4 freelancers share their advice for taking the right risks

4 min read
Katie Perry
  •  Oct 12, 2017
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There is no ignoring the rising momentum of the freelance movement. No matter what industry you’re in or what skill set you possess—be it design, engineering, writing, or something else—you might have felt the itch to ditch the single-employer life for more entrepreneurial pursuits.

As cities around the world like Chiang-Mai, Lisbon, and Berlin are capturing the interest of digital nomads, freelancers are organizing in places like New York and Los Angeles with the support of trusted groups like the Freelancers Union. In fact, the New York City Council passed the landmark Freelance Isn’t Free Act, designed to protect the rights of freelancers in the 5 boroughs.

Related: How to price your freelance design work

Beyond its forward-thinking freelance-friendly policies, the conventional character of New York has made the city home to tens of thousands of independent workers who are inspired by the unique challenges (and opportunities) inherent to living there. This rising independent creative class—explored in a new short film created by the freelance software company I work for, AND CO, in collaboration with Daniel Soares—is redefining the term “freelance” within an increasingly independent economy.

Here are some lessons from the film’s stars, who represent 4 of the most creative freelancers we could find in the city that never sleeps. You can watch the full film below or at

Follow your envy

Do you ever see someone else pursuing their passion and think, “Why not me?” Part of becoming an entrepreneur is leaning into that twinge of envy.Twitter Logo Helen Levi, owner of Helen Levi Ceramics, and a freelance potter and photographer, recalls looking around her at others who had taken the leap and thinking, “I want to do this.”

Of course making the move to freelance requires more than guts. You need a game plan for how you will support yourself independently, as well as a business strategy for realizing your professional ambitions as a free-standing entrepreneur. Along with these logical steps, though, you need to have the confidence to believe you can achieve what you’re setting out to do. Most great businesses start with a risk, yes, but they also begin with a vision and the conviction that it can be accomplished.

Start here:

  • Make an envy listTwitter Logo—that is, people you wish to emulate. Study (or just ask!) how they got started, paying close attention to their business strategy and approach to finding work.
  • Assess market fit for your skill set: Are others selling similar services? Are companies hiring for your particular skill set?
  • Start taking informational/introductory meetings (yes, before you quit your full-time job!). Chum the waters a bit before going in for the kill.

Draw a line in the sand

Beginnings are always roughTwitter Logo,” says Alex Trochut, an award-winning designer, illustrator, and typography artist who has worked with everyone from Katy Perry to the Rolling Stones, but just because starting your own business is hard doesn’t mean it’s not well worth your effort.

In fact, many great success stories were born from humble beginnings. Barry Gordy founded the legendary Motown record label with a $500 loan. Hugh Hefner started Playboy with a meager $600. As the saying goes: Everyone’s gotta start somewhere, right?

“When it comes to freelance, beginnings are always rough.”

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You could waste months or even years waiting for the “right” time to go out on your own, or you can create a game plan that will allow you to forge your own career path while still being responsible and mitigating some of the associated risk. Ashley Nowicki, founder of AUCTOR, advocates for aspiring independents to build a financial safety net before taking the leap, which might mean saving your proverbial pennies for a few months before giving notice.

Start here:

  • Calculate your estimated living expenses for 3 to 6 months and start building your safety net to prepare for when you turn freelance
  • Read this free book on how to launch your freelance career
  • Calculate your estimated tax obligation

Be an optimist and a realist

The life of an independent professional might seem like a dream to outsiders. Certainly, making one’s own hours or living one’s life as a digital nomad abroad might seem ideal to someone who is shackled to a 9-to-5 desk job, but this career path comes with its fair share of challenges.

“It’s not like the movies,” notes Zipeng Zhu, who runs an independently owned and operated creative studio, DAZZLE, from his Brooklyn home.  

Being a solopreneur isn’t “like the movies,” says @zzdesign. But for NYC’s top creative freelancers, it’s so worth it.

Earlier this year, AND CO launched a global study on the state of freelance. In our interviews with hundreds of independent professionals, an interesting trend emerged: Although most freelancers said they were not more financially stable since going independent, nearly 70% of them said they were happier and that their quality of life had improved.

Freelancing is hard work and it can be marked by the highest of highs and the lowest of lows, but many independents will say that the challenges are well worth the freedom and flexibility this career path provides.

Start here:

  • Be a doer about the hard stuff. As a freelancer, there are a few things you must be completely on top of for your own security (and your sanity, too). This includes health insurance, tax obligations, business ops (like invoicing) and the like.
  • Be a dreamer about the future of your business. Think big! Where do you see your business going and what are the short- and long-term steps needed to get there?
  • Be real with yourself. An independent career path isn’t for everyone.Twitter Logo Do a little soul-searching to decide whether the ups are worth the downs.

Embrace your purpose

Freelancers today are wired differently than you might think. While many people go independent to build their own career paths and take control of their financial futures, the vast majority are after it to fulfill a deeper need. Each of the creatives we interviewed in SOLO NYC expressed their passion for starting each day with a distinct purpose that is all their own.

Says Adriana Urbana, a creative chef who is pioneering a format for at-home dining in Brooklyn, “Every day I wake up wanting to work.”

Becoming an independent might mean making more money. Or, it might mean taking a pay cut in favor of more free time and flexibility. No 2 freelancers are the same in this regard, which is the beauty of owning your own career destiny. What keeps you happy, sane, financially secure, and motivated is uniquely your own. Choose the opportunities and career strategy that work for you—and don’t be afraid to revisit these choices and optimize along the way.

“What gets you out of bed in the morning?”

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Start here:

  • Identify your personal North Star. What are you most passionate about? What does your business stand for? Write it down and revisit it a few times a year.
  • What gives you purpose? How does your approach to work cater to your personal and professional preferences?
  • Check in with yourself on a regular basis to avoid burnout

Want even more insights? View the short film below, and follow AND CO’s SOLO project for future profiles on creative freelancers who are living out their dreams around the world.

Collaborate in real time on a digital whiteboard