do before anyone else is. Always give yourself permission first.

I’m just saying,

If you’re looking to convince someone that you’re insane, polyphasic sleeping is a great place to start.

And convincing someone you have insane work-ethic is a good first step.

Polyphasic sleeping was my first permission slip of many towards mastering business and design. Use your imagination to find your own. If you want insane results, come up with an insane permission slip, and just do it.

Hello polyphasic sleeping.

Goodbye social life.

I had to warn my parents that I was going to be a zombie for the first week or two, and I might need to cook in the middle of the night to help keep me awake.

My mom hated the idea at first, but learned to accept it. Bless that woman’s heart for putting up with my insanity.

My Daily Process:

Wake up, Read, Nap
Lift weights, cook, nap
Ride bike, read, nap
Plan my “work”, cook, nap
Write music, nap
Execute “work”
Nap

All that time my head revolved around design or programming. Sometimes dreaming about it.

Soon enough, I was convincing myself I was an expert in design.

The sequence was constantly changing, but the bolded ones were usually in that exact order. I interchanged lifting, biking, writing, and cooking in-between the creation process.

Consume.
Create.
Repeat.

*But don’t forget to strategize and visualize a tangible end-goal before doing either.

“If you think adventure is dangerous, try routine; it is lethal.” — Paulo Coelho

I did this everyday for over a year. Weekday or weekend, rain or shine. Friends inviting me out, or nobody speaking to me for days. There was only one thing I could do.

In the past year I’d read over 50 books so my head was full. I cut back a little on the reading to spend time producing instead of pure consumption.

Hemmingway’s Trick:

Another important thing was that I try to stop right at the peak of my excitement– allowing that I’d already gotten something difficult and tangible done that day.
This way, I was always eager to get back to work tomorrow.

Chapter 3 Tough Love:

Success is Harder Than you Think

What I thought would take 3 months ended up taking 18 months. Which is another good lesson within itself:

6x Your Expectations:
Take how much time your goal could take (if everything runs perfectly smooth), then multiply it by 6.

Understanding this will eliminate your downsides.

Quality things take time.

Slow is smooth, and smooth is fast.
— Jocko Willink

Always go for the long term wins on projects you’re passionate about. No, not even passion is enough. If you only ever do accept passion-projects, you’ll be ahead of 99% of your competition. But that’s easier said than done.

Myth: The Overnight Success

If there’s one myth that I constantly fall for, it’s the myth of the overnight successes. I was naive and stupid enough to think that I would be able to figure how to be self-employed within a month.

I was way off. I brought my bare living expenses down to $40/m, so it gave me some ceiling room for error. Majorly due to my awesome parents helping me with rent and food for a few months (also getting rid of things like my smartphone). This was mission critical. I’m incredibly grateful for it, because not everybody has that convenience.

Being wrong about the timeline paid off. If I’d known how long it would take, I might have put it off for a “better” time.

Which means, I probably never would have jumped.

I’ve learned to trust my gut when it feels time to jump.

There is never a good time. If there was, it’d be right when you feel that malaise of comfort seep in. That’s when you fucking jump.
You either jump now or risk missing your true potential.

“Someone once told me the definition of Hell: The last day you have on earth, the person you became will meet the person you could have become.”
— Anonymous

A few months later I cashed my first check, I think it was a 50% deposit for $450.00– not quite what I had in mind, but it was a start.

I know I said it took 18 months, but that’s how long it took to be able to move out of my parents on my own.

When things take 6x longer than expected, it’s easy to get discouraged.

I’ve read a lot of Navy SEAL biographies and memoirs, which I’ve always found to be a quick fix for times of discouragement.

I always remind myself something I read in SEAL Team Six: Memoirs of an Elite Navy SEAL Sniper:

The author, Howard Wasdin, says that when people would ask him for advice on becoming a Navy SEAL, he would automatically try to talk them out of it.
The point was that if he could talk someone out of doing it, he knew they didn’t have what it took to succeed. He was saving them from wasting a lot of time.

“We choose to go to the moon in this decade and do the other things, not because they are easy, but because they are hard, because that goal will serve to organize and measure the best of our energies and skills, because that challenge is one that we are willing to accept, one we are unwilling to postpone, and one which we intend to win, and the others, too.”
– John F. Kennedy

Keep that kind of resilience close to your heart, and don’t seek for any external validation. If you look to those close to you for approval, you’re going to fail. Because they don’t see you like you do, it’s nothing personal.

Successful people are usually bred by fire. It ignites when they finally see who they were born to become. It’s not an option. You couldn’t talk them out of it to save their life.

Nearly a year later, I had a handful of small projects under my belt. I was still living with my parents, but more comfortably now. My polyphasic sleeping days were over and my social life was back. Rock climbing, road trips, and camping were in full effect– but I was still extremely focused on work.

