The Art of Freelancing Like a Boss, According to the Folks Who Do It

Jeffrey Hazelwood/CNET

Jamie Brindle has been freelancing for 16 years and is on a mission to “demystify” the freelance world. In 2020, amid a shaky job market and widespread rejection of corporate hustle culture, he started helping beginner freelancers become their own bosses. 

The expansion of remote work, advances in AI and the growth of influencer platforms have all led to a kind of self-employment boom. As Gen Zers and millennials find new ways to upgrade their skills in a flexible work setting, the traditional 9-to-5 has become less inviting — and less reliable. 

“People are finally coming over to my side and agreeing that building something for yourself is the safe option now,” Brindle told me.

Financial instability is not a minor factor. Plenty of full-time professionals rely on part-time side hustles and gig work to compensate for stagnant wages and the high cost of living. Working as an independent contractor can feel like a life raft during tough economic times. Whether by choice or necessity, millions of people are turning to freelancing as a long-term business strategy.  

“If you lose a client, you’re inconvenienced,” said Brindle. “If you lose your job, you’re unemployed.” 

The term “freelancer” often brings to mind ride-share drivers or creators working from home. Yet the self-employed span nearly every industry and skill level, from entry-level musicians to highly specialized brand consultants. In my research, I discovered a world of artists, technicians, developers, strategists, writers, coaches and tradespeople, each carving their own path. 

In 2027, freelancers are projected to make up more than half the US workforce, according to Statista. A majority freelance workforce has numerous political and economic implications for future generations. What does a country of nearly 90 million independent contractors look like? 

Better yet, should you follow the trend? Whether you’ve recently lost your job or you’re following your passion, this article focuses on tips to get started building your own business. Shaped by real-life insights from seasoned freelancers, this practical guide can help you thrive in this expanding work model. 

How to move from full-time employment to freelance work

Freelancing is not always a choice. If you’ve recently been laid off or left your job out of necessity, you won’t necessarily have the luxury to plan for self-employment. But in today’s competitive job market, setting up your own gig could be the easiest way to guarantee some income. 

One of the biggest hurdles is getting started. First, identify your strengths and narrow in on what you’re offering. Then tell everyone you’re available for work. 

“If you create a persona for yourself, market yourself and your business, and create that reputation, that’s what eventually will bring people to you,” said Jeannette Smith, a freelance content writer and editor. Over the years, Smith has cultivated an impressive following, with 11,000 connections on LinkedIn.  

When making the leap from a conventional employee to an independent contractor, don’t wipe your slate clean. Use the experience and connections you’ve built over the years to devise a business plan and reach out to prospective clients. 

“Everything that you’ve done in your 9-to-5 is a launch pad for your freelance work, your network, your skills,” said Tia Meyers, CEO and founder of Freelancing Females, the world’s largest community of women in the freelancing field. 

If you need guidance, the Freelancers Union, a nonprofit with over 500,000 members, can provide advocacy, education and access to benefits. Executive director Rafael Espinal said the organization can connect you to fellow freelancers and provide assistance for everything from creating contracts to setting rates. 

1️⃣ Understand the business

If you’re committing to freelance work full time, you might need to formalize your business by registering with the state. Setting up a separate legal structure will give you liability protection, tax flexibility and the ability to secure loans. In Smith’s case, she created an LLC (a limited liability corporation) that allowed her to open a business bank account and keep her personal and business finances separate.  

Alternatively, anyone who is freelancing for occasional side income can be classified as a sole proprietorship. If you don’t want to incorporate or form a legal entity to run your business right away, you’ll report your income on your personal tax return. “Just be aware that as a 1099 employee (freelancer), no taxes are being withheld,” said Smith. “It is your responsibility to estimate your taxes due and pay them quarterly.” 

Ultimately, how you decide to structure your business entity depends on your goals as a freelancer and what legal and tax benefits you’re looking for. 

2️⃣ Build your reputation

A freelance business doesn’t grow magically. Once you begin taking on projects, it takes time to find your footing. Depending on the industry and your persistence, Meyers told me to expect anywhere from three months to 12 months to get consistent income and inquiries from clients. 

To build your reputation, Brindle recommends boosting your visibility on the professional networking platform LinkedIn, which he calls a “24-hour business conference.” But don’t treat the site like a portfolio or an online resume. Instead, use social media for discussion and commentary, where you can make ongoing contributions and maintain engagement. 

Brindle said that sharing posts about what your clients find valuable will favor the algorithm, which is designed to keep users on the platform as long as possible. 

3️⃣ Find your network

No one will know you’re looking for work unless you tell them. “Go to your past co-workers, send notes to friends, find a collective of people,” said Meyer-Grado. Communities like Freelancing Females, the Freelancers Union and local job boards advertise openings, help you collaborate on work and share client bases.

Creating a profile on talent marketplaces like Fiverr and Upwork can also do some of the lifting. According to Nikhil Purwaha, senior director of project management at Upwork, the site has thousands of job posts for freelancers across more than 125 categories, from marketing to software development to customer service. 

“We recommend creating a profile that highlights your core strengths, then browsing open projects that match your background,” Purwaha told me in an email. “Clients are often more interested in outcomes than credentials, and many are open to giving newer freelancers a shot if they show commitment, skill and professionalism.”

4️⃣ Grow your client base

To generate a loyal clientele, your outreach should be ongoing and diverse, ranging from in-person referrals and professional associations to smaller contract agencies. Once you start completing assignments and proving your reliability, clients are likely to come back to you. 

“The trust factor is the most important thing to build,” said Smith. “If clients like you, they will eventually trust you. And people tend to only buy from people they trust.”  

