Illustration by Marie Bergeron
Odds & Ends

Finding Your Career: The Power of Unorthodox Experiences

Career Pathfinding: The Surprising Advantages of “Dark Horse” Thinking

My first real job was as a student archaeologist. We were digging along Hadrian’s Wall in Northern England at the northernmost point of Roman expansion. I would wake up around 5a.m., grab English tea, and then bus 2 hours into the countryside side towards what could have easily been confused as a giant mud pit. 

When first applying for the job, I remember thinking that this would basically be my first stepping stone towards becoming Indiana Jones. What I encountered was the daily, 8-hour dust-tooth-brushing of 1,500-year-old cooking utensils.  

After around the second week, it became apparent that I didn’t quite belong. While my neighbors were meticulously documenting the precise geometry of dish fragments, I was sneaking away into the rolling grass hills of Durham, UK to write about the existential angst of not knowing what I wanted to do with my career. Suffice it to say that archaeology wasn’t my cup of tea. 

Suffice it to say that archaeology wasn’t my cup of tea. 

I spent the next summer cleaning the tanks of genetically engineered, bioluminescent fish. In the months preceding, I did nothing short of showing up on the doorstep of the principal investigator, human biology final exam score in hand. I wanted to be a neuroscientist. Thinking myself to be the fish-behavior equivalent of Will Hunting, the math genius MIT cleaning staff member  in

I wanted to be a neuroscientist. Thinking myself to be the fish-behavior equivalent of Will Hunting, the math genius MIT cleaning staff member  in

Thinking myself to be the fish-behavior equivalent of Will Hunting, the math genius MIT cleaning staff member  in Goodwill Hunting, I would spend the evenings scrubbing algae growths off of glass walls in a dark basement while reading about the mating behaviors of Haplochromis Burtoni, a strange color-changing fish native to Africa’s Lake Victoria.  

At the time, I was utterly confused and fairly lost. All that I seemed to know was that I didn’t want to be an archaeologist and that neuroscience, insomuch as it applied to rare fish behavior, was probably not for me.

It wasn’t until several years later that I fully realized the extent to which I had learned about myself during these two unorthodox experiences.

Dark Horse Thinking

While in grad school, we were exposed to a concept known as “Dark Horse” prototyping. The concept was simple. Once you have a sufficient implementation of what you might conceive as a satisfactory idea, put it on the shelf, and spend an equal amount of time prototyping something as unrelated and utterly strange as possible.

Working with the research arm of our corporate sponsor, we were tasked with designing “wearable artifacts to augment and extend the human experience.” During the first trimester of our work, we researched and implemented a belt that gave blind people directions through vibratory headings. We had invested our time, brainpower, and egos in this concept, and were quite frustrated when we were told to throw it out to pursue unconventional alternatives.

The following trimester was probably the most creative period of my life thus far. We built everything from gloves that quantified a person’s anxiety state throughout the day to electronic “smart” contraceptives. This freed us from the emotional handcuffs of ego investment.

The concepts we pursued were so strange that we stopped caring about whether or not we were on the “right” path. We were able to redefine our notions of normal or socially acceptable, and this gave us the freedom to explore things few others had.

Moreover, removing the psychological barriers we had created by trying to create something users would absolutely love allowed us to start a flywheel of progress. Once we returned to our original navigation prototype in the third trimester, we had an entirely new and fresh perspective on our target users. We were able to build something that blended the thoughtfulness of our original vision with the novel user features and insights we gained during “Dark Horse.” 

I find personal career journeys to share many of the same properties. Below are what I believe constitute the fundamental principles of Dark Horse thinking. 

There is no such thing as the absolute “right” path. 

“Does history record any case where the majority was right?”

– Robert Heinlein

I’m not sure if it’s because I spent my childhood immersed in fiction stories, but I’ve always subconsciously felt as if every “next-step” could be the pivotal moment in my life. Cinderella loses a crystal slipper and we wonder whether she would have lived happily ever after without doing so. The “pivotal next step” is an illusion of retrospect inasmuch as it is an illusion of narrative structure.

As Steve Jobs put it in the 2005 Stanford Commencement Address, 

“You can’t connect the dots looking forward you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future. You have to trust in something: your gut, destiny, life, Karma, whatever. Because believing that the dots will connect down the road will give you the confidence to follow your heart, even when it leads you off the well-worn path.”

As an exceptionally amateur chess player who can’t keep more than the combinatorial space of 2 future moves in his head, I have always believed that setting up powerful, large, open, idea networks of moves is the best way to insure that your future self will make good decisions.

