You don't have to wait until 67 to retire. Here's the math.

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On Tuesday, I got to do one of my favorite things inside this community: put a real expert in front of you and get out of the way.

Dan Pascone runs a wealth management firm called Tailored Wealth. What makes him different from almost everyone else in the money world is simple. He started as an individual contributor at a Fortune 100 company, moved into sales leadership, and built his firm on the side while still carrying a number. So when he talks about lumpy income, comp plans you don't sign until June, and the strange tax problems that come with a monster year, he's not reading it off a slide. He’s lived it.

We've been circling each other for over a year now. We bonded over a small disagreement with the FIRE crowd. You've probably heard of FIRE (Financially Independent, Retire Early). It's a noble idea. But almost nobody on this list actually wants to retire to a beach, clip coupons to survive, and wait out the rest of their life. You're wired to build and create things and help others. So, I landed on a better frame for people like us:

FINE — Financially Independent, Next Endeavor.

The goal is not to stop working, but to stop working your heart out to grow someone else’s business. Dan calls his version "hybrid retirement," and after walking many of his high-earning W-2 clients through it, he's noticed the same thing I have: the people who pull it off do two things well at once.

Marry those two, and the ability to walk away from corporate life to pursue your own thing without financial stress stops being a fantasy and becomes a natural occurrence.

Here's the framework he shared for doing this, from top to bottom.

This is the step almost everyone skips, and it's the one that makes the rest work. Before a single dollar gets moved, you decide what you're actually building toward. Dan calls the move underneath this effort scenario analysis, and it’s something he does for all his clients, including Inner Circle members in this community. The key is you don't need one perfect answer, you just need a few honest options.

If you want to leave corporate in three years, for instance, then you have to accept that a dip in income (or at least stability) will most likely occur and prepare for it while something new grows.

Maybe you want to take a two-year sabbatical and then buy into a cash-flowing “boring” business down the road (think laundromat, storage units, indoor youth soccer facility, etc.). Or, as I pursued, maybe you’re interested in monetizing the specialized knowledge you built in your sales career (content-to-commerce, coaching, consulting, and agency, or fractional work). You model a handful, and the ones that feel real start to separate themselves from the ones that don't.

→ Need help? Review Lesson 11 of Learning Path 5

Once you can see the next phase, you back into the money you’ll need during the transition and launch. Get clear on what's coming in and what's going out—during the corporate years, and conservatively, after them. Most sellers assume they have to replace their entire paycheck on day one. Dan's point, and it's a good one: if you've saved with the right strategy in place, you usually don't. A lower-income year isn't a failure. Handled right, it's one of the best tax planning windows you'll ever get.

→ Need help? Work through Lessons 1 - 5 of Learning Path 5

This was the line that stuck with the group. While you're a high-earning W-2 employee, you are, in Dan's words, the IRS's best friend. There's very little flexibility. But the minute you walk out of a corporate role, the entire tax code opens up to you — even if you never start a business. The options become unlimited.

He broke the tax world into three buckets you're already using, whether you’re aware of them or not.

Dan calls this life-driven investing, and it's the part most high earners get wrong. They invest everything for growth, then panic when they need to pull money out in a down market. Instead, you build your portfolio in liquidity bands — buckets tied to when you'll actually touch the money, not just how much you want it to grow.

That's the skeleton. It's useful on its own, and if all you do is sit with those four steps this week, you're ahead of 95% of sellers who earn twice what they keep.

But the skeleton isn't where the money is. The money is in the mechanics — the exact 2026 contribution numbers, the move that lets you access money before 59½, the way the wealthy borrow against their portfolios instead of selling, the mid-year tax plays you can still run before December, and the one strategy Dan handed out that I'd never seen offered anywhere.