Freelancers are (unfortunately) used to hearing questions from family and friends who don’t quite understand what they do or how it all works.

Yes, we get that working as an independent contractor can be challenging to wrap your head around. If someone has been a corporate desk jockey their whole career, they may need help to fully grasp the freelance thing. Questions naturally abound—How do you make money? How do you handle multiple clients? Do you ever get out of your PJs?

Younger folks’ career paths may seem relatively “unconventional” to older generations—but freelancing is fast becoming more the norm than the exception. According to research published by Fast Company, 48% of Gen Z workers are freelancers, with about half of working millennials also working as independent consultants in some capacity. By 2027, 86.5 million Americans will be freelancing—about half of the U.S. workforce.

While we understand some generational confusion, that doesn’t mean that the questions don’t get (sometimes very) annoying. While it may fall on us to educate about the freelance world, we can still have fun doing it.

Here are some top questions pesky family and friends will likely ask about your freelance career this holiday season—and how to respond.

1. “Do you actually make money as a freelancer?”

Cue the *eye-roll* — this one gets us every time. I mean, it’s not often you ask full-time professionals detailed questions about their salary. But believe it (or not), this is often one of the first questions lobbed when family discovers you’ve gone to the freelance side. At the risk of delving into a doctoral discourse on your financial history, you can nip this one by being concise and to the point.

How you might respond:  Yes, I’m making money—in fact, freelancers typically make more (often far more) as independent consultants than in traditional full-time jobs. Boom.

 

2. “When are you going to get a real job?”

Oof—this one rankles. Doing work consistently for several clients and getting paid for it is essentially the definition of j-o-b. While being a freelancer is not the prototypical norm, we are often better paid for our skills and experience.

How you might respond:  When this one is lobbed my way, I explain that while I don’t report to an office or work a classic 9-to-5 schedule, I am working all the time, often longer than those in more traditional careers.

 

3. “Aren’t you worried about your future?”

Ah, the future, the lovely “certain” future. Freelancers and standard FTEs alike are all susceptible to job insecurities. Layoffs are a thing—ask the high-paid folks from Twitter, Meta, and other tech behemoths who recently got pink-slipped. Most freelancers are acutely aware of the pitfalls of not having enough work to cover a slow month (or, gulp, year), which is why we cover our bases and plan for rainy days.

How you might respond:  Yes, I’m worried about my future, but guess what—you should be too, which is why you need a solid financial plan.

 

4. “So, what’s it like to not have a boss?”

Questions about freelancing can swing wildly from irritating to starry-eyed. For those frustrated by their own work leadership, imagining freelancers frolicking happily, with no upper management to contend with, is the stuff of fascination station. But it’s important to (maybe after having a weensy bit of fun with it) remind family and friends that being your own “boss” is not quite as glam as it sounds.

I share that I’m responsible for things I’d rather toss up the ladder, like accounting, insurance, payroll, and more. And the truth is everyone answers to someone. Yes, there’s no direct supervisor—but freelancers function at the mercy of their different clients. They are accountable to the people who write them checks, so it often feels like there are multiple bosses at once. Ouch. It’s not the pretty rose-colored Vaseline on the lens view that most people picture.

How you might respond:  Share that while you love being in charge of your workday and career trajectory, going it solo also comes with challenges.

 

5. “I bet you take vacations all the time, right?”

People often assume that freelancing is synonymous with jet-set trips to exotic locales. And while the ability to work anywhere is great, an actual “vacation” is one where you can actually unplug and disconnect from the digital grid—and typically requires quite a bit of advance planning.

I remind folks that there’s no PTO in the land of the freelancer. Shutting things down for a week or more involves planning ahead and oodles of communication with clients. It’s more complex than picking a cool destination, packing, and setting an out-of-office response.

How you might respond: ”While I do have the option to work from wherever, it can (somewhat ironically) be more complex to get away. True vacations require a lot of prep and planning, which means they don’t happen as often as they do in my fantasies.”

 

6. “What’s your five-year plan?”

Five years? Freelancers often don’t have the next five minutes planned. Sometimes there’s an idea of what one would like to accomplish in the next five years, while other times, it’s more about planning for next month. If you don’t have a five-year plan mapped out and color-coded, that’s perfectly fine. And even if you do but prefer not to go into detail about it, this genius response keeps the mystique.

