Markets have delivered three straight years of strong returns. If you have RSUs, stock options, or a concentrated position in your employer’s stock, your balance sheet might look better than it ever has.
And that is exactly when most people do nothing.
They don’t think they need a plan - because things feel fine!
I want to push back on that because “things feel fine” is not a financial strategy. It’s a feeling and for high earners with meaningful equity compensation, it may be one of the most expensive feelings you can act on.
Here’s what I see consistently with clients who have large RSU positions or concentrated company stock:
· When the stock is down, they don’t want to sell because it feels like locking in a loss.
· When the stock is up, they don’t want to sell because it feels like leaving money on the table.
There is always a reason to wait, it’s human nature to let the stock price determine which reason feels most convincing.
What rarely gets examined is the full picture of what “waiting” actually means.
Your salary comes from this company.
Your bonus comes from this company.
Your benefits, your retirement contributions, and now a growing portion of your investable net worth - all tied to the same single outcome.
But here’s silently what happens: the rising stock price does not reduce that concentration - it increases it.
When markets are strong and your equity is worth more than ever, you are not in a safer position. You are in a more exposed one - with more to lose if something changes, and less urgency pushing you to act.
Here’s the thing: when “the market is high” is actually when you should have a plan!
I am not arguing that you should sell everything at vesting, more that your decisions around RSUs, concentrated stock, and equity proceeds should be driven by a repeatable process - not by where the stock price is today, how you feel about the company’s prospects, or what the market did last quarter.
A disciplined framework answers questions like:
· “What percentage of each vest do I sell, hold, or redirect - and why?”
· “At what concentration level does my employer stock become a risk I need to actively manage?”
· “How do equity proceeds connect to taxes, cash flow, and long-term investing goals?”
· “What would change my approach, and what wouldn’t?”
These are not questions you want to answer for the first time in a down market, under pressure, when the stakes feel highest. They are questions worth answering when you have time, clarity, and optionality on your side.
Strong markets give you something that volatile markets do not: the ability to make thoughtful decisions without urgency forcing your hand.
The professionals I work with are smart, successful, and genuinely busy. Equity compensation planning rarely feels urgent when things are going well - and that is the problem.
The planning gaps I see most often are not complicated. They are simply unaddressed:
· No defined rule for how much company stock is too much
· RSU vesting events handled reactively, one at a time, without a consistent approach
· Tax withholding set at a rate that does not account for the full income picture
· Equity proceeds sitting in cash because there was never a clear decision about where they should go
None of these gaps feel critical when markets are up. They become critical when circumstances change (a layoff, a market correction, a major life event) and decisions need to be made quickly without a framework in place.
A question worth asking yourself right now is this:
“If your stock hit a 52-week high tomorrow, would you know exactly what to do?”
What would your answer be? Would you have a written well-defined approach? Something you could execute confidently and explain to someone else?
If the answer is not a clear yes, all that means the structure is missing, not the opportunity!
Having a plan in place is not about predicting where markets go from here, in fact, its the opposite! Nobody knows what the future will hold. This is about making sure your financial plan is driving your equity decisions, rather than your equity decisions driving your financial plan.
The best time to build that structure is before you need it.
If you have RSUs, stock options, or a concentrated position and want to think through your approach with more structure, I have put together a resource hub designed specifically for high-earning professionals navigating equity compensation decisions.
Access my Equity Compensation Planning Hub here!
Read more articles by Kyler Nielsen