If you're 35–45, earning $500k+, a lot of that from RSUs… Money probably stresses you out.
You’re not alone
Here’s what I hear ALL...THE...TIME....from tech professionals in your shoes:
1️⃣ "I'm earning more money than I ever imagined—why am I still stressed?"
2️⃣ "My RSUs feel like Monopoly money—how do I turn this into something real?"
3️⃣ "Why do I own so much company stock—and why does it keep me up at night?"
4️⃣ "I don’t want to hit 60 and my hard-earned equity vanishes in a crash."
Here's the simple truth
➡️ Complexity = Stress
➡️ Not having a clear financial system/plan = Stress
➡️ Too much company stock = Stress
How you fix it
Doing better ≠ higher returns. You're not stressed because you "aren't doing angel investing" or "didnt see the AI boom early and invest in Nvidia".
Doing better = having a plan and system for your money. Rather, you're stressed because a lot of money is coming in the door (🙂), a lot is going out (😔), the taxes are complex (😕), and you don't have a plan/system for it (👎).
You can create a system yourself, or partner with an expert
Both approaches can work. Its a function of your time, knowledge, interest, and psychology. For example, I recently helped five tech professionals:
➡️ Fix their RSU tax bill surprise every April
➡️ Sell their vested RSUs on autopilot ("Monopoly money" → diversified investments)
➡️ Reduce company stock exposure by 75% without triggering a huge tax bill
➡️ Smartly exercise ISOs and plan for AMT (with likely recoup in 1 year)
➡️ "FINALLY feel good about our money situation"
How you create a money system
Detailing out all the steps here could be the subject for 50+ future blog posts. But at a very high level, the key things you should know and tackle here are
Know Your Cash Inflows and Outflows. Know your income, expenses, and target/hit a healthy savings rate. 401k + cash savings of 20% or more of income will put you on a healthy path. And these savings are what fuel your money system.
(REITERATED) KNOW YOUR EXPENSES. This is the biggest miss I encounter. Everyone knows what their income is. But 98% of people either don't know, or materially under-estimate their spending
Have a plan for your stock comp. Lots of "good" choices here --> but they need to be purposefully chosen. "I didn't know what to do with my vesting RSUs so I just kept them"= an unintentional decision (and a high risk one at that).
Diversified, purposefully-made, risk-appropriate investing. Approach your investments unemotionally, know how much risk you can/want to take, and build a diversified portfolio. In most cases, don't own too much company stock.
(REITERATED) PURPOSEFUL INVESTMENT STRATEGY. There are many "good" ways to invest. But you need to have intentionally chosen your strategy + the reason why.
Tax knowledge + strategy. Have a good estimate of your tax burden and rates (there's 7-13 types of tax to focus on 😬). And know that withholding is weird on RSUs; ISOs/AMT are all sorts of odd; and most "sounds to good to be trust tax strategies" usually are (but some do exist). If you want to geek on on this, you can find more details here
Many other things too. Spending aligned with your goals, debt management, appropriate insurance, estate plans, employee benefit selection. BUT....getting the above 4 things right will take you a long way!