Whether it's "Happy Christmas" (which seems to have eclipsed the more traditional exhortation to be "merry"), "Happy New Year", or the religion-neutral American import "Happy holidays", so many hopes for contentment can have the unintended effect of seeming like a reproach, especially if we are not feeling as chipper as the season appears to demand.

It is often claimed that the "festive" period is one of enhanced misery for many, with rates of depression soaring as people grapple with family strife or loneliness that is in stark contrast to social expectations. There is conflicting evidence on this – calls to helplines like the Samaritans do increase over the holidays, but the suicide rate tends to dip, at least until the New Year kicks in. Nevertheless, the common perception of widespread seasonal woe, even if anecdotal, suggests that the forced imposition of "happiness" on a particular time of year can have unintended consequences.

However, there is another, much more useful phrase for describing the potential of the holiday period – "the season of good cheer". Whereas the word happiness implies an end state, the result of causes and conditions over which we may have little control, cheerfulness is volitional, a deliberate decision to be good-spirited. Indeed, it may be especially appropriate to rouse "good cheer" at times – such as midwinter – when outer circumstances seem wretched and we are more likely to feel downcast.

The value in distinguishing between "happy" and "cheerful" was underlined by the Tibetan meditation master Chogyam Trungpa Rinpoche. Trungpa was hugely influential in bringing Buddhism to the west in the 20th century, not least because of his precise and profound understanding of the English language and his ability to apply it in expounding Buddhist principles. He used to make a point of wishing people a "cheerful birthday" or a "cheerful new year", emphasising that we can make a decision to connect and identify with our basic wellbeing (also known as Buddha-nature), even when we are in the midst of suffering.

By making a conscious decision to be cheerful, including when we are in pain, we diminish our identification with unhappy circumstances and strengthen our confidence that we are not entirely at their mercy. This brings us choice – perhaps not over the circumstances themselves, but over how we relate to them. If we choose to respond with cheerfulness, we not only stand a better chance of weathering the storm, but we are subtly strengthening our ability to deal constructively and positively with life's inevitable insults.

I've learned a little of this through my own experience. During an almost-three year bout of depression and anxiety, I became stuck in negativity, digging myself further and further into a pit of despair. In an attempt to understand my gloom, I dove right into it – unfortunately this just strengthened my habitual tendency towards seeing the dark side of things, entrenching my sense of self as a "depressed" person, which as a result I continued to be. It's only when I learned first how to accept rather than fight than my mood, then to detach from it, and then finally to actively cultivate its reverse, that I was able to recover. I still have a predisposition towards melancholy, but by applying cheerfulness even, or rather especially, when I least feel like it, these days depression seems to overtake me far less often and for shorter periods.

The acceptance part of the process is important – cheerfulness should not be confused with the sometimes-nauseating "everything's-going-to-be-alright" approach that positive thinking gurus often appear to advocate. The purpose of cheerfulness isn't to deny that life is sometimes shit, it's that we aren't dependent on the happiness that comes from circumstances in order to find ways to wonder at it – as one Buddhist elder once asked me: "Rather than just liking the smell of roses, or hating the smell of manure, perhaps you could start appreciating that you have a nose?"

Wishing cheerfulness on others is a simple way of spreading what in Buddhism are known as "the four immeasurables" – love, compassion, equanimity and joy. Such a wish is not only expressing a desire for people to be happy, but that they might have the tools to cultivate a sense of wellbeing independent of whatever pains and pleasures they experience during the winter holiday season, or at any other time. And that, to me, seems like a wish worth making.