Hey friends,
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The events of this week have got me thinking about advice and how we should approach giving it out to others.
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​On the topic of advice: as always, please feel free to let me know your own thoughts on anything I’ve said by responding to this email or messaging me on Twitter. I’d really appreciate hearing what you have to say. It helps me clarify my own thoughts and make sure I live up to my promise of delivering valuable information.
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​Up until this point, I’ve always hated giving advice. When asked for my opinion from friends and family on the choices they were making, I often took the non-committal route of redirecting questions back to them and avoiding making a recommendation on what they should or shouldn’t do.

Based on my own experiences, the model that I had built up in my head for making decisions was that no one could help you make that decision. Being someone who looks inward instead of outward for the answers to my problem, I believed it was best to give the conservative response of “you should do what feels right” or “follow your heart.”

This came from a place of doubt and fear. I felt unqualified. Why should my opinion matter on this or that topic and how can I really be sure that what I tell them is the right thing for them to do. I feared that my advice would lead them in the wrong direction and couldn’t live with the responsibility of having somebody make a mistake based on what I had told them.

These fears came up this week when I was asked by a younger friend of mine for advice on what courses he should take come next school year.

Having been in his place just a few years back, I asked him a few questions including what his desired outcome was, what reservations he was having and what thoughts had come to him so far. I listened to what he had to say and told him what I thought he should do based on my experiences and what others had told me. I didn’t think much of it.

It was when he mentioned something about hoping to get the same grades as I did that I felt a great deal of responsibility. I realised that being someone who had done well in school, my words would likely weigh heavily on his decision. It scared me.

I thought of the people in my life who I looked up to and how everything they told me felt like sacred wisdom. Knowing that I could have the same effect on somebody else, I came away worrying that I had said the wrong thing.

Having time to think on the walk home, I thought back to how choices in my own life were influenced by the (sometimes not asked for) opinions of others and working through it all helped me come to this conclusion:
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When giving advice, taking a hard stance risks having the receiver go off in the wrong direction but taking no stance only assures that they go off having gained nothing.
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The conservative choice assures the chance of no significant negative outcomes but it does so at the expense of removing significant positive outcomes. This is the case with everything from business and investing to sports and relationships. Not asking your crush out assures that you don’t have to face the embarrassment of rejection. It also means removing the chance that you’ll be with the person you want to be with.

We add value to others’ lives by contributing a different perspective on the world. People look to those around them for advice because they want to escape the echo chamber of their own thoughts and look at their problems through the eyes of another.

Of course, you shouldn’t give advice on something you know little to nothing about. Providing things like financial 🚀 and medical advice should remain the responsibility of those who have some domain expertise and shouldn’t be taken lightly. But for most other things, your insights have value so long as you are (1) looking out and considering the best interests of the person seeking advice (2) explain where you’re coming from and (3) caveat it as an opinion to be weighed with many others and one’s own judgement.

Your words can help others see new insights, overlooked points and holes in their thinking. Whether or not they agree with what you tell them is up for them to decide. If they agree, they will have come away with a new answer to their problem and if they don’t, they’ll come away with a stronger conviction.
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Don’t fear giving advice, fear not providing value to others.
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See you next week,
Dylan

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Favourite Reading

​Tinkering Versus Goals​
Venkatesh Rao writes the blog ribbonfarm. His second project, Breaking Smart, is dedicated to exploring the new digital economy we find ourselves in and the implications it will have on our lives and the future of work. His collection of essays from 2015 serve as both biography and crystal ball for software ‘eating the world.’ Even if you lack an interest in technology, this is an interesting discussion on the two modes of problem solving founded on two ideologies old and new. Give it a read for an answer to the question of why ‘tinkering’ offers us a better way to solve problems.
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​The Problem with Optionality​
Options are financial instruments that give investors the choice of selling/buying a share at a given price without committing to doing so. Optionality stems from this idea of a non-committal widening of one’s options that many students seek out by pursuing jobs like consulting where they get a ‘broad’ set of skills and the chance to network with individuals and companies they could work with in the future. This piece is a word of caution on how maximising optionality can make for a stagnant life where we put off pursuing our dreams.

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Great Conversations

​[The Brandon Zhang Show] Brett Goldstein​
Brandon Zhang, writer and student at Columbia University, interviews Brett Goldstein of Launch House. The two of them talk startups, being multidisciplinary, not letting yourself be defined by your major and how to find work you’re passionate about.
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​[The Quest] Michael Seibel: From Justin.tv to Twitch​
​Justin Kan started justin.tv, the website that would become the streaming platform Twitch which Amazon acquired in 2014 for almost $1B. Michael Seibel who cofounded the company with Justin talks about his life going from a Yale dropout to political campaigner to startup founder to CEO of Y combinator. A great story about the unexpected twists and turns in our lives and how we should seek out opportunities that we may never come across again.

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A tweet to think about

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Quote that I’m reflecting on
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- James Allen