Leading Advisor Simon Reilly

How to Lead Without Burning Out Your Nervous System

Simon Reilly — Wed, 01 Apr 2026 14:00:00 +0000

Every advisor-turned-founder eventually reaches a point where the business runs faster than their nervous system can comfortably handle. It doesn’t happen all at once. It happens gradually — almost invisibly. A few more clients. A few more team members. A few more deadlines. A few more fires. A few more decisions. A few more expectations layered on top of the old ones. Until one day…

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How I’ve Improved My Use of ChatGPT: The Power of Containment and Isolation

Simon Reilly — Wed, 25 Mar 2026 14:00:00 +0000

Over the past couple of years, I’ve been using artificial intelligence—particularly ChatGPT—almost every day as part of my thinking, writing, and consulting work. What started as curiosity quickly turned into something far more powerful. Today, AI has become one of the tools I use to support my strategic thinking, accelerate writing, organize complex information, and help build systems…

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When Growth Makes You Feel Disconnected — And How to Fix It

Simon Reilly — Wed, 18 Mar 2026 14:00:00 +0000

There’s a moment in every founder’s journey that almost no one talks about. The business is growing. Revenue is up. The team is expanding. Opportunities are multiplying. From the outside, everything looks exactly the way you hoped it would look. And yet… inside, something feels off. Not wrong. Not broken. Just distant. It’s a quiet emotional disconnection — the kind that’s…

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Growth Isn’t Breaking Your Firm — Missing Leadership Architecture Is

Simon Reilly — Wed, 11 Mar 2026 14:00:00 +0000

Why Growing Firms Need a Leadership Operating System Most leadership advice focuses on what to do next. The next tactic. The next hire. The next piece of software. The next marketing idea. But at a certain stage of growth — typically when a firm reaches five to ten people — leaders discover something uncomfortable: The problem is no longer effort. The problem is clarity.

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If You’re Still the Hub, Your Business Can’t Scale

Simon Reilly — Wed, 04 Mar 2026 14:00:00 +0000

Every founder eventually reaches a moment when they look around and quietly realize: Everything still runs through me. Every decision. Every approval. Every exception. Every deadline. Every urgent issue. Every question—large or small. Even when there’s a team. Even when there are good people in place. Even when the business is technically “successful.” You’re still the hub.

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When Old Stories Shape Modern Leadership

Simon Reilly — Wed, 25 Feb 2026 14:00:00 +0000

Every leader carries an inner narrative that began long before their first job title, their first client, or the first time they were responsible for a team. These early narratives often operate quietly in the background, influencing how leaders respond under pressure, how they set boundaries, how they handle conflict, and how they interpret the actions of others. And the truth is this…

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Will AGI Put Your Advisor Business Out of Business by 2030?

Simon Reilly — Wed, 18 Feb 2026 14:00:00 +0000

Let’s suspend disbelief for a moment. The airwaves are filled with predictions that AGI will eliminate 70–90% of jobs within the next five years. Entire industries will collapse. The socioeconomic consequences will be catastrophic. Governments won’t be ready. Businesses won’t adapt in time. Anxiety levels are already rising. So let’s ask the uncomfortable question: Will AGI put your…

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Your Legacy Starts Long Before You Consider Selling

Simon Reilly — Wed, 11 Feb 2026 14:00:00 +0000

Most founders think legacy begins when they start planning to sell, transition, or step back. But the truth is far more revealing: Legacy starts the moment you begin leading. Every decision… Every habit… Every conversation… Every standard you reinforce… Every standard you tolerate… Every emotional pattern you bring into the business… All of it becomes part of the legacy long…

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Why Your 2026 Breakthrough Depends on What You Remove, Not What You Add

Simon Reilly — Wed, 04 Feb 2026 14:00:00 +0000

Do you understand that attracting your success in 2026 and beyond is more about subtraction than addition? Most leaders don’t. And that misunderstanding is quietly sabotaging otherwise bold, well-intentioned growth plans. This distinction crystallized for me during a recent 2026 business plan review with one of my clients. Their plan was ambitious, thoughtful…

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Stop Hiring the Person You Interview — and Start Hiring the Person They Really Are

Simon Reilly — Wed, 28 Jan 2026 14:00:00 +0000

Every leader has experienced this moment: A candidate interviews beautifully. They’re polished, enthusiastic, articulate, and confident. You walk out thinking, “Finally — this is the one.” But weeks or months later, you realize the person you hired… is not the same person you interviewed. Their follow-through is inconsistent. Their communication style is different than you expected.

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