Will Burns never thought of himself as a gambler. He wasn’t the type to bet on sports games or sit at a blackjack table in a casino. The thrill of winning didn’t outweigh the certainty of losing—primarily when the odds were structured against the player and tilted heavily toward the house.
From his very first job at the age of fifteen, Burns knew that money came only through hard work. To throw it away chasing a slim chance of a payout wasn’t in his nature. Yet while he avoided games of chance, Burns was no stranger to risk. His life and career tell a different story, shaped not by avoiding uncertainty but by stepping directly into it when the moment called for courage.
Burns didn’t grow up with political connections in Chicago. He didn’t inherit a network of powerful friends or a clear path into public office. Every rung he climbed was through his own initiative, and many times, that meant taking a leap when the outcome was anything but sure.
In 2007, one of those leaps presented itself.
A state representative had recently died, and her seat was filled on an interim basis by the representative’s secretary. In theory, this appointment would help ensure continuity with the deceased officeholder’s staff.
Still, in practice, it quickly became controversial when the new representative broke with other lawmakers and voted against a gun control bill that was part of Mayor Richard M. Daley’s 2007 public safety agenda. The vote made her politically vulnerable ahead of the following year’s primary.
Democratic leaders in the district knew they needed a strong challenger. And in a district where Democrats held overwhelming sway, the winner of the primary would almost certainly win the seat in November. Their first choice, Candidate A, was recruited with high hopes and firm support. But almost immediately, problems surfaced. Candidate A ignored advice from the very party leaders who had pushed him into the race. Frustrations grew, doubts multiplied, and within weeks, confidence in him all but collapsed. The search began anew.
That search led to Will Burns. At the time, Burns had already spent more than a decade in the trenches of policy making, legislation, and politics. He had forged relationships, acquired domain knowledge on public education that few others had, and enjoyed the trust of important institutional actors affiliated with his cause.
But saying yes would be difficult. The election was fewer than six months away, so there was no time for an exploratory campaign or even to take a poll. Running also meant leaving the position of deputy chief of staff in the Senate President’s office—a stable and influential job that he had worked hard to earn.
It also meant figuring out how to support his family without the steady paycheck, all while dedicating himself entirely to a campaign that would demand every ounce of energy and focus.
And Burns knew firsthand how all-encompassing that commitment can be. Campaigning is not a nine-to-five affair; it takes over your entire existence. A candidate’s day consists of meetings with donors, discussions with potential supporters, work on policy and messaging, coordination with staff, events in the community, and with organizations that have invited the candidate to appear.
Days start before dawn at bus stops and end long after dark at people’s homes hosting neighborhood gatherings. Even holidays provide little relief. You hand your life over to the campaign for as long as you’re a candidate—your friendships, your family, and even you yourself become secondary.
The safer path would have been to decline. He could have stayed in his role, avoided the stress of financial uncertainty, and watched the race from the sidelines. No one would have faulted him for it.
But that felt like running away for Burns. He had spent years dreaming of being a legislator, knowing full well the kind impact good, strong legislators can make in Springfield. He also knew something else to be true: chances like this don’t come around too often. To let it pass by might be to miss out on an opportunity forever.
After careful but brief conversations with trusted advisors and his family, Burns made his choice. He stepped in.
The risks were real, but so was the opportunity. And above all, Burns believed in himself. He thought he could compete, and he felt he could win. More than that, he wasn’t willing to look back years later with regret, wondering what might have happened if he had taken the leap but instead chose to stay safe.
For Burns, the campaign was more than an election. It was a test of his courage, faith, and character. To say yes meant to bet on his sweat, relationships, and determination to outwork everybody else in the race. It was a gamble without escape clauses, but one he had to take if he wanted to get closer to the goals he had set for himself.
Looking back now, Burns sees that moment as a turning point in his life. The leap into uncertainty reinforced a lesson he had long understood: dreams are rarely handed down like heirlooms. For most people, dreams are earned through risk, through sacrifice, and through the willingness to face failure head-on.
Will Burns’ story vividly illustrates this. He didn’t gamble at the casino table. He gambled on himself. He gave up ease and security for the prospect of public service. His risk wasn’t calculated in dollars but in devotion, stamina, and daring to commit when you aren’t sure where things are headed.
Ultimately, that decision to take the leap made all the difference. Burns showed that while avoiding unnecessary losses is wise, some risks are worth it. Because when the chance to pursue your calling arrives, hesitation alone can be the biggest loss of all.
