My spouse recently purchased 4000 shares of company stock when it hit a 20 yr low inside their 401K plan. The stock has a 53% payout ratio & a 50 yr 8% avg. annual dividend increase, 12% last 10 years. I was against this concentration of assets in a single stock but its a done deal and can be sold if needed. One of the quirks of holding company stock in a 401K is you can elect to recieve the dividend instead of reinvestment back into the 401k (You pay only ordinary income tax, no penalties, tax is not withheld, shareowner repsonsibility). The thought I had was take the dividend which is about $5000 per year and use it towards fully funding roth IRAs in diversified mutual funds for both of us or if that goal is already reached begin funding a taxable account with a tax efficient mutual fund. Id be interested in any thoughts on this. I think the risk is it would be easy to say hey lets go to Hawaii the heck with funding roths were not guaranteed any tomorrows. I realized all experts say do not hold more than 10 to 20% of assets in company stock. Have explained it all to spouse-- repsonse is who cares what the stock price is were buying a consistent cash flow. Spousal arguments would consume a separate thread. 13 years from retirement.