Doing Things You're Not Qualified for

June 3, 2019

Success was achieved by exceeding expectations — as my old English teacher said, we all got really good at “hoop jumping”; enthusiastically, competitively, and with complete acquiescence, jumping from hoop to hoop: get good grades, extensive extracurriculars, hours of community service, attend a well-regarded college, build your credentials.

The problem is two fold. The first is that those are the expectations of others — they are things that you were told to want and come from your culture; they are not your own expectations for yourself. The other is that after college, there are no longer clear expectations — the prescribed hoops to jump through are ambiguous, less tangibly achievable, and far between. If you proceed to do what you think you’re expected to do instead of what you want to do, then when things go wrong — as they inevitably will — you will stand there frozen on the stage of your life doubtful and despondent. If you instead do what you love and things go wrong — as they inevitably will — you become resilient.

The constant is that things will predictably go wrong. The variable is how much you love what you’re doing when things do go wrong.

Forging your own path though is hard. Not knowing what lies ahead is scary, but “insecurity and difficulty are the feelings of driving your own ship” and the challenge afforded by the difficulty of figuring it out is a requisite for learning. While it may be easier and feel safer to pursue a path already laid out, a desire for convenience can be a hindrance to learning, particularly as you proceed further into the hoop jumping scheme. As standard of living increases with each hoop, items that were formally aspirational, once obtained, become obligations, taken for granted, and non-negotiable for each subsequent hoop. Hoop jumping in this way begets convenience.

Convenience, by definition, seeks to alleviate friction and struggle in our lives; it works to efficiently automate away tasks that challenge us and require effort. While convenience is well-intentioned in its attempt to make our lives easier and save time, time saved does not equate to productive use of that time. Convenience serves as a bridge to complacency, and complacency stifles self-development.

If you will struggle regardless, why endure the struggle of complacency when you can instead grow from the struggle of doing something that you love?

The “occasional reminder that you’re kind of dumb is a critical humbling exercise”

This is why I think feeling under-qualified in forging your own path is OK. The vulnerability of humility and the erosion of complacency is where the opportunity for learning is the greatest. The sentiment of “Imposter Syndrome” feels misplaced and overly pessimistic***; Imposter Syndrome is stepping outside of your comfort zone and playing to an unknown higher standard that elevates you to progress towards that standard. The resilience that results from the combination of things going wrong, having no idea what you’re doing, and having a genuine love of what you’re doing is awesome.

A recent study demonstrates how people’s most enduring regrets in life result from not living up to our own expectation of our ideal self, not from failing to live up to other’s expectations of our ought self (see self-discrepancy theory). The same researchers had found that people’s largest life regrets were things they had not done, rather than things they had done. Live to avoid end of life regrets. Focus on your own ambitions rather than those vapidly laid out for you by others, and seek out those who challenge and push you towards your ideal self (1). No one knows what you like better than you do, so you have to be your own advocate (2).

An aside on doing things you’re not qualified for: if you have the ability to forge your own path, recognize your privilege to take on risk. While being able to pursue something you want is an incredible opportunity, it means you have the margin of safety to prioritize desire over need in the first place. In the serendipitous confluence of factors where an opportunity simultaneously satisfying desire and need arises, take advantage, but heed the underlying privilege involved in the ability to do so.

No One Really Knows What They’re Doing.

I sure don’t….We always aspirationally look up to people who seem to have figured it all out. However, at some point, you reach a comparable stage to where those people whom you perceived as all-knowing and wise stood and realize that everyone, at every stage, is winging it. They’re making better informed decisions, drawing from experience as they ascend, but they’re pretty much always charting uncharted waters nonetheless. I’ve found the aphorism holds: the more you know, the more you realize how little you know. So exercise humility and understand you always have something to learn from those around you.

With that…On being colorblind, qualia, and subjectivity of observation.

“Radical open mindedness…requires you to replace your attachment to always being right with the joy of learning what’s true.” — Ray Dalio

There’s a disconnect between academic skeptics and real world pragmatists.

Skeptics will identify real world problems and propose hypothetical binary solutions that ignore the nuance of choice and trade-off while belittling the complexity of the people whom their solutions would in theory serve. That is all assuming skeptics will entertain solutions in the first place; frequently, I’ve found they simply cast baseless aspersions (haters gonna hate). Don’t completely ignore these skeptics, but unless they collaboratively work with you to come up with real solutions, don’t let their hypotheticals and scrutiny dictate your direction.