 

How you might respond: ”While I could tell you, it would ruin the surprise.”

 

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Bottom Line

The best overarching advice for annoying questions about your freelance career? Get curious about their curiosity. Why are they asking—are they just curious? Concerned? Jealous? Both? It will help guide how much fun or seriousness you inject into your responses. So, when Uncle Larry asks when you’re going to get serious and go to law school, you can let him know that you’d love to chat about this but must check on the roast and then lament how you’ll be sitting on opposite sides of the table. Or, get a little cheeky and tell him you’ll get right on that as soon as you get his tuition check.

 

About the author.

An award-winning creator and digital health, wellness, and lifestyle content strategist—Karina writes, produces, and edits compelling content across multiple platforms—including articles, video, interactive tools, and documentary film. Her work has been featured on MSN Lifestyle, Apartment Therapy, Goop, Psycom, Yahoo News, Pregnancy & Newborn, Eat This Not That, thirdAGE, and Remedy Health Media digital properties and has spanned insight pieces on psychedelic toad medicine to forecasting the future of work to why sustainability needs to become more sustainable.

I get asked a lot about how I’ve landed in the various roles I’ve explored throughout my working life. I’ve had a lot of different jobs, and sometimes feel like I stumbled into a career just by taking leaps and trying things out. The secret to my success? A mix of luck and gumption, probably.

I’ve never really considered any of my shifts a full-on career change, preferring to think of them as shifts or evolutions into something adjacent. Perception is reality, baby, and that’s how we frame the story. Looking back over the past 15 years, here’s an outline of the various phases I’ve moved through, how the shifts played out, and the lessons learned along the way.

Before we dig in, I want to be absolutely clear that this journey came with a lot of help, a lot of privilege, and a lot of luck. None of us are islands. Every successful pivot comes with help and other people who can open doors or at least crack open a window.

 

 

PHASE 1: BROKEN OPTIMISM

Inspired by Rachel Weisz’s character in The Constant Gardener, I decided I wanted to study journalism in college. I thought I could make a difference by exposing hard truths and launching a career in investigative journalism. Throughout my college years and my internships, I realized that the industry had been shifting, and not in a way that seemed to value what I wanted to offer. Also, SPOILER ALERT, Weisz’s character dies on the job, which I maybe should have considered.

I also started noticing very legitimate anxiety issues and found myself too identified with my writing to ever feel good about submitting it on time. I suffered from crippling perfectionism, which made it hard to work on a deadline. Eventually, I decided to put that dream away, and just figure out a way to get a job in New York where I would eventually figure things out.

 

LESSONS:

• You may not major in your eventual career, but you can lay the groundwork for solid recommendations and a portfolio.
• Self-esteem and mental health issues, when unaddressed, can lead you to slowly sabotage yourself.

 

 

PHASE 2: CHAOS 

I moved to New York under the backdrop of Occupy Wall Street and the wake of the Great Recession. Unemployment rates were still high, so snagging a role fresh out of college was a challenge. I felt directionless and desperate but managed to plow forward and apply to every gig I was remotely qualified for. I tapped into Craigslist, alumni networks, every contact I had made in my various internships, parents of friends who were based in the city, and on and on we went. This is what we call planting seeds, and it can be so frustrating not to see results from the sheer volume of it all.

Within one week, I had a part-time job that paid $10/hour working as an assistant to a photographer’s agent, which I landed through a connection I made at a former internship. A few months later, I had lined up a few more gigs, including web production, copywriting, hostessing, and bartending. The hustle was very real that first year in the city. I did a lot of unpaid work and interviewed for a lot of weird gigs — thank you, Craigslist — but managed to stay afloat.

Eventually, one of the seeds I had planted sprouted, and I landed an interview at Sony as a quality assurance coordinator. Not the role of my dreams, but it was in tech and music, full-time, and at a big company. I was thrilled. I got the job, would be paid hourly, but did not get benefits which was okay because I was still on my parents’ insurance.

