Step 2 of Saving Taxes Your Way: Ask
You measured where you are and where you say you want to go. Now stress-test the destination.
Most people project a financial future and accept it. They pick a number (a million dollars, ten million, whatever feels big enough) and start grinding toward it without asking why.
That’s the expensive way to do it. And I don’t mean expensive in money.
The One Question
Asking is one question. Why do you want what you think that you want?
It’s a process of elimination. When someone asked Michelangelo how he took a block of raw marble and created the Statue of David, he said he just removed everything that wasn’t David. That’s exactly what we’re doing with your financial goals. Take the raw thing and cut away everything that isn’t what you actually want.
Most people never do this. They hold onto the full block.
The Dragon That’s Actually a Lizard
There’s a story about a Wall Street banker grinding 80-hour weeks so that one day he could make partner, pull three million a year, and finally do what he really wanted. Someone asked him what that was. He said he’d buy a plane ticket and ride his bike through China.
That trip costs less than $5,000. He was giving away half of the most physically capable years of his life for something he could put on a credit card.
Then there’s the Mexican fisherman and the Harvard businessman. The businessman is on vacation in Mexico (barely, since his inbox followed him there) and he wanders down to the docks one afternoon to clear his head. A fisherman pulls in three beautiful yellowfin tuna. The businessman asks how long it took. “Only a little while,” the fisherman says. “Why don’t you stay out longer and catch more?” The fisherman looks at him. “Because this is enough.”
The businessman can’t let it go. He lays out the whole plan. Fish more, scale the operation, build a fleet, set up distribution in New York, take the company public, sell it for twenty million dollars. “And then what?” the fisherman asks. “Then,” the businessman says, “you can sleep in late, fish a little, take a siesta with your wife, have dinner with your family, and play guitar with your friends at night.” The fisherman smiles. That’s what he does now.
The point isn’t that ambition is bad. The point is that most people are chasing a dragon that turns out to be a lizard. The goal they’re grinding for is already in reach. They just haven’t asked the right question.
Ask Why. Then Price It.
So ask why. Get specific. Keep going until you hit the real answer.
The dream is a $10M house in Key West. Why? Island life, ocean air, sunrise from bed. That same feeling exists in Brazil for $3K a month.
The dream is early retirement. Why? Time back, freedom from the inbox, mornings that belong to you. Run the numbers on what that actually costs. A lot of people find they’re already there, or a lot closer than they thought.
The dream is generational wealth. Why? You want your kids not to start from zero. That’s a specific number, not an infinite one.
Once you know why, you can price it honestly. And once you can price it honestly, the path is often shorter than you ever thought, which means you can set the next goal. Then the one after that.
Redefine Your Goals If Necessary
If the answer to “why” changes the destination, redefine your goals before moving on. Go back to the ideal financial statements you built in Step 1 and update them to match the honest version of what you want. The numbers should reflect the real life you’re funding, not the one you assumed you wanted before you asked.
This isn’t a one-time exercise either. Every year or two, ask the question again. Goals shift. Kids grow up. Businesses sell. The destination ten years from now isn’t the destination you set today. Keep it honest.
Where Tax Strategy Fits
Once your goals are honest and you have a real target, tax savings become a very long lever. The question shifts from “how do I make more money?” to “how do I close this specific gap faster?” Cutting what you pay in taxes is often the most efficient answer. Higher ROI than working more hours, with no additional revenue required.
Picking Your Vehicle
After you’ve redefined the goal, you pick how you’re going to build toward it. Business equity, stocks, real estate, liquid assets. No universal right answer. The right vehicle comes down to three filters.
First, what’s optimal? Optimal means the highest return for the lowest investment, given where you already are. Someone already maxed on real estate loss limitations isn’t going to get the same ROI from another rental as someone who’s never owned one.
Second, what’s convenient? This is where your statement of net worth does the work. Where are you already putting capital? What’s already on your balance sheet? The easiest move is usually a one-degree shift in a direction you’re already heading.
Third, what do you prefer? Your P&L tells me this. Money doesn’t lie. If I can see twelve months of where your spending’s going, I know what you already like doing. The best strategy’s the one you’ll actually stick to, and what you’re already doing is a strong signal.
The intersection of those three is your vehicle.
The Cost of Skipping This
If you never ask, you’ll probably still hit your goals (assuming you live long enough). But you’ll spend years grinding toward a version of success that isn’t what you actually wanted. You’ll get there and wonder why it doesn’t feel like you thought it would.
The cost is time. And time, unlike money, doesn’t compound. You can’t get it back.
Trim the fat now. Figure out what you actually want and what it actually costs. You might find the life you’re working toward is already within reach. And if it’s not, at least now you’re working toward the right thing.
Resourceful beats resources.
Stay smart,
Jonathan Sussman CPA
