I used to like to make myself sad, so I would listen to Bill

Gillian Jacobs once revealed a confession of the heart, both tender and strange: “I used to like to make myself sad, so I would listen to Bill Callahan as Smog.” At first, these words may seem paradoxical—why would one seek sorrow deliberately, when life already offers grief in abundance? Yet within this admission lies a profound truth about the human spirit: that there are times when sadness itself is a form of nourishment, a way of entering more deeply into the mystery of existence. To choose melancholy is not always to despair, but to allow oneself to feel fully, to cleanse the soul through tears.

The origin of her sentiment rests in the power of music itself, and in the particular artistry of Bill Callahan, whose work as Smog is marked by quiet, haunting lyrics and melodies that reveal the weight of solitude. Jacobs, like many seekers of art, turned to his songs as one turns to a mirror, seeing within them her own unspoken longings and hidden sorrows. In listening, she did not merely consume sadness—she cultivated it, she dwelt in it, as if sadness itself were a teacher. And indeed, it often is.

History offers us many examples of those who, like Jacobs, sought the bitter cup of melancholy willingly. Consider the ancient poets of Japan, who composed haiku and tanka about the fleeting beauty of cherry blossoms, not to celebrate joy alone but to contemplate impermanence and loss. Their sadness was chosen, not forced upon them, yet it deepened their appreciation of life. Or think of John Keats, who spoke of “the beauty of melancholy,” suggesting that sorrow sharpens our ability to see the world’s wonders more vividly. Jacobs’s practice belongs to this lineage: the deliberate embrace of sadness as a means of illumination.

There is also wisdom in recognizing that to choose sorrow is to reclaim power over it. When grief comes uninvited, it can crush the heart; but when we step into sadness by choice—through music, poetry, or meditation—we learn to walk with it, to understand it, to let it pass through us without destroying us. Jacobs’s tears before Smog’s mournful songs were not signs of weakness, but of courage: the courage to face the shadows of the heart, rather than flee them.

The deeper meaning here is that sadness and joy are not enemies but companions. Without sorrow, joy cannot be fully known. Without melancholy, delight loses its depth. Jacobs’s confession teaches that there is value even in seeking sadness, for it tempers the spirit, makes us tender, and opens our hearts to the struggles of others. It is when we have sat willingly with our own sorrow that we learn how to comfort the sorrowful around us.

The lesson for us is this: do not fear sadness, and do not despise the moments when you choose to dwell in it. If a song moves you to tears, let the tears flow. If a story reminds you of loss, let the ache teach you compassion. The danger lies not in feeling sorrow, but in denying it, in hardening our hearts against its lessons. By allowing ourselves to feel, even by choice, we remain human in a world that often urges us to numbness.

Practical wisdom follows: seek balance. Do not drown yourself endlessly in melancholy, but do not avoid it entirely either. Let sorrow be like winter—cold, yes, but necessary, for it prepares the earth for spring. When you feel drawn to songs, poems, or memories that stir sadness, take the journey. Listen, reflect, and allow that sadness to make you gentler, wiser, more patient with the fragile humanity of others.

Thus Gillian Jacobs’s words endure as more than a memory of youth: “I used to like to make myself sad, so I would listen to Bill Callahan as Smog.” They remind us that sadness, when embraced with intention, is not destruction but purification. To choose to feel deeply, even when it hurts, is to live more truly. And in this, we learn that the soul, like music, carries many notes—some joyful, some mournful, but all essential to the symphony of being alive.