My company's stock price reached a new high today. Over the last year, it has gone up about 50%. This is great for me as I have quite a lot of shares through my company's employee stock purchase plan. So then the question becomes should I continue to hold onto my shares, or should I sell some or all of them and take the profit (minus the not inconsiderable taxes)? And when? This is, quite literally, the million dollar question. And I don't have an answer. All I know is that this account is very important to me as it's what I'm going to live off during my sabbatical when I finally get laid off or choose to quit. Which feels like it could happen this year (even though I said the same thing last year).