Will progressively investing with moderate-to-high risk help secure a future?
There are a few flaws in your reasoning: I know my portfolio will always keep going up, No, it won't.  You'll have periods of losses.  You are starting your investing in a bull market.  Do NOT be fooled into believing that your successes now will continue indefinitely. The more risky your portfolio, the bigger the losses.  The upside of a risky portfolio is that the gains generally outweigh the losses, but there will be periods of losses. I honestly don't believe that it's possible for me to end up losing in the long term, regardless of risk. I think you vastly underestimate the risk of your strategy and/or the consequences of that risk.   There's nothing wrong with investing in risky assets, since over time you'll get higher-than-average returns, but unless you diversify you are exposing yourself to catastrophic losses as well.