Struggling

I’ve had a few recent personal setbacks. I tried to get a speaking gig at a conference I thought I’d be a good fit for — rejected. I got an intro to a magazine editor, who, after what I thought was a productive and good conversation over the course of weeks, rejected me for her publication. And after writing for another publication for many months and getting a ton of traffic, another editor won’t return my emails. To top that off, we missed some goals we set for ourselves at Highrise for June.

Yeah, I’m struggling.


When I got into high school things were tough. I somehow got into all these honors and advanced classes from doing well on placement exams but struggled with how hard the classes were. Eventually I figured it out with the help of some great teachers and hard work. But I was shocked sophomore year, when, during the first week of the new school year at a class assembly, I was called up on stage in front of 400 of my fellow students and given an award for having the highest GPA of my freshman class.

Whoa. It dawned on me maybe I was actually a pretty good student even amongst all these other smart kids. And so I just got even more competitive. Could I keep this #1 GPA up?

But sophomore year got even harder. First, there was the schedule. I was involved in at least 5 clubs, tons of extracurricular activities, and all-year-long volleyball training. And second, now I found myself in my first AP (Advanced Placement) class: AP Art History.

Trouble began right away when I made a poor impression on the Art History teachers. These guys were assholes and in my opinion terrible teachers. I really didn’t like their flavor of teaching. But I tried insanely hard, and still did really poor in that class. You can score a 1–5 on an AP test. I don’t think you can even get a 0 unless you don’t take the test. I got a 1. My GPA in that class wasn’t hot either, and with that I saw my class rank slipping.

By junior year I was stressed out. I just couldn’t keep up with the things I wanted to do and maintain the top class rank I wanted. And it felt awful. What was I going to do?


I’ve gotten some advice recently:

Wise words. Just go; do your thing.

In high school, I just gave up trying to actually meet the demands of my schedule and getting the top rank of my class. For some classes, I even stopped turning in all my classwork on time. I just couldn’t pull another all nighter and keep my sanity.

I remember for one of my classes, I just didn’t hand in the project we were supposed to do. A few days later I dropped it on the teacher’s desk and said, “I hope I can still turn this in.”

Not only that but I did the project in a really fun weird way that I wouldn’t have been able to unless I had taken that extra time.

The result: I got a 100% on the project. And he took off 10% for turning it in late. 90% not too shabby. I started doing that for other classes. If I was stressed on time, I got more sleep, did better work on it, and just turned it in late, for still great grades even with some time penalties.

I realized maybe I didn’t have to take all this so seriously. Maybe I was even paying attention to the wrong things. Maybe I should instead maximize for how much fun I could have and what I could learn from the work instead of maximizing things like my class rank. Maybe I should just do it my way.

From then on, I enjoyed the rest of my time in highschool. And here’s the thing, I still ended up with a great GPA, and a high rank in school. I can’t tell you anymore what it was, still top 10, maybe even in the top 5. But I can’t remember, because I stopped looking. I stopped caring about it.

Instead, just doing as good a job as I could within some sane limits of my time and well being, and optimizing for my happiness, still produced great work. I was happier, and succeeded with what I wanted.

I didn’t give up when I was struggling, I kept going, but in my own way.

Ever spend some time thinking about what you are optimizing for? Is it stuff you have a real hard time controlling? Are you trying to out-do your competition by spending a great deal of time comparing how you stack up against them? Would you be better off still working hard, but making sure you were optimizing for how much fun you were having doing it?

A wise reminder from my precocious two-year-old. Worth thinking about as I go through some new struggles today.

Just go; do your thing.

P.S. If you enjoyed this article, you should follow my YouTube channel :) And if you find yourself struggling while organizing your own small business, check out how Highrise can help!