Freelancing Pros and Cons: Key Benefits, Challenges, and How to Decide if Freelancer Life Is Right for You

It’s the dream for many: freedom from the 9–5, the ability to be your own boss, and the option to work from anywhere — whether that’s your kitchen table or a beach in Bali. Freelancing can offer more control over your time, your income, and your work-life balance. But like any career path, it comes with trade-offs. Before you take the leap, here’s what to expect — the pros, the cons, and how to tell if this lifestyle fits your personality.

What is freelancing?

Freelancing is more than just working from home in sweatpants — though that’s definitely part of the appeal. At its core, freelancing means being self-employed: offering your skills or services to multiple clients without being tied to a single employer. You’re in charge of what you do, who you do it for, when, where, and for how much. According to Pew Research Center, US-based self-employed workers are more satisfied, more fulfilled, and feel more valued than those in more traditional jobs. As many as 62% say they’re very satisfied with their work, compared to just 51% of traditional employees.

It’s a model that’s grown massively in recent years. From designers and writers to therapists, developers, and consultants — more people are leaving traditional jobs behind in search of flexibility, autonomy, or simply a better fit. Statista projects that in 2027, 86.5 million people will be freelancing in the United States and will make up 50.9% of the total US workforce.

But freelancing isn’t for everyone. You need to be okay with risk, self-management, and the occasional dry spell. If you like structure, predictability, and having someone else call the shots, freelancing might feel more chaotic than freeing.

Pros of freelancing

There are many pros to freelancing — let’s get into it.

Freedom and flexibility

Freelancing gives you something most jobs can’t: control. You set your schedule, choose your clients, and work where you want — whether that’s a quiet home office, a local cafe, or a different country every month (sounds interesting? Check out our top eight locations for digital nomads). Need to take a Tuesday off and work Sunday instead? Go ahead. Want to only work with clients in a specific industry? You can. Bonus: no rush hour, no dress code, no awkward team-building.

For me, this flexibility has been a game changer. I’m a full-time freelancer now, but when I was working in an office, the standard 9-to-5 felt like somewhat of a mismatch. My most productive hours are early in the morning — from around 6:30 to 10:30 — and then again in the evening, from 5:30 to 8. That long stretch of midday office hours used to feel like a slog. Now I can structure my day around my own rhythm.

Of course, all of that comes with a caveat: no one’s going to manage your time for you. You’ll need to build your own structure — but if you do, freelancing can give you the freedom to design a workday (and a life) that actually works for you.

The biggest misconception about freelancing is that it’s inherently less stressful or easier than a 9-to-5. In reality, the mental energy you spend switching between pitching, delivering, and managing your own brand can exceed what you’d ever spend in a single role. For instance, when I lead rebranding projects for clients, the lines between “work” and “life” often blur, making it essential to set strict working hours even when nobody’s watching.

{{Mac Mascorro}}

Creative and career control

Another perk of freelancing is the ability to shape your work around what actually interests you. You get to pick your projects, build your brand, and grow your skills on your own terms.

In a full-time job, your role is usually predefined. You inherit tasks, systems, clients, and expectations — and whether or not they suit you, you’re expected to deliver. As a freelancer, you decide what kind of work you want to be known for. You can double down on what you’re best at, experiment with new services, or refine your freelancer niche over time.

It’s also one of the fastest ways to upskill. Because you’re managing every part of the business — not just the craft itself, but also pricing, communication, client service, and marketing — you tend to learn by doing, fast.

Of course, it’s not always glamorous. You might take on projects you’re not in love with to pay the bills. But even then, you’re still making that call — and that level of agency adds up.

Upon graduating from college, I transitioned quickly to freelancing as a digital consultant — I was forced into it, not because I had a choice… The best part of freelancing was that I had a direct connection with clients — you feel every success, every failure, and you learn at a fast pace… I learned that resilience and adaptability mattered more than technical skills.

{{Martin Weidemann}}

Higher earning potential

The ability to earn more than you could in a traditional job is yet another advantage of freelancing. There’s no manager capping your salary, no rigid pay scale to climb — just the open-ended potential of what you can negotiate and deliver.

