Why? Why? Why? Why? Why? Why? Why?

I teach an introductory entrepreneurship class, and one of the first questions I ask students is why they chose to take it.

They raise their hands for one (or multiple) of the options below:

1.     You’ve always had an entrepreneurial spirit. (Maybe you had a lemonade stand as a kid or have a side hustle now?)

2.     You love Shark Tank.

3.     You want to be really, really rich.

4.     You already have a killer idea.

5.     Or... the elective just looked cool.

Most hands usually go up for option 3: I want to be really, really rich. The next most popular choices are 1 and 5.

I like to start here because what I’ve learned from working with students and established entrepreneurs over the years is that even if being “really, really rich” is the surface-level motivation behind a venture, the real reason usually runs much deeper.

Actually, money usually isn’t the reason at all.

So, the next question I ask is: “Okay, you want to be really, really rich. Why?”

That answer leads to the next why, which leads to the next why... and that’s when the fun begins. More importantly, that’s when we start uncovering what wealth actually means to them.

Asking why isn’t unique to my introductory entrepreneurship class. The practice has been used in business for decades and, more recently, adopted by the personal development world.

One of the best-known versions is the 5 Whys Approach, originally developed by Sakichi Toyoda and used at Toyota to identify the root cause of a problem by repeatedly asking one simple question: Why? 

Traditionally, the 5 Whys has been used to solve business and operational problems. More recently, a similar approach has been used in personal development to better understand the deeper motivations behind our goals and actions.

One modern version of this Q&A game is known as 7 Levels Deep. I first heard about the exercise through Dean Graziosi, author of Millionaire Success Habits. On a podcast, he described 7 Levels Deep as one of the most impactful exercises of his life. He pointed out that “we think it’s because I want to get out of that job, I want this freedom, I just want more money, I want to take the better vacations, and it’s seven times deeper than that.”

I can confirm this based on dozens of conversations I’ve had with students.

“I want to be an entrepreneur so I can buy a yacht.”

Okay. Why?

After the next six whys, it usually turns into something more like: I want financial freedom, so I never feel controlled or helpless by my life circumstances.

Now, what’s more motivating? Is the yacht or reaching a level of financial freedom that gives you the autonomy to have more control over your quality of life?

It’s option two…but the yacht is just a fun extra!

I think this is an exercise we can all consider when we feel stuck or lack motivation. Maybe getting up for the gym at 5 a.m. isn’t particularly motivating, but prioritizing your health so you can one day play with your grandchildren, something your own grandparents never had the opportunity to do, is. Maybe going back to school to finish a bachelor’s degree feels overwhelming, but knowing that a degree could become a foundation for generational wealth might be what lights your fire.

When I first did this exercise, I was contemplating whether I should continue pursuing my Ph.D. I was overwhelmed, burned out, and the finish line seemed out of sight. So, I started by asking myself the first question: Why did I start the program in the first place?

Why, after why, after why, I uncovered that I wanted to earn a credential that would give me the opportunity to impact even one student who might be doubting their own potential. That was it! That was enough to get me through quantitative analysis.

It’s so easy to get stuck on the surface-level thing. But sometimes, getting to that surface-level goal becomes a whole lot easier when we understand the deeper reason we want it in the first place. One of the simplest ways to get there is, you guessed it, asking why.

Children are naturally great at this. If you have a two- to five-year-old (or have interacted with one recently), you already know what I mean. You can probably hear that sweet little voice already: “Why?” And then, approximately three seconds later, “But…why?”

It’s their natural way of making sense of the world around them and connecting with the people in it. We’ve always known how to do this. Somewhere along the way, though, we stop asking quite so many questions.

So, if you’re stuck, start with why. Then ask it six more times.

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Find one thing that brings you joy today.