While I wanted to do something “more creative” long-term, I really enjoyed my team and the work I was doing. Unfortunately, lack of monetary advancement and sexism lead me to seek greener pastures. My roommate suggested a staffing agency he had worked with to help me find my way, but instead of being placed by them, I became a recruiter.

 

LESSONS:

• You can harness various skills to reach unexpected places.
• Sometimes the seeds you plant take a while to sprout, but you’ll be grateful to your past self when they do.
• Lean into every network connection you can; reach out respectfully and without expectations.
• Be gracious, listen, say thank you, and mean it.
• Sometimes a toxic environment can drive you out of a potential career path.

 

PHASE 3: STABILITY

That’s right! I finally found a salaried full-time role with benefits and all at Creative Circle. I joined the New York office as a recruiter, using my creative/tech experience as a base, and built off that with training and experience. Did my heart still long for creativity? Yes. And you know what? I got to explore my creativity after hours since I was making more money and finding stability. I took improv and storytelling classes. I took piano and voice lessons. I started therapy and worked through the self-esteem issues that sabotaged my college writing dreams.

Having those three years of stability was life-changing for me. I got on top of my health, learned about myself, and built a savings account. But something was still missing for me. I explored a range of passions that led to signing up for trainings, mentorships, and certifications so that I could do the part of recruiting I liked best, helping people. I decided I would try my hand at freelancing. I expressed my wishes to my manager, and we parted ways on excellent terms (this will be important later).

 

LESSONS:

• Financial stability and independence can be game-changers.
• Maintaining your mental health and integrity is more important.
• There are ways to part ways amicably. Maintaining professional connections can only help you. (Obviously, if your employer is manipulative and unethical, this does not apply. Burn that bridge and never look back, but make sure you have evidence of their misconduct just in case.)

 

 

PHASE 4: CALCULATED CHAOS

I took a stab at entrepreneurship, teaching yoga, reading tarot cards, and offering one-on-one mentorship and coaching. This was an ever-evolving process that launched me back into that hustle zone, albeit with a little more cushion and a little more freedom. I worked all kinds of gigs, in all kinds of environments, with all kinds of people. I designed workshops and classes, packaged offerings at events, worked with long- and short-term clients, and had the space to study and explore various areas of interest.

A lot happened during this time, but eventually, I made my way back to my home city and tried to continue what I had started. However, it became clear I couldn’t do things in the same way anymore. I started shifting, focusing more on mentorship, and allowing myself to imagine something different. I had never intended to live like this forever, and was realizing perhaps all my interests and hobbies shouldn’t become my job. It was time to pivot once more, I just didn’t know what that would look like yet.

 

LESSONS:

• Your passion could lead to a career, or it could lead to a valuable learning experience.
• You can monetize the things you love, but you can also walk away when it’s not working anymore.

 

PHASE 5: EXTERNAL CIRCUMSTANCES

After one year back in Miami, I suffered a concussion four months before the onset of the COVID-19 pandemic. This had the unfortunate effect of making the already challenging logistics of my work untenable. Teaching yoga in Miami was way harder than teaching in New York. Needing to drive, often during rush hour to teach classes made it so my dollars per hour earnings were often way below minimum wage if you include prep and travel time. Once I sustained the injury, the effort doubled as driving at night would trigger headaches and nausea, I also couldn’t look at screens for more than a few hours a day. It was a rough time.

I had to spend a lot more time resting, which was hard and made me feel helpless, but with the support of my family and then boyfriend/now husband, I made it through and realized it was time to pivot once more. In my explorations, I reached out to my old manager (the one I left on great terms with), and picked up some copywriting and admin work. I was really lucky to ride out the pandemic with a few of my mentorship clients and some supplemental income. I also moved in with and married the boyfriend. It was a hard time, but a good time.

You’ll notice this was not a full pivot, but rather a rolling with the punches kind of situation, where I picked up work when I was able and switched to meet my abilities and needs. Sometimes we don’t get to pick our pivots. We just work with what we have.

 

LESSONS:

• Control is an illusion.
• Notice your limitations, and ask for help.
• Sometimes you can’t do things the way you used to. Sometimes it’s unexpected.

 

PHASE 6: FOCUS

Staring at a new phase of life, I had some choices to make. While post-concussion symptoms lingered, they were infinitely more manageable, and I had developed methods of soothing and coping whenever they cropped up. After over a year of preparing, my husband and I were ready to embark on a four-month journey across the country. The plan was to put everything in storage and then find a home and start a family upon our return.

