My company has an employee stock program in which employees put a percentage of their paycheck into the company for a period of time, after which they can purchase shares at the lower of the start and end market price of the period, less 15%. At the end of the period, employees can sell and thus gain a profit of at least 15% (minus ordinary taxes).
My investment philosophy is that which involves only investing in no-load, low fee mutual index funds tracking the S&P. However, I believe the employee stock program would result in a higher profit that can be reinvested in a mutual fund, as opposed to forgoing the employee stock program and investing strictly in the mutual fund.
The shares in my company's employee stock program just vested and I wish to sell it and move into a no-load, low-fee mutual index fund tracking the S&P. This will be my first time doing so, out of a 401K.
The question arises as to the mechanism by which I do this-- lump sum investing or dollar cost averaging.
I intend on holding these stocks for 10-30 years before selling, depending on whether or not I wish to start a business or obtain a down payment for a home. For the time being, I will never add to this mutual fund except for when I sell the stocks in the employee stock program, as my total investment dollars are allocated to the 401K and the employee stock program.
I am inclined to sell tomorrow morning and transfer the returns in a lump sum into a mutual fund tomorrow afternoon. I am a long term investor, and if the market crashes tomorrow evening while I invested a lump sum at the height, I won't sweat it as I wouldn't touch the money for at least 10 years (assuming I even start a business; otherwise it would be 20-30 years). If the market goes up for 6 months and then crashes, the gains in those 6 months would be irrelevant as I intend on investing for the long term.
In other words, if I am a long term investor focused solely on no-load, low-fee mutual index funds, should I spend the time and transaction costs on dollar cost averaging when I receive a lump sump, or should I just invest it all in one lump sum and be done with it?