💰 How to navigate a career change without losing financial ground

☕ Good morning!

Career transitions can be pressure cookers. 

When you’re leaving a role at the top of your game, be it founder, operator, or senior exec, you’re not just updating a title, you're stepping into the rarest of personal financial windows. 

This unique opportunity allows you to collapse tax years, recode equity outcomes, and rearrange long term liquidity like a black-belt optimizer– basically a financial planner’s perfect storm. 

Still, it’s easy for the uninitiated to fumble the mechanics. They sprint for a counter-offer. They passively cash out RSUs. They leave money on the table because the 401(k) rollover link was easier to click than working with a real planner.

The thing is, doing this correctly helps you win the next wealth decade, almost on autopilot.

📊 Equity moves like a portfolio, not a pay stub

Every option you’ve been granted is a contract, and every contract means risk. 

Don’t treat ISOs and RSUs like individual lottery tickets; they should be treated like positions in a multi-asset portfolio that evolve by time, tax exposure, vesting triggers, and expiration cliffs. 

You should be thinking more like a family office than someone at the craps table, hoping the roll of the dice falls favorably.  

Start with the mispriced risk.

If you’ve got ISOs, it might be worth considering converting them early when income is low to optimize Alternative Minimum Tax clock start.

Got RSUs? Manage cliff timing to spread income across tax years. 

NSOs? 83(b) early exercise is brilliant when pre-IPO valuation swings go turbo.

Blackouts? Map them across both companies to avoid being stuck during liquidity windows.

To be clear, every financial situation is different; if you’re confident in your company’s trajectory being a rocket ship, you’ll want to project different scenarios from there. Let the math help steer the wheel, not solely your subjective feelings. 

Don’t forget: Layering liquidity through advisory roles or consulting retainers keeps the income curve predictable, and makes equity moves safer by design.

🚀 Navigating a Job Change?
Don’t leave money on the table. Our Executive Job Change Guide breaks down key strategies to optimize your equity, minimize taxes, and secure your financial future.

Learn more and get access here: Executive Job Change Guide

📍 Your zip code is worth millions

California doesn’t forget. 

Emily learned that after she moved to Nevada and learned CA would still claim state income tax on her exercised NSOs. Why? Because she earned them when her W-2 said “San Francisco.” 

Brutal, but legal.

Moving states to save on taxes isn’t anything new– SALT can be a doozie. 

Fun fact, between 2018 and 2022, over 125,000 New York City residents moved to Florida, resulting in a $13.8 billion loss in adjusted gross income for NYC. 

Many of these folks were high-income earners seeking lower taxes, better affordability, and improved quality of life. The top 1% of NYC taxpayers contribute 40% of the state’s income tax revenue.

To get clean, you need to plan ahead. 

Lock in your new domicile fast; that’s your license, voter registration, mailing address. Not after you execute, but before.

Trace where your comp was earned, not paid. Smart modeling separates CA- and NY-derived income even post-departure.

Got upcoming liquidity in Year 2? Move in Q3 of Year 1. A full year earns a cleaner tax separation.

Looking for a more advanced move? Some dual-residency scenarios allow community property splitting, valuation freezing, or upstream gifting before big events. 

Is it complex? You bet. But for multi-million dollar equity stakes, it’s really worth looking into. 

Track every W-2 and 1099 for misassigned withholdings. You owe taxes to the states where the value was created, not necessarily where it landed.

🛑 Making Sense of the Inflection Point

Most execs see a job change as an emotional or title-driven event, but the real unlock is treating this rare moment as a generational wealth constructor. 

If you care about financial independence, legacy design, or simply outplaying the tax code, it starts with modeling these transitions like they’re IPO events.

Thinking like an earner got you where you are, but for this specific time period, you need to think like a builder and financial planner. 

Consider things like building liquidity layers, side income streams, and driving geographic arbitrage whenever possible. Know your wealth horizon and the low income tax tools at your disposal, and leave nothing to chance. 

We’ve helped clients think through the equity, tax, and location puzzles that come with career transitions, not just so they “don’t mess it up,” but so they can actually use it to accelerate long-term freedom. 

If you’re thinking about making a move, make sure you have a goal you’re actively moving towards rather than just checking boxes. 

Keep in mind career change isn’t just a transition between companies, but a brief pause to design your next financial chapter. 

Stay savvy, stay proactive, and keep your financial future bright.

Until next week!

This information is not intended to be a substitute for specific individualized tax advice. We suggest that you discuss your specific tax issues with a qualified tax advisor.

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