Let’s Discuss The WHY
By Jason LaRocca | Vice President of Operations | March 13, 2026
So, I’ve been diving into Simon Sinek’s book “Start With Why” over the last few weeks, and it’s made me think quite a bit differently about my professional life. There is a LOT of good material in this book, but if I wanted to boil it down to one simple phrase, it would be this:
If you want to truly connect with your clients, with your employees, with the market for whatever business it is that you run, then WHY you do what you do is more important than WHAT you do or HOW you do it.
Passion is ignited in people when values and beliefs align across like-minded individuals and groups. What follows from there is either going to be a more or less effective expression of how what you are doing aligns with those core beliefs, brought to market via a set of products with an underlying leadership philosophy driving its execution.
This seems like a pretty simple concept, and I also believe it is a true one. But I have to wonder how many of us truly show up to work each day with our beliefs in the forefront of our mind. We clock in each morning and clock out each night, and we go through an endless to-do list filled with tasks and meetings and the like. I wonder how many of us think of those task lists, or those meetings, as a way of animating the beliefs that lie beneath them. Do we really feel engaged? Or are we going through the motions?
I had ZERO clue what I wanted to be when I “grew up” and entered the workforce. I was an English major at Boston College, and could have doubled as a philosophy one. I vaguely thought I would become a professor of writing or an editor of books until I “broke through” with my own writing. I thought of passion and work as being mutually exclusive of each other. You should follow your passions on your own time. Work is what you did to pay the bills. And I thought it was inauthentic to think of it any other way. You probably don’t need me to tell you how that all ended up – several years of floundering from job to job, blowing through money I had saved, with no clear direction for the future. I didn’t have an end goal, so of course I didn’t have a path to follow either.
I ended up in the mortgage industry by accident. I needed a job. I started out as a temporary employee for a company called First Nationwide Mortgage Company, working 8 hours a day 5 days a week pulling staples out of documents, taping the holes I made after pulling out those staples, and blacking out bar codes in order to make the documents ready for imaging. That was all I did for the entire day. I would be lying if I said I was passionate about it, but I realized I was at a point where I needed to discover my passion for SOMETHING at work, or I was going to enter a danger zone that was going to be hard to escape. So, I put my head down, worked hard, and believed that something better would emerge.
Two decades later, two companies later, and a half dozen promotions later, I am still in the mortgage industry, currently managing Operations for Investor Services at Westcor Land Title Insurance Company, and I don’t plan on leaving for the rest of my career.
I discovered two things about myself as my professional career progressed over these last two decades. You can call these two things my “why,” if you like. I discovered that I absolutely love leading people, and I discovered that I equally love building client relationships. Everything I have done in my work career, at least everything that feels important to me, has revolved around those two areas. They are the reason I show up to work each day. Like any great love, I have developed these passions over time. I haven’t always been good at them. I have had mis-steps and mistakes. But at my core, I believe in these two things. And if you believe in something, you WILL find a way to honor your belief. It’s the only way to be authentic to yourself at the end of the day.
It strikes me that I spent a lot of time last year in my blogs writing about our products and services in Investor Services, and the management philosophy that underpins the delivery of those products and services. All of that is well and good, but in Simon Sinek’s terminology, I was only talking about WHAT we do and HOW we do it in all of the pieces I wrote. I wasn’t talking about the WHY behind it. And at the end of the day, the WHY is the most important piece. I want people to understand the values that drive the business I manage. I want you to know WHY I do what I do. And I want you to have a real sense for WHY you may want to work with me and my team.
In many ways, I couldn’t have ended up in a better place than Westcor if I wanted to be the leader I set out to be as I started to find my passion many years ago. I never got to meet our late CEO Mary O’Donnell in person, although I spent many hours with her in conference calls in my 5 plus years under her greater leadership. Mary NEVER forgot the why in her leadership of our company. She NEVER stopped talking to us about why Westcor existed and why it was special. Simon Sinek would have LOVED her. Westcor exists to be different, to be fun, to be the upstart challenging the status quo. But more than anything, and Mary constantly articulated this to us, Westcor exists as a business in order to operate like a family in how we treat each other, and in how we treat everyone else we come into contact with. As you can imagine for someone who loves leading people, and loves building client relationships, all of those things are beautiful music to my ears. And really, to my soul.
Next month I will articulate more about WHY I think my beliefs as a professional and as a leader help separate us from every single other vendor you can work with in this space. But this month, I want to simply say thank you – thank you to Simon Sinek for making me dive deep into myself these last few weeks. Thank you to Mary O’Donnell for helping to create a company that feels like home to me. And thank you to every employee and client I’ve helped lead over the course of my career. You are the reason why I love showing up for work every day.

















