Planning for the future kinda sucks, ammirite?

Since moving to Austin, TX I've taken a moment to re-examine what skills I've developed, highlights of my personality, and how that aligns with established career paths. In this post I will take you through my thinking and provide some of the tools I created to analyze the future.


I believe we should approach the most important aspects of life in a holistic fashion. That means, when I say future, I consider how it impacts:

  • my experience
  • the story of my life to look back on someday
  • how it effects other people
  • whether it builds my personal values
  • what hobbies are developed
  • impact on health
  • and - finally - money

You may already notice something different in my approach here. These aren't organized in any particular order besides the last one. I optimize my choices toward the experience, including still being happy if I were ever poor again, but just know that doesn't necessarily mean you need to do that too. The thought process and methods here are for you to take, break, mold, and form to fit your needs.

Imagining Our Greatest Potential

It is necessary to understand there are subconscious stories that shape our actions. These assumptions limit the ways we express ourselves and risks we take on any given day. This is part of our ego which is a carefully and meticulously crafted character. We are taught from a young age that strong resumes build this character for the better and to show obedience toward other external demands or compliments.

I don't play by others' rules and suggest you don't either. The system is too rigged and geared towards the consumption of our life force, relations, and planet.

Have you ever taken a little risk like listening to new music, wearing fun clothes, or doing something original only to have others become your greatest critic? How about when a stranger compulsively lashes out in an attempt to keep the world perfectly ordered? Perfect based on their own perception of order, I may add. As-if given divine right by the establishment to keep you in line.

This happens to every brave little thing I do, so I stopped caring.

To truly manifest our greatest potential it is necessary to let go of these external influences. They represent other peoples' limits.

Taking ownership of our character sheet also takes destiny into our own hands. Why live a life trying to appease everyone else when we've already consumed our culture? Is this really how it's meant to be? Those people are often broke, loveless, and miserable anyway.

I say no, it is not, but it seems so because we're all told this is how the world works. We're told this by our parents, teachers, community and no one knows any better. Our success is often met by confusion or fear rather than curiosity.

The thing many successful people understand that others don't is that the world is what we make of it. Detached from societal expectations is where our creativity and the real human experience awaits.

Fake it til' you make it is a tactic for overcoming barriers but first the person faking it needs to have goals rooted in self. We typically replicate other examples of success, which is useful, but my advice is to be careful of your influences. That video game streamer has no life balance, doesn't read any good books, and barely fucks. Don't pursue the most obvious versions of success, successful people already sit in those roles.

Imagining our greatest potential means starting with a blank page. We owe it to ourselves to be our greatest supporter. Leave it to others to try and limit our potential. They'll try but succeeding in the face of it will makes the experience so much richer.

If you are an entrepreneur or want to cut out a more personalized path into the future, my recommendation is to strengthen your imagination and avoid zero-sum mimic games.

Avoid Zero-Sum Games

Zero-sum games happen when we mimic each other and is the cause of most conflict. It is also arguably killing our ability to innovate.

Examined by Rene Girard's Mimetic Theory🔗, as we copy each other we inevitably desire the same things thus resulting in more competition. More imitators lead to the originators being more convinced they made the right decision. This heightens competition further, drawing more people in. This feedback loop leads to conflict, upsets, and bubbles.

Note: The nature of copying each other is also disingenuous and persuades us from carving our own path, which is another reason I recommend against it.

We see this play out all the time on YouTube and social media. A YouTuber finds a successful formula and then everyone else copies it, never quite achieving what the original was while also making it very competitive. The "How To Make $100k Per Month Course" quick-business ads on Facebook is another recent example but we can see this in many areas of our life when more than one person desires the same thing.

In zero sum games, no one creates new culture, innovation, or meaningful value while the industry squeezes everyone involved and draws more in.

