Freelancing Mistakes: 20 Career Killers Common to New Telecommuters

freelancing mistakes

Have you recently traded your onsite employee status for the flexibility and independence of life as a telecommuting freelancer? If you’re one of the more than 13 million self-employed U.S. professionals who work from home, according to, take stock of these freelancing mistakes that could kill your career before it gets off the ground.

Top 20 Freelancing Mistakes Common to New Telecommuters

1. Failing to Secure a Contract 

Freelancing without a contract is like swimming in open water without a life vest. Can you stay afloat without one? Probably. But what if something doesn’t go according to plan? A contract is your protection. It holds you accountable for work you have agreed to complete and it is your defense against being ripped off by clients.

2. Not Knowing Your Worth 

The professional independence associated with telecommuting as a freelancer doesn’t only pertain to work location; freelancers also have the ability to set their own rates for services rendered to their clients. Unfortunately, new freelancers are notorious for undervaluing their work.

When determining freelancer rates, Forbes contributor Laura Shin recommends focusing on these three factors to strike the balance between a rate that sits well with clients as well as your bank account: 1) Your budget; 2) Your skill level; 3) Your time.

3. Avoiding Your Tax Payments 

One of the most costly freelancing mistakes new telecommuters can make is neglecting to pay their taxes. Unlike employees, freelancers are responsible for withholding their own taxes and most likely paying quarterly estimated taxes rather than only filing a return once per year.

Here are a couple of additional tax requirements freelancers cannot avoid:

  • If you earn more than $400, you are responsible for paying income tax and self-employment tax (Social Security and Medicare)
  • Clients paying you $600 or more must provide you with a 1099-MISC form

Related: Freelancers—How to Prep for Tax Season

4. Treating Deadlines as Optional

Merriam-Webster defines a deadline as “a date or time before which something must be done” or “the time after which copy is not accepted for a particular issue of a publication.” As a freelancer, don’t make the mistake of looking at your list of deadlines as merely a suggestion for when your projects should be completed. Consistently meet your deliverables or your time as a telecommuting freelancer could quickly meet an end.

5. Over-promising and Under-delivering 

Speaking of deliverables, agreeing to complete more projects than what your capable of handling isn’t impressive. If you’re new to a project and want to wow your client, adopt the strategy of under-promising and over-delivering. Set the bar to a goal slightly lower than one you know you can achieve, then sit back and watch your client be dazzled as you sail over the bar.

6. Relying on One Client for a Majority of Income 

This freelancing mistake is a real-world application of the adage “don’t put all your eggs in one basket.”

Landing a good-paying contract with a well-established client right out the gate is a dream scenario for new telecommuting freelancers, in that it inspires a feeling of job security similar to what they’re used to experiencing as an employee. However, freelancing and job security are neither synonymous, nor mutually exclusive. Rather than gambling on one client for the majority of your income, seek contracts from multiple income sources. This way, if one contract abruptly ends, you aren’t scrambling to make ends meet.

7. Being Too Eager 

When you’re a self-employed telecommuter, just because have the luxury of working from home doesn’t mean you should never stop working. Making yourself too available will eventually lead to feelings of resentment not only for the abundance of projects you’ve agreed to take on, but potentially for the very idea of working from home as a freelancer.

Related: 7 Quick and Easy Steps to Overcome Job Fatigue

8. Abandoning Your Network 

Transitioning to a home-based job means you get to leave behind office politics and your stall in the cubical farm, but it does not mean you should abandon all elements of your former, non-telecommuting occupation—namely, your network.

In addition to helping you combat the sometimes isolating effects of working from home, remaining connected to your professional network will provide you with a pool of potential job application endorsements and industry resources to reference for upcoming projects.

9. Caving to Distractions 

Television, household chores, errands, sleeping in, and family friends who pop over for a visit are serious distractions for up-and-coming freelancers. Ensure you treat your freelance career with the same respect you’d give to a traditional, onsite office job. Your dirty dishes can wait.

10. Neglecting to Save or Back-up Your Files

“The dog ate my project” doesn’t work as an excuse when you’re no longer a doe-eyed eight-year-old. Help prevent lost files and missed deadlines by frequently saving and backing up your files as you work toward completion.

11. Mismanaging Your Time

As a freelancer, you can best manage your time by establishing a regular routine that balances your professional and personal responsibilities. Start with setting a schedule that requires you begin and end work at the same time every day, then incorporate daily to-do lists or utilize a time management app to take your productivity to the next level.

Related: Telecommuting Productivity Hacks: 10 Insider Tips from VV Team Members 

12. Thinking of Your Job as a Hobby 

Every new telecommuting freelancer needs time to adjust to life as a remote, self-employed professional, but this doesn’t mean you can be lax in your work ethic, especially if freelancing from home isn’t an endeavor to only earn supplemental income. Being a successful, self-employed freelancer requires internal motivation and respect for telecommuting as a legitimate work model.

13. Accepting Every Project 

Give yourself permission to be selective about the types of projects you elect to complete. Instead of accepting every proposal you’re offered, consider whether the project will add value to your résumé. Crafting a portfolio of work that is, as often as possible, focused on a specialty within which you excel will lead to more lucrative future offers from clients knocking on your door for a taste of your subject matter expertise.

14. Not Following Up with New Project Ideas 

Once you have completed a project for your client, send a follow-up message with a note of thanks for the opportunity, a request for feedback, and a pitch for new projects you want to complete on behalf of the client.

