Thank you for this insightful piece on the common pitfalls first-time founders face. Your candid reflections and practical advice serve as a valuable guide for those navigating the early stages of entrepreneurship.
Honestly I love seeing someone write as you do Ryan, sharing your past "mistakes", realising in full effect the situation, self-perceptions being altered with growth, and of course great tips every time. I don't plan on being a leader, but if by God's will I happen to "lead" anything ever, I've got some good stuff to start with. Thank you!
Wow. That really makes me smile. I am really glad that you enjoy the authenticity — truthfully, that is the whole basis of my Substack. I got so tired of how boring the picture perfect lessons are in most leadership books.
Your manager showed true leadership not by reacting in pride but by guiding you with wisdom. Instead of getting upset when you boldly said you were aiming for his position, he chose to direct you with care, helping you grow into a better version of yourself. That’s a rare kind of grace. Sometimes, all we need is one person who sees beyond our overconfidence and chooses to lead us with heart. A true leader carries both strength and compassion. Thank you for sharing your story.
Thank you so much for reading and giving me your thoughts Sae! This piece did not get much traction but I really enjoyed writing it. So any and all feedback is appreciated. :)
I agree with literally ALL of your points. I was upset at the time but it was probably the best thing for me.
This is gold. Seriously. That transition from high-performing individual to leader? It's like suddenly being handed a map in a language you don't speak and being told to guide a tour group. The 'sink or swim' approach so many companies take is truly baffling. You're spot on btw! They train for output, not for actually leading humans. And surprise, surprise, those are two wildly different skill sets. One could say that I have had my fair share at seeing leadership fail tremendously, both up close and from a safe distance.
That whole 'if you're good at your job, people will naturally follow' myth? It's the leadership equivalent of thinking if you can bake a great cake, you can automatically run a Michelin-star kitchen. Nope. Leading requires a whole different kind of emotional intelligence, the ability to navigate the human mess, not just the task list.
Your story about wanting your boss's job early on? So relatable. That overconfidence of youth, thinking your individual brilliance automatically translates to leading a whole damn operation. Bless that manager for his patience and for actually leading you instead of just firing your arrogant behind. That 'you don't know what you don't know' line is brutal but so true. And the path he laid out – taking a step back to build a real foundation? That's the kind of mentorship that actually shapes careers.
The fact that you're now working on protocols to support new hospital managers speaks volumes. It highlights just how widespread this problem is–promoting based on tenure or individual success and then just leaving people to flounder. It's not their fault; they were never given the right tools.
And amen to taking your growth personally. Waiting for a corporate handout is a recipe for stagnation. Finding mentors, reading, listening, having those real, uncomfortable conversations – that's where the real breakthroughs happen.
Your top 5 mistakes? I see echoes of those in so many new leaders (and let's be honest, even some seasoned ones). Avoiding difficult conversations because you want to be liked? That 'nice trap' is a leadership killer. Doing instead of delegating because 'it's just easier'? Short-term gain, long-term burnout for everyone. Thinking control equals leadership? Newsflash: it breeds resentment and stifles growth. No defined expectations? It's like asking your team to run a race without a finish line. And changing too much, too soon without input? That's ego tripping in a hard hat.
'Progress, not perfection' should be the leadership mantra. It's about learning, being intentional, and being real with your team. They don't need a flawless robot; they need someone who listens, learns, and leads with actual care.
This whole piece is a much-needed reality check for anyone stepping into leadership. It's not a promotion; it's a completely different job. And recognizing those rookie mistakes early on can be the difference between building a thriving team and watching it slowly implode under the weight of good intentions and a lack of real leadership skills.
Thank you for this insightful piece on the common pitfalls first-time founders face. Your candid reflections and practical advice serve as a valuable guide for those navigating the early stages of entrepreneurship.
Using a sports analogy. Great players don’t (often) make great managers / coaches.
What a wonderful leader you had to give you insights on how you can be better. And good on you for taking these things as you growth 💯
Couldn’t agree more, Astrid. I kept in touch with him for a very long time.
I wonder what ole JP is up to these days.
Honestly I love seeing someone write as you do Ryan, sharing your past "mistakes", realising in full effect the situation, self-perceptions being altered with growth, and of course great tips every time. I don't plan on being a leader, but if by God's will I happen to "lead" anything ever, I've got some good stuff to start with. Thank you!
Wow. That really makes me smile. I am really glad that you enjoy the authenticity — truthfully, that is the whole basis of my Substack. I got so tired of how boring the picture perfect lessons are in most leadership books.
Your manager showed true leadership not by reacting in pride but by guiding you with wisdom. Instead of getting upset when you boldly said you were aiming for his position, he chose to direct you with care, helping you grow into a better version of yourself. That’s a rare kind of grace. Sometimes, all we need is one person who sees beyond our overconfidence and chooses to lead us with heart. A true leader carries both strength and compassion. Thank you for sharing your story.
Thank you so much for reading and giving me your thoughts Sae! This piece did not get much traction but I really enjoyed writing it. So any and all feedback is appreciated. :)
I agree with literally ALL of your points. I was upset at the time but it was probably the best thing for me.
RYAN! THIS! FTW!
This is gold. Seriously. That transition from high-performing individual to leader? It's like suddenly being handed a map in a language you don't speak and being told to guide a tour group. The 'sink or swim' approach so many companies take is truly baffling. You're spot on btw! They train for output, not for actually leading humans. And surprise, surprise, those are two wildly different skill sets. One could say that I have had my fair share at seeing leadership fail tremendously, both up close and from a safe distance.
That whole 'if you're good at your job, people will naturally follow' myth? It's the leadership equivalent of thinking if you can bake a great cake, you can automatically run a Michelin-star kitchen. Nope. Leading requires a whole different kind of emotional intelligence, the ability to navigate the human mess, not just the task list.
Your story about wanting your boss's job early on? So relatable. That overconfidence of youth, thinking your individual brilliance automatically translates to leading a whole damn operation. Bless that manager for his patience and for actually leading you instead of just firing your arrogant behind. That 'you don't know what you don't know' line is brutal but so true. And the path he laid out – taking a step back to build a real foundation? That's the kind of mentorship that actually shapes careers.
The fact that you're now working on protocols to support new hospital managers speaks volumes. It highlights just how widespread this problem is–promoting based on tenure or individual success and then just leaving people to flounder. It's not their fault; they were never given the right tools.
And amen to taking your growth personally. Waiting for a corporate handout is a recipe for stagnation. Finding mentors, reading, listening, having those real, uncomfortable conversations – that's where the real breakthroughs happen.
Your top 5 mistakes? I see echoes of those in so many new leaders (and let's be honest, even some seasoned ones). Avoiding difficult conversations because you want to be liked? That 'nice trap' is a leadership killer. Doing instead of delegating because 'it's just easier'? Short-term gain, long-term burnout for everyone. Thinking control equals leadership? Newsflash: it breeds resentment and stifles growth. No defined expectations? It's like asking your team to run a race without a finish line. And changing too much, too soon without input? That's ego tripping in a hard hat.
'Progress, not perfection' should be the leadership mantra. It's about learning, being intentional, and being real with your team. They don't need a flawless robot; they need someone who listens, learns, and leads with actual care.
This whole piece is a much-needed reality check for anyone stepping into leadership. It's not a promotion; it's a completely different job. And recognizing those rookie mistakes early on can be the difference between building a thriving team and watching it slowly implode under the weight of good intentions and a lack of real leadership skills.