Thoughts & Perspectives from A Reluctant Freelancer, Part 1
- Erin Ratliff
- Feb 9, 2024
- 10 min read
Updated: Jun 2
When life hands you lemons, go freelance.
Like so many, I fell into freelancing accidentally and thus, quite reluctantly. I had actually had fantasized about the freedom and flexibility of being self-employed for years but fought that idea tooth and nail -- clinging to the familiarity and stability of traditional 9-5 employment.
I believe everything in life happens in the right timing and in the right way, but more often than not it's going to be what you planned on. It's going to happen in the way you least expect it.
For me, it was unexpectedly losing my job due to Hurricane Helene. After hundreds of applications and dozens of interviews, I still had no offers at the 8-month mark. As a single mom who was already financially struggling to make ends meet, this was a devastating and shocking blow, full of many sleepless nights and tear-filled days. My unemployment benefits ended and I had no choice but to dive in.
This was actually not the first time I had found myself suddenly unemployed and considering freelancing seriously. In the previous year I was let go of my comfy marketing agency role just before the holidays. Thankfully I was able to find a job within a few months, built up more fantastic resume experience and portfolio work, but then lost it again at Helene. Another devastating blow. The universe really kept giving signs that I refused to see.
I didn't just want to have an income, I NEEDED an income for survival. I was thrown/thrusted into unemployment amidst a terrible job market and even after applying to dozens of jobs per week, I felt stuck and scared. Finally going on 8 months without a paycheck I had no choice but to figure out how to make money, and quickly.
What they say is true: "Necessity is the mother of Invention, and Desperation is the father of Brilliance.” And when there is a will, there's a way!
I was kicked out of the nest and from there it was sink or swim. I had to learn the ropes of self-employment qucikly I had to learn to not only use my skills, but also to sell myself. This post is just the beginning of my story!
I didn't choose the Freelance life, the Freelance life chose me.
First, what is a Freelancer?
Freelancers, or 1099 workers, are small business owners who operate independently and set their own hours, terms and value.
Other common names for freelancers include...
Independent Contractor (IC): A self-employed individual who provides services to a business or individual under a contract. They have control over where, how and when they work and may work for multiple clients simultaneously.
Creative/Creator: Individual (writer, marketer, designer, photographer, software engineer, artist) who sells creative skills and outcomes
Coach, Consultant or Advisor: An individual with specialized knowledge and specific domain expertise, who sells their perspective and advice and/or solves problems
Fractional Officer: Synonymous with "part time"; often used in conjunction with executive leadership roles like CMO
Solopreneur: An entrepreneur who building a business fully on their own.
Note: Freelancers may also resonate with the terms Influencer, Founder, or Thought Leader. Every Freelancer is different! It's also ok if you don't want to call yourself a Freelancer at all, thus avoiding any stigmas out there or the pressure to be or do things a certain way.
At the end of the day, your job title doesn't really matter. People just want to hear about how passionate you are about the services you provide! It's much much more important to clearly share WHO you help and the pain/problem you help them resolve.
Example: Instead of "I am a _____" try... "I help____ escape/avoid/relieve/solve ______ to create ______in their lives and work."
What a Freelancer is Not:
An Employee - an individual who is hired by an organization or business to perform specific tasks or roles in exchange for wages or salary.
An Agency: A team of people selling creative skills / outcomes
"out of work," "broke," "lazy," "hard to work with" or "unemployable"
Note for employers: If you’re looking for someone to work 40 hours a week, attend team meetings and trainings, complete yearly performance evaluations, and represent your company at all hours, hire an employee, not a contractor.
Need more clarification?
You might be a Freelancer if...
you pay all of your own taxes, SSI, health insurance and the like
you make more than $600 with a client, and they are legally required to send a 1099 in January.
You might be an Employee if...
you completed a W2 form from the IRS upon hiring
someone else is responsible for withholding employment taxes, SSI, and any other taxes
Why is this important?
A Freelancer (IC) is a legal classification that impacts an individual's taxes and employment status with the federal government, state government, and the IRS and State Treasury.