Of course, the client has the option to reject your proposal, but the client also may be so impressed and inspired by your initiative that the result is a new contract offer. If the client does take a pass, maybe they’ll be kind enough to offer suggestions for other industry contacts in need of your services, and if not, at least you made the effort.

15. Making Assumptions

“Assumptions are the termites of relationships.” 

—Henry Winkler

Rather than allowing assumptions to devour your foundation as a telecommuting freelancer, follow this rule: Don’t assume. ASK—

  • A: Alert your client to changes in project elements, goals, and scheduling
  • S: Set expectations upfront and revise objectives as needed
  • K: Keep in contact, which cultivates a policy of open-door communication

Related: Remote Collaboration: Methods for Effective Virtual Communication

16. Failing to Establish Boundaries 

Contrary to the practices implemented by far too many clients, the line between employee and independent contractor is not a fine one. The IRS makes clear distinctions between these two professional classifications, and it’s critical that all new independent contractors know and understand their rights as self-employed persons, which lessens the likelihood they’ll be misclassified by their clients. The U.S. Department of Labor (DOL) has also launched a DOL Misclassification Initiative with 37 states to provide education about employee misclassification and ensure all workers receive the protections, wages, and benefits to which they are entitled.

17. Forgetting to Update Your Employment Documents 

Each time you complete a project for a new client, update your résumé and revise your cover letter to include your most recent work history and highlight the new skills and experience you have acquired. Remembering to update your employment documents as you complete projects will save you time and frustration down the road when you need to quickly apply for new contract offers.

18. Disregarding the Importance of Social Media 

Social media is an invaluable tool for self-employed professionals working to build their brands, engage with like-minded professionals, stay up-to-date on industry trends, establish themselves as industry experts, and connect with new clients. Disregarding the benefits of social media and the new doors it could open for your career could prevent you from realizing your full potential.

19. Ignoring Personal Projects 

It’s understandable that new telecommuting freelancers have tunnel vision for diving into their initial contracts and watching those first self-employment dollars pour in, but they shouldn’t altogether reject their own passions. Ignoring personal projects often puts new telecommuters on a fast track to professional burnout, because they feel as though they are giving all of themselves away. We suggest setting aside time each week to devote your talents to a personal endeavor.

20. Dismissing Your Instincts

No matter how desperate you are for work, go with your gut when it comes to accepting job offers. If something about the client or type of work the client’s offering sets off your internal alarm, breathe and reconsider the proposal. When applying to freelance jobs, take our advice on how to avoid scams.

Become a Virtual Vocations Member and Explore Thousands of Freelancing Opportunities

It’s Virtual Vocations’ mission to ensure our members receive fast access to the most current and best virtual job listings anywhere, including thousands of opportunities to telecommute as a freelancer in more than 40 top career categories.

We’re unlike other job boards because we publish hundreds of new telecommute job vacancies every day, ensuring each job posting will allow you to work from your home office at least 20% of the time.

We even provide Virtual Vocations members with options for customizable email alerts, giving job seekers instant access to newly published telecommute job openings curated based on their job search preferences.

Why register? Here’s a sampling of some of the exclusive Virtual Vocations telecommute job resources designed to give job seekers the highest opportunities for success in their telecommute job searches and connect them to the right telecommute jobs and clients:

  • Action plans and downloadable resume templates
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  • Search Filters that allow you to search for human-screened telecommute jobs by job category, type, telecommute status, travel requirements, and more—all to ensure you are applying to the most appropriate telecommute jobs for your experience level, skill set, and job flexibility needs
  • A team of experienced customer service professionals ready to answer your questions about utilizing Virtual Vocations during your telecommute job search via phone at 1-800-379-5092, email at, and Live Chat Support on our Homepage

Visit our Services Page to learn more about these and other remote work perks you can utilize during your telecommute job search.

Employers: Use Virtual Vocations to Post Unlimited Freelance Telecommute Job Openings at No Cost

The Virtual Vocations Employer Portal gives telecommute-friendly companies streamlined, secure permissions to post their telecommuting job openings for free as well as receive applications from from Virtual Vocations’ member list of high quality job candidates—half of whom work from home as freelancers, according to the Virtual Vocations 2016 Year-End Statistical Report.

Companies who elect to become Virtual Vocations Employer Partners will not only be able to post an unlimited number of telecommuting job openings for free, but also enjoy a multi-faceted promotions package ensuring their telecommuting job openings receive maximum exposure through the following avenues:

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Visit the Virtual Vocations Employer Portal to post your telecommute job openings at no cost and join more than 3,500 employers using Virtual Vocations to find and hire top quality telecommuting talent.

Have you made your own freelancing mistakes? Share your advice for new telecommuters when you connect with Virtual Vocations on Facebook and Twitter. We’d love to hear from you! 


VVlogoJoining Virtual Vocations grants you access to our hand-picked telecommuting jobs database. Our family-owned company is committed to helping you find quality job leads. We strive to help make your work-at-home job search faster, easier and safer by bringing you scam-free jobs that offer some form of telecommuting or virtual work.

Learn how our service works, browse job leads by location and career category, or search hundreds of hand-screened telecommuting jobs to find legitimate work-at-home job leads that match your skills and background.

About Kimberly Back 770 Articles
Kimberly Back is the Content Division Manager at Virtual Vocations. Prior to beginning work with Virtual Vocations in 2012, Kimberly was a subscriber and advocate of Virtual Vocations' services. She has exclusively worked from home since 2009.