So what did this next pivot look like? It was a complex series of proposals, applications, freelance work, and endings that spanned almost the entirety of 2021. I knew I wanted to fully step away from the more “woo” aspects of wellness after seeing its predatory nature unravel over the course of the pandemic. (If you’re interested in learning more about that, I would start with the Conspirituality podcast). I also knew I needed to keep things simple until after our cross-country trip and make sure any big commitments and changes didn’t start until 2022. I knew I wanted to home in on working towards practical solutions that are more rooted in community than individualism. That led to the following:

I had picked up more freelance work doing some internal sourcing in addition to writing.

I applied for graduate-level social work programs and enrolled for a January 2022 start. (I chose the most flexible/affordable program available so I wouldn’t have to take out loans and could continue working.)

I stopped taking new coaching clients, eventually saying goodbye to my last mentee by the end of January 2022.

I pitched a version of my current role, and a new department was eventually born.

In many ways, the various twists and turns have led me here and I had to use that to my advantage. The number one question I had to answer was why am I the best person for this job. What are the skills and experience only I can bring to the table? Boom, pivot.

 

LESSONS:

• Timing might not be everything, but it’s a lot.
• Having colleagues in your corner makes a big difference.
• So does knowing your worth.

 

About the author. 

Alessandra is your friendly neighborhood writer, coach, and facilitator with a varied history of experience from digital agencies and corporations to yoga studios and gyms. Her expertise and interests range from fitness and wellness to self-care and personal development to intersectionality and justice to science and creative cultivation. She has worked on and off with Creative Circle since 2014, originally as an NYC recruiter, later as an internal sourcer, and currently as a community wellness and culture specialist as well as a contributing writer for this here blog. You can find up-to-date offerings or sign up for her newsletter at alessandracalderin.com.

 

I’ve lived in Bed-Stuy for over eight years and I am still discovering its many offerings. The neighborhood, which birthed artistic legends such as Lena Horne, Harry Nilsson, and Jay-Z, boasts a rich cultural legacy, and is still chock-full of artistic inspiration today. It’s also the perfect neighborhood to explore on foot, as the route from Bed-Stuy to Fort Green can be traveled along quiet, tree-lined residential streets, as opposed to busy, traffic-filled avenues.

Do The Right Thing Way

Along Stuyvesant Avenue between Quincy and Lexington is Do The Right Thing Way, the filming location of Spike Lee’s 1989 masterpiece. While Sal’s Pizzeria is no longer standing, the film’s “Bed-Stuy Do Or Die” mural has been recreated at the corner of Stuyvesant and Lexington, along with another mural, on the opposite corner, commemorating the film and its beloved characters. A great photo op for any fan of the film.

Stuyvesant Heights Historic District

This residential district is a refreshing addition to any walk. It boasts a number of quiet, tree-lined streets, on which sit gorgeous, historic red brick and brownstone row houses. The icing on the cake is the southern section of Stuyvesant Avenue, which contains the final group of rowhouses to be built in the early twentieth century. These breathtaking, neoclassical structures are particularly beautiful in the fall and spring, when their architecture can be glimpsed among the trees shedding their leaves or bursting into bloom. There are also a number of freestanding mansions in this area, including the Otto Seidenberger House, which was used as a set in the HBO series Boardwalk Empire.

Tompkins Avenue

After leaving Stuyvesant Avenue, walk west along the pleasant, residential streets to Tompkins Avenue, which is one of Bed-Stuy’s main thoroughfares, filled with restaurants, locally-owned shops and bars, and plenty of spots to sit with a coffee and people watch. On weekends during the summer months, Tompkins is closed to traffic, and pedestrians walk, shop, and mingle with local artisans who set up booths along the route.

Dear Friend Books

Dear Friend Books is a beautifully designed, meticulously curated shop on Tompkins Avenue that specializes in vintage books, magazines, and ephemera. They serve coffee and other non-alcoholic beverages (I am told they soon hope to have a liquor license) that can be enjoyed while browsing the shelves or sitting under an umbrella in their backyard patio space. I’ve picked up several art and design books here, and will definitely be going back for more.

