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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  1. Happy belated & thanks for sharing about your journey Jason! A major shift in perspective for myself is learning how to let lose and have fun like a simpleton.

    Having done sport at a competitive level too, I tend approach life with a structured and methodical approach. This affects my down time where I am stuck in logical  work mode and prefer intellectual conversations.

    While I get the part about being a go getter, I have since learnt to immerse myself in play time better. For example appreciating the fun vibes at a festival and lowering my criteria for jokes and laughter among friends. 

    I’m much happier and able to connect with more people now. Also more well rested and productive when its time to return to work.

  2. Jason, I appreciate your blog and your drive to be the best you can be.  Thank you.

    My perspective on why one should strive to be the best one can be has shifted over time (I’m 65 years old now).  I’ve been through periods of time when athletic or academic or even business achievement were important to me.  Being seen by others as successful, talented, etc. was ego-gratifying.  I enjoyed it and wanted more.  And that turned out to be the challenge because there wasn’t always more to be gotten.  Nowadays, I think the neuro-scientists would say that these were dopamine rushes.  I’ve had other periods of time when I wanted to be happy.  Happiness can be a great but also fleeting way of being.  Having a family, building a business…these were experiences that weren’t always “happy” but they were fulfilling in many ways.  Sometimes sad and tragic things happen (you’ve talked about overcoming your athletic injuries, for example). I’ve experienced divorce, lawsuits, homelessness, bankruptcy, deaths of family members…sometimes it’s hard to see why one should continue to strive to be the best one can be. But from my perspective, I think that there’s no other way of being because there’s no other way of living a meaningful life, one where you can have both happiness and fulfillment in spite of what external circumstances occur.

  3. Jason – came to you via Scott Britton a few weeks ago. Love the blog. Happy birthday bud!

    What made my mindset strong in many aspects was the idea of “being comfortable being uncomfortable”. I wrote a blog post detailing my journey that begin entering Junior year of high school. I began socially awkward, the definition of an introvert in every way (well, all the bad ways, not the good ways. Still an introvert and proud of it! So don’t read that as an extrovert ideal). I learned that the best way to grow was to embrace discomfort, and even seek it out. I did a lot of different things to do this – Mixed Martial Arts, Ballroom and Latin Dancing, leadership programs, certain types of jobs, and so on. It carried out into my work and dating life as well.

    I still believe that to be one of my most important attributes, both personally and professionally – being comfortable being uncomfortable. It changes what you do in all aspects of your life!

  4. My 22-year old self was fresh out of college and bright-eyed and bushy-tailed about starting a company. However, being young and naive, I thought the idea made or break a startup. If I could send a message back through time, I would share the following principle with my younger self:

    “Get the right people on the bus, the wrong people off the bus, and the right people in the right seats.”

    This is a quote by leadership studies author Jim Collins from his book “Good to Great.” Collins argues that the team trumps the idea. His bus analogy attempts to make the point that, while your destination may change, as long as you have qualified and capable people in your company you can successfully course correct. In contrast, even the best idea will sink a weak team.

    At age 28, I’ve pursued a handful of startup ideas. Reflecting on my mistakes, I think I often over sweated the idea rather than the people with whom I pursued it. Six years older, I now take Collins’ point to heart and focus more on the individuals with whom I hop on the “bus.”

  5. thaironius Thanks for sharing Thai! I do think sometimes we over emphasize the idea and overlook how important the people are around you.

  6. Hi Jason, thanks for that cool post, happy birthday retrospectively!
    I also turned 28 this year. What I have learned, is to ignore “the game”. :)
    I find usefulness plays much stronger physics on the market than human irrationality. If I sell an elixir that makes people 20 forever, I don’t need to game it.
    I agree that it can be gamed, just like the lotto can be won; I just think the inherent risk is too high, and one’s learning is not adding up in a concentrated direction, while persistently moving in one direction does add up. Thus I think it is bad investment.
    I spent 13 months chasing the irrelevant for just another 2 weeks, while I had a working product that needs no tricking just loads of work. I thought I could cut corners with fast money.
    Hope you don’t mind the disagreement :)

  7. Let me see. As life goes along, I realize I might never be good at business. So instead of trying to be good at business stick to what I am good at. I would consider myself a very good software engineer, so I am sticking with that now. But there is still the desire for huge financial success. So, I decided to build something that will sell itself.  I am trying my hands at creating Artificial General Intelligence.

