Out of the thousand articles I’ve written, there are few that I genuinely like. Most of those I feel are mostly correct or useful, upon reflection, are still lacking in a lot of ways. Sometimes they’re too wordy, the research is too sparse or there are obvious counterarguments I ignored.
I feel the same way about all of my books, and all of my products. Since I wrote Learn More, Study Less , several years ago, I’ve done at least five major renovations (although often as different packages, rather than a complete replacement to its predecessor). Even after five generations, I’m still not satisfied with my work, and it will probably take me another few thousand hours of work before I might be.
Looking back at when I did the MIT Challenge , I see the flaws in my design. I can think of dozens of ways that would have make the project more successful, more generalizable to others or more interesting. I’m not finished yet, but I’m sure I’ll look back on this current project  with a similar eye for its shortcomings.
Because I live in a Western society, where any lack of self-praise that doesn’t border on oblivious narcissism is somehow an illness that needs to be cured, let me stress: I think this a good attitude to have about your own work.
Too Much Self-Esteem?
If you look throughout history, or across other cultures, it’s hard to see why self-esteem in your own work is currently seen as an indispensable virtue. Eastern cultures historically valued modesty and a focus on process rather than your accolades. Even Western culture’s roots recognize the danger in self-praise: pride did, after all, make the short-list of deadly sins.
Today, self-esteem seems to be the quality one can never have enough of. Almost any problem, from depression to narcissism, somehow stems from not having enough self-esteem. Every successful person is painted as someone with unwavering faith in themselves and their talents.
There’s definitely a point at which, below that, having too low an opinion of your work is crippling. You end up obsessing over details instead of going out into the real world and getting feedback. Maybe you’re below that point, in which case this entire article doesn’t apply to you. I don’t know.
But, I feel, just as there is definitely a lower-threshold where insufficient self-esteem kills your motivation, there’s definitely an upper threshold where it blinds you to feedback. When you think too highly of your ideas and your work, then you can’t see the flaws which should be improved for the next iteration.
Balancing Self-Criticism and Praise
Since knowing exactly where those limits lie is difficult, I’ve found it’s better to employ a rule of thumb: your past work, which needs no motivation since it is already complete, is optimally viewed in a more self-critical light. Your current work, which needs commitment to a plan and less wavering, needs more of your inner motivational speaker.
When I worked on the MIT Challenge, I tried to avoid criticism of the project as much as possible. Not because I knew the criticism wasn’t valid, but because I knew it probably was. My critics had a point: self-grading isn’t perfectly accurate, the value of college has a lot to do with accreditation rather than knowledge, college is about more than just book knowledge, computer science isn’t terribly important to the career of a writer. However, mid-project there’s little you can do with these criticisms other than have them suck away your zeal.
Now that the project is complete, I’m more than happy to entertain those criticisms, and often agree with them to some extent. I don’t need faith because the work is already done—I can instead view my own work with a critical eye, looking for information that can improve the next iteration.
As a blogger, I think the form of this introspection is equally important as its skew. I generally don’t rely on reader feedback (good or bad). Of course, I use it on clear-cut cases of bugs that need to be fixed or features that need to be reworked in a product. Hard data for quantifiable metrics or benchmarking against writers who you feel better you along a specific dimension work well. But the general waves of love-or-hate comments you get as a writer are a terrible proxy for the actual quality of your work.
This last step though, of going through your past work and dismantling all the conviction you built up along the way, isn’t a fun step. It aches to look through the thousands of hours that could be dismissed with a simple objection. Or that a possibly wrong idea has been etched into the thesis of a book.
If your only desire is to feel good about yourself, then, by all means, skip this step. It’s not nearly as fun as being your own biggest supporter. But if your work matters to you on a deeper level than just its emotional or material rewards, I don’t think it’s one you can afford to ignore.