From the financial crisis of 2008-09, some lessons were learnt. No matter whether you dollar-cost invest or time-cost invest .. which is essentially spreading your purchases over time or dollars points, there is simply no way to rationally or logically think about stocks. Stocks are disjoint from a company. I mean fundamentally they are tied up and in theory, company does well then stock does well. But still there is a bit of disconnect between stock prices and company performance. There were lot of financial companies leaders who routinely said something, meant something else while the public reports showed more losses and hence the stocks were on downslide. There is little that can be done when leaders in public firms start telling one-sided truths. The key take away was that you cannot be 100% in stocks. Or 100% in bonds. Just look at the GM bonds crisis which was brokered by govt which left the stock holders in dust while giving some cents on a dollar for the bondholders. Big fishes survive while smaller ones are eaten raw. So tread carefully. No matter what - Diversify. Even if some god comes up from above and tells you that stock XYZ would be the best performer in the next 10 years, still go and diversify. When I say diversify, I mean home, rentals, real estate, Reits, Stocks-US/Emerging/Index/Active/Dividend, Bonds-US/Emerging/Index/Active/Dividend. Over time you could get comfortable with some. I like the Emerging bonds more than US bonds, Index bonds more than Active bonds. For dividend, maybe buy the individual bonds. Basically, diversify. Have cash too. This is often underestimated. I have been thinking of putting cash in local banks and credit unions where they still give in the 1% APY range. Online savings accounts like Discover, GE, Axis, Ally bank, Ever bank, Barclays or American Express are pretty good these days.
The main lessons from 2008 that needs to be drilled is not to count on others. After diversification, put the money in lower ranges rather than higher ranges. If something is in all time high, like it is now in 2014/15, just stay put. Markets come up and go down and keeps on doing this thing. In future, this is going to be more pronounced. Companies frequently change. Most are bought over and undergo transformation. GE is transforming highly now. Many index components are different. Dow of 2009 is different from that of 2014. I wonder where Dow of 2009 would be now had they not changed the components and weight.
Invest more in your own career and more importantly get the skills to strike out on your own. There is nothing in the rat race. You are better off consulting or working independently. When you are fulltime make sure you are up to date on skills. I see many folks with full-time simply delegate as they settle down on managerial roles with families. After that it is all political and no business or technical skills. That road is just dead-end. Better, just start your own company some time and start it on your side work and on weekends and then slowly scale it up. These days most projects are modularized. So even if you start a company, the HR and payroll are outsourced. You can get someone in India for your IT stuff and someone in America for your Accounting/Tax needs. You can computerize your solutions and have people work remotely which pretty much lets you focus on the business. The core business is where you could apply your skills. Once you have a good set of patents or business trade dress, or a portfolio of these, you could always sell them or just scale them and maintain them. Back to investing, 2008 was a big change for me. For many in gen X and millennials it was rather a rude awakening that markets would not keep going higher and that there are lies out there and you have to fend for yourself in the wake of the realization that Social security might not even cover major portions of the retirements. So be on your own, this is the time when the individualism is going to be truly tested and the more individualistic and hard-working/self learning folks who use knowledge and data to make decisions would be the stand outs. Rest would be living off-hand outs. Another lesson or observation during 2008 was that when shit hits the fan, all principles go to dust. Legends and big characters choke in the face of disaster and pressure. So many giants were liars and cheats and simply started begging for bailouts from governments instead of accepting that they failed. Once you fail, you get out like the other workers that you have been firing all these years. You stand back in the line. Work your way up. Nothing of that sort happened. It seems once you have money and are steep in politics anything goes. Wonder how such men sleep at night. Anyhow, I digress.
Point is you are on your own. Learn and upgrade your skills. Coding/Trading/Handling finance and cars/homes etc. are basic skills needed along with work. Forget about the iphones and igizmos and start accumulating experiences.