Mr. Lif was a corner piece of the Definitive Jux puzzle, as important to its cause as co-founder El-P, Cannibal Ox, or Aesop Rock. The Bostonian nonconformist took an analytical approach to writing that attempted to drill home on-the-nose messages. His debut album, I Phantom, remains one of Def Jux’s seminal achievements and it is still his best work to date, a concept album on how black people are disenfranchised by the American system. He has always been equal parts revolutionary and educator, finding his way through carefully-articulated syllabic mazes in search of hard truths. He doubled-down on this in his last two albums, the surging class evaluation Mo’ Mega and its heavy-handed followup I Heard It Today. After a seven-year absence from rap, he has returned with Don’t Look Down, his first album on Mello Music Group, a sharp technical marvel and a meditation on all that’s brought him here. This is a record of the weary lecturer, one who has long been fighting the good fight with little to show for it. But Mr. Lif doesn’t ever wonder if it was all really worth it; he merely acknowledges the cost.

Unlike past sanctimonious lyrical displays, which read like condensed civics seminars, these raps are riddled with mentions of missed opportunities and internal self-doubt, and they’re delivered with a dryness that only enhances the candor. The what-ifs here are personal, not historical or conspiratorial. “Well I’m sitting at my table now, hands crossed, blast off/ Thinking ‘bout some opportunities that I had passed on/ Hindsight is 20/20, thinking isn’t helping any/ Drinking will just serve to end me/ Progress, am I making any?” he raps on “Everyday We Pray.” It's a peek into the exhaustion of the lifelong renegade: When your life’s work is beating your head against the walls of the political establishment, it’s natural to wonder if it has actually done any good.

Lif has sought to use his career to explain complex ideas to strangers, yet he’s spent just as much time making basic ideas complicated. “The goal is to search deeper and go smarter and think harder,” he raps on “Let Go,” but overthinking has always been one of his weaknesses. Don’t Look Down keeps things relatively simple, opting for narratives and wordplay that are far more approachable. What ties the whole experience together is his cautious optimism, along with his still-firm belief that struggle builds character. Don’t Look Down openly acknowledges doubt but never succumbs to it, instead using it as a balance for self-righteousness. There aren’t any regrets, only lessons learned. The emotional (and literal) centerpiece for the album is “A Better Day,” which opens with a snippet of Dr. Martin Luther King, Jr.’s speech “I’ve Been to the Mountaintop.” In it, Mr. Lif uses the full arsenal—his lyrical dexterity, his reflexive flow, and his observant eye—to paint a vibrant picture in broad strokes.

And yet the best moments on the album are the free-wheelers, records that aren’t anchored by any weighty concepts, allowing him to just be the proficient rapper that he is. On “World Renowned,” the fun-loving energy of Del the Funky Homosapien rubs off, and over a skipping loop it sounds like both tag-team partners are having a good time. Lif snuggles into the undulating wave on the Edan-produced “Whizdom,” which billows around him. The best of these is “Mission Accomplished,” which reunites the Perceptionists and finds the two emcees finishing each other’s syllabic yarns in call-and-response. It’s in the moments when he isn’t tethered to any belief system that Mr. Lif sounds most liberated.