mistakes mistakes and more mistakes

Every year, the fan favorite and most widely read newsletter I send is a list of the things I’ve screwed up in my business. It’s what gave birth to my podcast, Why Are We Shouting?, where I used to shout weekly about what I’d messed up this time.

This year? A twist. In my efforts to remind you that nobody in business knows what they’re doing – not even if they’ve been in business for 20+ years – I’ve turned my mistakes into questions. Maybe they’re yours, too?

Why are time zones so hard for me?

I haven’t met a single person who hasn’t screwed this up. Time zones continue to confuse me, torment me, and they always make me look bad. Last week I missed two calls with people in Germany and California. How I still mess this up I’ll never know.

How come I rely on systems as though they’re flawless?

I build systems, tweak them, and rely on them. Then I’m shocked when they break. I’ve set up a Google Sheet to remind me when to follow up with potential clients. On the day that the code fails and I stop getting reminders, my follow-up game dies. This happens at least once a month and I’ve got no idea how to fix it. Same with socials. I’ve hit publish on content and believe the system’s going to work perfectly, forever. Then it skips a post. Or the algorithm changes. I gasp and scream about what the world must think of me.This is especially excruciating when I think I’ve clicked publish only to discover that I never did. Systems are never perfect. When they fail, I feel exposed and helpless. Turns out, no system can save me from being human.

If divorce, perimenopause, and eldercare are a few of the many transitions we go through, why do I leave them out of business conversations?

I’ve worked so hard to leave the big stuff out of business interactions. Who taught me that being vulnerable about my struggles would make me look weak when they actually connect me more deeply to you? I noticed this habit several years ago and now work to weave the word hormones into many of my conversations. Buttoned-up business expertise isn’t what builds relationships. Authenticity does.

Why are we so afraid to tell our customers and clients when we don’t know the answer?

In a world where answers are instant and expertise is automated, admitting uncertainty can feel like I’m giving people a reason to tune out. I’ve been conditioned to equate knowledge with value and value with worth. But I’ve taken the very long road to realize that it’s just not true. It humanizes me to say “I don’t know.” People crave information, sure, but curiosity and courage far outweigh a simple answer. Is it getting harder to reveal uncertainty now that AI can give us alllllll the answers? I don’t know.

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If there are two things I know about business owners, it’s that change is inevitable, and we never don’t make mistakes. That’s how we get better at what we do.

But we get it backwards. We think we’re doing it all wrong so we talk ourselves out of moving forward when that’s exactly where we should be headed.

See you soon,

jill