<prompt> Human: Hi, I am 22 and working as a software engineer in San Francisco. I just accepted an offer at a late stage startup think Uber, Lyft, Airbnb and received an offer of 140k salary, a 10k sign-on bonus, and 400k worth of RSUs that vests over 4 years.I already have 100k saved from my previous jobs over the past 2 years and it is distributed like so:60k - Stocks with ETrade 35k in 3 stocks and the rest in 3-4 others27k - 401k with Fidelity moving to Etrade10k - Lending Club5.5k - Roth IRA with WealthfrontSome background: I originally had 70k in my Etrade account, but lost 10k in both Go Pro and Lending Club over the past few months. I have not sold and am hoping they make somewhat of a recovery before realizing my losses. I realized that if Id saved most of my money in cash when the market was unusually low a few months ago I could have made an easy profit with the recent recovery. My strategy now is to sell off my holdings at a reasonable price and wait for the market to dip again so I can buy when everything is cheap. I moved my 401k money to Etrade to do the same.I realize I have a problem with diversification, but cant seem to shake the speculation bug despite having lost a fair bit on stocks already. Is there something that can be done to both satisfy this craving and still be somewhat safe?UPDATE: I recognized that I was being pretty dumb with my above strategy and needed more people to tell me this, thanks! Im planning to dump 55 of my portfolio into VTI, put 25 into Lending Club notes and keep the other 20 in cash for speculation. Any advice on this?  <response>: My strategy now is to sell off my holdings at a reasonable price and wait for the market to dip again so I can buy when everything is cheapThis is called timing the market and if you could consistently achieve this you could make millions in asset management. Spoiler alert: Fund managers are not able to do it, its unlikely you will.Your stock portfolio is extremely undiversified - less than 10 stocks, something also tells me that those probably are in 2-3 sectors. There is nothing bad in underweighting a sector or two, especially if you have natural exposure to it through your job, but trying to beat the market by selecting 2-3 sectors is not gonna work most of the time.How much time can you spend researching the companiessectors a week? If you said 10 hours then Id say youre extremely committed, an average analyst in asset management will be doing same thing for 50 hours and will have significant information advantage. Average analyst has very hard time outperforming the market.You would not sit at a poker table with the pros, so why would you think you can do better than pros here?It is fine to pick some stocks yourself and overweight them, but only as a part of well diversified portfolio and to a limited extent.Find a diversified allocation and stick to it. Have some reasonable small percentage of your investments set aside for your own bets if you need to.PS. 