Diving into freelancing and building my own company wasn’t something I ever thought I would be doing. I admired people who did it, but the idea of being an entrepreneur myself was scary and uncertain. I tried muffling the little voice in my head that was whispering, “Well, what if?” and “Why not you?” with loud music and a steady paycheck.
Over the course of my adventure in NYC, I have launched creative ad campaigns during the day and produced events at night and on weekends as soon as I was out of the office. It was delicate juggling several projects at once, and it got to the point where I could quietly admit to myself that I was being torn between two things I was passionate about. My side hustles were rapidly blossoming into exciting opportunities and I spent time wondering if I was ready to take a leap of faith — right up until I took the leap.
An opportunity came along I couldn’t say no to — one that involved me flying halfway around the world to Dubai to help a dear friend Jelena launch The Confetti Project internationally. It was challenging and liberating; there was chaos and excitement in equal measure that reassured me producing these kind of creative events and connecting communities across the world was what I was being called to do every day. So I decided to make a change.
While the road has been wild, the only thing I wish I had known was that an invaluable resource like the Hustle Fest: From Full-Time to Freelance conference existed when I was struggling through the transition to start freelancing.
Turning side hustles into full time pursuits
Hustle Fest was started by Jillian Richardson and Melissa Wong to help would-be freelancers ease themselves into the transition and have the necessary tools and resources right at their fingertips. If you haven’t read the brilliant Badass Women profile the Nooklyn team wrote about Jillian and how Hustle Fest all came together, I highly recommend you get inspired and read it here.
With the sun streaming through the windows of Rise NYC, Hustle Fest kicked off bright and early at 10 AM on a Saturday. We all checked in, picked up a workbook, picked out some wicked stickers provided by Moo, and enjoyed coffee from Cafe Grumpy. There was a collaboration station where people could write down their “Ask” (what they needed help with) and their “Give” (what they could offer others) as well as sign up for one-on-one coaching from anything from wellness and goal-setting, to finance and negotiating rates as a freelancer.
It was exciting to be embraced by a community of fellow freelancers at various stages of their own journeys. While a majority of attendees were still in full-time jobs, they were all chasing dreams and came looking for advice on how to sharpen their skills in order to transition into freelancing. No one had all the answers. Attendees shared their fears and struggles and bonded with like-minded individuals, fully recognizing that they were not alone in exploring what it would mean to freelance full-time.
Diving in and designing our futures
As the first session “Designing Your Life” kicked off at 11 AM, Jillian and Melissa had all of us open our workbooks and start looking at the wealth of potential we each possessed. In order to “conquer” our career transitions, Jillian and Melissa had us start broad and write out a list of 10 things other people would say we’re good at, followed by all the possible careers and job titles we could hold. Then we focused in on the people we could help, audiences we could reach, and the potential problems we could each solve.
With each step, we went deeper, drilling down until we could each articulate three vision statements of who/what we were, who we could help, and what we could help those people/the world understand or do. We had a mock cocktail party where we introduced ourselves to people and tried on different personas/careers we were crafting. Being able to articulate and own each vision statement was empowering and it was easy to see how people lit up when they were talking about the ideas they’d be bringing to life.
Jillian and Melissa challenged all of us to come up with questions we’d need to answer to approach different career paths and reflect on what steps we would need to take to answer our questions. It was fun to crowdsource questions and hear what other people were wondering about and where they were trying to go in their own careers. It was clear Hustle Fest was all about collaboration and supporting one another, not about competing for the same jobs or keeping all our knowledge locked away in our own heads.
Getting some coaching (and working on “not dying”)
Over a lunch of gourmet sandwiches and GT’s Kombucha, people grouped up by desired industry and slipped away for one-on-one coaching with coaches that have graced 30 under 30 lists and have a proven track record of success. Each coach specialized in different areas including wellness, pricing/negotiating, productivity, finance planning, confidence and mental training, leadership mindset, and career transitioning. There was a strict no laptop policy and we had all been encouraged to put our phones on airplane mode. We were genuinely making connections free of distractions and exchanging contact info by writing down our information in our notebooks.
After lunch, we dove into presentations on “not dying,” aka the ins and outs of managing health insurance with Oscar, as well as how to finance like an adult and handle taxes like a pro with Brooklyn Plans. BestMe taught us how to set realistic goals for ourselves and how to break them down so they wouldn’t seem so impossible to achieve. We set about writing down specific income and client goals and accountability plans and participated in mock interviews.
As the day was winding down, Jillian and Melissa talked about setting up useful morning routines. Suggestions included journaling as soon as we woke up, eye gazing with ourselves for 10 minutes to increase self-compassion, and staying on airplane mode for the first couple hours of the day to work on curing our smartphone addictions. We were given an extensive list of resources, and workbooks in hand, we had actionable next steps we could set about accomplishing over the next week, month, and quarter, alongside fellow aspiring freelancers.
Keep on hustling
I found Hustle Fest invaluable in providing both a built-in support system of peers, and tools to help me continue sprinting after my dreams. The coaches Andrew, Chris, Meg, Oona of Anoo World, Cynthia, Stephanie, Leanne, Dena, and Hayley were rockstars, speaking to each of us with enthusiasm and wisdom.
The most important things I learned attending Hustle Fest included articulating what I wanted and needed help with, as well as getting insight into planning out my finances. There are several pitfalls to watch out for when it comes to adjusting rates as a freelancer, learning to negotiate contracts, filing taxes properly, investing, and keeping a close watch on profit and loss. Before meeting Jillian and other freelancers back in January, I felt like some days I was scrambling to figure things out day to day, but the resources Jillian and Melissa brought together for Hustle Fest made the complexities of transitioning to freelancing much more manageable.
I’m excited to see how Hustle Fest evolves in the future and where we all dive in, in the next few months! For now, you can follow Hustle Fest on Facebook to get updates!
If you’re interested in chatting with the Hustle Fest co-founders — you can connect with Jillian via The Joy List, Instagram, Twitter, and check out her personal website! You can also follow Melissa and New Women Space on their website and Instagram for their upcoming events!