The Word is Change

If you’re looking for a broader, more affordable selection of reading material, head on down the street to The Word is Change, which sells both used and new books, with a special focus on social justice and history. They also buy books, which can be exchanged for cash or store credit.

Herbert Von King Park

Named for community leader Herbert Von King, this beautiful green space serves as a kind of centerpiece to the surrounding neighborhood, à la Washington Square or Tompkins Square in Manhattan. On weekends you can walk along its meandering paths and see friends picnicking, families hosting cookouts, and dogs chasing frisbees. It also has a decent lawn area, which is perfect for spreading a blanket and reading a book. Near the center of the park is an amphitheater and cultural center, which hosts classes and programs for the community.

Harold and Maude

Harold and Maude is one of the most special vintage stores I’ve been to in Brooklyn. It carries a nice variety of styles at affordable prices, as well as a selection of antique records, jewelry, and tchotchkes. The only downside is its miniscule size, which can only comfortably accommodate around three people at a time. I recommend going on a weekday to avoid the influx of fashion-hungry hipsters.

Mr. Friendly

Walk two blocks west from Von King Park and dip into Mr. Friendly Pet Supply. Even if you don’t have a furry friend, this holistic pet store is a treat for anyone with a taste for design. Their branding is clean, playful, and yes, friendly. They make all of their products onsite in their studio, and the result is a collection of unique and affordable treats, toys, and branded merch.

Bedford Avenue

Now it’s time to head to a more bustling area: Bedford Avenue, near Bed-Stuy’s western edge. Full of bars, coffee shops, and restaurants, this is a prime location if you are looking for a night out in the neighborhood.

First stop is Do Or Dive which, as its name suggests, is a no-frills bar with cheap beer, frozen cocktails, and a cash-operated jukebox. Owned by the same people as two other favorite Brooklyn dives (Luckydog and Skinny Dennis in Williamsburg), this is a great spot to come to with friends for a day drink or six, particularly in the warmer months, when the giant outdoor space is packed with energetic Brooklynites.

When the weather gets colder, head next door to the polar-opposite Dynaco, which, with its dark, cabin-like atmosphere and open fire pit, feels like a cozy wooden lodge, perfect for a glass of wine or a hot toddy.

If you’re not in the drinking mood, go one more down to Playground Coffee, adjacent to which is The Annex, a small bookshop which specializes in works by POC and Queer writers and artists. Then take your coffee and purchases across the street and look at the famous, two-story Biggie Smalls Mural, at the corner of Bedford and Quincy.

On the other hand, if you’re really looking for a party, head one block west to Franklin Avenue and see what’s going on at C’mon Everybody, a popular LGBT nightspot known for its dance parties, art shows, and live music. (Chances are you will see some of the same people from the previous spots.)

Whether you’re a weekend visitor or eight-year resident, Bed-Stuy is a treat for anyone needing creative inspiration. Whether it’s architecture, music, film, antiques, or nightlife, the neighborhood is filled with an array of places to explore and gather artistic fuel. Or, if what you need is to clear your head, the neighborhood’s streets and parks are the perfect location for a picturesque walk or a peaceful rest with a book.

Additional recommendations:

Marian’s
Neighborhood jazz bar with nightly music, comedy and more.

Chez Oskar
Tasty French bistro with a cozy interior and craft cocktails.

LunÀtico
Fancy cocktails, delicious small plates, and nightly music make this a must for any jazz lover.

The Billie Holiday Theater
One of the nation’s premier Black playhouses, this theater’s alumni includes performers such as Debbie Allen and Samuel L. Jackson.

Burly Coffee / Better Read Than Dead Books
Cozy, quiet coffee shop combined with an impressive selection of used books.

Lovers Rock
Fun, unique bar offering tropical drinks, reggae music, and dancing.

Sistas’ Place
Cozy, relaxed spot for jazz, poetry, and art.

About the author. 

Daniel Nolen is a writer, designer, and performer in New York City. He has written about design, music, film, and theater, and can be found regularly and happily taking in concerts, shows, and exhibitions around the city. He also co-hosts the weekly comedy/variety show Cast Offs, every Monday at 8pm at Club Cumming in the East Village.

