When Ambition Leads to Failure

Photo by Rob Bye

Someone asked me the other day what personality trait I had that’s responsible for the success I’ve had in life. There’s two things to that question I’d like to unpack. The personality trait, which I’ll cover in another post soon, but maybe even more importantly, what is this “success” they spoke of? :)


I’ve founded and run various software companies. Today, I run a company with tens of thousands of happy and paying customers that generates millions in profit.

I don’t say this to brag. I’d never brag about this. I don’t feel like I have anything to brag about.

Because I simply don’t feel successful. There’s so many things on my plate right now that I’m chasing. Company growth. Audience growth. Team growth. Personal growth. Experiment after experiment. And most of those experiments don’t work out.

I feel like I’m constantly chasing my idea of success and never reaching it. Why is that?


Something struck me in a reread of David and Goliath, Malcolm Gladwell’s most recent tome about underdogs.

He writes an analysis comparing graduates of STEM degrees at Harvard and Hartwick College. Harvard is #1 on Forbes list of Top Colleges. Hartwick is #509.

As you’d expect, the top Math performers can more easily be found at Harvard than Hartwick. The top third of STEM (Science, Technology, Engineering and Math) degree students at Harvard scored an average of 753 on the math portion of their SAT. That’s near perfect. The bottom third at Harvard — an average of 581.

Is that good or bad?

Well, if you compare it to Hartwick… Of the folks enrolled in STEM degrees there, the top performing third of students scored an average of 569 on their Math SATs. The worst math student at Harvard is a better math student than any, even the best, student at Hartwick — on average of course.

Again, this probably isn’t surprising.

What was surprising however is the percentage of STEM majors who actually graduate with a STEM degree.

Top students at Harvard 53.4%. Bottom students at Harvard 15.4%. Top students at Hartwick 55%. Bottom students at Hartwick 17.8%.

Practically identical. And that’s strange.

Students who have tested better at math going to the most elite school in the US, are dropping out at a higher/same rate from STEM degrees than students they perform better than at Hartwick.

What we’re seeing is the Big Fish Little Pond theory introduced by Herbert Marsh, a psychology professor at the University of Oxford.

Marsh described it as “equally able students have lower academic self-concepts in high-ability schools than in low-ability schools.”

In other words, we feel worse about ourselves when we compare upwards. So worse, that it might even cause us to change our behavior and goals because we don’t think we can hack it.

If only we had a different perspective we’d see how far we’ve come.


Since I graduated from college in 1999 all I wanted to achieve was to run a software company. Trouble was I was a chemical engineer without any software experience. I took a job at Accenture (Andersen Consulting back then) as a glorified secretary, writing down meeting minutes, and making sure people had read and signed whatever document they needed to.

It was terrible, but at least it was a foot in the door to worlds I wanted to be part of. Technology. Business.

The goal still looked bleak. I didn’t have the skills to actually even make software yet, but I put my head down and tried to move forward. I’d stay late at work every night, using the fast internet (I was living with my parents and they had dial up AOL) to download Java and start practicing how to make things with software. It felt like it was taking forever. A lot of nights where people were going out with friends, I was at home working on some programming problem. Eventually, eventually, I had some aptitude to start building really cool things, like the prototype I showed up with to my Y Combinator interview in 2006 convincing Paul Graham to take a shot on us to start a company.

Back then I think it was easier to understand success. I was trying to be a software entrepreneur amongst a group of consultants who only talked about being entrepreneurs.

Today some of my friends run the most trafficked, or the fastest growing, or the most profitable businesses you can think of.

And it’s great. But it doesn’t always feel great. :)

I know there’s people out there reading this in the exact same situation. You keep comparing yourself up. Wanting more. Ambition is wonderful, but only when it motivates you to keep going.

There’s an ugly flip side when it causes you to think you should give up when really you’ve already come so far.

So what’s the solution?

Adam Grant, another great author and professor at the Wharton School of the University of Pennsylvania offers a helpful thing to remember:

Get acquainted with your former self. Compare your current accomplishments to your past expectations. And for a few minutes, before you’re jolted back to the present, you’ll feel contented. Maybe even proud.

P.S. If you enjoyed this article, you should follow my YouTube channel,where I share more about how history, psychology, and science can help us make better decisions. And if you find yourself organizing your own small business and sales, check out how Highrise can help!