It's also crucial for businesses to ensure compliance with labor laws and tax regulations. Misclassification can lead to legal and financial consequences, including fines, penalties, and potential lawsuits.
In other words, it's not something to take lightly.
The IRS considers three main categories of evidence to differentiate between an employee and an independent contractor: Behavioral Control, Financial Control, and the Type of Relationship.
What goes into Freelancing?
Being a freelancer is SO much more than just executing professional quality deliverables, outcomes and waiting for the next project or assignment. There is so much that goes on behind the scenes.
A freelance business is like an iceberg – an overwhelming amount of it sits below the surface, unseen to the masses.
Why? Because you're a team of 1 wearing MANY hats every single day. You’re the Director, Manager, Coordinator, Specialist and Assistant. You're the...
sales team
marketing team
finance team
operations team
legal team
IT team
HR team
admin/support team
You're every role and every department, from top to bottom. All in one human body. No pressure...
In 2022, 60 million Americans performed some kind of freelance work, which represents an increase of three percentage points from the prior year.
Debunking The Myths of Freelancing
Myth: Freelancers have no job security
Truth: Technically speaking, nobody has job security. Anyone can be let go or lose their job at any time, for any reason. With freelancing at least you have a significant heads-up if the business isn't making money, giving you a real chance to pivot or turn things around.
Myth: Freelancing is chilled and relaxed.
Truth: If freelancing was truly easy, then everyone would be doing it. Social media tends to glamorize entrepreneurship. It doesn't tell you the full story, only curated highlights. Sure, you can choose your own hours, but the work also demands you always be "on" and that you wear many (ALL) hats.
Unless you're on vacation, truly being off the clock as a freelancer is rare. While intensive, focused client work (PR outreach, content creation etc) may only take 4 or 5 hours of the day, your mind is occupied for much longer in research or ideation. There's also the unbillable time where you're drafting emails/proposals or in networking or prospecting. And don't forget the time needed to market your own biz or develop your personal brand.
Some weeks will be more packed than others. Some days are busier than others. Your freelance schedule is yours to create. Whether you want to work 2 hours or 20 hours, that’s up to you based on your individual financial, personal and professional goals.
Like everything in business and life, it's about tradeoffs. There's happiness and fulfillment (AND plenty of challenges) to be found no matter which route you go.
Myth: Freelancing is not a "Real" Job
Truth: Freelancing is 100% a real, legitimate job requiring real work and making real money. Millions of high-achieving people like myself wouldn't be doing it if it wasn't!
Myth: You can make six six-figure income as a freelancer
Truth: While hitting 6 figures is possible as a freelancer, it is also somewhat rare. That is a huge achievement and career win. But let's also celebrate all the newbies and underdogs who:
were brave enough to take the leap and give something a go that some only think about
just secured their first client
are building a way of working in order to spend more time seeing the world or their loved ones
just make enough to feel slightly more "comfortable"
are choosing to freelance to improve their mental health and wellbeing.
It's important to avoid comparison to other's progress or success. Freelancing is not a competition. The benchmark of success you set for yourself is the most important one of all. If you’re covering your basics while putting some savings away and enjoying your life with flexibility and freedom, then you're doing better than most. In fact, you're blessed beyond measure.
Myth: Being your own boss is the best life choice.
Truth: This all depends on how much self-discipline and focus you have. While its great to have the opportunity to decide who I work with, how often I work and when, sometimes it can be helpful to have someone else hold you accountable or give you a kick in the butt that you need. This is where you can have your own personal cheerleaders come in (perhaps a partner, friend or family member or someone from your mastermind)
Myth: Everyone should try freelancing.
Truth: Not everyone WANTS to go out on their own. Not everyone has the same values, goals, needs or motivators. Your path is worthy, no matter what. Whether you choose entrepreneurship, freelance, or an in-house career, what matters most is that it aligns with what YOU want out of life. Neither path is harder/easier/better/worse – they're just different. For some, freelancing is a temporary solution. For some it's a longterm commitment, a life by design.
