~Hello World~
Welcome to the first edition of the QuarterliesFive
Weekly newsletter where top CEOs, investors, and senior leaders answer five thoughtful questions on leadership, decisions, meaning, and the moments that defined them.
New editions will arrive every Thursday morning. I’ll keep these same five questions for the first 12 weeks, then introduce a new set for the next season.
Starting with Michael Fassnacht, who is not only a close friend, an investor in my company Gatherset, but also a trusted mentor and one of the first people I’ve consistently called over the years when I’m assessing important decisions.
Have fun reading!
Michael Fassnacht is President & Chief Growth Officer of Clayco, one of the largest design-build and construction firms in the United States.
Previously, he served as Chicago CEO of advertising giant FCB, then as Chief Marketing Officer for the City of Chicago, and later as President and CEO of World Business Chicago, where he led the city’s global business attraction efforts and helped bring major companies, investment, and jobs to Chicago.
Over the past decade, he has become one of Chicago’s most powerful business leaders, a behind-the-scenes fixer, and a key power broker, known for building partnerships across the public and private sectors to strengthen the city’s position as a global hub for business, innovation, and talent.
What feels more fragile now than it did earlier in your career?
I think many of us feel fragile when the pace of change becomes overwhelming, or when we don’t fully understand the forces driving it. That’s where many of us find ourselves today where both of these forces are bigger than rarely in mankind’s history.
Change can be exciting, yet it also has a way of making us more anxious and vulnerable. Perhaps that’s because this moment of change touches all three core dimensions shaping our lives: political, economic, and social.
Change can be exciting, yet it also has a way of making us more anxious and vulnerable.
What does ambition cost that people don’t talk about enough?
Many people aspire to a highly successful career, one marked by prestigious titles, financial rewards, and external recognition. What’s often overlooked is that the higher one rises, the more visible one becomes, and with that visibility comes less freedom in everyday behavior, both professionally and personally. With each promotion, the behavioral “box” grows smaller.
Those who fail to recognize these boundaries may step outside of it, often facing unintended and negative consequences. You can read about these kinds of situations almost daily in the news, when someone lost their job because they didn’t understand that dynamic.
The higher one rises, the more visible one becomes—and with that visibility comes less freedom in everyday behavior.
What decision looked wrong publicly but felt right privately?
When I became CMO of the City, I brought a higher risk tolerance and a willingness to experiment into the Mayor’s Office. As a result, Mayor Lightfoot and I were criticized for several campaigns, including “Chicago. Not in Chicago.”
While some of this work faced significant public scrutiny, I still consider it among the best of my professional career, both for its breakthrough creativity and talk value, and for fundamentally shifting the risk profile of how a city like Chicago could be marketed.
Some of the work that faced the most criticism ended up being the best of my career.
Where do smart, successful people like yourself most often deceive themselves?
Many successful people underestimate the role that luck and good fortune have played in their professional journey. It’s easy to attribute success solely to personal brilliance
and hard work.
In reality, success is often shaped just as much by timing and happenstance, as well as by the support and sacrifices of many others along the way. Recognizing this, and openly acknowledging it, is one of the best paths to being humble and grateful.
Recognizing the role of luck in your success is one of the surest paths to humility.
What are you more protective of today than your title or income?
Absolutely my family. Once you have children, there isn’t a single day that goes by without worrying about them, wondering how they’re doing, or asking yourself if there’s anything more you could do for them.
Their happiness quickly becomes more important than anything else. You are as protective of them than you could ever imagine. But simultaneously, you need to give them space, freedom and the opportunity to make their own mistakes. It’s painful to
watch but absolute necessary.
The hardest part of parenting is loving your children enough to let them make their own mistakes.
