Book Review: And You Will Call It Fate

And You Will Call It Fate, Timothy J. Hillegonds, University of Nebraska Press, March 2026, print, 170. 

Reviewed by Philip Janowski.

And You Will Call It Fate is a memoir by Chicago author Timothy J. Hillegonds. The narrative begins in the early 2000s when Hillegonds enters a complex business relationship with Sean Dempsey, a former football player turned owner of a financial services firm. (Let it briefly be stated that the identities in the book, besides the author’s, are concealed.) The title comes from a Carl Jung quote that introduces the text: “Until you make the unconscious conscious, it will direct your life and you will call it fate.”  

In 2002, Tim (as he is largely referred to in the memoir) is a twenty-four year old waiter at a Baker’s Square restaurant, having dropped out of college several years ago.

We learn quickly that he is a partier with both a drinking problem and a cocaine problem. Less quickly we learn that he’s left behind a string of crimes and debts, as well as a young daughter, in Colorado. Tim is likable, though, and as with many young people, keeps his night life hidden. Dempsey meets Tim at Baker’s Square and offers him a job at his company — perhaps Dempsey sees a younger version of himself in Tim. Tim sees a chance for a better life, and accepts. 

This offer from above begins Tim’s journey of self-development, a process Jung called individuation — the journey to recognize yourself in all your aspects, good and bad, and in so doing, both accept and become your truest self. Dempsey is no angel, however, and to face your dark side is no picnic. Dempsey is an archetypically masculine man, fairly out of touch with his emotions, and so liable to burst into rage. Sometimes this rage results in violence. He is also presented with archetypal masculinity in his role as a mentor, practically a father figure. Tim truly admires Dempsey, who has achieved financial success and resonates with power. He helps Tim too, even arguably to the point of saving his life. 

Tim’s alcoholism worsens to the point that Dempsey fires him. Dempsey, however, was a former alcoholic, and he offers Tim a nearly miraculous deal: Dempsey will send Tim to one of the best rehab centers in the country, all expenses paid. He will even pay for Tim’s child support during the stay. Tim accepts, and while at the rehab center, participates in Alcoholics Anonymous. When Tim returns to Chicago, Dempsey rehires him. 

The temptation to drink and use hard drugs persists — after all, it’s one day at a time. But even if it’s an uphill climb, Tim’s journey is still upward from this point forward.  

Other challenges appear during the struggle for sobriety: Tim seeks to reconnect with his ex and daughter in Colorado where authorities still pursue his arrest. Dempsey relocates his work to North Carolina and takes Tim with him, leaving behind the city that Tim loves. And finally, when Tim tries to leave Dempsey to forge his own career path, Dempsey sues him for everything he has.  

And You Will Call It Fate is a captivating reflection on a man reaching for a better life and achieving it. Tim and Dempsey’s tumultuous relationship rightfully form the core of the memoir, with Dempsey being both the helping hand from above and the enraged bull that seeks to destroy Tim when Tim no longer fits Dempsey’s definition of loyalty. The gray morality is smartly handled, and even by the end we cannot see Dempsey as a monster. He lives in a state of toxic masculinity—a theme that is explored several times throughout—but it is the kind of toxic masculinity that many are willing or are tempted to follow. Strength and skill are attractive traits, even when used for destructive purposes. It is part of Tim’s journey to unentangle himself from the destructive side of these qualities and achieve a more balanced self.