Where There’s a Will, There’s a Way

Sh*t That Isn’t True

Drew Dudley
Drew Dudley
5 min readMar 21, 2017


It’s interesting to discover what people have found to be true about life and leadership, but it’s fascinating to hear what they’ve found to be false. In the “sh*t that isn’t true” blog we explore cultural clichés and lessons you should “unlearn” on Day One.

Daniele Zanotti, President & CEO — United Way Toronto and York Region

Daniele Zanotti is the CEO of United Way Toronto and York Region, the largest United Way in the world. In his words, his job is “the perfect platform for system change, an ability to invest in good programs, do research, work with government on policy, and fundraise with individuals all committed to make a difference.”

The son of Italian immigrants, both of whom worked two jobs as he grew up, Daniele’s Italian roots played a big role in teaching him the ideas he now classifies as “sh*t that isn’t true”.

Wisdom from the Shoe Shop

“I spent a lot of time as an immigrant kid with my Nonno, my grandfather,” began Daniele. “He was a shoemaker. I had an opportunity a few times to visit in the summer in Italy before he passed away. We’d all be sitting in his little shoe shop — me, the local priest, the bread maker — as he was making shoes. While I was there I’d hear a couple of Italian sayings — as you call them ‘cultural cliches’ — that really stuck out to me. For a long time I carried them with me, but recently I’ve started to change how I feel about them.”

Daniele paused, and I realized he was taking a moment to figure out the translation from Italian.

“One was ‘A qui vuole, non mancano modi’,” he said. “Loosely translated in English it would be, ‘where there’s a will, there’s a way.’ I was always of the belief that, listen, if you got drive and you’re hungry, there’s a way. You’re going to get there and you’re going to do it on your own. It’s the concept of pulling yourself up by your bootstraps — where there’s a will, there’s a way.

A Collective Way

“But I don’t know now if I am as convinced about that anymore — the importance of individual drive,” continued Daniele. “I fully believe now that community and the wraparound supports that an individual gets are ‘the way’. I also feel that the way out of poverty, or the way to opportunity, is not as direct, linear, and fast as it was even when I was growing up, Drew. That worries me. I don’t know if the journey out of poverty today is as much about individual drive as where you’re born, who your friends are, and the social economics around you.

“How would you make that saying better?” I asked Daniele. “If you had to incorporate what you’ve learned since that day with your Nonna, how would you revise it?”

“I think we’d want to consider ‘where there is a will, there must be a shared and collective way.’”

“Might I call it a United Way,” he said with a laugh.

“I think this idea of individualism, while appealing in our culture, is fundamentally flawed,” Daniele continued. “No one gets there — whether you’re an entrepreneur, a political leader, or a community champion — no one gets there on their own. Despite your will, we need to rely on each other and our shared assets and skills to deliver.”

There Must Be Many Wills

“So you’re saying the phrase ‘where there’s a will, there’s a way,’ focuses too much on the individual,” I asked, trying to ensure I was clear on what he was saying. “What you’ve really come to believe is that it can’t just be one will. It has to be many wills.”

“That’s right,” confirmed Daniele. “Often, despite an individual’s drive and effort, we have many people working two jobs to make ends meet and still living in poverty. There’s no lack of will. But there are structural or system changes that need to be made to facilitate a way out. I think we need to reimagine the value of community and collective and united, versus individual pathways.

“Is it possible that the phrase ‘where there’s a will, there’s a way’ reinforces the idea that if you’re still in poverty it’s simply because you don’t want it bad enough?” I asked.

“Yes,” responded Daniele. “And I think that the reality of poverty is far more nuanced and complex. Every day I meet with individuals who are working very hard, in fact I would say harder, to cope and survive than many would be if they were working. The battle to lift out of poverty is not individual as much as it is collective and community.

What’s Your Leadership Community?

Last week, Bill Robinson identified the idea that “it’s lonely at the top” as some “sh*t that isn’t true”, and I see that idea echoed in Daniele’s thoughts as well: like climbing out of poverty, leadership has often been seen as an individual endeavour, with your success entirely dependent on your personal skills, dedication, drive and “hustle”. However, as Daniele pointed out, success in complex endeavours isn’t determined by the work of a single leader, but by the effectiveness of the leadership community that is built to support the goals and vision in question.

In fact, I was surprised to hear my second interview subject in a row use a specific term, “lead from the middle”. Daniele dropped it as we wrapped up the call and I asked him what advice he’d give himself on “Day One” of high school:

“I think I would offer two things around leadership,” he said. “Lead from the middle, and co-create. The bulk of the best ideas always come from the margins. They always come from the people you surround yourself with. That’s the magic of leading from the middle and servant leadership. Make those two things your starting point. Never create on your own. Always seek bigger brains to co-create.”

One of the toughest leadership skills I ever had to learn was to start assuming that all of my ideas were flawed in some way. I didn’t do it to get down on myself, but rather as a constant reminder to seek out feedback from the leadership community I built around me. After all, I long ago learned that many hands make light work, but many minds make great work.

As such, great leadership required great community building. Choose the minds that surround you carefully, and recognize that even if you’re smarter than every individual in the room, you’re never smarter than the collective wisdom of the room.

Daniele Zanotti Bio

Daniele Zanotti is the President and CEO of United Way Toronto and York Region — the largest United Way in the world. In 2015 he led a record-breaking $100-million campaign for United Way agencies, programs, and initiatives. Prior to his time at the United Way, Daniele served organizations like the Rexdale Community Health Centre; the Regional Municipality of York; Family Day Care Services; and Villa Charities Foundation. He has been a member of the steering committee for CivicAction, and has volunteered on the boards of the Toronto Region Immigrant Employment Council (TRIEC); the Human Services Planning Board of York Region; and the Vaughan Community Health Centre.



Drew Dudley
Drew Dudley

Founder & Chief Catalyst of Day One Leadership. West Wing junkie. Collector of penguins. Did that TED talk on lollipops.