Too Much Company Stock? You Need a Rule, Not the Right Day

A few weeks ago I sat on a call with a man in his late forties.

Twenty-two years at the same tech company. Good salary. Two kids. Twelve years left on the mortgage.

And €760,000 sitting in two stocks.

Almost all of it in the company that employs him. That one position is up 682% over five years. Up 224% in the last twelve months alone.

Some of those shares were handed to him at around $20. They are worth close to $400 now.

He knows what he should do. He has known for a while.

"I just kind of couldn't face dealing with it all. I just left it."

"I'm just paralysed with indecision."

He is not greedy. He is not reckless. He is stuck.

And the trap he is in has a design flaw that almost nobody sees coming. His words again:

"The more the shares go up, the harder the decision becomes."

Every good quarter makes selling feel more expensive.

Every new high makes him wonder whether another one is coming.

The reward for being right is a bigger problem.

Now count how many bets he actually has on that one company.

It pays his salary. It funds his pension. And it holds three quarters of his net worth.

That is not diversification. It is the same bet, three times.

You already know this shape. It is a company town. The plant is the employer, the landlord and the local economy all at once. While it does well, everyone does well. When it closes, you lose the wage, the house price and the buyer in the same week.

He can see it coming, too. His company has let tens of thousands of people go in the past year and a bit, and he told me plainly that as he gets older and more expensive, there is a target on his back.

So the one event that would take his income is the same event that would take a chunk out of his savings.

That is the risk. Not the share price.

The obvious objection is the one already forming in your head.

But what if it keeps going up?

It might. I have no idea.

I spoke to someone recently sitting on €500,000 of shares in the company that employs him. A year and a half ago they were worth more than a million.

Nobody rings a bell at the top. I cannot tell you what a single share price will do next, and neither can anyone charging you for the prediction.

There is a second reason he has not moved, and he named it himself.

The gain is so large that the tax bill will be large too.

"My capital gains on these things are going to be colossal."

I understand the flinch. Then look at what that sentence is actually saying.

A big capital gains bill means the bet paid off. Nobody gets handed one of those for being wrong.

And in Ireland you pay 33% on the gain, not on the holding. The tax takes a slice of the win. It does not take the win.

The bill is also smaller than the one in his head. The gain is measured from the value on the day the shares landed with him, not from zero. And he does not have to sell the whole position in one tax year.

Nobody has ever told me they regretted paying tax on a profit.

Plenty have told me they regretted watching a profit disappear before they ever got to pay tax on it.

So here is what I said to him, and it is not a stock tip.

He does not need to pick the right day. He needs a rule.

Decide how much you want out. Decide the date. Sell a fixed slice every month until the position is a size you can sleep beside. Then stop letting the chart make the decision.

The point of a rule is that no single day has to feel right. Because no day ever will. On a stock that has been good to you for twenty years, every day feels too early, right up until the one that feels far too late.

I am not standing above any of this. I did the same thing.

In early 2020 I added up my own money for the first time. €191,000. Two thirds in my Salesforce pension, one third in Salesforce shares.

One company. The same bet, three times.

On the 31st of March 2020, in the middle of the Covid crash, I sold every Salesforce share I owned and bought the entire global stock market instead. A friend told me I was crazy. The share price then doubled in five months and I felt sick about it.

Six years on, the whole market has long since left that single stock behind.

I still write down what I am worth on the last day of every month. I do not publish that number. My 1:1 clients have seen it for two years, and it is one of the things I will keep showing inside the membership, along with what moved each month and why.

What I will say here is the part that actually matters, because it is the part you can copy. I did not get that decision right by being clever. I got it right by refusing to keep making one bet three times.

If you hold shares in the company that pays you, the question to answer this weekend is not whether the stock is any good.

It is what happens to you if the stock and the job go on the same day.

I have written before about why a price tag is not a promise, and this is the same risk seen from the inside, by someone who is living it.

I also wrote a free playbook that shows exactly how I think about company shares. When to sell. How the tax really works. And how to stop your employer quietly becoming your entire portfolio. You can get it here.

This is the exact kind of decision I am building into the membership I am creating in the open. The first 50 founding members lock in the lowest rate it will ever have, for life. Doors open in September, and the waitlist hears everything first. You can join the waitlist here.

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