I regret not doing it when I had the opportunity. It’s kind of like a company match, in that they’re basically giving you free money if you contribute.

That said, there is still risk associated with any investment.

Just to be clear, this is ESPP type for a publicly traded company? What are the EU rules for holding?

For me, at Fortune 500 company it’s been great. Not super sexy growth, but most of my lots are stable. And even lots that have lost value have not really fallen below the discount price. I think the challenge for me was the combo if ESPP as well as Stock Option and RSU’s quickly led to a place where I was/am overexposed to the company for my non retirement investment. You need to be disciplined to annually, or quarterly, selling shares and reinvesting to diversify.

On the downside, if shit hits the fan with your company, it sucks. You could lose your job and lot of value in stock if you have so much. That said, if you believe in the company and already have a somewhat diverse portfolio of index funds or other holdings, it’s probably a no brainer to opt in.

Take the free ones. Ignore the discounted ones, don’t buy them.

There is too much concentration in your livelihood when you invest in your employer. For example, and I know too many examples of this, if your employer starts doing badly, you can not only lose your job, but they might move out of town leaving your home in a state where you may need to sell it in a depressed market. Often the shares you would have invested in the company are worth too little to sell. Your assets, your job, your home, all take a hit at the same crazy time. Not worth it.

Instead, invest in broad-market index funds. Go to Bogleheads where they discuss this and ask there. If you like momentum, arguably the greatest investor that has ever lived, Warren Buffett recommends a split between 90% SPY or IVV (S&P500) and 10% cash. The S&P500 is something like a momentum fund of the top winners of the US economy, and constantly changing.

Your employer is only trying to tie you down and have real skin in the game so that you’ll work harder. Ignore the tendency.

Best of luck.

It makes a huge difference how big the company is, and how easy it is to sell shares. (I am also making the fundamental assumption the company is public, if it is not then there is no guarantee at all you can ever sell the shares). If your company is traded on a major exchange, and there are lots of shares traded per day, the it is likely you will be able to sell them when you need to at a competitive price (subject to any restrictions they place on you as an employee to sell).

Large publically traded companies in the US call this an “Employee Stock Purchase Plan” and if this is offered as part of an ESPP, then the company is likely large enough to count.

Then, there is a separate matter of whether the company is a good investment at all. And even if it is, you may not want to invest in your employer at all, because your salary is already tied into their performance, and you may not want to tie your investment strategy in to the same company. However, there is nothing preventing you from selling ESPP shares as soon as your company lets you do it after purchase, and if you do that you can get an immediate guaranteed return, with very little risk. You will have to pay taxes on your profit, but not the money you put in to buy shares.

It makes your taxes a little more complicated, but not overly so, and you may clear enough to pay an accountant to do your taxes anyway.