Though Fiverr and Upwork can help you get started, many independent contractors don’t recommend relying on them as the foundation of your business. Sites like these have “pay to play” elements or take a percentage of each transaction as commission. As a result, online gig-work marketplaces are often saturated with low-paying clientele. “They can create a race-to-the-bottom mentality, where freelancers are outbidding each other to secure work,” said Espinal. 

According to Brindle, the majority of your clients should come from your own networking and promotion, and only 10-15% from freelancer platforms. 

5️⃣ Market your niche 

Marketing involves educating prospective clients about your unique service and demonstrating your brand’s niche — a way of planting the flag as a category leader. “If a freelancer comes to me and says, ‘I don’t know how to get leads,’ 99.9% of the time it’s because they don’t have a niche,” Brindle said.  

For example, if you’re trying to generate clients as a personal fitness trainer, you’ll stand out if you specialize in something more exclusive, like helping executive women over 50 reach their strength-training goals. “Specificity is your ally,” he said. 

Once you’ve found your niche, focus on the deliverables, not the skill itself. What will the results be? What should your clients expect? What problem will you solve? Translate everything to the language of ROI to guarantee a solid return on investment, said Brindle. 

6️⃣ Determine your price

Before you set a price for your services, create a budget sheet of your business costs and work backwards. Independent contractors should put aside 40% of their take-home earnings to cover taxes and professional expenses, according to Espinal. 

“Consult with other freelancers in your industry and see what they charge,” said Smith. Then figure out your “happy price” by considering all the project details — length, time commitment, resource costs — to set a figure that feels fair for the value you’re offering. Though you might not have a set price for your services out of the gate, have a goal of what you’d like to be charging in a year or two. 

Ideally, according to Brindle, you’re pricing in a way where you could technically subcontract every job — i.e., hiring another freelancer to do the work — and still meet your annual revenue goals. Though a lot of freelancers advertise hourly rates, consider charging based on the project or the solution you’re offering, not the time it takes. Brindle says not to allow the client to set a ballpark figure. “You’re the expert, so you should be the one to present a budget to them,” Brindle said. 

The benefits of freelance work 

Becoming a business owner comes with different responsibilities, new types of management and increased flexibility. While you might start off working more hours than you had in the past, you’ll eventually familiarize yourself with pacing, tracking your hours and working when you’re most productive. You also aren’t limited by an income ceiling, so you can always make more money by taking on more projects. 

“The beauty of freelancing is your choice to work when you want, and to work with the clients you actually want to work with,” said Meyers. Whereas traditional employment locks you into the same focus area, freelancing allows you to take your skills to the next level or build something unique based on what you love to do. 

In today’s uncertain job market, being an independent contractor can give you increased freedom, according to Espinal. “In a traditional 9-to-5, you don’t have control over whether or not you go to work the next day. You have an employer who makes that decision for you,” he said. 

Top advantages to freelance work: 

☑️ Set your own schedule 

☑️ Choose your own clients 

☑️ No salary ceiling  

☑️ Flexibility to pivot 

The downside of freelance work 

Not everyone is comfortable with marketing their business or managing their time and finances. As a freelancer, you’ll have to be willing to sell your services and get used to keeping receipts for expenses, paying quarterly taxes and reconciling your finances monthly. “I recommend getting a bookkeeper if you can, because there are just so many rules that change every single year,” said Meyers. If you can’t afford to hire someone, try different platforms or accounting software such as QuickBooks and HoneyBook. 

One major disadvantage to freelance work is the lack of benefits. You won’t get paid time off, a retirement account match, short-term disability, health insurance or anything else that typically comes with an employment compensation package.  

You’ll also need to be prepared to give up a steady paycheck and get used to a more erratic income stream. “Payments from clients aren’t always prompt, and sometimes you have to chase them down,” said Smith. In some cases, clients could refuse to pay entirely, which makes it even more important to have a written agreement when taking on projects. According to Espinal, around 75% of freelancers accept work without a contract, leaving them vulnerable to noncompliant clients. 

If you go into freelance work to fulfill your passion on a full-time basis, be careful you’re not living and breathing work. An otherwise fun hobby, like baking, could become particularly grueling if you’re trying to transform your personal kitchen into a cookie factory. Staying motivated requires being cognizant of work-life balance to avoid burnout. 

Main disadvantages of freelance work: 

☑️ Inconsistent payments from clients

☑️ No included insurance or retirement benefits

☑️ Ongoing expenses and taxes

☑️ Fatigue from not setting boundaries 

Final tips for new freelancers 

➡ Be bold

When starting out, you’ll face a lot of rejection and ghosting. “But you have to keep believing that the next opportunity is going to be the big break,” said Smith. Don’t be ashamed to market your business however you need to, she added. 

Remember that a lot of your clients will hire you not only because of your skills, but also your character. “Don’t be afraid to share your personality,” said Meyers. 

➡ Get a website

A business website shows off your portfolio and is great for search results. It also demonstrates that you’re human, Smith told me. If you don’t have a website, make sure you have some type of web presence (substack, landing page, social media), so clients can see your work and contact you easily. 

Once you have a web presence, don’t force your clients to scroll through multiple pages to know what you’re selling. Meyers recommends creating clear packages and service offerings. 

➡ Prepare the financials 

First, prioritize building up an emergency fund to cover at least six months of expenses in case of unexpected circumstances. Factor in all your business overhead expenses ahead of time: software, equipment, gas, meals. Study the tax rules to know exactly what you can claim as a deduction. 

You’ll also want to make sure you can afford to pay health insurance out of pocket and contribute to a retirement fund. If you’re interested in other insurance offerings besides health insurance, Espinal said the Freelancers Union provides some benefits, including disability, liability, and life insurance, to members at a fraction of the cost.