To abstract this, prioritize spending time with people who can be constructive while maintaining a doubtful position of skepticism. Being able to have “Thoughtful Disagreement” is super important (3).

On $ & Investing with a $38k Starting VFA Salary

(See linked PDF below…all my thoughts on money)

VFA $ Breakdown - JPS.pdf

For much better articulated and well formulated ideas on investing, please read @morganhousel’s — …one of the highest value/word reads.

Other Things I’ve Come to Believe Are True

  • *** Optimism isn’t so much an attitude or state of mind. I think it manifests as a creative force. Optimists seek to realize and create the positivity they envision. (4). Conversely, I think pessimism is a pernicious force and similarly prescient in that pessimists will realize the negativity they envision.

  • I learned a lot more from video games than many of older generations would care to admit. To dismiss video games is no different than to dismiss books…they momentarily afford traversing an alternate reality constructed by someone with something to say or a story to tell; only the medium differs. Things I’ve learned from video games include: work ethic, investing (power of compounding and exponential growth), economics (tragedy of the commons, power of incentives, trade-offs, present bias, risk-aversion), statistics, project management, time management, power of team (some things you just can’t do alone), object-oriented thinking, power of specialized knowledge.

  • Having to both educate and sell makes selling sufficiently more difficult.

  • Technology doesn’t really matter; people’s feelings about technology matter. What’s in it for people matters more than what allows for it to transpire; experienced benefits are more powerful than promoted features.

  • There is a huge opportunity to modernize government.

  • Setting tangible goals for improvement is better than generally trying to improve; you need to be able to measure progress.

  • Twitter, curated properly, is the most valuable and powerful social network at the moment.

  • You don’t need to be on the coast to be successful. Furthermore, I think the perspective gained by leaving your nest — whether you grew up on the coast or in middle-America or anywhere else — is pretty important…We certainly live in bubbles. As Mark Twain notes in The Innocents Abroad:

Travel is fatal to prejudice, bigotry, and narrow-mindedness, and many of our people need it sorely on these accounts. Broad, wholesome, charitable views of men and things cannot be acquired by vegetating in one little corner of the earth all one’s lifetime

  • Job creation is really hard. When I signed on to Votem, I joined the founder/CEO as the first employee with Leopoldo Peña. Since then, our team has grown to over 20 people. However, when businesses set out to solve a problem, job creation is not typically the problem to solve. Job creation results from businesses succeeding. (2019 Update: Votem has failed). Votem never set out to create jobs explicitly; Votem set out to elevate the democratic process to an unprecedented level of verifiability, accessibility, security and transparency. Companies can only hire people as they succeed as a business.

  • In spite of the shilling and hype blockchain has garnered over the past two years, the promise of blockchain is real. I think it is emerging as the single most interdisciplinary technology bridging computer science, finance, behavioral economics, psychology, law, cryptography, monetary policy, governance, and politics…I remain as excited about the space as I did leaving college.

  • On blockchain’s protagonist, Bitcoin is a hedge against organized government and traditional stores of value and an insurance policy against centralized monetary policy failures.

  • Clevelanders are simultaneously the most prideful and self-deprecating folks around; it’s wonderful.

Things with High Benefit-Cost Ratios

  • Showing up and being reliable have a remarkably high payout for how little they actually require. Trust is built largely by just doing what you say you’re going to do.

  • Taking Good Notes. Take notes on everything. Notes will pay great dividends and your future self will thank you for them. Building on note taking, writing galvanizes ideas in your head and makes them durable and referable. It does so to a clarifying degree that thinking about those ideas alone cannot achieve. Write more ideas down, your future self will also thank you for these (5).

  • Being on time.

  • Cold outreach is far more effective than most people realize. If you can surmount the mental hurdle discouraging it, you find that people — even those you may think are completely inaccessible — are actually pretty receptive to a directed well-crafted note. If you don’t ask, you don’t get.

  • Similarly, when applying to a company, a relevant well-crafted cover letter goes a very long way toward differentiating your candidacy. On the same vein, sending thank you notes is minimal effort and maximal impact.

(1) thanks Leopoldo Peña

(2) thanks mom

(3) see Ray Dalio

(4) thanks to @morganhousel

(5) thanks to David Gardner (@DavidGFool)