<prompt> Human: TLDR: First job with Restricted Stock Units RSU as compensation and I have vested to the point where 25 of my net worth in combined retirement and non-retirement funds is in a volatile tech company stock. Great gains! Freaking me out! I would appreciate diversification advice that helps minimize taxes 24 bracket. Im proposing my plan at the bottom.Im working to keep the size of this post small by guessing conservatively at relevant information. Ask if I omitted something important! This is a new reddit account because my family, outside of my spouse and children, has a history of needsemergencies that increase with my wealth.Background: Financial stability is important since I grew up living hand-to-mouth. I achieved a zero net worth 20 years ago and since have built wealth by minimizing recurring expenses and saving aggressively. I saved conservatively until my emergency fund covered a year of living expenses, then invested aggressively via increasing 401k contributions. Taxes are my greatest recurring expense My career has grown considerably since and I have minimized lifestyle creep to maximize savings for college and retirement. My current job has two firsts. I stuck around long enough to vest the 401k employer contribution AND it pays with RSUs that vest over several years. I got luckygreedy because any attentive risk management would have had me sell off my companys shares before the stock price went up dramatically.Decreasing Risk Tolerance: I invest aggressively for long term growth and have never timed the market. I easily weathered the bad financial events that happen every seven to ten years - early 90s recession, 2001 dot-com bust, 2008 financial crisis, and here I am in 2018 thinking that were way overdue for the next one. I can weather the next crisis but my children will need college funds in the next six years. Im concerned that I will be withdrawing before things can recover from the next crisis. Im about 20 years away from retirement, sooner if I can make it happen.The questions and concerns Im trying to address: I have too much company stock as both relative to my net worth and as a absolute single investment. What is the maximum percentage of my net worth inclusive or exclusive of retirement funds that should be held in a single volatile tech company stock? Whats too much for a single stock? I assume at 25 377k of 1.5m I am exposed to considerable risk and should diversify. How can I diversify while minimizing taxes? Which investments should I chose when I diversify? Should I adjust my stocksbonds ratio? Should I consider a backdoor Roth IRA?Current numbers: Theyre grossly rounded so they might not add up perfectly. Net worth is 1.5m: 775k retirement: 610k traditional IRA Betterment 90 stock 10 bond plus 165k 401k 380k liquid: 50k safety net with the balance invested Betterment 90 stock 10 bond 417k home equity I live here, cantwont moveCurrent company stock holdings are worth 377k. Heres how they break out: 241k is liquid vested over time, paid income taxes at vest, effective tax rate varies based on appreciation and capital gains treatment 29k will incur a 1 effective tax rate most recently vested with minimal gains at income tax rates 50k will incur a 6 effective tax rate newest shares taxed at capital gains rate with minimal gains 69k will incur 9 effective tax rate The remainder has 9 effective tax rate 136k is in retirement 96k in traditional IRA 40k in 401kMy proposal:Im guessing at a 10 target. It really is a guess. Im open to advice to go higher or lower. Im also open to reinvestment advice. SellReinvest all 136k of retirement shares with no taxes to be paid until disbursement when retired, reducing the stock to 15 of net worth Sell 79k of the 16 tax rate shares, pay 3k in taxes, put the 76k proceeds into the Betterment taxable account reducing the stock to 10 of net worth. Change Betterment allocations from 9010 stockbond to 8020 I have no idea if or how a backdoor roth IRA applies to this situation.  <response>: This is a scenario in which you should seek professional advice from a fee-only CFP and a CPA. Dont make investment decisions with huge tax ramifications based on advice from Reddit. 