An even click-batier title than How to start iOS contracting.

I believe that advice is helpful up to a certain point, after which it becomes detrimental. There are many articles written on why advice can be bad, so I’m going to focus on the two reasons that I believe are novel. They are: 1) The person giving advice isn’t the same as you. 2) Advice-givers are generally incentivized to be overly-conservative.

Before we explore these two reasons, I want to clarify my thoughts on the postive aspects of advice. Of course, advice is a net good. Without it, everyone would have to, for example, burn their hands on the stove to learn that it’s hot.

In a broader sense, learning by reading is a form of advice. Reading or similar learning mediums are absolutely necessary for the progress of society.

Problems with advice arise when it’s about something personal, and when you’ve achieved some experience.

Advice-givers are not you

Generally, when someone gives advice, they’re describing what they would do in your position. However, that person has different goals, life experiences, etc. than you do. It’s very hard to filter someone’s advice through that lens even when you’re consciously trying to do so.

A more concrete example: I’ve always struggled with what direction I want to take my career in. I read a lot of biographies [1], and because my desire is to achieve financial wealth, and I currently work in the technology sector, that leads me to read biographies about successful technology entreprenurs. The problem with that is, I’m not like a lot of them!

So, I would read Bill Gates’ biography, and I would feel bad about myself. His goals were things like: intellectual prestige, creating the best software and working with new technology. My current goals are: respect, financial wealth and interest in the opposite sex. [2]

Because my goals didn’t align with Bill’s, I would assume I’m on the wrong track, or I have a bad moral compass. In reality, my goals are shared with many successful american males. I’d argue that a majority of american musicians and athletes have the same goals as I do. I just don’t have the same goals as Bill.

You may think that you can filter out the differences between yourself and the advice-giver, but it’s quite hard. Their way of thinking will seep into your thoughts, especially if it’s someone you hold in high regard.

Advice-givers are overly-conservative

Humans generally over-value negative events relative to positive events. Because of that, advice-givers usually are more concerned with not having their advice “come back to bite them”, rather than create the best possible outcome for you.

A particularly salient example: I’m part of a Slack group for iOS developers. [3] We have a channel for freelancers such as myself.

Recently, a member asked for advice on what is a valid business expense and what isn’t. People were suggesting he couldn’t even expense meals! If one of us suggested he could expense that meal, and he went to jail for tax fraud, he would absolutely remember who gave him that advice. However, if he was successfully able to expense that meal, he would not remember who saved him that $12 in taxes.

As a result, everyone gave him overly-conservative advice.

This post is still under writing. I’m unsatisfied with it so far.


[1] I read biographies for the purpose of achieving success using a similar method as the subject of the biography. Because of the way I use the biography, it’s a form of advice.

[2] I’m quite uncomfortable sharing these goals in a professional context. However, I think total honesty on my part will create the best results for the reader.

[3] It has been one of the best sources of learning I’ve ever experienced. Tech-utopianists argue that because of the internet, humans won’t need to cluster creators together in cities to achieve the positive combinatory effect you see in tech in SF now, or art in Florence in the 1500s. This group has been the best example I’ve experienced in support of that argument.