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Don’t Start with “Why,” Ask Some of These Questions Instead

Oct 28, 2020 | Business & Enterprise

Reading Time: 7 minutes

Apple computers. Harley-Davidson. Leadership. Inspiration. If you didn’t know better, you’d’ think Simon Sinek’s Start with Why was written by a Baby Boomer with a hardon for TED Talks.

If you’re anything like me, after reading this much-touted book, you might also have wondered if Sinek had as much adulation for Elizabeth Holmes. After all, she duped a large swath of corporate America with her totally incredible “why.”

Now, for those of you unfamiliar with the book, its basic prescription is that if you answer why you’re in the game first, you’ll be the richest, most successful man to have ever lived.

Something like that. Just ask Steve Jobs, okay?

Or oh, wait. He’s dead. And was apparently not as inspiring leader as Sinek thinks but little more than a horrible, brittle “manager” of people.

In fairness, other people and businesses make an appearance in the New York Times Best Seller Start with Why. And to Sinek’s credit, the book is decently written, if generic.

But I first became suspicious of the book after its prescription completely failed me. More on that in a moment.

Who Is Simon Sinek to Tell Us to Start with “Why?”

First, one thing stood out to me when I was first introduced to Sinek.

No one seemed to be asking who this guy was or where he came from. Sure, you can find no end to the references after he became a feature on the lecture circuit with Start with Why. But who is he to tell us how to run companies and businesses? Or be successful leaders?

Well, a quick look at his bio and a search around the web, and you’ll find, before the consultant and corporate world latched onto him…

  • Simon Sinek had very little experience starting or running companies. In fact, it seems his only experience was typical consulting with a Blogspot on the side.
  • He appears to have never held any significant decision-making role in any organization.
  • His resume doesn’t indicate much familiarity with leadership IRL.
  • His understanding of corporate history, as we’ll see, was superficial at best.

No, Sinek was just some marketer. That’s literally it. Just another dime-a-dozen, wanna-be NYC marketer.

How much could he possibly know about developing success? Or running anything?

How My Business Failed to Benefit from “Why”

Naturally, you might wonder what brings any weight to my observation about starting with “why.”

And the answer is fairly simple: I originally put my “why” first. And got it wrong. I would paid for it in time, effort, and a little bit of my sanity.

Here’s how…

When two friends offered to help me find my “why,” I thought, sure. Not one to turn down a book, I purchased Start with Why and Find Your Why right away. At worst, I figured, we’d get some good conversation out of it all.

Of course, it didn’t hurt that you get a captive audience where all you have to do is talk endlessly about yourself.

And the session was good. Or at least, it felt good in the moment. However, what I discovered was a bit of what I’ve already known: I like to tell stories. In fact, I’ve been saying so since I was five years old. And I’ve been a ferocious reader since about that time too.

But that’s not the problem.

It would take me another year or so to come to a realization. And that’s how telling stories is not what I actually do for other people or what I find most rewarding.

No, what I enjoy most, and find myself doing over and over again, is creating stories that other people tell. And sometimes they tell those stories for years and years to come.

A subtle but very important difference.

Although my marketing agency was modestly successful, it was more of a ghostwriter for others, if you will. And it drove me absolutely crazy. Long nights, tons of monetary investment, lots of stress. And for what?

You see, after working with numerous small and medium-sized organizations, I realized that it was something else entirely that had always excited me, for profit or not. And that’s being an architect for organizations… studying, building, and re-designing them.

Trying to start with “why” got it all way off for my business. It also didn’t make me a better leader, more inspiration, or more successful.

And that’s how starting with “why” got me in the wrong place.

Where a Theory of “Why” Falls Short

But maybe you’re thinking all that means is that I got my “why” wrong initially. And now I’ve corrected that problem.

Let’s dive in a little deeper to see why that’s not the case.

The truth is that Sinek’s  “Theory of Why” doesn’t reflect how people truly act. Or the intricacies of human psychology and sociology. Sure, we often do search for the reasons behind our strongest desires. We often also want meaning and value in our work, our personal lives, and beyond.

Still, this is a remarkably trivial observation, especially in the 21st Century.

This is the reason “why statements” often are little more than bland, generic platitudes. Don’t believe me? Simply take a look at Sinek’s very own, expertly-crafted “why statement.”

To inspire people to do the things that inspire them so that, together, each of us can change our world for the better.

That sentence might as well have been ripped right out of the worst corporate HR meeting in history. It is utterly, magnanimously devoid of meaning. It says absolutely everything and nothing. And it’s little more than #inspirationporn with no advantage against competitors. You couldn’t get any worse unless you wrote something like…

To tell my company’s story so I can empower leaders and change the world.


What are we, as business and civic leaders, supposed to do with that?

