Having been a stand-up comic since 2001, I’ve always had some familiarity with Mike Birbiglia, from his first appearance on Comedy Central’s Premium Blend, through his more extended specials, late night spots, and albums. Although I did briefly meet him once as he toured through my hometown, my general awareness of him is as an outside observer, filtered through his recorded material. He always struck me as an artist who was still trying on different hats, trying to figure out where he belonged. Moving standard monologist jokes into guitar act type of stuff, before really hitting his stride as a storyteller.

With his 2012 film Sleepwalk With Me, based on his one man show and book of the same name, Birbiglia again shifted into the role of filmmaker. Fairly successfully too, Sleepwalk With Me is the rare film that really captures the life of a struggling stand-up comedian, a messy and hard journey that strains relationships and constantly tests our commitment. Birbiglia’s fictional surrogate character’s ‘big break’ isn’t a writing gig for the world’s biggest comedy film star, or a competition that will make or break his career, it’s just a series of mediocre-pay road gigs that for the first time really make him believe he’s gonna make it.

Sleepwalk With Me could have been a fluke, the culmination of the ludicrous fate of a habitual anxiety-induced sleepwalking condition plaguing a comedian who just happens to have an established gift for making painful stories into hilarious material. Yet, here Birbiglia is back again with Don’t Think Twice, another exploration into the world of comedy, this time improv, and toll it takes onto those who make it their lives. While not a true sequel to Sleepwalk, it draws from enough of the same pathos to feel like a spiritual one.

The general theme of Don’t Think Twice can be summed up in a line from its trailer, “your twenties are all about hope, and then your thirties are all about realizing how dumb it was to hope.” If Sleepwalk With Me was Birbiglia’s ode to the first steps into a career in comedy, Don’t Think Twice is a bookend, a love letter to those whose careers have stalled, are in decline, or perhaps were never really much to begin with.

As a comic in her mid-thirties, who has had some decent breaks but is far from famous, Don’t Think Twice was a difficult film to watch at times, a sentiment I’ve heard echoed from several of my peers. The only other movie I can remember that best depicts the fearful gaze into the void of obscurity that comes from a life in service of a faded dream is Darren Aronofsky’s The Wrestler. A gaze best presented in Birgiblia’s Miles, the most veteran member of the group who makes his living teaching improv to beginners.

Miles has seen former peers and now even former students (Keegan-Michael Key’s Jack) surpass him, soon to forget him entirely. Miles is deeply bitter and lost, clinging to a memory of a single audition for Weekend Live over a decade earlier. There’s no indication that Miles has ever had any other opportunities or that he’s even pursued them if he had, instead choosing to blame others around him for his position in life and sleeping with his students to trick himself into believing he’s still that 23-year-old with a chance.

It’s a big risk for the director and writer to cast himself as a fairly unlikeable character like Miles, but it pays off well with the occasional glimmer of goodness that we know could shine out more if he just let go of his resentment. I know Miles so damn well. I’ve met so many of him over the course of my career, and I think many of us are terrified that one day we’ll look in the mirror and see Miles there. When you’ve been pursuing a dream for your entire adult life and yet still linger on the fringes, it’s hard not to.

The flip side of this is Gillian Jacobs’ character Sam, who skips out her own audition for Weekend Live and seems to simply want to just do improv forever, exactly as she has been. I related most to Sam out of all the characters. She’s someone who loves performing, feels most at home doing their shows, but seems frustrated, perhaps even frightened of the business part of show business. I see Sam in every writing packet I didn’t send out, or every festival I chose not to send to. The film makes the solid argument that Sam is actually right where she needs to be, but as audience members accustomed to seeing characters take a journey, it feels jarring to be told, no, this character doesn’t need help, she just needs to be left alone. While I’m not as content to stay at my level as Sam is, I share a kinship with her as someone who has spent the last several years shedding the baggage of that I’m “supposed” to do and instead carving out my own journey through this business in the way that makes me happiest. (Although ironically for me, doing so led me to the biggest successes in my career.)

I won’t go so far as to call the movie’s characters failures, because I don’t think the film or Birbiglia himself views them that way. They’re portraits of dreamers, of people who have continued to chase the vague idea of stardom, living in a world that so narrowly has defined what the term “making it” even means. The great tragedy at the heart of so many of the characters’ arcs is that had their lives continued exactly as they were at the start of the film, scraping by a day to day existence in order to continue doing their shows at night, they all might have stayed pretty happy. Not unlike Sleepwalk’s fictionalized road comic, they’ve actually made it.