That said, this higher level of income doesn’t just happen the day you decide to take on your first client as a freelancer. To make the most of freelancing, you need to know your value, set the right rates and market yourself consistently. If you’re after a high-paying freelance job, but are unsure where to start, Solowise has you covered — check out our list of top 14 best-paying jobs for freelancers right now. 

Your earning power also depends on how well you manage your time, scope, and client pipeline. The good news? You can adjust your pricing and workload as your skills grow, and unlike salaried roles, you’re not waiting a year for someone to approve a raise.

I keep detailed records of seasonal patterns in mental health needs. January and the holidays are always busy, but summer can be surprisingly slow as families travel. I now book lighter client loads during busy months to avoid burnout and save extra during peak times to cover the inevitable summer dip when half my clients are on vacation.

{{Anne Marie White}}

Tax perks and write-offs

Nobody likes to talk about taxes, but unfortunately, when you’re a freelancer, you’re the one who has to take care of them since you don’t have an employer to withhold them automatically from your salary. Tax rules vary depending on where you live, but if you’re in the United States, there’s an extra layer: the self-employment tax. On top of regular income tax, freelancers are responsible for both the employer and employee portions of Social Security and Medicare.

If you’re confused about why I’m including all this tax stuff as a pro of freelancing, I have one thing to say: deductions. Deductions reduce your taxable income, which means you owe less in taxes overall.

There’s a whole lot of stuff you can deduct: software,  equipment, even part of your utilities or internet bill — as long as you keep good records. You may even qualify for a home office deduction if you’re using a part of your home for work exclusively and regularly. It’s not fun, but with the right system, you can make taxes work in your favor. Check out our detailed freelance tax guide here to get a better understanding of what you can deduct.

Here’s a video from TurboTax to help you make sense of transitioning to being fully self employed, from the point of view of taxes.

Cons of freelancing

And what are the downsides, you ask? Read on!

Unstable income and unpredictable workload

One month, you’re drowning in deadlines. The next, you’re refreshing your inbox praying for a project. That’s the freelance cycle: inconsistent workload, delayed payments, and the constant low-level anxiety that it could all dry up tomorrow.

Even if you do have a solid gig going on, you might still be waiting a long time to get paid. Something like Net 30 could turn into Net never — especially if your client’s accounting department is disorganized or just slow. If you find yourself in this situation, check out our guide on what to do if a client doesn’t pay for a service.

It doesn’t have to be a dealbreaker, though. Over time, it gets easier as you get used to dealing with this chaos. You’ll learn to manage your finances, such as setting aside money during busy months and keeping an emergency fund, and figure out how to spot the warning signs of a late-paying client. And if work ever dries up unexpectedly, there’s no shame in jumping on Upwork or Fiverr to fill the gap while you line up the next thing.

No built-in benefits or paid time off

Since you work for yourself, there’s no HR department sending you holiday calendars or approving sick leave. For freelancers, every day off is unpaid — whether it’s a vacation, a bad cold, or just burnout. You’ll also need to sort out your own health insurance, retirement contributions (which can actually help you lower your taxes), and any other benefits you want to have.

It’s one of the tougher trade-offs of self-employment, but not unmanageable. Many freelancers factor time off into their rates, build in recharge periods between projects, or set up separate savings accounts for things like healthcare or holidays. Some even plan ahead by creating “buffer months” or treating time off as a line item in their pricing.

You’re a one-person business

One thing I wish I’d known before freelancing: how critical it is to institutionalize your own processes and self-structure, not just for client projects but for your own pipeline and mental clarity. Early on, I once let a promising idea with a health food startup stall simply because I failed to create internal deadlines for myself—no boss means no built-in momentum unless you set it.

{{Mac Mascorro}}

You know this already — freelancing isn’t just doing the work — it’s being the entire business. You’re the strategist, the marketer, the account manager, and the billing department, all rolled into one. For some, it’s empowering. Others might find it overwhelming. 

