Let’s talk about the trade-offs between taking the time to do your homework on something and getting ahead through decisive action.

My father is running for a seat on the school committee of my hometown and I’ve been helping him put together his website. His initial list of campaign priorities emphasized broad themes: academic excellence, teacher quality, things that few would disagree with.

I’ve pressed him for details how exactly he plans to fulfill these priorities. More teacher training? New classroom technology? Overhauling the teacher hiring process? He would demur, not wanting to advocate for any specific policies before he has a better understanding of his constituents. Sure, the election is months away, but with a better known candidate also in the race, I’m concerned his nebulous platform won’t win him any new supporters. [1] Continue reading

This is an excerpt from my book, How to Get What You Want (a primer for ambitious people).

We all know that teenagers are highly susceptible to peer pressure. That’s why parents are often concerned when their children are hanging out with “the wrong crowd”. But eventually we grow out of that phase, and learn to make decisions on our own right?

Not quite. Consider something as simple as purchasing a snack or a film on an airplane. Continue reading

We make comparisons between business and sports all the time. We talk about hitting a home run, taking more shots, playing defense. But one of the challenges of business, compared to sports, is the rarity of the unadulterated victory. Whether it’s a friendly pick up game to a state title to the Olympics, winning a competition offers something pure and simple. A true win. Yes, the victory may be temporary – next round, next game, next season – but it’s still very real, very tangible. Continue reading

Editor’s Note: I’m on a two-week trip to Peru! Follow on me on Twitter for updates. I had a little down time after an exhausting surf lesson and wanted to share one of my favorite pieces on change research. – Jason

We can learn a lot from the lessons of other people. This is why we always ask older people what they regret most in life: by hearing their perspective, we can hope to avoid their mistakes.

It’s a new year and many folks are thinking about goals, resolutions, and habits for 2014. I’d like to offer a resource from a great study done by researchers at Dartmouth and Harvard that analyzes 119 stories of either successful or failed attempts at “major and sudden change”.

“Personal Accounts of Successful Versus Failed Attempts at Life Change”

Todd Heatherton (Darthmouth) & Patricia Nichols (Harvard) Personality & Social Psychology Bulletin 1994 Continue reading

angry and cocky

I was talking to some folks about applying to Y Combinator [1] and preparing themselves to found a startup more generally. One point that I found myself talking about, especially in terms of timing, was the two distinct emotions that I that many founders seem to posses, especially in the early days. [2]

They have an intense dissatisfaction with something in the world and an irrationally large sense of confidence about themselves.

As any founder will tell you, doing a startup is hard. Being passionate about the market you’re tackling, having a love for building great products —  that’s all well and good. But when push comes to shove, there are few things more motivating than being a little pissed off.

When you’re mad, you work harder, you hold out longer, you move faster. You might be mad at the big players who are screwing over consumers, mad at your old boss who turned down your promotion request, mad at all the investors or media people who don’t get what you’re doing.

And that anger is fuel.

Paired with the anger is thinking you are the shit. To take the plunge and do a startup is to implicitly say:

“Despite the fact that most startups fail, I think I can succeed. And thus I believe I’m smarter, more capable, more persuasive than the majority of founders.”

It takes some cockiness to say that. Think about Elon Musk, Steve Jobs, Mark Zuckerberg, Paul Graham, Jack Dorsey. [3] In their own way, each had a tremendous belief in themselves: their vision, judgement and abilities.

When I started Ridejoy, I had a chip on my shoulder, in part because the CEO of the startup I worked at once told me I was “a bit junior”. And yet he had dropped out of college to start that company and was the SAME AGE AS ME.

I’ve always had a unreasonably large amount of confidence and I did believe that I was better than other founders. Getting into Y Combinator certainly supported that thesis. [4]

By no means were these qualities “everything you need” to be a success. In fact, you’ll still most likely fail. But if you were thinking about making the leap asked me if NOW was the time to start your company, I’d ask: “Are you feeling a little angry? And a little cocky?”

FOOTNOTES

[1] If you don’t already know, I’ve written a 92 page guide to applying to Y Combinator – you can get it for free if you sign up for my email newsletter

[2] Clearly this is anecdotal evidence —  and yet our brain is wired to respond to stories and data of this nature. Take from it what you will.

[3] Same deal as [2] – correlation doesn’t prove causation, but sometimes it can suggest it.

[4] I say that at the risk of sounding like an douche, but I’m just telling the truth. When you’re in the top 7% of thousands of teams who apply to YC, you start to feel a little special.