Category: Entrepreneurship
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When Busy is Just Scared with a Better Mask
You cut the overhead. It made sense at the time. Actually, the numbers demanded it. The org chart got leaner. Positions were eliminated, the team shrank, the structure simplified. It was the responsible call. The leadership call. And then quietly, without announcement, the work that used to belong to other people became yours. You are…
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The Paralyzed Analyst—The Neverending Pause
You don’t want to look foolish as you feel the shockwaves of the latest numbers. You know it’s stupid to stop the digital campaign or disrupt the plan of care mid-stream, but you just can’t help but react. You desperately search for the reframe, the call to action, the shift. But here, procrastination is reframed as…
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Posting Into The Void
On the Meaning Famine and What’s Really Happening to Us Are you the person who listens to podcasts on the commute, during the run, while fixing dinner, or adjacent to your kid’s Babe Ruth game? Are you on YouTube at midnight and again first thing in the morning? Doom scrolling before you’ve even left your…
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A Thousand Tiny Goodbyes
It was nothing. It’s expected even, right? Part of the ebb and flow. That’s where your mind goes as you read the polite message declining the renewal. The rationalization arrives before the disappointment does. It arrives so fast you almost miss the fact that something just landed. Something that stings a little. Something that, if…
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The Loneliest Job In The World
“You are performing with a confidence you don’t entirely feel, for people who need you to feel it.” I’ve worked with entrepreneurs for over twenty-five years. The fearless leaders who can’t talk about what they really feel are the ones I think about most. Entrepreneurship requires that you show up confidently, allaying everyone else’s fears…
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The 6 AM Email
By Sydney Ashland She sent the email at 6:00 am, from bed, without a second thought. She had been rolling over an issue from work that had been mentioned the previous day. It was only said in passing. It wasn’t something she had even agreed to research, but before she fell into bed, she felt…
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Your AI Coach Doesn’t Know You’re Lying to Yourself
On The Seduction Of Being Understood By Something That Can’t Feel The Weight Of What You Are Avoiding The Observation The AI coaching market just crossed $5 billion. Venture capital is thrilled. Your nervous system remains completely unimpressed. I’m still trying to catch my breath. Every week I watch another breathless announcement: an app that…
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Two People. One House. Two Completely Different Worlds.
On the invisible battle happening behind closed doors in high-achieving homes. She scanned the driveway again for the twelfth time or maybe it was the fifteenth. She’d lost track. It wasn’t that big of a deal, at least that’s what she kept telling herself. It was just an argument. Couples argue. She knew this better…
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THE STARTING POINT
What Change Actually Looks Like Before It Looks Like Anything People want to know what change looks like. They imagine a moment. A shift. Something dramatic and visible, a decision made, a boundary held, a new version of themselves stepping cleanly into view. That’s not what I see in this work. What I see is…
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You Look Like You Have It Together-But Do You Feel Like It?
She sat in boardrooms in corporate America. She knew how to read a room, how to speak with authority, how to hold her ground in a meeting full of people who assumed they were the smartest one there. She dressed well. She delivered. She performed so exceptionally that she almost convinced herself it was the…