Overview

Description

This highly interactive discussion invites participants to explore the tradeoffs of creating an unconventional life.

What happens after you create the life you thought you wanted?

Together we’ll reflect on what we’ve gained, what we’ve lost, and what we’re still trying to figure out.

Many of us have made important life choices in pursuit of greater freedom: entrepreneurship, remote work, travel, relocation, unconventional careers, or designing life on our own terms. These choices can bring tremendous rewards - autonomy, growth, flexibility, adventure, opportunity, and meaning.

They can also create unexpected challenges around belonging, relationships, community, identity, partnership, and home. This highly interactive discussion explores the tradeoffs of creating an unconventional life. Together we'll reflect on what we've gained, what we've lost, and what we're still trying to figure out.

Expect thoughtful conversation, meaningful connection, and practical questions you can continue exploring long after the session ends.

Meet Your Facilitator: Aenslee

Aenslee works as a leadership coach with founders, executives, and other high-performing individuals navigating the complexities of transitions, relationships, and the challenges that emerge with increasing success and responsibility.

Originally trained as an engineer, she has spent much of her career living and working internationally, building an unconventional path across countries, careers, and ways of thinking.

She is a lifelong athlete, and more recently has taken up ultrarunning as another way of exploring endurance, challenge, and what it takes to grow through discomfort. Her work sits at the intersection of leadership, performance, and human development, focused on the kinds of questions that don’t have simple answers.

https://www.aensleetanner.com/

Why Join?

Many conversations within entrepreneurial, remote work, and travel communities focus on the benefits of freedom. Far fewer explore the complexity that often comes with it.

This workshop creates space for the parts of the story that are often left out:

• Loneliness despite independence
• Building community while constantly moving
• Navigating changing identities
• Relationships across countries and lifestyles
• The tension between freedom and stability
• Creating a sense of home

Whether you’re a founder, freelancer, remote worker, expat, traveler, or simply questioning traditional life paths, you’ll find a welcoming environment to explore these topics with others.

What to Expect

This is not a lecture, networking event, or self-improvement workshop. Instead, it is a facilitated conversation designed to create space for honest reflection and meaningful dialogue.

Throughout the session, participants will explore questions such as:

• What does freedom mean to me today?
• What have I gained by choosing an unconventional path?
• What have I sacrificed along the way? Where do I experience belonging?
• How do relationships change when life looks different from the norm?
• What am I still searching for?

Through guided discussion from our host Aenslee and shared perspectives, participants will have the opportunity to connect with others navigating similar questions and experiences.

No preparation or prior experience is required, only curiosity and a willingness to engage.

Photo Gallery

Expect:

• Thoughtful conversation
• Small group discussion
• Personal reflection
• Diverse perspectives
• Meaningful human connection

Who Can Join: Open to anyone interested in exploring the realities of unconventional living, working, and personal growth.
Format: Facilitated open dialogue and group discussion
Experience Level: No previous experience required

Frequently Asked Questions