How to tell your boss that part of your job sucks.
Fri Jan 23 2026
Ever stare at your computer thinking "there HAS to be a better way to do this"? Like that task at work that takes 3x longer than it should. The one everyone complains about but nobody fixes.You know it needs to change. You might even know HOW to fix it. But telling your boss? That feels risky. What if they think you're just complaining? What if you come across as difficult? What if they say no and then it's just...awkward?In my early 20s I was the silently suffering employee. Now I'm the boss wishing people would just TELL me when something's broken before we waste months (or years) doing it the hard way. So I pulled Stacy in for this one to get her take on both sides of this conversation.
In this episode, we cover:
How to decide if it's actually worth bringing up (or if you just need a Coke and a walk)
The 9 questions to ask yourself before approaching your boss
How to approach different types of bosses strategically
What to say (and what NOT to say) to look entrepreneurial instead of difficult
When to just quit instead—because sometimes that IS the answer
Fair warning: This is a long one. But if you're thinking "I can't do another day of THIS"—it might be exactly what you need. Want more? Check out the full blog post with all the details at https://mayecreate.com/?p=125633
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Ever stare at your computer thinking "there HAS to be a better way to do this"? Like that task at work that takes 3x longer than it should. The one everyone complains about but nobody fixes.You know it needs to change. You might even know HOW to fix it. But telling your boss? That feels risky. What if they think you're just complaining? What if you come across as difficult? What if they say no and then it's just...awkward?In my early 20s I was the silently suffering employee. Now I'm the boss wishing people would just TELL me when something's broken before we waste months (or years) doing it the hard way. So I pulled Stacy in for this one to get her take on both sides of this conversation. In this episode, we cover: How to decide if it's actually worth bringing up (or if you just need a Coke and a walk) The 9 questions to ask yourself before approaching your boss How to approach different types of bosses strategically What to say (and what NOT to say) to look entrepreneurial instead of difficult When to just quit instead—because sometimes that IS the answer Fair warning: This is a long one. But if you're thinking "I can't do another day of THIS"—it might be exactly what you need. Want more? Check out the full blog post with all the details at https://mayecreate.com/?p=125633