In this insightful discussion, Andy Wright (CEO Streamtime and Founder of Never Not Creative) explores the delicate balance between confidence and cockiness with Simon Lee (Chief Creative Officer at The Hallway) and mental health educator Aimee Davies (The Hey Mate Project). This common professional anxiety affects creatives at every level, whether pitching to clients or interviewing for dream roles. The conversation reveals that authenticity beats sales pitches every time, while self-awareness about not wanting to appear cocky is actually your greatest asset. Simon and Aimee share practical strategies for speaking confidently to important people without losing your genuine voice.
We’ve all been there – standing in front of someone whose opinion really matters, trying to showcase our abilities without sounding like we’re completely up ourselves. It’s one of those delicate dances that can make even the most seasoned creative break out in a cold sweat. This question strikes at the heart of professional anxiety many of us face, whether you’re pitching to a dream client or networking. Andy Wright, Simon Lee and Aimee Davies together bring different perspectives: Andy shares how to foster genuine confidence as a leader and community builder, Simon explains it from years of hiring and leading teams who must balance humility with selling ideas, and Aimee highlights the mental health and self-awareness side that helps you avoid arrogance by staying authentic.
Aimee immediately identified the core solution to this dilemma: authenticity trumps everything else. "Where I find we can really balance that confidence versus that cockiness is through our authenticity," she explains. Rather than delivering a rehearsed sales pitch that you might not fully believe in, she suggests "really demonstrating whether that’s making a list of your achievements and how you really feel about them and leading into that."
The key insight here is that people can spot inauthenticity from a mile away. When you lead with genuine evidence of your work and honest feelings about your accomplishments, "that translates a lot better than a sales pitch which we may or may not believe and a lot of the time people can see straight through as well."
Simon brings a refreshing perspective from his experience in leadership roles. He admits to struggling with this balance himself, sometimes being "overconfident or even arrogant at times or then the other way be too recessive." His solution? Complete honesty about both successes and failures.
"Be open about the things that you haven’t done so well," Simon advises. From his experience interviewing candidates, he reveals: "I love to know the things that they’ve actually stuffed up – in fact I sometimes ask that question... I actually often learn more from that than I do from the biggest success."
This approach removes the pressure to be perfect and allows for genuine human connection.
Both Aimee and Simon highlight something crucial: the very fact that you’re worried about coming across as cocky is actually a massive advantage. As Aimee points out, "the people who are cocky don’t have self-awareness."
Simon reinforces this: "The fact that you’re asking this question speaks to self-awareness as well, so understanding that you don’t want to come across cocky means that you know how you might be perceived, which I think is a really big thing that is very valuable."
This self-awareness puts you in a fundamentally different category from those who genuinely are arrogant – and it shows.
Simon’s overarching advice cuts through all the complexity: "Be yourself." He emphasises that you shouldn’t "feel uncomfortable about talking about your achievements" while also being honest about areas where you’re still growing.
His practical warning is particularly valuable: "Don’t feel that you have to put on a hat and pretend to be someone else because ultimately if you did manage to kind of get yourself through a situation by pretending to be something else, you will ultimately be found out."
The conversation reveals that balancing confidence without cockiness isn’t about finding some magical middle ground – it’s about being genuinely yourself. When you speak from a place of authentic experience, acknowledge both your strengths and growth areas, and maintain awareness of how you’re coming across, confidence becomes natural rather than forced.
Remember, the people worth impressing are those who value honesty and authenticity over polished perfection. Your self-awareness about this challenge is already putting you ahead of the game.
CCO & co-owner of The Hallway, creating ideas with real-world impact. Led the Boys Do Cry campaign, reaching 100M+ and inspiring men to seek mental health support. Mentor, speaker & dad of two.
A mental health educator and counselor, combining years in the creative industry with nearly five years in therapy, now runs The Hey Mate Project to provide tailored support for creative professionals and organisations.
Founder of Never Not Creative, CEO of Streamtime & co-chair of Mentally Healthy, driven to make the creative industry fairer & more human. Believes great work should never cost wellbeing.
