For Tim, "I want to make a lot of money" isn't a real goal, it's a placeholder for one. It sounds like an answer, but it doesn't actually tell him anything he can build a strategy around, because wanting money in the abstract doesn't explain what that money is supposed to do for someone's actual life. So instead of taking that answer at face value and jumping into tactics, Tim asks the follow-up that most people never get asked: great, but why? What are you actually going to do with being rich? What does that money buy you that you don't already have? That single question is where the real coaching starts, because the answer to it is almost always more revealing than the original goal.
This is where Tim's approach shifts from business advice into something closer to psychology. Money, on its own, isn't a destination, it's a tool, and different people are reaching for that tool to solve completely different problems. Some people want money because they grew up without security and they're chasing the feeling of never having to worry about a bill again. Some want it for status, to prove something to themselves or to people from their past. Some want it purely for freedom, the ability to make choices without financial pressure dictating the answer. Some want it to take care of family in a very specific way. None of those underlying motivations are wrong, but they lead to very different definitions of "enough," very different tolerances for risk, and very different paces someone should actually be working at to get there sustainably.
That's exactly why skipping the "why" is so dangerous in coaching. If Tim just took "I want to make a lot of money" and handed someone an aggressive growth strategy, he might be pointing a person who actually wants security and stability toward a high-risk, high-burnout path that technically produces more revenue but never actually satisfies the thing they were chasing in the first place. Money without a clear why behind it has a way of never feeling like enough, because the person never defined what enough was supposed to look like. Tim's seen agents hit six figures, then seven figures, and still feel exactly as anxious and unsatisfied as they did when they started, because they were optimizing for a number instead of the actual life that number was supposed to create.
Getting someone to articulate their why also changes how they show up day to day, not just their long-term strategy. Someone chasing money to escape a childhood of financial instability approaches setbacks completely differently than someone chasing money to prove a point to a family member who doubted them. Both are powerful motivators, but they carry different emotional weight, different burnout risks, and different signs of when the goal has actually shifted. Tim can't coach any of that effectively without understanding the psychology underneath the surface-level answer, which is why the why matters just as much as the what, if not more.
This is also where Tim's coaching differs from a lot of the generic advice floating around the industry. Plenty of coaches will happily hand out a growth plan the moment someone says they want to make more money, because a growth plan is easy to sell and easy to package. Tim's approach is slower and requires more patience from both sides, but it produces something a generic plan never can: a strategy that actually matches the person following it. Two agents can say the exact same words, "I want to make a lot of money," and walk away from that conversation with completely different roadmaps once Tim understands what's actually driving each of them.
For anyone in real estate, insurance, or sales who's ever answered "what do you want" with some version of "to be rich," this clip is worth sitting with honestly. The follow-up question is uncomfortable because it forces real self-reflection instead of a convenient, socially acceptable answer. But it's also the difference between chasing a number forever and actually building a life that feels finished at some point.
Bricks and Risk is the podcast dedicated to real estate, insurance, and building your business, hosted by Sean Mooney and Tim Garrity, with additional wisdom from a network of local and national experts.