Lost in Y Community

The home of "both/and" people

Executives, entrepreneurs, and professionals building portfolio careers, making connections, and moving forward together.

Lost in Y is a professional community for people who don't want to choose one professional identity. Here you can combine a role, consulting, entrepreneurship, investment, and meaningful work, within a network built on trust, personal relationships, and mutual give.

Portfolio careerProfessional communityOpportunities & connections
"Both/and" people, in their own words

People who don't fit one box

Just a small glimpse of the range of people who make up the community.

CEO & board director at a public companyER physician & startup founderVP marketing & real-estate entrepreneurProduct manager & academy creatorSenior official at the Ministry of Defense & startup mentorE-commerce entrepreneur & founderAccountant & e-commerce brand builderNonprofit CEO & board director
My story

From a personal search to a community of 3,500+ members

Itamar Assaf at the MassChallenge program, Boston, 2016Boston, 2016

In 2016, at an entrepreneurship program in Boston, something happened that I didn't expect. I was exposed to a new world, high-tech and academia, but the real lesson I learned wasn't about fundraising, it was about building relationships.

In that moment I asked myself: "why not bring this culture to my friends in Israel?" I looked for multidisciplinary, curious people like me, who didn't want to fit into one professional box, but to connect worlds and build their own path.

Over the years I've met thousands of executives, entrepreneurs, and professionals. Through deep conversations, meetings, and joint work, it became clear to me that many people are looking for more than another networking group. They're looking for a professional space that allows honest consulting and real connections.

That's how a community based on personal relationships, trust, and mutual give was born. Not a mailing list, not a contacts database, but a network of people who help each other think, progress, and create opportunities.

The community in the field

Real people. Real meetings.

Lost in Y wasn't built only in groups and on screens. It grew from meetings, conversations, events, and personal relationships, conversation after conversation.

The strongest network isn't made of contacts. It's made of people who know, trust, and are willing to help each other.
Community meetupsOpen conversations between people from different worlds, around challenges, ideas, and opportunities.
One-on-oneIn-depth meetings that let you know someone beyond a title, understand a need, and create a precise connection.
Connections that carry forwardA first introduction that turns into a partnership, consulting, an opportunity, or a new professional step.
What happens in the community

Professional spaces, shared purpose

Every space in the community is meant to help members think, consult, meet people, and create opportunities. Some of the conversation is quiet and focused, some open and active, but all of it is built on trust, professionalism, and mutual value.

The Announcements Channel

Insights and opportunities, no noise.

A quiet, focused channel where I share insights, business and professional opportunities, quality roles, tools, and content relevant to "both/and" people.

The Business Arena

A place for connections and working together.

An active space for consulting, finding partners, suppliers and clients, sharing knowledge, and creating professional and business collaborations.

AI Builders

Learning and applying AI in the field.

A space for executives, entrepreneurs, and professionals who want to use AI in their work and business. Sharing tools, use cases, processes, and practical experience.

Professional Opportunities

The next step, when you're ready for it.

Focused channels for professional opportunities, management roles, projects, consulting, and relevant connections, from the community and network built around it.

Our approach

The world has changed. Careers need to change too.

AI is changing roles, companies are cutting headcount, and career paths are no longer as predictable as they were. The community exists to help people build resilience, stay relevant, and expand their range of action.

Portfolio career

Not leaning on a single role. Combining a role, consulting, projects, ventures, and investments, building a professional mix that fits your life stage and goals.

Managing your career

Not waiting for the market to decide for you. Developing capabilities, building relationships, examining opportunities, and making professional decisions by choice.

Speaking candidly

In a trust-based space you can consult about professional challenges, changing direction, pricing, compensation, and organizational politics, and get a perspective from people who know the reality.

Voices from the field

Why join the Lost in Y community?

"I always felt I didn't fit one traditional box. Here I found the tribe of "both/and" people, and it's the most precise place to plan my next career move."
Senior product management executive
"As a founder who sold a company and was at a crossroads, I found a discreet, ego-free space in the community for eye-level consulting."
Serial entrepreneur & founder of an acquired tech company
"This community opened doors I didn't even know existed. It's not regular networking, it's building long-term relationships."
Entrepreneur & executive search specialist
Frequently asked questions

What's worth knowing before you join

What is the Lost in Y community?
Lost in Y is a professional community for executives, entrepreneurs, and "both/and" people. It's a trust-based space for sharing knowledge, consulting, making connections, and building a portfolio career.
Who is the community for?
Executives, entrepreneurs, freelancers, consultants, and professionals who want to think ahead, build professional relationships, and create more than one possibility in their career.
What is the "both/and" model?
It's an approach that lets you combine professional worlds, for example an employee role, consulting, a venture, investments, or meaningful work. Instead of choosing one identity, you build a mix that fits you.
Can I join if I'm a salaried employee?
Absolutely. Many community members work as employees, manage teams, or lead areas within organizations. The community fits anyone who wants to expand their options and be part of an active professional network.
How long does joining take?
You fill out a short intro form. After a fit check, you can schedule a 15-minute intro call and get access to the relevant spaces.

Want to build the next step together?

Joining the community is based on mutual fit and a wish to create value. That's how we keep a professional, high-quality, trust-based space, where members can consult, make connections, and grow over time.

I personally review every request. If it looks like a fit, I'll send you a link to join the community.

Nice to meet you

The first step to the Lost in Y community

Tell us a bit about yourself, your professional path, and the connections you're looking for. These details help us get to know you and continue the join process.

Prefer to talk first? Book a 15-minute intro call ↗

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We'll use these details to process your join request and follow up by email and WhatsApp.