TL;DR
9/10. Ego at three stages: when you are aspiring, when you have succeeded, and when you have failed. Better than The Obstacle Is the Way because the argument cuts against the reader instead of encouraging them, and because the success section is aimed at exactly the person likely to be reading.
The claim is that ego is not confidence and is not ambition. It is the need to be perceived a particular way, and it costs you differently depending on where you are.
Aspiring, it substitutes talking for working. Successful, it makes you unable to hear anything corrective. Failing, it makes you unable to accept the situation and start again.
The three-part structure mirrors the earlier book and the content is harder. This is the one I return to.
Why is talk cheap?
Because announcing a project delivers the recognition you were going to receive for finishing it.
That is the sharpest sentence in either book and it explains a behavior I have watched for thirty years. Somebody tells everyone about the book they are going to write. The telling produces the response, the interest, the sense of being a person who writes books. The reward has been collected and the work becomes optional.
Holiday cites research on this and the research is contested, which does not much matter, because anybody who has announced a project instead of doing it recognizes the mechanism from the inside.
The practical instruction is uncomfortable and correct. Do the work quietly and let the finished thing be the announcement. For a writer that means not telling people you are writing a book until there is a manuscript, which almost nobody manages.
What does ego do to a successful person?
This is the section almost nobody writes, and it is why the book is better than its predecessor.
Advice assumes a climbing audience. Books are sold to people who want something they do not have, so the entire genre is aimed at the aspiring, and the failures of the successful go undocumented because nobody is buying a book about them.
Holiday spends real pages on it. Surrounding yourself with agreement, because disagreement has become expensive for the people around you. Interpreting luck as skill, which is the standard error and which compounds because success provides no feedback distinguishing the two. The inability to take a correction from anybody junior, which cuts you off from the only people who can still see clearly.
And entitlement, control, and paranoia, which he treats as the characteristic failures of people who have got what they wanted and are now defending it.
What about failure?
The third section deals with ego when things have gone wrong, and its argument is that ego makes failure permanent.
A person without much ego assesses a failure, extracts what is usable, and starts again. A person with a great deal of it cannot do the assessment, because the assessment requires admitting the thing happened and was partly theirs, and so the failure becomes an identity instead of an event.
The chapter on the difference between being wronged and being ruined is the useful one. Plenty of things are genuinely unfair. The question is what you do afterward, and ego answers that question by demanding the unfairness be acknowledged first, which frequently means nothing happens at all.
Does Ego Is the Enemy have the same flaws as the first book?
Yes and it survives them better.
The examples are chosen to fit, the history is compressed, and a reader who knows one of the figures well will find the treatment thin. That is the standing problem with this format.
The difference is that the argument holds without the examples. Take out every case study and the claim that the need to be perceived a particular way will stop you at each stage of a career survives intact, because the reader can test it against their own behavior.
That is not true of everything in this genre and it is not true of the first book, where the case studies are carrying more of the load.
Verdict
The best of Holiday’s three, and the one worth rereading. If you take one thing, take the observation that announcing a project provides the recognition you were going to get from finishing it, which is why the announcement so often ends the project.
Read the success section even if you do not feel successful. It is a description of a failure mode you will not notice from inside it.
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