Work.

I got so sick of that word.

People would say, what are you doing?

“Working.”

It felt wrong to call it work. It was more like spreading Legos across my bedroom floor and playing.

That’s my personal guide to knowing when I’m working on the right thing.

When it reminds me of playing legos as a kid, I know I’m working on the right project.

Speaking of which, the next project I did was one of the most fun– and it jumpstarted my whole career.

Chapter 4 The 5 Natural Emotions:

How to Jumpstart a Creative Career

At the time, I was co-founding Jackalope Marketing, with my friend. We had just finished putting in long-hard hours on a website mailout campaign to 100 “targeted” companies or so.

We got not one response. It completely flopped on it’s face. Some of our envelopes got returned to us all torn to shreds.

I felt like we got lucky that it failed, because after doing some cold-calling I realized these “targeted” companies were fucking bottom-feeders. We targeted them solely because they had the shittiest, most outdated websites.

It was my first advertising investment and I lost every penny. But what I learned was that companies with shitty websites have shitty websites because they’re shitty companies. Sure, there are exceptions. But I’m not going to spend my time searching for these unicorns.

Established companies that show no regard to their digital presence or design quality– do them a favor, just let them keep their money and die.
Don’t kill yourself saving them.

I was lucky, because the last thing I wanted was a bunch of low-paying web clients calling me every night with fires to put out and pictures of their dogs to upload.

The 80/20 Principle:
Cheap clients are the worst. They often suck up 80% of your time and only make up for less than 20% of your revenue.

I was trying to convince my biz partner that we should pivot. I thought producing videos would be more fun than developing websites– but I was getting a lot of resistance.

At this point, he had moved to Austin and was doing a full-time internship. I was the only one working full-time on Jackalope at the moment, so I probably shouldn’t even be asking for permission.

I needed to jump again.

Taking Action

I decided to write my own permission slip. I bought JackalopeMedia.com and told him that it was going to be my video production department.

He definitely wasn’t as excited as I was about it, but that’s what I’m saying– it’s not personal. You’ll meet this kind of resistance your entire life until you’ve shocked your peers enough that they stop doubting you. I thrive in this resistance, so I didn’t take it personally.

This move solved every road block. I couldn’t believe I wasted so much time being afraid to simply do what I wanted to do.

I was repressing my anger, holding a straight face, and in turn allowing it to silently boil my blood– which wasn’t benefiting anyone at all.

Then one night while reading, I stumbled across a description of how my emotions work in a favorite book of mine. I suddenly understood why I was so disturbed, because I could visualize my emotional process. Therefore, I could understand it. And it was coming from a place of love.

I felt better already. I had to share it with people immediately.

I contacted one of my favorite bloggers and showed him an infographic concept I’d thrown together. He agreed to share it with his audience when I finished it.

The infographic actually turned into a 2 minute animation video you see above. We went all out on it, so it ended up taking over a month. For zero money, I worked four 80–100 hour weeks.

Teach What You Need to Learn

I channeled my business frustration into creating something to teach others how to deal with their anger– which in turn helped me understand and deal with my anger.

It’s an incredibly useful feedback loop for working through personal issues.

It simply came down to realizing that anger was perfectly okay, and that if my lack of creative control was pissing me off, I simply had to just take action and do my own thing without asking for permission. Anger doesn’t mean freaking out or acting violent, it just requires proactivity.

That responsibility was on me.

This video taught me that it’s actually good to be pissed off sometimes. It’s a primal instinct that helps us survive. Repressing it is unhealthy.

So Jackalope Media was born. In the video, it represents the baby playing in the street. I’d saved it for now.

But it would be kidnapped from me less than a year later.. (more about that in Pt II)

A Case for Pro Bono and Spec Work

Most designers are appalled by the thought of doing pro bono or spec-work. And then there’s some who plant the seeds of their careers off of it. A small few know the true power of it. They use it to build their portfolio, experience, and exposure. I know many creatives who have built their entire careers on the back of pro bono work.

This pro bono video got over 250k views thanks to some shares from big social channels like Upworthy, SpiritScience, and HighExistence.

I still haven’t got one single lead from this video directly, but it triggered an avalanche…

We did the video without asking for anything in return, and it paid off.

Jordan Lejuwaan, the founder of HighExistence (co-founder of Futurism, and on Forbes 2016 30 under 30), hired us to do another video a few months later, but this time– paid. Our first paid video project, and it was slightly bigger than any of the web projects we’d done at that point.

My biz partner was now finishing a year long internship in Austin, TX– so we moved him back to Utah so he could work with me full-time on this and projects to come.

Fell In Love with Austin

“Austin knows how to party! #shakespearesaustin #dirty6th #firstnightinaustin”