Hustle Fest: From Full-time to Freelance

Helping professionals enter into the “solo” space

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Event Planning and Production

Curriculum Development

Partnership Outreach

Project Management

User Research

Community Management

Communications Strategy

Writing / Social Media 

Team: 2 founders, 10 volunteers

Time Frame:  4 month planning cycle, 8 hour event

My Role:  Event designer, producer and workshop host

The Challenge

Many people are unsatisfied with their 9-5 jobs and want to work for themselves to pursue a career they are more invested in - but they don’t know how to start.

Many events and workshops for freelancers are all fluff. There were few events that addressed the biggest fears of going freelance: getting clients, making enough money, self-management.

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The Solution

My co-designer Jillian and I saw a need for a resource that was approachable and supportive, but also empowered people with practical skills and resources. We produced a total of three day-long summits each attracting 100 professionals from a range of different fields.

Each event had a “marketplace” of career coaches for attendees to engage as potential ways to continue their professional development. Jillian and I ran a “design your life” and “goals” workshop during the conference, creating all original workshop content for the playbooks attendees could take home.

We reached out to many companies and orgs to provide additional programming and support. We curated a speaker list with independent consultants and employees from companies like Oscar Health and Brooklyn Plans and secured financial and in kind sponsorship from companies like The Muse, Fiverr, Rise NYC, ThoughtWorks, GT Kombucha, Cafe Grumpy, Brooklyn Brewery.

Hustle Fest #2 Attendees

Hustle Fest #2 Attendees

Understanding who we were solving for

Every workshop topic and content piece was informed by the user interviews and surveys we conducted ahead of each event.

  • We heard from every attendee about what their biggest fears were and what they most wanted to learn.

  • We collected information about what industries our attendees wanted to work in and facilitated lunch groups organized by industry.

  • We created a “give” and “ask” board where people could connect professionally and feel a part of a generous community.

  • After each Hustle Fest we performed a retrospective on what went well and where we could improve with the help of a coach

Negotiation Workshop by Hillary Black for Hustle Fest #2

Negotiation Workshop by Hillary Black for Hustle Fest #2

Hustle Fest Logo

Hustle Fest Logo


Each time we collected feedback from attendees we felt affirmed that we were providing a unique service that left people feeling energized and equipped. We felt confident enough to increase the ticket price and secure nicer venues each time.

The positive testimonials from attendees made it clear that we had fulfilled a real need for people looking to make the oftentimes intimidating leap into self-employment. Several people told us that Hustle Fest changed their lives.

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