The Atlassian Co-Founder’s Guide to Conquering Impostor Syndrome
Most entrepreneurs are leaving money on the table. The average sales funnel converts just 2.35% of visitors, but the
Most successful entrepreneurs have a dirty secret: they spend half their time wondering when someone’s going to figure out they’re winging it. You’d think building a billion-dollar company would cure that feeling, but it doesn’t. If anything, the stakes just get higher.
Mike Cannon-Brookes knows this feeling intimately. The co-founder of Atlassian—the Australian software giant worth over US$50 billion—has felt exactly the same way for the past 15 years. Understanding impostor syndrome entrepreneurs face becomes crucial when you realise he’s learned to turn that feeling into his competitive advantage.
The Billion-Dollar Founder Who Didn’t Know What He Was Doing
Cannon-Brookes’ entrepreneurial journey actually began before Atlassian, with an early taste of both success and uncertainty. While studying at the University of New South Wales, he co-founded an internet bookmark management tool called The Bookmark Box with classmate Niki Scevak. The company was sold to Blink.com in 2000, giving him his first experience of building something valuable—and his first real encounter with impostor syndrome in the entrepreneurial world.
But it was Atlassian that would truly test his ability to navigate uncertainty. The journey started like many entrepreneurial tales: two university mates who didn’t want real jobs or suits. Yet the reality was far more precarious than it appeared. Cannon-Brookes and Scott Farquhar bootstrapped the company for several years, financing the startup with a $10,000 credit card debt. They were literally betting everything they had on their ability to figure things out as they went.
Today, Atlassian’s software helps millions of teams worldwide collaborate, and their tools have even made it to space aboard Mars missions. Yet the success hasn’t eliminated his impostor syndrome—it’s just given him a more sophisticated vocabulary for it.
“Most days, I still feel like I often don’t know what I’m doing,” Cannon-Brookes admits. “I’ve felt that way for 15 years, and I’ve since learned that feeling is called impostor syndrome.”
His early days were filled with moments that would make any entrepreneur cringe with recognition. When people called asking for “accounts payable,” he’d freeze, wondering whether they wanted money or were offering it. During board meetings, he’d frantically scribble down acronyms in his notebook to look up on Wikipedia later. Interviewing their first HR manager terrified him—how do you hire someone for a department you’ve never worked in?
These weren’t just growing pains. They were symptoms of something deeper: the persistent feeling of being well out of your depth, yet already entrenched in the situation. It’s not fear of failure or inability to do the job. It’s the sensation of getting away with something, coupled with the constant fear of being discovered.
The Night Everything Changed
The turning point came during Atlassian’s early success. Four years in, with 70 employees, they entered the New South Wales Entrepreneur of the Year competition at their auditor’s suggestion. Cannon-Brookes was so convinced they didn’t belong that he didn’t even attend the state ceremony when they won.
But they kept winning. State level, then national Young Entrepreneur of the Year, and finally—to everyone’s shock, including the announcer’s—Australian Entrepreneur of the Year overall. The Ernst & Young CEO’s first words upon opening the envelope? “Oh my God.”
This led them to Monte Carlo for the World Entrepreneur competition, where Cannon-Brookes found himself seated next to Belmiro de Azevedo, Portugal’s winner. Here was a man who’d been running his business for 40 years, employed 30,000 people, and generated four billion euros in turnover. Atlassian had 70 employees.
After a few wines, Cannon-Brookes confessed his feelings of inadequacy. He admitted they didn’t deserve to be there, that someone would eventually figure this out and send them home. The Portuguese businessman’s response changed everything: he felt exactly the same way, and suspected all the winners did too.
“This was a pretty big light bulb moment for me for two reasons,” Cannon-Brookes reflects. “One, I realised that other people felt this as well. And two, I realised it doesn’t go away with any form of success.”
Why Successful People Feel Like Frauds
This revelation challenged a fundamental assumption: that successful people don’t feel like impostors. The opposite, Cannon-Brookes discovered, is more likely true. The higher you climb, the more acutely you feel the gap between where you are and what you think you should know.
For many impostor syndrome entrepreneurs, this creates a vicious cycle. Success breeds more opportunities, which brings bigger challenges, which amplifies feelings of inadequacy. Yet this same cycle can become a powerful driver for continuous learning and growth when properly channeled.
