Highlights from #imakealiving NYC and Looking Ahead to Portland!

FreshBooks is on the road! Last month, we hosted #imakealiving in New York City. Next up: Portland, Oregon!

With great risk comes great reward—and for small business owners everywhere, this couldn’t ring truer! Plenty of heart, soul and labor goes into the creation and day-to-day of a small business. And guess what? FreshBooks is here for you every step of that journey. Last month, we hosted our third #imakealiving event of 2018 in NYC. Here’s how it all went down!

Highlights from #imakealiving NYC

The amazing panel included (Founder of ShankMinds: Breakthrough), (Filmmaker and Feminist Blogger), (Executive Director of Freelancers Union) and Steph Hoff (Creative Producer, Strategist and Marketing Innovator). The event was moderated by , Host of the Beancast Marketing Podcast and Co-Host of the #imakealiving podcast, season one.

#imakealiving NYC was hosted at Carolines on Broadway, a comedy club in the heart of Manhattan. Close to 150 freelancers and small business owners attended to listen in on inspiring panelist discussions.

When asked whether the driver of self-employment was passion or independence, panelist Caitlin Pearce talked about the changing face of full-time jobs and how many self-employed professionals have come to the conclusion that working for themselves isn’t a bad thing.

“I get to be my own boss, get to make the choice on what projects I take on and the people I want to work with,” she says.

But when it came to taking the plunge into freelance, Steph Hoff shared her perspective. “No one is going to give it to you—you have to reach out and take it,” she says. “I wanted to be an art director so I told people I was an art director. I started getting jobs because of it.”

Dream, Girl film creator Erin Bagwell discussed the hustle and passion she put forth in making the film, and that it wasn’t easy to reach out and ask for funding, despite the film’s initial success.

When asked about money (and why many creatives neglect to ask for what they deserve) Erin Bagwell shared her perspective. “For me, it was about the ego. It felt awful and I just really needed to swallow my pride and get over it. I really wanted my film to do well in the world, so I had to go out there and have uncomfortable conversations.”


Finally, the panelists talked about building security amidst the instability and constant hustle of self-employment.

“We find the freelancers that do the best have a robust network, people they can go to for referrals and can outsource work to,” explains Caitlin, as she speaks about the members of the Freelancers Union. “There’s a whole economy of services that have cropped up and been really helpful for freelancers.”

Looking Ahead to #imakealiving PDX

For the 4th city on our #imakealiving tour, we’ll be hitting Portland, Oregon. Each and every #imakealiving event helps to facilitate and inspire connections between small business owners—and we’re honored to be a part of it all. This time, we’re coming with a theme: Being Your Own Boss: How to Hustle and Own It. Ready to get the conversation going, Portland? We can’t wait to meet you!

Event: #imakealiving powered by FreshBooks
When: Wednesday, June 20th, 6:30PM–9:30PM PDT
Where: The Evergreen, 618 SE Alder Street, Portland, OR 97214 USA
Details: #imakealiving will host a diverse panel of people from different industries. They’ll share stories about their livelihoods and non-traditional career journeys. Our panelists will then show you how to harness that inspiration and apply it to your own career. Our goal is to motivate and empower you to break out of your comfort zone and take some chances with your career and marketing!
Cost: Free – seeing you thrive is all the payment we need!
Panelists Include: Aaron Draplin, Courtenay Hameister, Jack Phan and Nathalie Weinstein

about the author

FreshBooks is the #1 accounting software in the cloud designed to make billing painless for small businesses and their teams. Today, over 10 million small businesses use FreshBooks to effortlessly send professional looking invoices, organize expenses and track their billable time.



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