  8. RNAKAMOTO2 Fascinating – so your main attitude (be the best) has stayed the same, but your reason for doing it has changed? That’s awesome. Thanks for sharing!

  9. chegra That’s not an easy thought to swallow chegra – thanks for sharing it with us. Wishing you the best with your AI project!

  10. Bin Teo Charlie Hoehn has recently written a book about play and its deep value to keep us happy, healthy, and productive that you might want to check out. Thanks for sharing!

  11. Humility and Arrogance. I used to believe I couldn’t possibly be wrong. Now I’ve learned to accept that the possibility I am wrong is non-zero. 

    When I was “younger” (I’m 23) I used to believe I must be right when I thought I was right because I was intelligent, capable, etc. I knew I was right so there’s no way I could be wrong. However, over time, I went through experiences where, upon self reflection, I realized that even though I was wholly convinced I was right at the time, I turned out to be wrong. Sometimes completely wrong, but more often just slightly off, missing an extra perspective or detail that would have changed the whole situation if I knew it applied. For example, I thought the entire concept of investing was a perpetuation of wealth inequality so I refused to take on investors for my start up on that principle. The idea being that only if you had money could you invest, and having money is more dependent upon your birth than your hard work (more people are born wealthy than are made wealthy through work–I have absolutely no proof for this, perhaps this is another example of things I used to believe were right but aren’t) so the rich get richer and the poor get poorer. Now I know the institution isn’t designed to perpetuate wealth inequality, but it’s just natural a result of competing interests and the greater bargaining power of the rich. Another example is that I used to think I was exceptional at writing, and when I would get a bad grade I would think it must be because the evaluation system is broken since it is unable to appreciate what I bring to the table. Then I read my writing a few years later and was shocked at how childish I sounded. 

    One one hand, it is a good thing to always be able to look back at yourself and find mistakes: it means you’re learning and improving over time. On the other hand, it does create the possibility that you might not be doing the right thing with your life right now. Somehow, we must both be confident in our present selves and decisions, despite knowing we may realize we’re wrong. Finding out what you’re good at, and what you should take other people’s advice for will help with this. (more

    Thanks for the prompt Jason!

  12. Well I am still 27, soon to turn 28 and  27 has been a big year for me.  I have been seriously injured twice (ski injury to knee, bicycle injury, major surgery), I have started my own company (again) and I have been debating proposing to my girlfriend.  What I have learned this last year is that life is constantly changing, is highly unpredictable, and that the best course of action is to make the best of things/situations when they happen.  

    My injuries were a major setback for me, since I am an extreme athlete, but what I have been able to do with all of the time at home is hone my jazz piano skills, focus on the business and read about 40 new books, which has been an extremely fulfilling way of using my time.  I am ready for 28, kind of hoping it isn’t as painful as 27, but stoked for each moment I get to live.  Carpe Diem

  13. Nice response Jason. I totally agree with your view.
    For me it’s changing my perspective to using both western culture and my parents culture to full benefit. Currently I stay with the parents and this used to be a big part of my same because it goes against western standards.
    Considering I’m taking care of my parents and chip in rent money I feel more valid about the perspective and using the money I save to travel to other places.

  14. Hey everyone! So sorry for the delay here. I just did a random number generation between 1-9 since we’ve got 9 responses here. The number turned out to be three (Generator:

    In descending order, that means AttemptedLiving is the winner! Look for an email in your inbox bud!

    Thanks everyone for your great thoughts. It made my birthday that much more awesome.

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