Simon Sinek has a simple message: figure out why you do what you do. Most of us get lost in what we do or how we do it, then drift off and wonder how we end up in an unsatisfying place. By figuring out your "why," you can test what you do, and how you do it, to see whether it aligns with your "why." If it doesn't, it won't feel right. Too many misalignments and you end up in the wrong job, the wrong place, the wrong life.
His book is worthwhile, but it does spend most of its time talking about businesses. This is definitely important; businesses that are out of touch with their "why" are responsible for a great deal of destructive behavior in the world today. For example, did you know that when Sam Walton died, Walmart was one of the most loved businesses, by both customers and employees? Sinek claims that Walton did not effectively transfer his visionary "why" ("take care of people and they will take care of you") to the company, and that's why Walmart has fallen so far, to become one of the most reviled organizations.
If you just want to get the gist of the reasoning behind "Start With Why," his TED Talk is probably enough -- the book just makes a more in-depth case. What neither of them do, however, is give much help in the way of showing you how to discover your "why," which turns out to be a rather tricky process. The only help I found came in the form of a rather short-lived podcast (not by Sinek) which seems to end last November after 13 episodes (I haven't listened to them all; perhaps they decided that was all they needed). During some of the podcasts, the hosts talked about the discovery process for individuals and small businesses, and shed some light on it.
Applying this to my own experience, I have felt disconnected from my previously-chosen pursuit of computer programming languages for awhile now. "Start With Why" piqued my interest because it seemed like it might lead me to something more meaningful, so I started to ponder my "why."
Your "why" must fit with the important activities and decisions you make in your life, and when you find it you can think back on these and see them all fit into place. After a few days (admittedly in another country), it occurred to me that my why was "break the chains around our brains." This seemed to fit very well with all the things that really motivated me -- including my pursuit of higher-level languages. I saw us as being stuck, held back by older, less-productive languages so I've always tried to shake things up to move us to languages that allow us to do much more.
There's a problem with "break the chains around our brains" which shows the pitfalls of this process. Even though I can look back and see how my motivations fit that phrase, the phrase itself is not a "why." It is one aspect of "how," but in the end it doesn't say anything about why it's important for me to break those chains. Once the chains are broken, then what?
The process of discovering your "why" seems to require multiple passes. You get an idea, consider it for a few days, then realize you're mistaken. In my case, an important aspect of my "why" is transferring knowledge to others -- thus the writing and teaching -- but that's "how." So when people say they want to be writers, that's just describing a "how" activity. If you just want to write, you can find a well-paying job writing ad copy, but that's probably not what you mean. You might even have some particular genre you want to write, like travel or science fiction, but that doesn't produce a "why," but rather a "what." The "why" is more visceral, which is an important reason it's harder to pin down. Your "why" for writing travel or science fiction might be "to make people feel wonder."
The "how" and "what" can be traps. People often say they want to be writers, but how important is the medium? Perhaps you will find more inspiring expression in the form of video, or software apps. By limiting yourself to writing, you miss out on that. For a long time, I've thought of myself as "specializing in programming languages," but if what I really want is to enable people to be much more creative, or to provide much greater leverage over the world, then I've backed myself into a corner by focusing on the "what" (programming) or the "how" (various forms of teaching).
I haven't pinned down my "why" yet, but even the progress I've made so far has been liberating. If I can figure it out, then I have a clear basis for future choices, and a way to get back on track. Even if you don't read the book, watch the TED talk and I think you'll be convinced that it's worth the not-inconsiderable effort to discover your "why."
Update: It turns out they have an online course at StartWithWhy.com to guide you through discovering your own why.