Don't Follow Your Dreams (Too Far)

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. 

Build Yourself a Theory of Happiness

When planning for the future, one of the greatest challenges is that we're bad at predicting what will actually make us (un)happy. In other words, we lack a theory of happiness. 

A person from an average-sized town leaves everything behind and moves to London, only to find that they are crushed by the loneliness, high costs and stress of the big city life. Someone who achieved sudden wealth buys a big mansion in a gated community, wherein she starts to feel lonely and alienated, and finds herself missing the communal living of her student years. Another takes up an important job at a fancy firm, where the stress and long hours drive them to depression. 

In these examples, the problem is not with the choice itself. Some folks may end up happier moving to London, buying a big mansion or getting the fancy job. The problem is with the process, which is often faulty. All these choices happen to score high on prestige and monetary reward. Sometimes, being unable to identify the predictors of our happiness, we resort to the substitution principle:

If a satisfactory answer to a hard question is not found quickly, System 1 will find a related question that is easier and will answer it. (Kahneman, p. 97)

Hence we unwittingly default to proxies which are easier to measure, such as money or prestige. The question "which job will make me happiest?" becomes "which job will give me the most money or prestige?" Many important dimensions are lost in this conversion. 

The other problem is that we are bad at simulating how our life will actually be like under the new circumstances and how we will feel about it. When we try to simulate the future, we tend to fall on the inside view: we roughly imagine what the future would look like and see what feelings these images evoke in us; then we use these feelings as a cue to our future feelings and satisfaction. This is an understandable heuristic, but it's ineffective. 

Here's a better approach. 

First, you need to test your ability at predicting your happiness. It may help to set up a diary where you try to predict your happiness at different points in time, or conditional on certain events occurring or not, and then rating yourself on the predictions. I may set up a framework for this in a future post. 

Then take a scientific approach. Gather the experiences of others and the results of previous research. Formulate hypotheses, such as 'I would be happier with job X than job Y'. Devise experiments to test them, such as getting internships for X and Y and tracking your satisfaction. Finally, use the results to update your beliefs and formulate better hypotheses. This is how you build a theory of happiness. 

It's true, we can't always afford the whole process. Experiments can be costly, difficult to implement, and ambiguous in their interpretation. For example, if you were unhappy during internship X, is it because you actually don't like the job, or is it because of contingent factors, e.g. you didn't like the company, or the project you worked on was unattractive? 

Nevertheless, I find it useful to keep this in mind as the golden standard of pursuing happiness. And to be conscious of the heuristics I use to approximate it and their limitations. 

Whenever I make plans for the future, I try to at least implement the first step: putting aside easy proxies such as money and prestige, taking the outside view and gathering objective information. This is already a long way from the standard approach of simulating outcomes in my imagination.