When Success Becomes Your Biggest Obstacle
“I loved the event, great people, great energy, great drinks… but I’m still not entirely sure what Amanda’s Playbook is all about.”
That was the refreshingly direct feedback from my content manager’s father who attended last week’s live event. When I asked for his honest thoughts, he didn’t hesitate to voice the confusion that I suspected many others felt but were too polite to mention.
His candor was both a relief and a confirmation. The truth is, the ambiguity wasn’t a messaging failure—it was intentional, though that didn’t make it any less nerve-wracking to launch something I couldn’t perfectly define.
I stood there that day, surrounded by brilliant people who’d come to support something that was still taking shape, feeling that familiar tension between the instinct to have everything figured out and the necessity of beginning before clarity arrives.
Why We Wait Too Long to Begin
What I’ve been wrestling with goes beyond branding—it’s about our collective hesitation to start before everything is figured out, or before it looks ‘polished’ on paper.
The irony is that the more experience and ‘success’ gathered, the more we tend to convince ourselves that we need the perfect articulation before the first step…
That we need the full plan mapped out before starting.
Yet almost everything meaningful I’ve built began in that uncomfortable space of “I can’t fully explain this yet.” The digital subscription model that became my career started before anyone understood what subscribing to online content even meant.
The Status Paradox That Keeps Us Stuck
There’s a moment when you’ve built something, when you’ve reached a certain level, and suddenly the very achievement makes us afraid to do something else.
You begin protecting what you’ve built rather than continuing to build.
Running competitively taught me something they don’t put in motivational posters. After winning my first major race, my coach pulled me aside and said: “Now comes the hard part.”
He was right. Once you win, there’s nowhere to go but down. When you’re chasing, you have nothing to lose. When you’re being chased, everything becomes about not losing what you’ve already claimed.
That pressure transforms running from joy to preservation—each race no longer about possibility but about protecting position. The same dynamic plays out professionally. Success paradoxically makes us risk-averse at precisely the moment when continued innovation is most critical.
This Week’s Video
In this week’s video, I share insights that might change how you approach your next venture:
- How the “elevator pitch” trap prevents innovation—illustrated through my own experience learning the hard way.
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The dinner party experiment I’ve been running that proved something surprising about human connection.
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The warning signs that you’re experiencing “1st place handcuffs’ in your career—and counterintuitive action that breaks this pattern.
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An invitation to try our first community experiment—and thus become a founding member -where sharing your influence challenges connects us.
Note: I’m far from a motivational speaker, this isn’t a pep talk from someone who’s never felt the weight of reputation. It’s my thoughts from standing in my kitchen at 2am after the event, still in heels, eating leftover canapés and wondering if I just made the biggest mistake of my career—or finally found my way back to what made that career possible in the first place.
If you’ve ever caught yourself refusing to start until you can “explain it properly,” this one’s for you…
To your success,
P.S. Fair warning: the community experiment involves actual participation. Lurkers beware—I might just call you out by name in next week’s video. Consider that both a threat and an invitation.
Let’s Connect
💬 Reply to my personal email with your questions for our Q&A segment
🎥 Subscribe to Amanda’s Playbook YouTube channel for weekly deepdives
👥 Join our private Substack community
📱 Follow me on Instagram and TikTok @amandasplaybook
