The Connected Future Leadership Circle

The Connected Future

Assess-Connect -Grow -Lead

A private

Leadership Circle and

Trusted Advisor for executive women shaping their next chapter.

The Connected Future is a private

Leadership Circle and Trusted Advisor for executive women carrying meaningful responsibility — women who want better conversations, clearer decisions, and the thinking to match the life and leadership they are building.

You'll join a small circle of thoughtful, ambitious women and create a private AI-enabled Trusted Advisor shaped by your values, patterns, assessment insights, goals, and the version of yourself you are becoming over the next twenty-five years — so that you can make decisions that are genuinely yours, stay aligned with what matters most, and move toward your future with clarity, conviction, and an better room to think in.

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Two powerful forms of guidance, working together

The Human Circle

A curated group of ambitious women in similar seasons of growth, leadership, pressure, and possibility. You’ll have space for honest conversation, thoughtful networking, shared insight, and perspective you may not get in your day-to-day environment.

The Trusted Advisor

A private AI-enabled reflection partner built around your assessment insights, values, goals, patterns, and 25-year future self. It helps you think through decisions, understand your blind spots, and reconnect with the future you are trying to create.

The Integration

The circle helps you see what you might be missing. The Trusted Advisor helps you carry that clarity into your daily decisions. Together, they create a more grounded, future-focused way to lead and live.

What would change if your future self could help you make today’s decisions?

Most of us make important decisions from inside the pressure of the present.

We react to the meeting, the opportunity, the difficult conversation, the financial question, the career crossroads, the relationship tension, or the quiet feeling that life is not quite matching what we imagined.

Your Trusted Advisor is designed to help you pause and see more clearly.

It is not “just AI.” It is a private, personalized reflection partner shaped by your own values, patterns, goals, assessment insights (TrimetrixEQ, and others), and the woman you are becoming. Over time, it learns the language of your life — what matters to you, what pulls you off course, where you tend to over-function, and what your future self would want you to remember.

Example question you might ask your Trusted Advisor:

“I’m considering taking a bigger role, but I’m worried it will cost me more of my personal life. Help me think this through from the perspective of my 25-year future self.”

Your Trusted Advisor might help you explore:

What part of you is excited, and what part is afraid
Whether this decision aligns with your longer-term vision
What boundaries would need to be in place before saying yes
What pattern from your assessment may be influencing your decision
What your future self would thank you for protecting now

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Career clarity

Peer perspective

Better decisions

Sustainable growth

Who this is for:

The circle is designed around the realities ambitious women often navigate with very little honest space to process them.

For ambitious women leaders in their 30s, 40s, and early 50s who are ready for deeper clarity, stronger decision-making, and a more intentional next chapter — within a carefully curated cohort of women in a similar season of leadership, life, and growth.

This may be for you if you are:

Growing inside an organization
Leading a team or preparing for a larger role
Building or scaling a business
Navigating a career inflection point
Feeling successful on paper but unclear about what you really want next
Curious about AI, but wanting it to feel personal, ethical, and useful
Ready for more honest conversation than traditional networking usually allows

You do not need to have everything figured out. You do need to be willing to think honestly about the future you are creating.

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Testimonials

What Members Say

This is the networking forum I didn't know I needed! Jim has thoughtfully curated a group of like-minded female leaders and facilitated discussions that have allowed us to share perspectives and support one another as we navigate challenges. This group has allowed me the space to reflect on where I am, the leader I want to be and check-in on a regular basis on my vision for my future self. I recommend this to any woman who is looking to be in the driver's seat of their careers and design the future they want to have.

-Emily, member since 2024

The Connected Future Group is a smaller, more intimate group, and there's something about the consistency of coming together quarterly that I've really come to value. Each time we gather, I leave feeling a little more grounded and a little less alone in what I'm navigating. The women in this group are genuinely supportive, Jim is an excellent guide, and the conversations have a way of sticking with me long after we've wrapped up. It's not a huge time commitment, but it's become one I really look forward to. If you're looking for a community that's low-pressure but genuinely connected - one that adds real value and reflection to your bigger life - this is worth your time.

-Kristin, member since 2024

Connected Future has been a transformative experience, pushing me to grow both personally and professionally. Jim provided the tools and guidance that helped me evolve, think differently, and prepare for what’s ahead. He also brought together an incredible network of women who uplift, challenge, and support one another, creating a space where I felt seen and empowered in ways I never expected.

-Lindsay, member since 2024

It's hard to put into words what Connected Future has meant to me. Jim has created something rare: a room where women who are used to carrying a lot can finally exhale, be honest, and think out loud together. I've walked away from every session with something I needed, whether it was a new way of seeing a decision in front of me, a question I hadn't thought to ask myself, or just the reminder that I wasn't alone in what I was navigating. So much of that comes down to who Jim is. His care is real, his commitment is steady, and the women he's gathered are extraordinary. I'm deeply grateful to have been part of this, and I'd follow this work wherever it goes next.
-Paule, member since 2024

How it works:

1. Request an invitation
Share a few details about your role, stage, and what draws you to the experience.

2. Join a small curated circle
Selected women are invited into a thoughtful cohort of approximately 5–8 women. Members are matched into curated cohorts with women in a similar season of leadership, life, and growth — so the conversations feel relevant, grounded, and genuinely useful.

