Bearing the Burden: Why “It Should Be Easier Now” Endures
Released in February 1972 on the album Good Hearted Woman, “It Should Be Easier Now” occupies a quietly profound place in Waylon Jennings’ body of work. It is not one of his loudest outlaw declarations or a song built for radio dominance. Instead, it is a reflective pause—a moment where experience, regret, and emotional honesty take center stage.
From the opening bars, the song carries the weight of lived life. Jennings’ baritone, already seasoned by years on the road and a career shaped by resistance to Nashville’s polish, sounds weary in a way that feels earned rather than performed. There is no attempt to dramatize pain. Instead, the song allows emotion to surface naturally, shaped by restraint and restraint alone.
At its core, “It Should Be Easier Now” asks a deceptively simple question: once love is gone and time has passed, shouldn’t the ache fade? The song’s quiet power lies in its refusal to offer a comforting answer. Jennings presents a narrator who understands his mistakes, recognizes what has been lost, and yet remains tethered to memory. The passage of time, the song suggests, does not guarantee release. Sometimes it only sharpens awareness.
Musically, the arrangement mirrors this emotional honesty. Pedal steel drifts gently through the background, acoustic guitar anchors the melody, and the rhythm section stays deliberately subdued. Nothing competes with the vocal. The production avoids flourish, allowing space for Jennings’ phrasing, pauses, and subtle shifts in tone. Each breath feels intentional, as though the singer is choosing his words carefully, even as he sings them.
This inward focus is significant within the larger context of Good Hearted Woman. The album marked a turning point in Jennings’ fight for creative control, often associated with defiance and independence. Yet “It Should Be Easier Now” reveals another side of that freedom: the willingness to be vulnerable. Instead of playing the rebel, Jennings turns the lens on himself. He acknowledges emotional stubbornness, unresolved longing, and the quiet disappointment of knowing better but still feeling deeply.
Unlike many country songs of the era that told stories at a distance, this track feels personal. The narrator is not judging, preaching, or blaming. He is simply admitting that knowing something should be easier does not make it so. That honesty gives the song its lasting resonance.
For listeners who have lived long enough to carry emotional history—lost relationships, choices that still echo, mornings that feel heavier than they should—this song lands with particular force. It does not seek to console with platitudes or promise closure. Instead, it validates the experience of lingering feeling. It recognizes that healing does not follow a schedule and that emotional strength often looks like endurance rather than resolution.
What makes the song especially enduring is its lack of self-pity. Jennings never portrays himself as a victim. There is accountability in the lyrics, a quiet understanding that some burdens are self-made. Yet there is also compassion—for oneself, for the human tendency to hold on even when letting go seems logical.
In this way, “It Should Be Easier Now” reflects a deeper definition of maturity. It suggests that growing older does not mean becoming immune to pain, but rather learning how to live alongside it. The scars remain, but they no longer dominate every moment. They become part of the background, shaping perspective without defining it.
Decades later, the song still speaks because it tells a truth that does not age. Love leaves marks. Time helps, but not always in the ways we expect. And sometimes, the bravest thing a person can do is admit that despite everything, it still isn’t easy.
In “It Should Be Easier Now,” Waylon Jennings offers no solution—only recognition. And in doing so, he reminds listeners that honesty itself can be a form of comfort.
