<prompt> Human: Im 23 years old, single, 75k salary, living at home for the next 1-2 years rent free, car paid off, and basically the only thing I am responsible for paying is 15k in student loans which my parents are also helping me pay off.nbsp;Over the years, my mother has been buying Exxon stock under a custodial account, and she is giving me full control of all the shares. As of right now, the stock is worth about 55k with a dividend of 500 being reinvested every 3 months. I really want to start diversifying into some low cost ETFs, but I want to avoid paying the 15 capital gains tax from selling off the stock.nbsp;My goal is to save and invest very aggressively for the next 5 years. For the first 2 years, I was thinking of using 20 of my salary to pay off my loans and use 35 to be placed into investments. Ive been thinking of different options, and this is what Ive come up with:nbsp;Option 1: Keep the stock for now, but use the dividends to be invested into ETFs. Pay off my loans and use the bulk of my salary to investing into more ETFs. Once my mother retires in 2 years, I would start gifting her 12,000 of the Exxon stock annually so she can sell it and place it into ETFsother investments while avoiding the capital gains tax.nbsp;Option 2: Keep the stock permanently, and keep letting the dividends being reinvested into buying more shares of Exxon. I know I shouldnt keep all my eggs in one basket, but if I keep letting dividends be reinvested into more shares, I think it would be really nice receiving a residual income from the dividends 5 years down the line. While I keep the stock, I will pay off my loans and start diversifying from scratch into ETFsbondsetc.  <response>: You may be overthinking this. Depending when she acquired the Exxon stock, you may have almost no capital gains due if you sell some or even all of it. You can use losses on stock acquired at higher prices to offset gains. The stock was more expensive that it is today for much of the past ten years. If you go back further, it might be up 20share, so youd pay 3share capital gains tax on those shares, offset by loses on stock you sell that had a higher-cost acquisition price. 