This is an important concept and strategy which requires some self discovery. To answer this question, the first thing one must do is to determine if one is a long-term investors or simply here to speculate. The best quote on this topic can be found below.
Our opinion depends on the person and the situation. A trader should never average down, only averaging up. A long-range investor who feels the company is down steeply because of temporary factors, and is near Major Support, should certainly average down. But for near-term action, nothing beats averaging up. This philosophy of buy-high-sell-higher is based on the theory that if your original judgement was correct, you should put more money behind it, rather than throwing good money after bad, as you do when you average down.
James Dines. How The Average Investor Can Use Technical Analysis For Stock Profits, 1974. Page 141
Our strategy of observing companies at or near the yearly low implies that buy-high-sell-higher is out of our comfort zone. However, we respect the wisdom from other market observers and recognized the importance of speculation.