Entrepreneurship at All Levels: From Side Hustlers to CEOs

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Five entrepreneurs from different creative industries got candid about what it takes to go out on their own at the session “Entrepreneurship at All Levels: From Side Hustlers to CEOs” at the Find & Follow Your Passion conference on Saturday, October 25th.

Panelists included Kristin Sloan and Doug Jaeger of JaegerSloan; freelance UX & brand strategist Talisa ChangSarah Mendelsohn, blogger, publicist, and Communications Coordinator at The Gap; and Michael Jacek Gre, Partner at SWARM.

FindSpark Side Hustles & CEOs

Photo courtesy of Jenny Seto

Getting started is hard work.

The panelists agreed that starting a business or working on your own is not easy. Failures, reiterations and self realizations are par for the course. You should only take on the journey if you are passionate about the idea and ready to be flexible.

“Make sure it’s something you really believe in and you’re really excited about,” said Kristin Sloan. “It’s going to take tons of your energy, tons of your time and tons of your brain space.”

Sloan was a professional ballerina who built a website about dancing as a side project. That side hustle taught her about coding and production, skills she now uses at media production company JaegerSloan.

Be open to changing the idea and testing out different things, then figuring out what works best. Sloan’s partner Doug Jaeger called this the “live, learn cycle.” He became an entrepreneur after leaving his job and deciding to control his own destiny. His first venture failed, but he started over with JaegerSloan.

“The living can be kind of painful sometimes, that’s where the learning comes in,” Jaeger said. “A lot of the best things I’ve ever worked on in my life have happened between 11 at night and 5 in the morning.”

While all the ideas may keep you up at night – one panelist said he hasn’t had a good sleep in years – Talisa Chang advised to start small. Chang, a UX, copywriting, and branding freelancer, learned from starting events company Her Girl Friday that trying to accomplish too many things was overwhelming.

“Learning how to disengage from the obligations that are not truly obligations can help you move forward with something that you care about,” Chang said. “If you enjoy it you’ll do it. The minute you feel like you took on too much it will become really stressful.”

Sarah Mendelsohn, who does freelance PR and writing in addition to working as Communications Coordinator at The Gap, said she sometimes wonders why she keep going, but she believes that all her hard work will pay off in the future.

Be mindful about which clients you take on.

“When you’re working with people, imagine – are they going to be a complete nightmare, are they going to be a hangover that’s going to be there for the next 3 months, or will they be cool and laid-back?” said Michael Jacek Gre.

There’s a lot to consider when deciding whether or to take a project. Jaeger asks himself, is it interesting? Are the people rational? Will the work get attention? Will it make money? But, you’ll inevitably take on some bad clients when you’re getting started.

Chang said she checks in with herself when she is offered an opportunity. If it seems dicey, she might decline it. Even so, don’t burn bridges. A lot of work comes from recommendations and you never know where your network will take you.

FindSpark Side Hustles & CEOs

Photo courtesy of Jenny Seto

Keep track of finances.

“Knowing what cash flow means for you is so important,” Chang said. “Knowing you have a safety net lets you take a risk like taking an opportunity that pays less, or quitting.”

Talisa recommends putting a percentage of money away every time you receive a check. Remember that you’ll eventually have to pay taxes, and fill out a W9 instead of a W2. Report transportation if your company doesn’t cover those costs. Look into Expensify and Xero to keep track of expenses.

Continue to learn.

The panelists recommend authors Paul Graham, Ben Horowitz and websites A List Apart and Quora. Find thought leaders in your own field and take on a virtual mentorship. And get inspired by other awesome side hustles at sidehustle.me.

Adjust to life as an entrepreneur.

Because you’re reliant on yourself, figure out how you want to get things done and experiment with what works for you. Maybe you want to learn skills during the day and work at night while most people are sleeping.

When you’re dedicating a huge portion of your time to your project, you need to learn how to prioritize what’s important. It’s easy to get caught up and try to do everything at once, but it’s ok to save some tasks for later if they aren’t urgent.

Remember that it’s impossible to have all the skills you need and keep trying to learn.

“It’s a trade-off – do you want that freedom, knowing that it is going to be a lot more work?” said Gre. “It’s not less. But the reward is also so much greater.”

Are you thinking of starting a side hustle or your own business? Share with us in the comments.

Want to meet top companies, new mentors, and other awesome, talented young pros like you?Join us for Hustle Summit, the most epic networking event you’ll ever attend, taking place on Friday, January 27th, 2017 at Irving Plaza. We’ll connect you digitally and in-person to the coolest companies, greatest pros across industries, and your future life-long friends. Companies we work with include HBO, Scripps Networks, BuzzFeed, Blue Apron, IPG Mediabrands, L’Oréal, and more. Learn more & save the date at hustlesummit.co



About the Author

Danielle is a recent grad from University of Delaware freelancing about business and entrepreneurship in NYC. You can see what she's up to on her blog at and on Twitter .

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