How Has Your Perspective Changed? (My 28th Birthday Question Giveaway)

A few years ago, I started a birthday tradition on this blog, where I ask readers to respond to a question, and give away a sweet prize.

When I turned 26, I asked “What’s one thing you wish you knew when you were 26?” When I turned 27, I asked readers to tell me about an important decision they had made.

Last week I turned 28, and it’s time for a new birthday question giveaway!

One random commenter will win a hardcover or Kindle copy of Think Like a Freak, a really rad book by writer/economist duo Stephen Dubner and Steven J. Leavitt (authors of Freakonomics and SuperFreakonomics). I’m about halfway through and really loving it.

This year’s question is:

What’s something you’ve changed your perspective on as you’ve gotten older?

So to be fair, here’s my answer to the question:

As I’ve grown older, I’ve come to appreciate the need to “play the game” [1].

Science was one of my first and most enduring interests. I loved the idea that we can develop a rational understanding of the world through experiments, hypothesis testing, and hard data. I liked that we could develop clear lines between correct and incorrect answers. Things made sense.

I also struggled more ambiguous subjects like English and to some degree History, which required students to argue for theories which were mostly unprovable. Finally, I wasn’t very good at dating, a complex and confusing social dance which held quite a bit of ambiguity and some posturing (when I was too forward with Vivian, my middle school crush, she lost interest. WTF?)

Needless to say, I disliked the idea of “playing games” in romance or business. Why can’t everyone just say exactly what they think and express their goals plainly and clearly?

So for instance, when I was applying to colleges, I was offered a partial athletic scholarship to Stanford. My family and I were thrilled! It was my dream school. I had also been offered basically a full ride to the University of Minnesota, which was a wonderful school but it would be cold and the academic rigor simply not as high.

My parents wanted me to pretend to the head coach like I was still thinking about going to Minnesota, weighing that option. I disagreed vehemently. I knew, and my parents knew, we would have had me go to Stanford even if they gave me nothing! I thought it was almost unethical to not acknowledge that and take the partial scholarship offer.

Fortunately for me, my parents decided simply to speak to the coach themselves, and got the offer raised 10%, which over four years of school, saved something like an extra $16k.


Over many years of starting things, building things, and marketing things, I’ve come to appreciate “the game”.

I get that negotiation, sales, fundraising, dating, marketing and other human interactions are complex and intricate things. We make decisions for far less than “rational” reasons and power dynamics require people to do some amount of posturing, signaling and “game playing”.

If you don’t play the game, at best you might be considered a little awkward and strange, at worst you will be at a severe disadvantage in many interactions. Even if you choose to broadcast that you “always play it straight”, that in itself is a kind of game – like a no-haggle car dealership. So there’s basically no way out.

So as I’ve gotten older, I’ve gotten off my high horse, became pragmatic, and started learning how to play “the game”.

Your Turn

Ok, now it’s your turn. Tell me about a time when you’ve changed your perspective on something as you’ve gotten older! Celebrate my 28th with your story as a comment down below and you could win a copy of Think Like a Freak!

(A winner will be selected on Tuesday June 3rd at midnight Eastern)


[1] To clarify, what I talk about when I talk about needing to play “the game”, I mean the need to understand the complex social dynamics involved between people and adjusting your behavior and language to the situation and context. For instance, the way you talk to someone when you are trying to raise money for your startup is different from the way you might approach a customer is different from how you might approach an attractive person at a weekend BBQ.

I have read The Game by Neil Strauss and while I find many of the tactics employed by “pickup artists” distasteful, I think the core thesis of the book, that dorky unlucky-in-love guys can learn to become more successful with women is an important one.

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