The most dominant type of zero-sum games are corporate and University hierarchies. Especially if you agree that our future is in flux, I recommend avoiding them. Their pyramid structures are zero-sum by nature and make it incredibly difficult to climb, especially if you want to keep your humanity.

Start with Imagination

Imagination is the coolest thing ever since sliced bread. It is necessary to envision a future self that is great to aim towards. Without vision, we tend to find ourselves at the bottom of whatever someone else or a system gives us. It also enables us go with the flow when things change, develops confidence in our decisions, and enables creative problem solving.

A few simple methods to work this muscle:

  • Meditation🔗 (This is the most important skill)
  • Use time in bed to envision a future (How old are they? What are they into? Where are they? What are they doing? Do they have a family? Explore all possible answers for these type of questions)
  • Visit a Fortune Teller (This may sound ridiculous but this is what tarot cards are for and it works. What do you have to lose?)
  • Write the story of your life (Autobiographies are also the ultimate gift for your future relatives)
  • Read Fiction, I recommend this one🔗 (When everyone reads non-fiction for their zero-sum games, we read Fantasy)
  • Draw things, paint, play piano, dance
  • Go for walks, preferably in nature, with no headphones
  • Responsibly take psychedelics
  • Email my brother🔗 for help, he's an ex-investment banker that teaches Visualization
  • Ask for more ideas in our Discord server🔗

Identify and Plan Goals

Now our task is to take that imaginary vague or vivid idea of our future self and make it reality.

The place I started in researching potential career paths was to look at the end-result first. What job do I want to have in the future? For me it left three more obvious choices:

  • Chief Financial Officer (due to my past in corporate finance)
  • Creative Director (due to my creative side and ability to coordinate groups of people)
  • Chief Marketing Officer (due to my creativity, proven marketing, and finance backgrounds combined)

I then compare these options with the type of lifestyle I want to live and what naturally speaks to my inherent strengths. Due to this, I remove Chief Financial Officer from the running. Even though it has the highest upside income potential, I am more creative than structural and would not enjoy this as much.

So, this leaves Creative Director and Chief Marketing Officer as options. The next thing I did was look up these positions on job boards to see what their average salaries were and the necessary skills hiring companies wanted.

Design Director Necessary Skills ($130k - $140k / year)
  • Sketch, Axure, Invision, Flinto
  • Photoshop
  • Illustrator
  • Keynote
  • Responsive Web Design
  • Native Mobile Design
  • Information Design
  • Typography, Color
  • Flows
  • UI Specifications
  • Design Principals
  • Agile Software Development
  • Direct Response Design
  • HTML5/CSS3
Chief Marketing Officer Necessary Skills ($138k - $265k / year)
  • Facebook / Instagram Ads
  • Google (SEM, SEO, Display Ads)
  • Social Advertising
  • Video, TV, Radio, Print
  • Demand Modeling
  • Multi-Touch Attribution
  • A/B Testing
  • LTV Marketing Investments
  • Budget P&L Goals
  • SQL
  • Statistical Analysis
  • Quant Techniques (Regression Models)
  • Consumer Mindset (Psychology)
From this search I also gathered possible industries to enter:
  • Technology
  • Advertising
  • Media Production
  • Entertainment
  • E-Commerce

At this point, given my background, it would make more sense to build a career towards the CMO position. The next step is to search for blogs, LinkedIn articles, and other writings from people in these careers describing their profession.

As you read their work, ask yourself which of these professionals speaks your native language more? Understanding this is important because someday you will become a version of that person!

Pro-tip: Email CMOs and Creative Directors in your area to ask them about their work. This both makes introductions for potential relation and will give you the best insight. Plus, you never know, maybe they're hiring!

Based on these considerations, I would pursue Digital Marketing while learning the Creative Director skills on my own time so I can make the jump. After researching the different roles, becoming a Creative Director really has no specific path to take but it seems the most fun! That excitement alone helps make dreams become reality.

If you need help or want to brainstorm, join our Discord community🔗!