How important is it to ramp up your investments over time? I started from a non-investing position and am slowly investing everything in 2 week intervals over the course of the year. The goal is to normalize risk over time but I worry that I'm missing opportunities to invest as they are simply sitting in savings accounts. What is your perspective on this?
This is much more a psychology question than a finance question. On the finance side things are pretty clear: because all investments are expected deliver positive returns over time, the sooner you invest the higher your returns can be rationally expected to be.
Unfortunately, "expected to be" is not the same as "will be". This is where the psychology comes in. Bear markets do happen and sometimes those expected returns do not materialize -- at least not for many years or even decades. If we happen to be heading into a bear market you will certainly be glad that you waited. But there is no way of knowing if that is the case. Obviously, plenty of people do claim to have this knowledge of future bull or bear markets. But for some reason these people also tend to work 9-5 jobs and spend a lot of their time convincing others of this special ability of theirs instead of cruising the Tropics on their mega-yacht. Draw your own conclusions on their market-timing skills.
If some investments were obvious screaming bargains, then things would be simpler. But unfortunately that is not the case. Bonds range from somewhat to very pricey, Stocks might possibly be fairly priced, but certainly nowhere close to cheap (cheap was late 2008 and early 2009). Gold is obviously not cheap after its tremendous run of the past decade plus. Even cash is "expensive" as it's likely getting not too much more than 0% return for you, so it's not like you are getting compensated for deferring your investments.
I think of spreading out potential one-time investments over time as a way to minimize regret. Regret is a powerful and unpleasant emotion. Few people are immune from it completely. In extreme cases, regret of past actions can lead you into making new mistakes. It's very rational to minimize regret as long as the cost of doing so is not excessive. By spreading your investments over a year you are extremely unlikely to ever have to regret investing at the worst possible time. You will always be able to point to one date and say "well, at least I only bought a little bit there". About other dates you will be able to say "I wish I bought more then, but at least I got something on the cheap". And so on. Obviously all of your purchases could still end up under water after some time as a bear market accelerates. But there's no escaping bear markets completely. At least you will have some relative highlights to think back to instead of the crushing regret of buying everything at the top.
But make no mistake. All you are accomplishing by spreading out your investments over time is minimizing potential regret. If it ends up a profitable strategy it will be purely by luck -- not by design. By design this strategy will lose a bit (but likely only a little bit) relative to the buy-it-all-at-once approach. If you are finding yourself regretting the very choice of trying to minimize regret by spreading out your investments, then perhaps it's easier to just pull the band-aid off all at once and immediately commit all your funds earmarked for investing. Only you can know which choice will be easier on you psychologically or whether the psychological gain is worth the (small) expected loss of missing out some time in the market. Obviously, whichever way you go, make sure you are sufficiently educated on how to invest.