The Accidental CISO (AC) is an anonymous voice in cybersecurity who stumbled into the Chief Information Security Officer role through a mix of timing, skill, and necessity. With a background in IT operations and service delivery, AC found unexpected purpose, community, and a platform for candid reflection on security, leadership, and personal growth. He now hosts The Mindful Business Security Show, educating SMB leaders on practical security.

"I was just looking for a place to vent. I didn’t want to get fired for telling the truth."

"Security exists at the confluence of people, process, and technology—it's not just about tools."

"I'm more me under the persona than I actually am in real life."

In this episode, The Accidental CISO shares how he unintentionally stepped into a security leadership role, the power of anonymity, and how embracing his alter ego helped him find community, confidence, and a calling. He dives into the human side of cybersecurity, masking, and helping others through authenticity and honesty.

• AC became a CISO by accident, not ambition.

• He leaned into unfamiliar responsibilities and grew into the role.

• Sometimes, your catalyst finds you before you find it.

• Online anonymity gave AC a safe space to express frustrations and truth.

• He found a vibrant community that shared his struggles and passions.

• His persona became more “real” than the masked version of himself at work.

• AC believes in collaborative security—not saying “no” but saying “yes, and…”

• Security must align with business goals and risk tolerance.

• He views security as a multiplier when built with context and care.

• Risk is part of doing business and drives innovation.

• A mature approach balances safety with operational freedom.

• Security teams should advise, not own, risk decisions—that belongs to leadership.

• AC’s journey helped him understand and support his own neurodiversity.

• His experiences empowered deeper connection with his children, who face similar challenges.

• Real leadership starts with knowing who you are and finding your people.

Learn. Think. and Act. with us every Sunday. Our Sunday email is filled with sections dedicated to helping leaders Learn. Think. and Act. These short weekly emails will help you make a difference and accelerate speed to impact at work, with self, and within your family.
Subscribe here: https://www.findmycatalyst.com/learn-think-act-opt-in

Follow AC at - https://www.accidentalciso.net/

• "It is playoff hockey time—the best time of year."

• "If you're not a hockey fan, become one during the playoffs; the intensity is absolutely amazing."

• "Find a player, find a team, find a story—and enjoy your playoff hockey journey."

Mike and Jacqueline break down the opening round of the 2025 NHL Stanley Cup Playoffs. They compare their brackets, share hockey fandom stories, and highlight key players to watch. It's a mix of friendly banter, expert insights, and encouragement for new fans to fall in love with playoff hockey’s unmatched excitement.

• Playoff hockey demands unmatched intensity—players dig deep to win.

• Fans' passion creates lasting loyalty, driving deep team connections.

• Find your personal "playoff moment" to ignite passion in your work or life.

• Playoff upsets and overtime games show that anything can happen.

• Embracing uncertainty builds resilience and reveals hidden strengths.

• Catalysts often emerge from surprising, pressure-filled moments.

• Heart picks (like cheering for the Senators) bring joy even if risky.

• Emotional decisions, when thoughtful, can lead to meaningful experiences.

• Don't be afraid to follow your heart when finding your catalyst.

• Hockey communities create bonds that last beyond the season.

• Shared experiences and team spirit are vital for long-term motivation.

• Building a community around your catalyst can speed up your growth.

• Win or lose, playoff hockey is about the journey, not just the Cup.

• Progress, learning, and enjoyment are key parts of finding fulfillment.

• Focus on the small wins and personal growth along your catalyst journey.

Learn. Think. and Act. with us every Sunday.
Our Sunday email is filled with sections dedicated to helping leaders Learn. Think. and Act. These short weekly emails will help you make a difference and accelerate speed to impact at work, with self, and within your family.
Subscribe here: https://www.findmycatalyst.com/learn-think-act-opt-in

Mike Simmons is a leadership and operations expert who helps organizations drive growth through clarity and execution. He leads initiatives through Find My Catalyst, offering services in leadership, revenue, and operations.
Tim Dyck brings deep experience in recruitment and people strategies. He is the founder of Best Culture Solutions, helping companies build great teams with purpose.

Together, Mike and Tim dive into the nuances of fractional leadership, sharing hard-won lessons, memorable metaphors, and actionable insights.

"Don’t mistake knowledge for experience. And don’t mistake experience for expertise."

"If you’re hiring a fractional leader, make sure they’ve run out of gas before—because they’ll know how to get you back on the road."

"Learning is great. But presenting yourself as an expert without experience can do more harm than good."

Mike Simmons and Tim Dyck unpack the world of fractional work, using real-life analogies to explain the value of experience and the risk of surface-level knowledge. They share the difference between knowing, doing, and mastering—and how true expertise accelerates impact. A must-listen for leaders hiring with intention.

• Experience is knowing how far your vehicle can go on empty.

• True experts have broken down before—and know how to recover fast.

• Awareness, experience, and expertise are not the same—and each plays a different role.

• Surface-level learners can use the right words but may not deliver results.

• Using tools like ChatGPT doesn't replace real-world experience.

• Misrepresented expertise can harm organizations and delay progress.

• Fractional leaders must already know how to solve the problem you have.

• They're not there to “figure it out”; they’re there to execute.

• Expecting quick results means you need someone who’s already done the work.

• Complexity slows progress; simplify by removing what’s unnecessary.

• Clear next steps fuel momentum in leadership and operations.

• Fractional experts help reduce overwhelm and focus on what matters.

• Use readiness assessments before hiring fractional talent.

• Match the right expert to the right job—based on proven track record.

• Fractional success is rooted in fit, not just availability.

Learn. Think. and Act. with us every Sunday.
Our Sunday email is filled with sections dedicated to helping leaders Learn. Think. and Act. These short weekly emails will help you make a difference and accelerate speed to impact at work, with self, and within your family.
Subscribe here: https://www.findmycatalyst.com/learn-think-act-opt-in