I suspect the answer is buy more of Sinek’s books. And as a piece of marketing for Sinek, it’s worked wonderfully for the self-help junkies and human resources conferences. And helping him worm his way into some more attractive roles. Otherwise, as even general marketing advice, it rather incorrectly approaches the complexity of loyalty.

From the link, loyalty involves many factors, the most important of which is not knowing why someone is doing something necessarily. And when you’re in a competitive environment, it’s rather obvious to anyone with experience that small differences in “why” statements are unlikely to greatly affect people’s decisions to go with one thing over another.

Or to keep showing up for more while skipping your competition.

In fact, it’s a little narcissistic and grossly entitled to think anyone actually cares at all about why you’re doing something.

Worse yet, there is no real indication that successful businesses or successful leaders routinely start with “why.” Or even have a single, unifying “why” in the first place versus any number of more minor ones.

How Do Successful Organizational Leaders Actually Start?

And actually, two of Sinek’s opening examples in his book, the Wright Brothers’ historic flight and Steve Jobs, don’t appear to have started with “why” at all.

Take the Wright Brothers for example… Orville said they “thought only of getting off the ground” and later decided to hope the airplane might become an instrument of peace. In fact, a chance toy helicopter gift as children is more likely to have been the factor for flight today than the brothers knowing their “why.” (Further detailed here and here). And they attributed their success over others simply as their desire for fun.

Did you catch that?

While Sinek claims the Wright Brothers started with “why” — Surprise! History seems a little different. And involving a more sophisticated series of decisions.

And how about Steven Jobs? Here he is in his own words

[…] I’ve always been attracted to the more revolutionary changes. I don’t know why. Because they’re harder. They’re much more stressful emotionally. And you usually go through a period where everybody tells you that you’ve completely failed.

Catch that one?

Steve Jobs said he didn’t really know why, let alone having started with a “why” in the beginning. And when he was asked what the goal of it all was, he again repeated “I don’t know how to answer you. In the broadest context, the goal is to seek enlightenment — however you define it. But these are private things. I don’t want to talk about this kind of stuff.”

Not exactly the awe-inspiring stuff of Sinek’s leadership smut, even if Jobs waxed a little poetic about his optimism in what people could do with technology, from the same link above.

No, what we find in Sinek’s historic examples, including Wozniak, is something else. And that’s much more what we might call discipline and even masochism than any feel-good-in-the-moment inspiration or generic motivational tripe.

A Slightly Different Approach

“Because it’s there.”

British mountaineer George Leigh Mallory before his 1924 death on why he was attempting Mt. Everest

So, I’m going to advocate for a different approach. And one more with keeping in mind the many small and medium-sized organizational leaders I’ve been fortunate enough to know.

  • Stop paying attention to Simon Sinek’s #inspirationporn
  • Understand there is no right way to start a business or organization
  • Ask a Hell of a lot more questions in whatever order life demands

And since I’m right in the middle of generating new entrepreneurial endeavors, this process is right at the front of my mind.

How do leaders go about starting new, successful organizations?

Although, we can’t know for certain if any of my new ventures will be successful, starting with “why” is not at the forefront of my mind for all of my new efforts. And in actuality, the process is so much more complex.

Here’s a sample of the cascade of questions I’m going through…

  • What industries have positive outlooks this year?
  • What about some of these business ideas is different?
  • Could I tinker with that part of the process?
  • How does that business process work?
  • What do I know about this area of commerce?
  • What does average profit margins or overhead look like?
  • Do I care about that or do I want to hire someone for it?
  • Who might like this and keep buying it?
  • What step would be my next one?
  • Then what?
  • Where might this idea take me in the end?
  • Who might I become in the process?
  • What more might I learn about?

The best part is that your questions don’t need to be asked in any certain order. Some may follow in a sequence as you uncover possibilities and research. You probably won’t remember them all years from now.

But what’s clear is that you most certainly do not have to “start with why.” And that’s the true crux of the matter with Sinek.

When you own a business, you actually don’t always know why you started it. Sometimes it’s the raw achievement of getting somewhere. Other times, it’s the fun or the freedom.

Your view of why you started it even changes by the month or sometimes, the hour during the rollercoaster.

Sometimes, and I can speak from experience, entrepreneurs are just obsessive masochists. This is especially true when it comes to answering the question, “why should I keep going?”

You see, that’s because, there’s more to business than just starting them anyway. There’s also why you keep going day-in and day-out. Call it sheer force of will. Or insanity.

Or damn stupidity. Sometimes you will feel incredibly stupid on this journey. And you won’t feel inspired in any way for many months, let alone some days. I can assure you of that fact.

And as one entrepreneur to another, I’m here to tell you, contra Sinek, that’s perfectly fucking okay.

Because at the end of the day, there is no one magic trick to being a successful leader or winning businessman. And anyone who tells you otherwise is a fraud. Or selling something.

Or both.


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