『The Cage Door Is Wide Open. Are You Walking Through It?』のカバーアート

The Cage Door Is Wide Open. Are You Walking Through It?

The Cage Door Is Wide Open. Are You Walking Through It?

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What does it actually take to walk away from a very good life... and bet on yourself instead?Helena spent over a decade building her career through boutique agencies, two major corporate acquisitions, and an executive role as chief of staff, before identifying a gap in the market and founding Archive Digital, an enterprise e-commerce services company that's female-founded in a space where that's still genuinely rare. She had the golden handcuffs, the title, the stability. And she walked away anyway.We talk about what it's like to navigate two acquisitions at completely different career stages, why the chief of staff role is having a moment, what 10 years of sobriety taught her about building a business and sitting with discomfort, and why she believes women have a responsibility to engage with AI right now, not watch from the sidelines.This one covers a lot of ground and all of it is worth your time.What You'll Learn⭐ What two corporate acquisitions taught her about knowing when it's time to leave⭐ Why the chief of staff role is becoming more important in the age of AI⭐ How sobriety built the exact muscle she needed to start a company⭐ What it means to trust your intuition when your board is all male and nobody looks like you⭐ Why "corporate stability" is an illusion, and what to do with that realization⭐ Why women aren't just suited to engage with AI, they're needed to shape itKey InsightsBoth Acquisitions Taught Her What She Didn't WantHelena went through her first acquisition as an individual contributor and her second as chief of staff on the leadership team. The vantage points couldn't have been more different, but the lesson was the same: the bigger the company, the further from the customer, and the harder it is to do great work with integrity.The Chief of Staff Role Is Having a RenaissanceHelena's time as chief of staff to her CEO remains her favorite job. And she's seeing data that suggests the role is becoming even more critical with AI. Companies need integrators who can translate across functions, hold complexity, and keep the human element in the lead.Sobriety Built the Business Muscle Before the Business ExistedGetting sober at 23 and building a decade of personal responsibility, sitting with discomfort, and learning who she was without alcohol — all of it turned out to be the exact training ground for entrepreneurship. The imposter syndrome of showing up sober to a wedding in her mid-20s and the imposter syndrome of pitching a global CTO aren't that different. You just learn to sit with it anyway.She Reversed Her Board on Gut AloneIn her first board meeting after raising money, Helena reversed the company's planned tech direction with zero data — just her intuition — and told the board that. Having an all-male board means there's no one in the room who instinctively sees what she sees. So she's had to learn to trust herself first.The Cage Door Is Wide OpenCorporate stability is an illusion. Entrepreneurship is an illusion. We're all navigating uncertainty — but most of us are doing it from inside a cage with the door open, convincing ourselves we can't leave. Helena left. And she'd tell you: corporate will always be there if you need to go back.Timestamps02:16 What Archive does and who they work with03:14 Navigating two corporate acquisitions 09:24 Getting further from the customer — what drove her to start something new11:36 Did she always see herself as an entrepreneur?14:50 Raising her hand before she was ready 15:48 The chief of staff role: what it actually takes19:24 Why AI is making the chief of staff role more important23:28 The transition from corporate executive to founder26:51 Sobriety and entrepreneurship: the parallel nobody talks about29:44 Reversing the board's decision on intuition alone35:58 You're building a muscle you don't even know you need yet39:41 How her idea of success has evolved41:11 The golden handcuffs — and why she walked away anyway45:35 It's all an illusion of safety46:04 Women and AI: get on board or get left behind53:02 The legacy questionResources and LinksFind host Kristin Belden on LinkedIn or at https://www.BeldenStrategies.com https://www.linkedin.com/in/kristinbelden/Sign up for Kristin's newsletter Big Deal Energy: https://www.BeldenStrategies.com/newsletterConnect with Helena on LinkedIn: https://www.linkedin.com/in/hailshan/Check out her substack: https://superpoweredbyhelena.substack.com/If this conversation resonated, hit the follow button and share it with someone who needed to hear it!#womeninbusiness #femalefounder #entrepreneurship #womenintech #corporatetoentrepreneur #sobriety #femaleintuition #AI #womenleadership #careerreinvention #over40 #kindofabigdeal #kristinbelden
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