This phenomenon extends beyond business. Research on successful relationships reveals that one attribute of the most successful partnerships is when both partners feel their significant other is out of their league. They feel like impostors in their own relationship—and this drives them to work harder and stretch to be the best partner they can be.
Cannon-Brookes experienced this firsthand when he met his future wife through a case of mistaken identity in a Qantas business lounge. Rather than freeze or correct her error, he kept the conversation going. More than a decade later, they have four children together, and both still occasionally feel like impostors in their own marriage.
“Apparently, that’s one of the reasons that we’ll likely have a successful marriage,” he notes. The key isn’t eliminating the feeling—it’s not freezing when it happens.
The Tesla Moment: When Impostor Syndrome Goes Viral
Cannon-Brookes’ most public bout with impostor syndrome came through a late-night Twitter exchange that spiralled into national energy policy. Seeing Tesla claim they could solve South Australia’s power crisis with industrial batteries, he impulsively challenged them, asking if they were serious.
When Elon Musk responded that Tesla could install a 100-megawatt-hour facility within 100 days of contract signing, Cannon-Brookes found himself in the deep end of energy policy. Within 24 hours, every major media outlet wanted his opinion as an “energy expert.”
The problem? At the time, he couldn’t distinguish between a AA battery for his children’s toys and a 100-megawatt-hour industrial facility. He was experiencing chronic impostor syndrome on a national stage.
“I remember thinking to myself, ‘Shit. I’ve kind of started something here and I can’t really get out. If I abandon the situation, I’m going to sort of set back renewables in Australia and maybe just look like a complete idiot because of my idiocy on Twitter.'”
Instead of abandoning the situation, he chose to learn. Over the week, he absorbed everything he could about industrial-scale batteries, electricity grids, renewables, and economic feasibility. Along the way, he spoke with chief scientists, CSIRO researchers, ministers, and premiers. His efforts even earned him a passing impression of an energy expert on ABC Lateline.
The result? South Australia issued a battery tender with over 90 applications, and the national conversation shifted from theatrical politics to serious discussion about renewable energy infrastructure.
The Framework: How to Harness Impostor Syndrome
Cannon-Brookes’ experiences reveal a framework for turning the challenges that impostor syndrome entrepreneurs face from paralysis into progress:
Recognise the Water Is Deep The most successful entrepreneurs don’t question themselves, but they heavily question their ideas and knowledge. They know when they’re out of their depth and aren’t afraid to admit it. This isn’t weakness—it’s wisdom.
Don’t Freeze, Learn When you feel like an impostor, the natural response is to freeze or flee. Successful people keep the conversation going. They use their fear of looking foolish as motivation to rapidly acquire the knowledge they need.
Ask for Advice Without Shame Successful people don’t see asking for help as a character flaw. They actively seek advice to hone their ideas, improve their understanding, and fill knowledge gaps. The Tesla situation worked because Cannon-Brookes reached out to experts rather than pretending to know.
Turn Fear into Force The feeling of being discovered can be paralysing or motivating. Channel that energy into learning, preparation, and growth. Your fear of being exposed as inadequate becomes the driving force behind becoming adequate.
Accept Being Out of Your Depth Some situations require you to be in over your head. Growth happens at the edge of competence. The key is harnessing the situation rather than being paralysed by it.
The Australian Advantage
There’s something distinctly Australian about Cannon-Brookes’ approach to impostor syndrome. The cultural tendency toward self-deprecation and “tall poppy syndrome” actually creates an environment where admitting uncertainty feels more natural than in cultures that worship confident expertise.
This cultural context might explain why Australian entrepreneurs often punch above their weight internationally. When you’re comfortable with not knowing everything, you’re more likely to ask the right questions, seek the right advice, and adapt quickly to new situations.
For Australian entrepreneurs, impostor syndrome isn’t just a personal challenge—it’s a cultural feature that can become a competitive advantage when properly channelled.
