According to the American Psychological Association, more than 80% of people face feelings of imposter syndrome at some point in their lives, and the sense they haven’t earned what they’ve achieved. This phenomenon can feel even more acute for entrepreneurs as the high stakes of running a business often leave them questioning their own abilities.
We caught up with Mike McDerment, co-founder of FreshBooks, to explore how he’s faced imposter syndrome throughout the business development.
From starting a software business in his parents’ basement, to leading a firm with 500 employees and customers in over 100 countries, Mike shares practical insights on how embracing self-doubt can actually be a tool for growth.
| Listen to the full podcast episode here: Embracing imposter syndrome and fear with Freshbooks co-founder Mike McDerment |
What is entrepreneur imposter syndrome?
Imposter syndrome in entrepreneurship is the persistent feeling of self-doubt and insecurity that many business owners experience, even when they are objectively successful.
Psychology Today explains that individuals dealing with this issue “feel that they aren’t as competent or intelligent as others might think and that, soon enough, people will discover the truth about them.”
This phenomenon is particularly common among entrepreneurs because they face unique pressures such as high expectations, the need to innovate, and the ever-present risk of failure.
Typical challenges of facing imposter syndrome in business
Business owners work in a high-pressure environment where they are expected to lead with confidence and provide solutions to complex problems.
One common struggle is the fear of being “found out,” which can lead to overworking, micromanaging, or avoiding risks altogether. This fear is compounded when entrepreneurs feel they must meet the expectations of employees, clients, and stakeholders — despite not having all the answers. Or, as Mike McDerment candidly shared:
“All these people are looking at me like I have all the answers, and I’m just figuring this out.”
Another challenge is the tendency to dismiss accomplishments as luck or timing rather than hard work and skill, which can sap confidence and hinder decision-making. This mindset may also lead to unhealthy comparisons with other business leaders and further fuel the belief that others are more capable.
Why imposter syndrome can be a sign of growth
Though it sounds (and often really is) terrifying, imposter syndrome in business can be a sign of growth. That’s because uneasiness arises when you’re stepping outside your comfort zone and into uncharted territory, which is where real progress happens.
This is how Mike explains it:
“It's a root cause for me — if you're living right and putting yourself in challenging circumstances where you don't know what the outcome is going to be, imposter syndrome is a natural reaction.”
Rather than viewing imposter syndrome as a limitation, you should reframe it as evidence that you’re pushing the boundaries and taking on challenges that help you evolve as a business leader. This can mean many different things — scaling your business, pitching to a high-profile client, launching a new product, and so on — but such moments of self-doubt often accompany meaningful growth.
Business owners should try and transform imposter syndrome from a debilitating fear into a marker of ambition because, as Mike says, it “doesn’t go away — it’s just part of professional life and a life well-led.”
Tactics for overcoming entrepreneur imposter syndrome
Though it can feel like a double-edged sword, imposter syndrome doesn’t have to hold you back. On the contrary, it’s possible to use clever tactics and reframe your mindset in order to transform imposter syndrome into a success tool. Here are some ideas on how to do that.
1. Focus on progress, not perfection
Perfectionism is a common driver of imposter syndrome, making you feel like nothing you do is ever good enough. Shift your focus to progress instead:
- Break big goals into smaller, manageable steps
- Celebrate small wins along the way
- Reflect on how far you’ve come, rather than fixating on what’s left to achieve
This approach helps build confidence and keeps you motivated.
2. Take action despite fear
The best way to overcome imposter syndrome is to act. Fear tends to diminish once you start tackling a challenge. Even if you don’t feel entirely ready, remind yourself that learning on the job is part of the entrepreneurial process. You’ll start building confidence and competence with each step forward:
“Every time you're feeling it, it's like a test. It's like you're in school, you're writing an exam or something. And if you took the course, you're probably going to be okay.”
3. Create a strong support network
Another strategy is to surround yourself with people who truly believe in your abilities and encourage your growth. This might include:
- A mentor who’s been in your shoes
- A network of like-minded entrepreneurs who share their own struggles and successes
- Supportive team members who understand your vision
When you have a network that uplifts you, it becomes easier to push past self-doubt.
4. Reflect and reassess
Finally, make it a habit to step back and assess your accomplishments regularly. For instance, keep a journal or create a “win list” to document milestones or positive feedback. This practice helps combat the tendency to discount your achievements and reinforces a sense of self-worth.
Imposter syndrome probably signals that you’re on the right track
Let’s face it — nobody likes feeling like they don’t belong or that they’re not good enough. Imposter syndrome can be frustrating, even paralyzing, but it often points to something deeper: you’re on the right track. While uncomfortable, these moments are where the most significant progress happens. In the words of Mike McDerment himself:
“You’re facing imposter syndrome when you’re essentially in a period of growth, when you’re in a situation that’s going to force you to learn new things or to do something you haven’t normally done. And that should be exciting.”
