Which professions do most people dream of? I don't have data for this, but we can assume that most of them score high on visibility, status and pay; are desired by a great number of people; and are probably very competitive.
It follows that if you take the standard advice to 'follow your dreams', you will try to get into one of these professions, and you will likely fail.
This injunction to follow your dreams is usually complemented by another which calls for persistence in the face of failure. This implies a negative view of failure: it is an obstacle that you must overcome, a challenge that life and other people throw at you to test what you are made of. If you persist in the face of failure, you have the moral high ground, and you will eventually succeed. But if you surrender to failure, you are a failure yourself, and you are not trying hard enough. I would like to challenge this notion.
When you fail, it usually means that society does not want to sponsor your work. This can be framed as a case of information asymmetry. There are two explanations: either your work is valid (a "peach") and society is underestimating it, or your work is not valid (a "lemon") and you are overestimating it.
Who is more likely to be right? Probably society: after all, selection processes incorporate the aggregated knowledge and expertise of many, while it is easier for an individual or a marginal group to be deluded about the value of their work.
Yes, history records cases when underdogs were right and gatekeepers misjudged them, but this is the exception rather than the rule; and only exceptions make history. Most startups ideas are just bad, as are most books who end up on an editor's desk and most songs uploaded to Bandcamp. Even work which is not bad in itself (in the sense of low quality) can be excluded because it is not good enough for the market. A global and competitive market will have high barriers to entry. Some works may be excellent but lack a market. For example, even if I had the skills to write an excellent epic poem (I don't) I would not get the success that Homer or Dante had in their time, because nobody cares about epic poems today.
In other words: "wide is the gate and broad is the way that leads to failure, and there are many who go in by it." This should convince you that if you fail, you should probably take the cue and move on, instead of wasting time and resources.
Failure is good for you. It is a feedback message telling you that society wants you to focus on something else. Moving on is a sign of reason and maturity. It allows you to negotiate your role in the world and find an activity that is rewarding for you and useful to others.
Those who made it to the top followed their dreams and persisted in the face of failure, and they feel compelled to remind you of that whenever they get invited to a graduation speech. Young people who listen to them assume that their policy is responsible for their success. But most people who follow their dreams fail, and those who blindly persist in the face of failure are hurting themselves more often than not.
Capitalism has a way of turning irrational confidence into societal gains. The fact that 90% of startups fail is terrible news for whoever wants to found a startup. It also means that 90% of founders are overconfident. While failing a business is a serious blow for an individual, it is a small loss for society, which is more than made up for by the 10% of businesses that succeed and go on to create a lot of value. Consequently, as a collective it is profitable for us to encourage the 'follow your dreams' ethos, even if the behavior itself is damaging for most individuals who adopt it.
(This is somewhat analogous to how the alarm call in certain birds species works. The act of signalling a predator might endanger the individual by attracting unwanted attention, but it might still be profitable for its genes if it increases the survival chances for its kin.)
I do not mean to say that you should not be ambitious. You should aim high in your endeavors and try your best to do something great. And you should not give up too soon. But if you are trying to break into a field where failure is the likely outcome, you should aim to fail early (to save time) and fail safe (to save other resources). And when failure happens, don't be ashamed to take the cue and move on.
Related: ‘Never Settle’ Is A Brag.
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