Freelancing Vs. Traditional Work: Which Is Right For You?

There are many reasons those in the personal finance space, and other industries, decide to switch from the traditional workforce to a freelance career. Depending on how you work best, freelancing may have pros and cons that traditional employment does have. As well, the inverse may be true.

Ashley Barnett, Content Director of, was kind enough to discuss with me the pros and cons of being a freelancer and working in a traditional role with an employer. For most freelancers, the deciding factor is usually health and insurance, and benefits. However, as a successful freelancer for over 10 years, the deciding factor for Ashley was career growth and advancement. She also shared that initially, she had no plans to return to a traditional role until she was offered her current role. 

We also discussed the typical pros and cons of why we chose to freelance over traditional work and vice versa. Things like flexibility, remote work, steady income, setting boundaries, and career advancement. 

Pros and Cons of Freelance


  • Flexible schedule and freedom 
  • Many work-from-home opportunities are available
  • Be your own boss
  • Business expenses & write-offs
  • Ability to turn down things you don’t like


  • Responsible for your own benefits
  • Need to account for taxes in requested rates
  • Variable income and workload
  • Little room for growth or career advancement

Pros and Cons of Traditional (W-2) work


  • Benefits provided by employer
  • Taxes taken out of salary
  • Stable income and workload
  • Opportunities for growth and career advancement


  • Less flexible
  • Work from home may not be possible
  • Working for someone else
  • Tax write-offs go to employer
  • Potentially bad boss
  • Harder to say no specific tasks

Flexibility Vs. Routine

For those that need flexibility in their lives, freelancing is preferred because of the lack of schedule. Although freelancers often have deadlines, they can determine how much time a task will take and if their client gives them sufficient time to complete it. Traditional work provides structure and routine for those who prefer it in their working conditions. 


Freelancing may require a bit more of a learning curve than only completing specific tasks. Learning to run a business often comes with new skill sets. Such as doing your taxes or hiring someone to help you withhold the correct amount. Along with learning how to create invoices, some programs can do this for you and tell you how much tax to withhold.

As a freelancer being self-employed, expenses incurred can be written off on taxes. In a traditional role, writing off expenses is a bit harder. Employers may provide reimbursements or other ways of handling expenses for their employees.

Variable Vs. Steady Income/WorkFlow

Ask freelancers if they have always been paid on time and chances are none will say they have been paid on time for every invoice. Since clients often request invoices at the end of the month and sometimes request another 30 days to pay, there may be longer gaps in your income than in traditional work.

Freelancers often have variable months of work and income. The idea of periods of feast and famine. Many freelancers suggest having a larger emergency fund for the slower months. Traditional work often comes with a steady income and knowing that paycheck will come periodically. Traditional work always comes with a chance of layoffs or downsizing as well.

Setting Boundaries

Freelancers also have a bit more freedom to push back when clients push boundaries. Freelancers can more likely say no, drop clients, or charge premiums when boundaries are pushed. In traditional work, pushing back may not occur as frequently out of fear. Fear of being let go, fear of not getting promoted, or other fears like being seen as insubordinate. 

Benefits, Career Advancement & Career Growth

In the United States, health insurance is often tied to an employer. Employers get discounted bulk rates since the employees have options from a single company. For freelancers, individual options come with a premium price tag. Traditional work often provides additional benefits as well.

As Ashley mentioned to me, there are a few options for growth as a freelancer. Scaling as a freelancer usually means creating an agency or digital course. These options aren’t always suitable for every freelancer. 

Some freelancers work better as their own bosses. Meetings can be beneficial for employees. However, I often hear from those in traditional work about how wasteful meetings can be. Clients provide the work, but freelancers aren’t micromanaged by a potentially bad boss. The corporate hierarchy isn’t right for everyone. 

Along with the corporate hierarchy, many employers are now pushing back on work from home. Mixed results from studies are arguing that some people are more productive working from home and some aren’t. Freelancers often have the benefit of working remotely. Employees don’t always get this benefit, as employers make cases to return to the office. 

The Bottom Line

There are advantages and disadvantages to freelancing or working a traditional job. What may be a pro to some may be a con to others. Both types of work will have tradeoffs for everyone. 

When working towards financial independence, some of us only work traditional jobs. Others have been freelancing for most or all of their entire career. Many high-profile bloggers, podcasters, and YouTubers built their freelance portfolios while working traditional jobs. No rule says you can’t do both or switch at any time. 

The right choice depends on timing, your personal preference, and what helps you reach financial independence and life goals. Although freelancing may seem more advantageous for financial freedom, don’t discount traditional work. Freelancing may not be for everyone, and you can certainly reach financial independence without going that route.


Read More: How to Save for Retirement as a Freelancer

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