The Importance of Understanding Your “Why”

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For the last few years, I’ve been partaking in mentorship programs as a mentor to underrepresented individuals who are looking to break into tech sales. Without fail, the first exercise I complete with my mentees seems straightforward on paper but ultimately ends up being quite complicated and sometimes very emotional. I ask them a simple question: “What is your ‘Why’”? In other words, what is it that you want for yourself in your life?

More often than not, when people hear this question, they think of something that I would call the “surface-level ‘Why’”. For instance, a lot of people will say that they want to make a lot of money. That’s all well and good, but ultimately the hard-earned paper itself is not gratifying. There is something that the money provides to a person. Does it allow you to do something with your time? If so, why does that thing matter to you? Does it allow you to buy something for yourself or someone else? If so, why does doing that matter to you?

The reality is, you generally need to ask yourself “Why?” over and over again until you land on the real answer. I write about this a little bit in the early chapters of my book when talking about how to sell to people and the importance of getting to the real motivators of the individuals who you sell to. But if you want to get anywhere in your life, you need to understand and anchor yourself to your own “Why” at all times.

Quite simply, when you are anchored to your “Why,” you raise the stakes to the utmost degree. As Simon Sinek artfully discusses in his book “Start With Why,” people do not care about what you do, they are care about why you do it. And that is probably for the same reasons that I talk about when I write about the importance of shared values in sales. Your “why” represents your values, and people like to align with people who share their values. How you go about performing that act is of little significance in the grand scheme of things as long as you are on the same page holistically and desiring the same outcome. 

The same is true for us in our internal mindset. Your “why” is the most important thing to you. It is easy to get lost in the “what.” Let me explain what I mean by that by getting into my why.

If you asked me why I work in sales, I would tell you it is because I want to make a lot of money. But the reason I want to make a lot of money is because ultimately I would like to be a writer, and I would like to be able to afford to take that risk. And the reason I want to be a writer is because I like the idea of moving people and influencing others in a positive way. And if you ask why that matters to me, I would tell you that I went to a high school whose motto was “from those to whom much has been given, much will be expected.” I was relatively fortunate growing up. And if you ask why this all matters to me even still, I would tell you that giving to others has always brought me more joy than anything I could do for myself.

That is my “Why.” But if you focus on the “What” – which is making a lot of money – it is easy to start caring less. Because it is not the money itself that matters to you. It is what the money affords you the opportunity to do.

This may be controversial, but I always tell my mentees to be honest about their “Why” when they get asked about it in job interviews. A lot of time employers will ask the simple question “Why do you want to work at our company?” Most candidates give the same canned response: they like the company’s mission, they like the culture, they like the opportunity for themselves, or maybe they like that people ride around on scooters all day in the office and get company-sponsored candies in the kitchen. Whatever it is, it’s a commoditized answer.

When I interview for a job, I might brush on these things because ultimately they matter. But in the end, it’s always because I think it’s the best opportunity for me to be successful. And the reason I care about being successful is because I want to be a screenwriter someday. I don’t pretend that I want to work at the company for ten years. Hopefully by then I won’t have to any more. That’s just the reality.

But why do I want mentees to do this? Because it shows the employer that they actually have something on the line that truly matters to them. Who would you rather hire – someone who likes your company mission, or someone for whom success at your company is like life or death to that individual? I would take the latter any day of the week. I want people who are self-aware of why they are there and what they want for themselves and who have connected the dots on how my opportunity will deliver that to them. I also want to know what motivates them because it is my job to keep them motivated. It brings us closer to understand what matters to each other instead of pandering to one another about making the company executives rich, as if that is our real mission. 

In the course of my mentorship, I have run across some fascinating people and have been exposed to some tremendous “Why’s.” One in particular that stands out for me is an individual whose brother and dog died in the same week. This person went on a downward spiral with drugs and alcohol for about a year mourning his losses. One day, he woke up and realized that if his brother were alive, he would be very disappointed in him. He decided that day that his life’s mission was to make his brother proud and to honor his legacy. That is what motivated him to enroll in the tech apprenticeship program where we met. I think he was surprised when I told him he should talk about this in his job interviews. I did not instruct him to do that because I wanted anyone to feel sorry for him or to hire him out of sympathy. Actually the opposite. I wanted them to know why he was really there, and that it had nothing to do with their company. I wanted them to know this was a lot bigger than a paycheck for him. As it stands, this person has been promoted multiple times and is having tremendous success, and he is one of my favorite mentees I have ever had.

Unfortunately, for other people, their life circumstances preclude them from even being able to have a “Why” that is anything more than dealing with a tough economical situation. Another mentee of mine had a tough time with COVID with his whole family falling into debt. He quite literally needed to focus on building a career to erase that debt and to put his family back on the map. This is the unfortunate reality for those who are not as well off: they do not have the time or capability to think of a “why” that is anything beyond a financial why because they need to wrestle with their immediate circumstances. It is only when these individuals are able to put themselves in a more comfortable position that they can instead deal with the trade-offs of attaining their “Why.”

Here’s what I mean by that. In most cases if you are interviewing for jobs, you would not necessarily take the first job offer you get because you want to see what will be the best offer. But for someone who has child support due in two weeks and who would otherwise go to jail (which is a real story of another mentee of mine), you can’t just sit around thinking about “Why” and wait for the best offer. You need to take the first one out of necessity.

This is why I think it is so important that those who have the capacity and wherewithal to advise and help others try to lean in and do so. There are so many people I have met out there who have such awesome stories but never have an opportunity to truly think about anything they want for themself other than to stay alive or just scrape by. If your “Why” is to help others, help them understand their “Why” too.

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