 

 

 

Freelancing is hard. In addition to finding work, chasing down invoices, and managing sudden changes in income, freelancing typically comes without automatic access to the benefits that full-time employees receive.

Let’s take a look at the benefits freelancers have to make up for with their own time, money, and resourcefulness, and go over our options.

Disclaimer: I do not advise or endorse any of these options. I am not qualified to give health, financial, or legal advice. I also don’t endorse any of the organizations mentioned by name. They are just examples. This is just a simple informational layout to get you started.

Health Insurance

Because the United States is one of the only wealthy nations without single-payer healthcare, most Americans rely on their employers for health insurance. In fact, in a study of the healthcare systems of the 11 wealthiest nations, the United States came in dead last… by a lot. A big reason for this is a lack of equitable access and the fact that navigating the wild world of insurance policies can feel like wading through a Boschian hellscape.

Having a solid insurance provider can mean the difference between saving for retirement and bankruptcy, if not life and death. So what’s a freelancer to do?

The absolute easiest way to have health insurance is to have a spouse or domestic partner with a workplace plan. Doesn’t scream “independence,” but if you’re in a stable relationship and it works for you, it makes life a lot easier.

If you’re 26 or under, you can also remain on your parents’ insurance under the Affordable Care Act. Again, not for everyone, especially if you can’t rely on your parents, but another easier option if it’s available to you.

You can also qualify for Medicaid if you meet the Modified Adjusted Gross Income (MAGI) requirements or other need-based requirements or Medicare if you are 65+ years old.

Beyond that, it’s a wild world of marketplaces. You can use the public marketplace through the Affordable Care Act, private marketplaces through individual insurers, or a health sharing network which usually is religious in nature (but there might be a secular one out there).

You can also use something like Oscar Insurance, which is a private insurance company that offers more affordable options, or Freelancers Union which is an organizational network of freelancers that offers a range of benefits with the cost of membership. There’s also COBRA if you’re leaving a full-time role to freelance and want to continue your current plan (although it can be pretty pricey).

Creative Circle freelancers also have access to a range of plans through a vendor called Benefits in a Card (BIC) throughout assignments. The details are emailed to every CC freelancer upon accepting an assignment.

All that said, plenty of people opt out of insurance coverage and pay out of pocket whenever they need something. That strategy is obviously dicey though, especially in the event of an unanticipated emergency.

TL;DR — here are some of your top options:

• Get married or domestic partnered to someone with insurance.
• Stay on your parents’ insurance if you can.
• Check if you qualify for Medicare or Medicaid.
• Shop for public insurance at healthcare.gov.
• Check out insurance options through an organization like Freelancers Union.
• Shop for private insurance or try a consumer-focused alternative like Oscar.
• If you’ve left a full-time role, use COBRA to extend your benefits.
• Look into a health-sharing network.
• If you’re freelancing for Creative Circle, you’ll have access to plans through Benefits in a Card.
• Go without and use out-of-pocket payment plans and discounts if anything comes up.

For a more in-depth look at healthcare options for freelancers, check out this nifty blog post.

Indemnity + Liability Insurance

Depending on what you do, you may need some kind of professional liability and/or indemnity insurance. The purpose of liability and indemnity insurance is to protect you if someone tries to sue you, whether you make an error or they’re injured in your office space. There’s a lot of debate as to whether you really need it, but it all comes down to what you do and what your risk tolerance is. Most folks arguing for liability insurance are trying to sell it to you, but that doesn’t necessarily mean they’re wrong. Even for freelancers with solid engagement agreements and disclaimers, a signature may not protect you everywhere.

For more info, check out Freelancers Union.

More Insurance?

There’s also media insurance, life insurance, disability insurance, and business interruption insurance. What?? But if you want to be covered for every kind of scenario, I guess you have options. In researching for this piece I came across this article about a freelance journalist who got sued. Luckily the publication he wrote for defended him, but if you’re writing about touchy subjects and people who might take offense to your words, media insurance may be something to consider.

Check out more solid advice here. And, of course, you can consult with a lawyer, accountant, or other professional to see what your specific needs might be.

