I want to ask you a question that often makes people a little uncomfortable because we simply aren't used to thinking about our finances this way: What is important about money to you?

Usually, when I ask people this, their first answer is easy, surface-level things like "security" or "financial freedom". But my goal isn't just to help you set financial goals; it's to dig deeper and find the true "why" behind your money. Getting clear about our underlying reasons for doing things forces us to face some of the inconsistencies in our lives.

A few years ago, I was introduced to Caitlin, a highly successful executive. But she was working eighty-hour weeks and burning herself out. When we met, she shared that she was obsessed with hitting a massive, multi-million dollar portfolio target by the time she turned fifty.

When I asked her what was most important to her about money, she gave me a classic answer that I hear time and time again: "Independence." I pushed a little further. "What does independence actually mean to you, Caitlin?" "It means I can finally stop working as hard and start living," she replied. So, I painted a picture for her. "Let’s pretend you’re there. You’ve hit the number and you're 'living'. What is so important to you about being at that spot?"

Caitlin got quiet. She looked down, and when she looked back up, her eyes were welling with tears. "My dad died of a heart attack at 55," she told me. "He worked his whole life and never got to take my mom to Europe like he promised. I just want to travel the world with my family while we are still healthy enough to enjoy it."

And there it was. That was her real "why."

Your values might be completely different from Caitlin's, and that is perfectly fine. The key takeaway is that once she identified her true, underlying motivation, her entire financial picture gained sudden clarity. She realized she didn't actually need to grind until age 50 to hit an arbitrary, massive number. Instead, we worked on a gameplan where she would scale back to a fifty-hour workweek, and started planning a three-week international vacation with her family that year.

Answering this uncomfortable question gives you a powerful lens through which to view every financial decision you make. When you know what is truly important, it becomes incredibly easy to say no to the noise and distractions that pull you away from your values. As Stephen R. Covey famously said, "It’s easy to say ‘no!’ when there’s a deeper ‘yes!’ burning within".

For Caitlin, making memories with her family before it was too late was her "deeper yes". The same can be true for you, but you just have to be willing to ask yourself the hard questions.

~Alex