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I have built a pretty solid portfolio of stocks over the last 7 years. The majority of my portfolio is established, dividend-paying companies that have solid balance sheets and years of successful growth. This strategy has worked fairly well, as the stocks have gained value and the dividends add-up. A long-term investor watches their holdings gain in value over time. You may trim some stocks, add some new ones, etc. but if you are buying long-term established companies, you expect them to grow over time and build value in your portfolio. However, this also presents a challenge.

This makes it harder for me to double-up on stocks that I already own. I hate the idea that I purchased X amount of shares of a quality stock at $43, but now, the stock price is at $60, but it still looks attractive. I have a hard time pulling the trigger and buying more of the company’s stock at the higher price. Even though I feel the stock is still attractive, knowing that I will pay substantially more than I previously did per share is a concept I have to struggle to overcome.

This is a good challenge that exists because I have been accruing more cash with which I want to invest. If I only had a set amount of cash and I invested 100% of it in stocks, the opportunity to buy more wouldn’t be there, unless I sold some holdings to acquire others. But, since I have been lucky enough to continually add cash to my investment portfolio, it is the challenge I am faced with.

I need to remember that I am not competing against my initial stock purchase, but rather investing in the company as it stands at the current price. And actually, for any of these situations, you have a track record of knowing how the company has already performed for you. You expect long-term growth stocks to do just that, grow. A buy decision shouldn’t be made because of previous price point purchases, but rather, where you feel the stock stands today.