By Jack Dorsey
Estimated reading time: 5 minutes
"Expect the unexpected. And whenever possible, be the unexpected." This Jack Dorsey quote about courage lands with a jolt, framing life's uncertainty as both challenge and adventure. In a world eager for routine and guarantees, the words call for boldness—a mix of awareness and daring. The energy in Dorsey's advice can spark important changes and help us see unpredictability not as a threat, but as possibility. Whether in daily choices or long-term dreams, this reflection on the unexpected plants a seed of confidence, inviting us to step outside comfort and break new ground.
What Does This Quote Mean?
At first glance, "Expect the unexpected" sounds like a twisty riddle. But Jack Dorsey is getting at something very practical beneath the clever phrasing. He's talking about courage—the courage to face uncertainty not just with acceptance, but with readiness. Life never fully follows a script. No matter how carefully you plan, surprises will arrive: sudden opportunities, setbacks, new paths opening when old ones close. Expecting the unexpected means reminding yourself that surprises are the rule, not the exception. This mindset prevents disappointment, and turns shocks into chances to adapt.
The second half, "be the unexpected," goes beyond readiness. Here, Dorsey invites us to actively surprise others, and even ourselves. Instead of waiting to have surprises thrust upon you, become a source of unpredictability. This is not about being random or reckless, but about thinking creatively, acting with originality, and daring to do what others don't see coming. It's about being proactive, refusing to simply react to circumstances.
This Jack Dorsey quote about courage carries both a warning and a rallying cry. Life will diverge from your plans, so build flexibility into your expectations. More than that—don't just handle surprise; create it. In everyday actions and big decisions, stand out by thinking differently and acting inventively. It's this mix of anticipation and daring that fuels true resilience and progress.
How Can You Use This Quote in Life?
1. Welcome Change—Don't Just Brace for It
Change is everywhere: in your career, relationships, and even daily routines. Instead of stubbornly clinging to old habits, start expecting things to shift. Make it part of your regular thinking. When you anticipate change, setbacks don't rattle you as much. You develop an ability to pivot, adapt, and learn on the fly. It's a mindset powered by courage, echoed in the Jack Dorsey quote about courage itself.
2. Surprise Yourself with New Challenges
Getting too comfortable can dull your instincts. Choose to shake things up now and then. Sign up for something you'd usually avoid, like a public speaking workshop or tackling a tough project. Push past what feels predictable in your own behavior. By "being the unexpected" in your own life, you keep discovering skills and strengths you never knew you had.
3. Bring Creativity to Your Work and Interactions
In meetings, conversations, or creative projects, look for unexpected angles. Share a bold idea, ask a surprising question, or suggest an experiment others haven't considered. When you take initiative in this way, you help your team escape routine and see possibilities they might have missed. People are drawn to those who spark new energy and direction.
4. Respond Calmly to the Unforeseen
When sudden changes hit—a plan derails, tech fails, or an emergency crops up—pause before reacting. Remind yourself that unexpected twists are part of life's script. Stay calm, assess, and act with curiosity instead of panic. Over time, this habit turns surprises from sources of stress into opportunities to shine under pressure.
5. Be a Pattern Breaker
Sometimes, the most powerful move is to act against expectations—kindness to an adversary, humility in victory, or persistence when quitting would be easier. These unexpected actions can transform relationships, shift workplace cultures, or help you stand out for the right reasons. Pick moments to break the pattern and leave a positive impression.
By weaving these ideas into your daily routines and bigger choices, you do more than cope with surprises—you embody them. This approach makes you both resilient to life's shocks and memorable for your own bold moves.
✨ The Motivation Message
You are so much more than the patterns you repeat. The world around you will throw surprises, sure—but you don't have to stay on the sidelines! Every day, you have the power to breathe fresh energy into your actions, step into the unknown, and turn obstacles into openings. Imagine the spark you can ignite—in yourself and in others—when you choose to be the one no one saw coming. 🌟
You don't need to have all the answers ready. True courage is willing to adapt, to learn, and to lead even when the outcome isn't guaranteed. What matters most is choosing to participate fully, to meet uncertainty with a sense of possibility. Others will notice your spirit and draw strength from your example!
This is your time to move forward with your head high, fueled by both anticipation and boldness. Take that first step—share a daring idea, chase a new path, try what feels intimidating. Trust that by expecting the unexpected, and sometimes being it, you will shape a life that's vivid and uniquely yours. Start today!
About Jack Dorsey
Jack Dorsey, who was born in 1976, is a well-known American entrepreneur and the co-founder of Twitter and Square. Raised in St. Louis, Missouri, Dorsey has always been fascinated by technology and how people communicate. Throughout his career, he has championed the power of openness, direct action, and challenging the status quo. His worldview is shaped by curiosity and a willingness to take risks, qualities that helped him launch two of the most influential digital platforms of this century.
The quote "Expect the unexpected. And whenever possible, be the unexpected" is a window into Jack Dorsey's approach to both technology and life. It reflects his belief in constant adaptation and in pushing beyond boundaries—whether creating a new product, leading a team, or dealing with life's curveballs. Dorsey's broader message encourages us not only to be resilient but also to be brave enough to invent, disrupt, and surprise the world. This philosophy has made him a prominent figure in innovation, inspiring others to approach uncertainty with both readiness and intentional courage.
