Throughout Church history there have been two major ways to follow this demand. Monastic orders make the Liturgy of the Hours top priority, while other aspects of their day (work, meals, recreation, sleep) revolve around these times of prayer. There were even times in history when monks would allow themselves only one hour of sleep to have almost the whole day devoted to prayer. Lay persons, along with priests and sisters not living in monastic communities, follow “Pray always” by leading the best Christian lives they can while punctuating their day with prayer. Such periodic prayer can be a quick one-liner, a period of meditation, the Mass or any other “lifting of the mind and heart to God.” The two ways, of course, need to be more nuanced than this short description allows, but my point is that both are meritorious responses leading many to lead very holy lives.
Whether living in a monastery or “in the world,” all of us can aim to “pray always.” One technique is to have a “signal” reminding us to pray more often than our regular prayer. One signal I use is lifting my coffee cup when I sit to pray first thing in the morning. God and I hold our mugs like beer steins and tell each other “cheers.” Just one word, one second of time, one thought, and a smile between God and me. Often this first prayer of the day is my best prayer of the day.