The good news is, you don’t have to do everything from scratch, and you don’t have to do everything yourself. Tools and services exist to help you function like a business without the overhead. Think contract templates, hiring a tax professional when tax season rolls around, accounting software to keep on top of invoices and cash flow, and project management tools to keep yourself accountable.

The most common misconception? That if you’re good at your craft, it will be all worthwhile. In fact, I spent more time chasing clients and writing proposals than actually delivering project work…
The biggest downside is emotional fatigue, because you are wearing many hats: sales, finance, delivery, customer service. 

{{Martin Weidemann}}

Finding clients takes work

Getting good clients takes effort and it never completely stops. You need a pipeline, not just a lucky streak. That means marketing yourself, networking, sending cold emails, updating your portfolio, or tweaking your Upwork profile. Sometimes you’ll spend more time landing the job than actually doing it. 

It’s not always fun. But once you start building a reputation, referrals come easier, and your outreach gets sharper. You start attracting the kind of clients you actually want, and have the freedom to say no to those who aren’t the right fit for you. In the meantime, if you’re having a difficult time with this, Solowise has guides on how to find new clients on LinkedIn, Instagram, or through expert networks.

It can get lonely

For some, this is a blessing. For others, a curse. There’s no team Slack, no colleague to bounce ideas off, no after-work drinks. Just you, your tasks, and a lot of quiet hours.

Some people thrive in solitude, but even then, it helps to have connection with other people. These days, there’s no shortage of ways to link up. Peer groups, coworking spaces, virtual communities and peer-to-peer platforms like Superpeer, Lunchclub, or Freelance Founders  have become ubiquitous, and they don’t just stave off loneliness – they can actually make your work better. It’s also worth investing in emotional support (therapist, mentor, whatever works) to avoid burnout.

What I wish I knew: The emotional toll of being everyone’s support system while having nowhere to turn yourself. When I transitioned from hospital settings to private practice, I lost the built-in peer support and case consultation that comes with institutional work. I learned the hard way that investing in my own therapist and peer consultation groups isn’t optional—it’s essential for longevity.

{{Anne Marie White}}

How to know if freelancing is right for you

If you’re considering making the switch from full-time employment to freelancing, unfortunately, there’s no way of knowing beforehand if it’ll be a good fit. However, there are factors that can help you decide.

Freelancing might be right for you if:

• You’re self-motivated and comfortable working solo
• You’re okay with some risk
• You’re good at switching hats: creator one minute, accountant the next
• You’ve got marketable skills and the willingness to sell them

On the other hand, it might be a bad idea if:

• You need external structure or thrive on constant feedback
• You’re conflict-avoidant (negotiations are part of the job)
• You dislike admin, invoicing, taxes, or anything non-creative
• You want to log off at 5 p.m. and not think about work until the following day.

Beyond the logistical stuff, it also comes down to personality. 

To succeed, you need the ability to genuinely empathize and communicate—period. In consulting, I found that the longevity of my client relationships (like with health/wellness brands launching new product lines) always depended more on my listening and clarity than on my design or analytics skills. Processes and systems get you 80% there, but empathy and team mentality finish the job.

{{Mac Mascorro}}

The experts I spoke to for this article also pointed to traits like curiosity about your clients’ needs, a long-game mindset when it comes to building relationships, and the ability to set boundaries and prioritize your own time. You’ll need to get comfortable making decisions with limited information — and adapting quickly when things change (because they will).

Essential personality traits: Extreme comfort with uncertainty and the ability to compartmentalize. One week I might have three crisis calls from suicidal clients, the next week everyone’s doing well and it’s eerily quiet. Unlike hospital work where the chaos is predictable, private practice swings between intense periods and dead silence with no warning.

{{Anne Marie White}}

The bottom line

Freelancing can be thrilling, but it’s not magic. You still have to market yourself, manage your time, and chase up that late invoice. What you get in return is freedom — the good kind and the scary kind. Still unsure? You don’t have to go all-in overnight. Test the waters with a part-time freelance project, or start moonlighting alongside your day job.