Myth: "Just quit your job and start freelancing"
Truth: That's really bad advice. It's not as easy as point A to point B. It can take years or even decades to reach the point where you feel comfortable making the move to full-time. In this time you're...
testing and honing niches
learning the market
creating connections
growing your savings
planning finances
developing your craft
securing business operations
putting organizational systems in place
automating systems
building confidence
developing a portfolio
honing your personal and professional brand
releasing limiting beliefs
healing your nervous system
building your capacity
That's a TON of behind-the-scenes work, and it can seem to go at a snail's pace, especially if you're neurodivergent, marginalized, or have complex life circumstances. Go slow and do what you can part-time while you still have a stable income.
Remember, you can't rush genius. You can't build trust and experience overnight.
So, what makes a great freelancer?
A great freelancer is a reliable and dependable point-person for your business, helping you optimize productivity, streamline processes, and achieve greater success in your endeavors.
They...
bring valuable expertise, efficiency, and flexibility to your projects.
deliver high-quality work on time and within budget, helping you meet your goals and deadlines effectively.
offer fresh perspectives, innovative solutions and specialized skills for better results
offer their full attention, asking good questions and making tailored suggestions
do what they say they're going to do... underpromising but overdelivering
speak about their own expertise and give guiding advice
take charge - adjusting and pivoting approaches as needed
charge per project so that the focus is more on the outcome vs hours spent
Building Resilience
If you're a fellow freelancer at the beginning of your journey and you're confused, nervous and worried, please know that's normal.
It takes time (months!) to align and find your stride. It's a process to understand how much more there is to do other than just your on-paper skillset that you're used to.
At the end of the day, being SELF-employed is a lot more empowering than being UN-employed. But it's not without it's challenges and risks.
When you've spent your whole life working to building someone else's dream, and then suddenly asked to build your own it's going to feel uncomfortable. Terrifying, even. But also terrifyingly beautiful.
If you're like me and you’ve had some side hustles brewing behind the scenes for a while now, I see you. If you're like me and you've kept your talents, skills and ideas mostly hidden in the backseat, I see you. If you're like me and you've always felt too afraid and insecure to go all in, I see you.n
When we work hard for something we love it's called passion. When we work hard for something we don't love, we call it stress.
Wrapping It Up
I am still incredibly new to freelance, I have TONS to learn and a good few mental barriers to overcome, even afterall these years of avoidance and resistance. I know this is going to continue to take a lot of self-discovery, grit and patience, I know there will be losses and hiccups, but with each one I will become stronger and wiser.
Freelancing is not for the faint of heart. It is a journey filled with ups and downs, challenges and triumphs, where each day presents a unique opportunity for growth and self-discovery. This path requires resilience in the face of uncertainty, determination in times of doubt, and perseverance amidst setbacks.
Yet, amidst the challenges lie moments of profound reward and fulfillment. You get the flexibility and freedom in
controlling your time
being your own boss
charting your own course
shaping your destiny
pursuing your passions
defining success on your terms
You also get the thrill of seeing your hard work come to life, knowing that every success is a testament to your dedication and unique talents. While freelancing is not a one-size-fits-all lifestyle, it may be especially beneficial for creatives, visionaries, empaths and other energy-sensitive souls. It means 100% ownership and control, which is deeply empowering.
At the end of the day, Freelancing isn't just a career. It's a calling. A journey of endless possibilities, and a rollercoaster of emotions and experiences. But isn't this what makes life work living? Every day is a different adventure and you're giving it your all.
Cheers to the gig economy, shameless self promotion and trying new things imperfectly but bravely, cringey but courageously!
Freelancing is Life in Color.
Want to work with a trusted freelancer who embodies integrity, heart and soul? I offer a variety of marketing services to support healers, coaches, and wellness practitioners in our collective mission to serve the greater good? I look forward to connecting soon!
Erin Ratliff is a holistic business coach and marketing strategist specializing in organic growth + visibility for heart-led soul-preneurs and energy-sensitive self-starters seeking personal and planetary healing.
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