The Transformative Principle of “Go Around”

jellyfishPink.JPG
3 min read

I recently listened to a podcast episode where Tim Ferriss interviewed chess prodigy Josh Waitzkin. Halfway through the interview, Josh shared a story about his son Jack.

Josh and his family were staying at a small cottage in Martha’s Vineyard one summer. One day, Josh’s young son Jack attempted to open the front door of the cottage but it was locked. Josh told him to simply “go around” to the backdoor that was unlocked.

From that day forward, Josh used the phrase “go around” to instill a default behavior in Jack: when faced with an obstacle, always look for a way to “go around” it. Sometimes this meant physically going around, but more often it meant mentally or psychologically finding a way to get around an obstacle or challenge.

I love this principle because it’s simple and useful. When life throws you shit, you have two choices: go around or complain. The default behavior for most people is to complain. Why? Probably because complaining feels so good in the moment and it gives you an excuse to avoid the hard work of going around.

It feels even better when you have someone to complain with. Or, better yet, if you can find a whole crowd of people that enjoy complaining, you guys can form a little community, turn yourselves into permanent crabs, and jump into a complaining bucket together to live in. You won’t make any progress or overcome any major obstacles, but man that’s gonna feel so good to have a reliable group of amigos to complain with.

The problem, of course, is that complaining leads to long-term stagnation. You never get anywhere. This is why it’s so important to cultivate a mindset of “going around” obstacles.

The Java Nightmare

In college I had to take an Intro to Computer Science course to learn the basics of Java programming. There were only two professors who taught the course. One was a notoriously strict grader who could let an entire class fail without flinching. The other was a laid-back guy who was more lenient with his grading.

I landed in the class of the first professor. On day one, she told us bluntly, “look at the person to your left and to your right. Out of you three, only one of you will pass.”

She wasn’t wrong. Half of the class dropped by week five. But the curious part wasn’t why the students dropped, it was how they dropped. When faced with a difficult assignment, one student would complain openly about how the instructions were unclear or the work itself was too difficult. It didn’t take long for another student to chime in and agree.

Pretty soon, half the class had jumped on the complaining bandwagon. Finally, when the first student dropped, more and more students began to drop like a line of dominoes.

Of course the assignments were difficult and the instructions were usually unclear, but it was still possible to complete them. You just had to choose to go around the unclear instructions and difficult nature of programming instead of complaining about the work.

So, although the class was a complete nightmare and I constantly considered retaking the course with the easy professor the following semester, I chose to push through and ignore the siren calls of the complaining crab bucket. I passed with a B.

Real World Obstacles

Passing a difficult class is one thing, but the obstacles we face in the real world on a daily basis are a whole different ball game.

The cost of college is rising fast. Most middle-class wages have been stagnant for years. Healthcare is messy. The price of daycare is outrageous. Sometimes you don’t get that bonus, pay raise, or promotion that you deserve at work.

But this doesn’t mean we can’t find ways to go around these obstacles. 

I graduated college debt-free by attending an in-state college and working part-time retail jobs throughout my undergraduate years. For some students, going to a community college for the first two years can decrease tuition costs significantly. For others, scholarships can help offset student loans.

Despite stagnant wages, there has never been a better time to start a side hustle. For me, I tutor students in stats outside of my day job. For others, there is Ebay, Craigslist, Rover, Airbnb, and a laundry list of other ways to earn extra money.

Choosing to live in a home that suits your needs, embracing a bit of frugality, and keeping expenses like cellphone payments, dining out costs, and entertainment in check can help you build up your savings rate.

Choosing to invest your money in low-cost index funds can save you tens of thousands in investment fees over the course of decades. 

Despite the financial obstacles we all face, there are ways of getting around them. It might take time and it might require us to get a little uncomfortable, but it leads to far better outcomes than choosing to complain.

Next time you find yourself facing a shitty situation, an unfair circumstance, or a difficult dilemma, fight off the default urge to complain about it on Facebook and instead look for ways to go around.


My favorite free financial tool I use is Personal Capital. I use it to track my net worth, manage my spending, and keep an eye on my monthly cash flow. It only takes a few minutes to set up and it makes tracking your finances simple and easy. I recommend trying it out.

Sign up to have my most recent articles sent straight to your email inbox for free ?

Full Disclosure: Nothing on this site should ever be considered to be advice, research or an invitation to buy or sell any securities, please see my Terms & Conditions page for a full disclaimer.

5 Replies to “The Transformative Principle of “Go Around””

  1. “..the siren calls of the complaining crab bucket.” That right there is worth cross stitching on a pillow or putting on a motivational poster.

    Thanks for the excellent read!

  2. “look at the person to your left and to your right. Out of you three, only one of you will pass.”
    Ack, I think a professor said that to us but it wasn’t about his class. He said that about how many of you will hate your job vs not hate your job for life. Which is much more depressing haha!

    Great message, complaining on Facebook does no good 🙂

  3. I immediately thought of “go around” the way pilots do. If they realize they are too fast or too high or something isn’t configured right for landing at the last second they have two choices, to force an unsafe landing or to increase the throttle and “go around” for another, better prepared, attempt. It isn’t the same as going around an obstacle to find another way to solve the problem but it has applications. Sometimes the locked door doesn’t have to be avoided you just need to circle back to where the spare key is hidden and make another approach.

  4. I have to chuckle over this a bit, I sometimes complain to Mr. Dragonfly and vice versa when we run into obstacles (it can be something trivial) – so we get the angst out of our systems so we can move on to potential solutions. One good thing is that we are “too” honest with each other after each “bitching” session and we are gracious of each other’s being candid and most time, we find solutions (the work-around) and if there things we are so stuck in, we always let them sit for awhile to see if the same emotional/financial impacts persist. I do not see a quick venting/complaint to be a bad thing but when you dwell on it, you start drawing some like-mind people to add to negativity instead of options to work things out.

    1. Haha nothing like a “bitching session” to let out your frustrations and then move on. I think it’s only natural to get angry / frustrated as a gut reaction, but the more you start to look for solutions instead of dwelling on problems, the easier it becomes to change your gut reaction to problem-solving.

Leave a Reply

Your email address will not be published. Required fields are marked *