When Impostor Syndrome Becomes Your Superpower
The key insight from Cannon-Brookes’ journey isn’t that impostor syndrome disappears with success—it’s that you can transform it from a liability into an asset. Here’s how successful entrepreneurs make this transformation:
Use It as a Reality Check Impostor syndrome often signals that you’re pushing boundaries and taking on challenges that matter. If you never feel out of your depth, you’re probably not growing fast enough.
Let It Drive Preparation The fear of being exposed as unprepared can motivate extraordinary levels of learning and preparation. Cannon-Brookes’ crash course in energy policy turned him into a credible voice in national energy discussions.
Make It Fuel Humility Leaders who feel like impostors are more likely to listen, ask questions, and consider alternative viewpoints. This humility often leads to better decision-making than overconfidence.
Channel It into Authenticity Admitting you don’t know everything creates connection with others who feel the same way. Cannon-Brookes’ honesty about his uncertainties makes him more relatable and trustworthy as a leader.
The Warning Signs: When to Pay Attention
Not all impostor syndrome is helpful. Here’s when it might be signalling real problems:
When It Prevents Action If the feeling consistently stops you from taking necessary risks or making important decisions, it’s become counterproductive. The goal is forward movement despite uncertainty, not paralysis because of it.
When It Becomes Chronic Self-Attack There’s a difference between questioning your knowledge and attacking your worth. Healthy impostor syndrome focuses on skill gaps; unhealthy versions attack fundamental competence.
When It Isolates You If impostor syndrome prevents you from seeking help or building relationships, it’s working against you. The most successful response involves reaching out, not withdrawing.
Practical Steps for Entrepreneurs
Based on Cannon-Brookes’ experience, here are practical strategies for how impostor syndrome entrepreneurs can transform self-doubt into competitive advantage:
Create Learning Systems When you feel out of your depth, have a systematic approach to rapid learning. Identify key experts, reliable sources, and structured ways to absorb information quickly.
Build Advisory Networks Surround yourself with people who’ve navigated similar challenges. Having advisors you can call when you’re in over your head transforms crisis into opportunity.
Document Your Wins Keep track of situations where you felt like an impostor but succeeded anyway. This evidence base helps counter the feeling that you’re perpetually unprepared.
Normalise Not Knowing Create a company culture where admitting knowledge gaps is rewarded, not punished. This makes it safer for everyone to acknowledge when they need help.
Focus on Learning Speed Instead of trying to know everything, focus on becoming excellent at learning quickly. This skill matters more than existing knowledge in rapidly changing environments.
The Paradox of Expertise
Cannon-Brookes discovered something counterintuitive: the more successful you become, the more you realise how much you don’t know. This isn’t a bug in the entrepreneurial experience—it’s a feature.
“I’m extremely aware of feeling like an impostor right now,” he admitted while giving his TED talk on the subject, “as I’m up here, some sort of pseudo-expert on a feeling that I couldn’t even put a name to a few months ago.”
This self-awareness creates a paradox: the moment you truly understand impostor syndrome might be the moment you feel it most acutely. But that’s precisely when it becomes most useful.
Moving Forward with Uncertainty
The entrepreneurial journey is fundamentally about navigating uncertainty with incomplete information. For impostor syndrome entrepreneurs, this feeling isn’t a personal failing—it’s a rational response to being in situations that require you to stretch beyond your current capabilities.
Cannon-Brookes’ advice isn’t to eliminate these feelings but to harness them. Use the discomfort of being out of your depth as motivation to learn faster, ask better questions, and build stronger support networks.
The entrepreneurs who thrive aren’t those who never feel like frauds—they’re the ones who feel like frauds but keep the conversation going anyway. They transform uncertainty into curiosity, fear into preparation, and doubt into determination.
Your impostor syndrome isn’t evidence that you don’t belong. It’s evidence that you’re growing, pushing boundaries, and taking on challenges that matter. The feeling might never disappear completely, but with the right approach, it can become one of your most valuable tools for success.
As Cannon-Brookes learned through building Atlassian, winning unexpected awards, and accidentally becoming involved in national energy policy: it’s okay to be out of your depth, so long as you don’t freeze and you try to turn it into some sort of force for good.
The next time you feel like an impostor, remember that you’re in the company of some of the world’s most successful entrepreneurs. The question isn’t whether you belong it’s what you’ll learn and who you’ll become while figuring it out.
Source: YouTube
