I’ve heard it said that the “real” answer to any question is buried only 3 layers deep. You have to ask the question, then ask the question beneath that, and then go one level deeper — then you arrive at the true answer. As an advisor, I’ve learned from many of the greats that the answer a client is seeking often lies somewhere between me asking a better question and them surfacing a deeper answer. And these answers are never black or white, right or wrong, smart or foolish. In practice this means that “simple, everyday questions” like: “My tax bill was really high last year - can it be lowered?” “Should I max my retirement accounts?” ”How much can we afford to give to this ministry we really care about?” ”Are we saving enough for our kids college? How much should we even save?” Each have miles of context beneath them, influencing the answer we hope to get, the plan we might’ve already committed to (regardless of the advice), and the baked in assumptions we brought into the conversation. These easily-google-able questions are anything but simple. Tax strategies are packed with trade-offs, compliance requirements, and implications for future-you. Same for your retirement accounts. And that question about giving first requires you to define “enough” which means taking an honest look at your needs, wants, goals, and surplus cash flow (if there is any). They weave into marriage roles, career decisions, core beliefs, emotions, family of origin, religious convictions — and I’m just getting started! It’s easy to see how a client could get lost in complexity and give up before ever arriving at a decision. A common term for this is “analysis paralysis” (and I can tell you from experience — this is a terrible place to be!) Here’s a simple framework to help you navigate from the question you’re asking to the deeper tensions holding you in indecision: * Start here: The Tactical Ask: “What should I do?” This is the pain point that usually triggers the google search, the text to your friend, colleague, or professional. * The Emotional Drivers: “What am I afraid will happen if I don’t do this? … What will I regret if I do?” Emotions are so important. They’re windows into our souls and tell us a lot about our internal world. God cares about that world and wants to meet us in it. Emotions should never drive the bus or fly the plane, but we ignore or underestimate them at our own peril. * The Foggy Gap: “Where does my analysis fizzle due to lack of information or clarity? Are there actual learning gaps here?” Oftentimes, complex situations have multiple moving inputs and myriad variable outputs. They’re not sequential, binary, or simple. And evaluating the trade-offs does require a lot of information. Finding the gaps can be helpful for your analysis. * The Faith Question: “What am I believing about God’s provision—and what am I trying to control?” You can certainly start here, but I strongly advise that you also end here. Once you’ve done your best to love the Lord your God with all your mind — distilling the questions, motives, emotions, and information you need — surrender it to Jesus and ask what He thinks. Let me walk through a (hypothetical) example. Say I’m talking with someone like Aaron. He’s been thinking about Biblically Responsible Investing after hearing his pastor mention something a while back. Aaron feels tension knowing his portfolio doesn’t match his convictions, but he didn’t know there was a better way. As a Christian, I know it’s wrong to profit from things that grieve and hurt the heart of God… but let’s face it, you can’t just invest in companies you go to Sunday school with. I’m also hearing these funds can underperform, and they cost more. So… is it better to just invest like the world and then use the money for Kingdom growth? That’s not a dumb question. And it’s thoughtfully approached by many faithful Christians. So when I hear something like that, here’s how I try to walk through it with him: Step 1: The Tactical Ask On the surface, Aaron’s asking about investment strategy because his current plan feels out of alignment with his faith. But he’s concerned about fees, performance, etc. Also his current advisor might not offer this investment approach. Step 2: The Emotional Drivers Underneath that, there’s grief. There’s also uncertainty. He wants to be faithful, but he’s not totally sure what “in alignment” actually means in the real world. And he’s afraid of making a sincere choice that costs his family later: higher fees, potential underperformance, maybe working extra years because retirement gets pushed out. Step 3: The Foggy Gap (where your “enough line” is missing) For Aaron, “biblical investing” sounds good, but it’s hard for him to define. And without clarity on “enough,” it’s tough to know what he really needs for retirement anyway—what he’s on-track for and what kind of trade-offs he can actually afford to make. When the finish line is fuzzy, most everything else is too. It’s like you’re on a lifelong journey to a destination you haven’t totally mapped out yet. You never quite know if you’re on-track to get there — or even where “there” is. This lack of clarity turns everyday financial questions into foggy indecision that leads to frustration and lack of execution. Step 4: The Faith Question And then we end up where these conversations usually lead: if he’s convinced there has to be a way to reconcile this tension, what is he really believing about God’s provision? And where is he trying to buy certainty or control with the “right” strategy? Underneath it all, he’s not just afraid of underperformance. He’s afraid he’ll choose faithfulness and accidentally hurt his family. He’s afraid he doesn’t have enough margin to “get this wrong.” Aaron’s not alone. Maybe you’re Aaron. And maybe, like him, you just needed permission to slow down long enough to ask yourself those 2-3 “deeper questions”—so you can make decisions with clarity, conviction, and open hands. And this is why I keep coming back to the “enough line.” When you don’t know what “enough” is for your family, every decision feels like it could be the one that breaks you. So you grab for certainty: the perfect strategy, the perfect fund lineup, the perfect tax move. But when you can draw a sober, realistic enough line in real numbers, something changes. You can finally see what’s required… and what’s available. And that’s where conviction stops being a weight and starts becoming a path. So here’s the real question: Do you actually need “the best” strategy… or do you just need an “enough” line you can trust? This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit faithandfinance.substack.com