Sick Pay, Paid Time Off, + Unemployment

The great part of freelancing is you can choose your time off. The downside, of course, is you don’t get paid for it. While some sick pay options were granted during peak COVID in the form of tax breaks, that seems to be over permanently. Ditto for unemployment benefits which were offered to a certain extent under the CARES Act as Pandemic Unemployment Assistance, in addition to PPP loans which played a similar role in replacing lost wages. However, now that those funds and programs are running out, we’ll probably land right where we started.

Some states do have sick leave laws, so you’ll have to check to see if your location qualifies you for any sort of compensation (which Creative Circle does apply to its candidates in those states), but if you’re contracting or working with your own private clients, it likely won’t apply to you either way.

The solution for the average freelancer is to make sure your rates are high enough to cover yourself when you fall ill or want to take a vacation. However, places like Freelancer’s Union now offer plans you can pay into to receive paid leave benefits.

Parental Leave

When it comes to parental leave, freelancers will have to make hard choices about how they want to manage their business. Reducing clients, ending projects, and taking time off to care for a little one without even a partial paycheck to balance the load can be stressful and intimidating. Unfortunately, the United States has no mandated protections in place for expecting contractors, and few if any companies offer any sort of benefits to freelancers or part-time employees. (They aren’t even required to pay their full-time employees on paternity leave, just guarantee they will have a job upon their return after 12 weeks. And that’s just for the birthing parent.) All we can do is our best to plan and save for any intended leave of absence.

Tax Withholdings

Odds are when you’re freelancing, you’ll get a 1099-NEC or 1099-MISC (this differentiation is new) at the end of the year instead of a W-2 which is what someone employed full-time would get. (Why are tax forms so complicated??) That means you don’t automatically pay your taxes with each paycheck. My first freelancing gig in 2012 had me on a 1099 and I, a fresh out of college financially illiterate noob had no idea I was supposed to save some of those paychecks for tax time. I got slapped with a hefty bill and was very freaked out.

We live, we learn, and now I meticulously calculate every little thing. I keep a running spreadsheet that tracks my income, business expenses by category, quarterly estimated tax payments, and more. Some folks with larger businesses might prefer a more automated system like QuickBooks; others may hire their own bookkeeper. It all depends on how much you make and how much time you have. There are tons of financial planners and accountants that can help you make the best decision for your business if you are like me and didn’t get the tax 101 in your younger years.

Here’s a more in-depth look from TurboTax. But remember, there are FREE sources for filing taxes online if you want to do this yourself and not pay for TurboTax. There is an episode of Hasan Minaj’s Patriot Act that dives deep into TurboTax.

Note: If you’re freelancing for Creative Circle, you’ll actually receive a W-2, so as long as you fill in the right deductions, you won’t have to worry about withholdings while on assignment.

Retirement Savings

Another arena where freelancers are on their own is when it comes to retirement savings. While some salaried roles may offer a pension (which is unfortunately way less common for non-government jobs these days) or a 401K plan (hopefully one they match), a freelancer must save on their own. The most common options would be a Traditional or Roth IRA, and there are also some folks who can put together their own 401K plan if they make enough. Consulting with a financial professional would be a good option if you don’t know where to start. Many institutions like Fidelity also offer assistance to prospective account holders.

Wellness + Transportation

While this one is more of a perk, it’s important to consider how much money you’re spending in these areas. Some wellness costs like gym memberships can be offset through health plans. Meanwhile, transportation should either be factored into your rates or negotiated into a contract if you have to travel onsite for meetings and projects, especially with rising gas prices.

Are you a freelancer? Do you have more tips or questions about navigating the wild world of our unhinged and unsupported reality? I’d love to hear from you! Feel free to email me: acalderin@creativcircle.com

 

About the author. 
Alessandra is your friendly neighborhood writer, coach, and facilitator with a varied history of experience from digital agencies and corporations to yoga studios and gyms. Her expertise and interests range from fitness and wellness to self-care and personal development to intersectionality and justice to science and creative cultivation. She has worked on and off with Creative Circle since 2014, originally as an NYC recruiter, later as an internal sourcer, and currently as a community wellness and culture specialist as well as a contributing writer for this here blog. You can find up-to-date offerings or sign up for her newsletter at alessandracalderin.com.