Investment: $997/year

3. Participate in quarterly guided sessions
Each quarter includes approximately 3 hours of structured conversation, reflection, and peer perspective.

4. Build your Trusted Advisor
You’ll create a private AI-enabled Trusted Advisor shaped by your assessment insights, goals, values, patterns, and 25-year future self.

5. Continue evolving it between sessions
You’ll receive weekly prompt ideas and optional monthly bonus sessions to help your Trusted Advisor become more useful over time.

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What the experience includes

Founding Membership: $997/year

Your $997 founding membership includes :

Small cohort circles

Each circle includes approximately 5–8 women, creating enough diversity for rich conversation and enough intimacy for trust.

Quarterly guided sessions

The current core time commitment is approximately 3 hours per quarter.

Optional onboarding session

Members may attend an optional 1-hour onboarding session to understand the process, the circle, and how to begin using the Trusted Advisor.

Trusted Advisor setup

Your initial Trusted Advisor setup takes approximately 3 hours. After that, you can spend as much or as little time developing it as you choose.

Weekly prompt ideas

You’ll receive weekly prompt ideas to help your Trusted Advisor evolve with you and become more useful over time.

Bonus monthly sessions

Optional 1-hour monthly bonus sessions provide additional support, conversation, and learning opportunities.

Networking and reflection

The sessions are designed with room for sharing, discussion, and real connection — not just content delivery.

Do you really know yourself?

Do you know your operating system — how you make decisions, what drives you, and how you work best?

Are you clear on the gap?

Are you honest about where you are today — and clear on what stands between you and where you want to go?

What if your future self became your advisor?

How would it change things if your 25-year future self became your mentor, guide, and trusted advisor?

Why this matters

Better decisions require better mirrors

Many capable women are making high-stakes decisions without enough honest reflection, trusted perspective, or future-focused support.

You may be surrounded by people, yet still feel like there are very few places where you can talk openly about ambition, uncertainty, leadership, money, identity, purpose, aging, reinvention, and the life you actually want.

The Connected Future was created to give you both:

A circle that sees you clearly.
A Trusted Advisor that helps you hear yourself more deeply.

The gap between the life you dream of and the life you are experiencing is not usually about intelligence or effort.

Often, it is about patterns, assumptions, competing responsibilities, old definitions of success, and decisions made without enough space to think.

This experience gives you that space.

About The Team

Heather McCulloch

Co-Founder & Operations Lead

Heather brings together human development, business experience, operations, and practical AI automation to help turn The Connected Future’s vision into a clear, trustworthy member experience. She leads the behind-the-scenes structure, including systems, onboarding, funnels, automations, and AI-assisted coaching tools, ensuring the platform can scale without losing its human connection.

Read Heather's Full Bio..

Jim Dryburgh

Co-Founder & Visionary

Jim brings decades of coaching experience, leadership insight, and future-focused thinking to The Connected Future. Inspired by his work with ambitious women leaders and the legacy of his late spouse’s passion for supporting career women, Jim helps shape the frameworks, tools, and vision that guide members toward greater confidence, recognition, and possibility.

Read Jim's Full Bio..

Built at the intersection of coaching, lived experience, and intelligent systems

Frequently Asked Questions

Is this a networking group?

Not in the usual sense. It is more curated, more thoughtful, and more structured than typical networking.

Is this coaching?

Not in the traditional one-to-one sense. It is a guided peer experience centered on perspective, judgment, and growth.

Is this focused on career or personal life?

Primarily career and leadership, with the understanding that work-life balance, ambition, and sustainability are part of the same conversation.

Is the Trusted Advisor private?

Your Trusted Advisor is designed as a private reflection space for your own thinking, goals, values, and decision-making. It is not a public group tool or shared community chatbot.

We will provide guidance on how to set it up thoughtfully, what to include, what not to include, and how to use it in a way that feels safe, useful, and personally aligned.

Who is this best suited for?

Women aged 30-50 in meaningful leadership roles who want a more intelligent, grounded, and sustainable way to think about growth.

Do I need to be experienced with AI to participate?

No. You do not need to be technical or already using AI in your work.

Part of the experience is helping you create a private Trusted Advisor in a way that feels clear, personal, and useful. The technology is simply a tool. The deeper purpose is reflection, clarity, and better decision-making.

Step into a circle of women who understand the weight of ambition, and create a private future-self Trusted Advisor to help you make decisions with more clarity, confidence, and self-trust.

What next?

You do not need to wait until something feels untenable to make better decisions.

Founding Membership

$497/year

Your founding membership gives you access to the full Connected Future experience for one year, including the quarterly circle, guidance to begin building your private Trusted Advisor, weekly prompt ideas to help it evolve with you, and optional monthly bonus sessions for deeper reflection and connection.

We are currently forming small founding circles.

If this feels aligned, we invite you to request an invitation. We’ll ask a few questions so we can understand where you are in your leadership, career, and life — and whether this is the right fit for you at this stage.

Founding cohorts are intentionally small. If there is not an immediate fit, we may recommend a future cohort or waitlist.

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© 2026 The Connected Future. All rights reserved. The content and experience provided are for educational and personal development purposes only and are not intended as medical, psychological, legal, or financial advice.

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