In other words, don’t worry about making the perfect next move to seal all the chinks in your armor while accomplishing all of your goals.

Make the minimum effective move that diversifies the position for your future self while leveraging your immediate strengths. Unless you are Neil Armstrong stepping foot on the Moon for the first time, a series of minimum viable moves is much more effective than one highly optimized step.

Doing something is more important than waiting to do the perfect thing. 

“The decent method you follow is better than the perfect method you quit.”

– Tim Ferriss, The 4-Hour Body 

There is a property known as the Pareto Principle, named after the Italian economist, Vilfredo Pareto that states, “For many events, 80% of the effects come from 20% of the causes” (Wikipedia, Pareto Principle).

You may have of heard the name in your introduction to economics class in the widely taught model of ideal resource distribution known as Pareto Efficiency. In venture capital, it is a commonly held belief that 20% of portfolio investments cover the costs of 80% of the fund. In software engineering, we often observe that 20% of bugs cause 80% of failures.

I could go on and on, but why is this important?

I believe that 80% of the progress we make towards identifying fulfilling careers is the result of 20% of our efforts.

What does this mean?

You’ll learn more about yourself in the early periods of jumping in and trying something new than you would by mapping out the perfect solution from a stagnant vantage point or by hammering away at incremental self-improvement.

Our CEO, Steve Myers, describes something he calls the “progress vs. motivation curve.” This is a mental model he uses to describe the balance between making progress on something versus having the motivation to continue working.

The minimum viable “win” often provides enough motivation to start a chain reaction towards huge gains in productivity.

During initial training, the United States Military requires all cadets make their beds perfectly first thing every single morning. It is believed that this starts the day off with a win. This success can be the spark that ignites motivation through a grueling training program.

Many of us have that perfect vision of what we wish we could do. Whether it’s learning a new language or building an iOS app, the utter magnitude of our dreams is often the element deterring us from their pursuit.

To risk cliché and quote Nike, “Just do it.”

You will rarely regret it.

This allows us to navigate beyond the perils of decision paralysis, something we are almost always faced with when encountering a world of options. 

Tunnel vision is real.

The Innovator’s Dilemma describes a phenomenon where successful companies who devotedly emphasize the needs of current customers often fall behind when failing to adopt technologies to meet the needs of future customers. There is a common pattern where companies are actually dis-incentivized to push disruptive innovations to market as they would risk competing against the core products of their businesses.

Clarence Hickman, a Bell Labs engineer working in the early 1930s developed a technology known as magnetic recording tape. Originally used in answering machines, this technology is the foundation of modern hard drive magnetic storage. Without it, there would be no Amazon, Apple, Facebook, or Google. The only problem: it took 60 years for this technology to reach consumer’s hands. 

Bell Labs, a research arm of AT&T, ordered Hickman to shelve his technology and stop development, fearing that it would disrupt their monopoly on the telephone market. For a public business with shareholders, board members, and the hot breath of Wall Street on its neck, it is no surprise that we observe a lack of incentive towards disruptive ideas.

On the individual level, these same principles apply, fueled by the momentum of our egos. Even Albert Einstein, the epitome of disruptive thought, struggled with this.

Holding to a belief in the deterministic properties of nature, Einstein, towards the end of his life, denied many of the insights unveiled through quantum mechanics, the birth child of his own work.

Tunnel vision is real, but it can be avoided.

Sometimes the answer to our problems isn’t working harder. Sometimes, you have to be willing to accept the principles of diminishing returns on a given path, reframe, refactor, and in my impression, get a fresh perspective.

Otherwise, the comfort and satisfaction that “good” provides will continue to outweigh the effort required to go from good to great. 

Timeboxing a path can be incredibly powerful.

Your efforts behave like an ideal gas. They expand to fill the container they are given. This principle, also known as Parkinson’s Law, lies behind most of the frustration and success we experience in life.

Google’s ATAP or Advanced Technologies and Projects Group is one of the most innovative technology groups in the world and has invented everything from modular smart phones to phones with a human-like capability to map your space and motion. ATAP is famously known for its DARPA-inspired two-year time limit to develop, design, and manufacture its goals.

If DARPA and ATAP do it, why not try it?

One major advantage of internships is that they allow us to try out a career without the pressure of staying beyond the summer. This allows us to try things out without feeling the way my grandfather described when he walked into his first job at the United States Forest Service as “the career and office that will consume 80% of my waking life.”

Try something out for a couple years and then force yourself to try something entirely different. It will either make you realize how much you truly appreciated the original career or you’ll find yourself on a new, fulfilling path. 


Andrew Berberick

February 5, 2016

San Francisco, CA