<prompt> Human: Hi PF, 30M100kyr Silicon Valley The company I work for has started do really well over the past three years. Ive been enrolled in their ESPP plan since then, and a 30k contribution during that time to has grown to 150k. I realize that I am extremely lucky to be in the situation that I am in and Im thinking of taking a year off 2017 and helping some family members and friends, and just relaxing for a bit. Perhaps travel or learn some new skills. Im not the type to blow all that money and I would live as I do now, but with an abundant amount of time for a year. No major expenses during that time either, as housing will be taken care of and car is paid off. I am fairly confident I can get the same job or similar job after the year is over. My question is, do you guys think this is a good idea? What would be the best time to sell all that stock and avoid the largest tax? Lets assume Ive held all the stock for over two years, that means I would only have to pay long term capital gains tax on the whole amount 15 correct ? Am I missing something else? I was thinking of selling everything in January 2017 so that all that stock would not add to my current income for 2016. Does that make sense? Does the 150k minus capital gains count towards my income for 2017 and would I have to pay taxes on that amount even though its from stock and not obtained through employment or business ventures?Edit: Thanks everyone! After reading through most of the comments, Ive concluded that :1 Having all that money in one stock is stupid, and I completely agree. If I had 150k in cash I definitely wouldnt have bought the stock, but 30k, perhaps I would have. I wasnt planning for it to grow this much and have this much risk, it just turned out like that. I need to diversify when I sell. 2 Make sure that I have enough for an emergency fund. I think I should be okay on this front. As I mentioned in a comment below, I just need an emergency fund saved till the end of the year and then use the stock sold for the rest if I take that route. I have 5k in savings 2k in checking. That in combination with a few other adjustments in lifestyle should cover the emergency fund. 3 Talk to a CPA on how to minimize the amount of tax I need to pay, and see if there are other options that are a better fit for my situation. A few people mentioned splitting the year between two calendar years and part time, as well as few other things. I need to investigate these options with a CPA. 4 Its a personal decision. If I feel like the pros of a year off hopefully building new and lasting life experiences greatly outweigh the pros of working a year and being financially sound, the I should do it. I really want the year off to travel and learn new skills, which I have tried doing now but couldnt accomplish due to time constraints. I plan on learning skills that are relevant to my career as well, so I wouldnt become stagnent and have more opportunities when I return to the job market. A few people have said theyve done this and the life experiences alone are worth the financial risk. I think its 5050, but personally Id take the risk, especially at this age. Thanks for all the advice PF! Let me know if Ive missed anything. Assistant: Sorry to backtrack, you have 157K in assets and 150K is in stock. Is that all of the assets you have? Do you really have 96 of your assets in your companys stock?Human: Yes thats correct. I know its weird, and I should definitely shouldve diversified, but remember I wasnt expecting to have a large percentage of my assets in company stock, it wouldve been a much much smaller percentage had the stock not gone up so much. Thats also the reason why Id like to sell soon, so Im looking to pay as little tax as I possibly can. I also have a car at 10k value now, and 30k in 401k. Forgot to mention 5k in a savings account which I should definitely move to a high yield savings account that earns a lot more interest which Ive read about on this sub.Assistant: I know its weird, and I should definitely shouldve diversified, but remember I wasnt expecting to have a large percentage of my assets in company stock, it wouldve been a much much smaller percentage had the stock not gone up so much.It is very risky to have 95 of your assets in one idea. so Im looking to pay as little tax as I possibly can.Talk to a CPA. I also have a car at 10k value now, and 30k in 401k.Do you have any debt? Do you have any money saved up in an emergency fund?Human: No debt, and emergency fund is whats in my savings account. Assistant: So 5K is all you need for 3-6 months?Human: 5k isnt all I need to survive with my current lifestyle, but its enough to get by for 5-6 months. Ill try to change my lifestyle accordingly. I was also counting on using some of the sold stock in case an emergency came up.  <response>: 5k isnt all I need to survive with my current lifestyle, but its enough to get by for 5-6 months.That is what an emergency fund does. 3-6 months of expenses saved up. 