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6 Signs You’re Not Ready to Be a Freelancer (and Tips to Improve)


It’s very common to hear people say they want to quit their job and be their own boss, but is doing so plausible for you? What are the challenges you can expect as a newbie freelancer?

Here are six signs you’re not ready to become a freelancer and what you can do to improve.

1. You Avoid Risks

Freelancing as a career is fundamentally riskier than a job. While an employee has the security of fixed monthly payments, a freelancer rarely ever enjoys the same level of financial stability. This is perhaps the biggest drawback of choosing to freelance over employment.

As a freelancer, you might have to face clients ghosting you, not paying on time, not paying at all, breaching contracts, cutting ties with you without notice, and much more. If you tend to avoid taking risks and repel uncertainty, freelancing will be much harder for you.


Find clients who have long-term recurring work rather than short-term one-off gigs. The latter doesn’t give you enough business. To do that, it’s advisable to avoid content mills like Upwork or Fiverr and reach out to leads directly via email, call, social media, or messaging apps.

2. You Lack Communication Skills

 Woman talking on the phone and looking at a laptop
Ivan Samkov/

While some clients are easier to talk to, most are a bit skeptical—and rightfully so—because of the reasons we discussed above. If you can’t hold a conversation with a new lead, they may assume that you’re either unqualified or not interested in working with them.



Learn to address your clients’ concerns proactively and make them feel understood. Remember, it’s your job as a freelancer to facilitate the conversation. Here are a few good questions you can ask new leads:

  1. How urgent is this project? What problem will it solve?
  2. Are you currently losing revenue due to the lack of this service?
  3. How valuable is this project going to be in the long run?
  4. What metrics do you use to judge the quality of the work?
  5. Do you have any more doubts that you’d like me to resolve?

Notice how the questions are about the client and not about you. This signals that you have a service mindset, i.e., an inner desire to help your clients succeed. The idea here is to make your clients feel like you’re on their side and want the best for them.

Related: Client Red Flags Every Freelancer Should Be Aware Of

3. You Don’t Know How to Market Yourself

Every working professional has to market themselves to display their employability. But doing so is more difficult when you’re self-employed, due to one big reason: trusting a freelancer is a lot harder for companies than trusting an employee.

Clients often hesitate to work with freelancers due to the obvious uncertainties it leads to. After all, hiring someone from your city to come work in your office is not the same as hiring someone from a different country who you know nothing about.


Make it a habit to collect recommendations on LinkedIn from your previous clients and build a personalized online portfolio. New clients worry that you won’t live up to expectations. They need social proof. A solid online presence on social media can help with that.

Related: Things Clients Look for When Hiring Freelancers

4. You Don’t Know How to Negotiate

An illustration of someone paying money to the beneficiary

It’s one thing to bring in new leads and a whole other thing to convert those leads into paying clients. To bridge that gap, you need to be good at negotiation. Without it, you can’t convey to your clients how your prices are in sync with their project requirements.


See things from the client’s point of view. If you were hiring a freelancer, what would be your biggest concerns, especially in terms of time and money? Here are a few to help you think:

  1. How is hiring you better than hiring an employee?
  2. Would you require constant supervision and support?
  3. Would working with you be really bothersome?
  4. How frequently will you send invoices?
  5. How flexible are your terms of service?

Related: How to Raise Your Prices as a Freelancer Without Losing Clients

5. You Rely on Others for Motivation

In the case of employment, it’s a manager’s job to motivate an employee under him. In other words, the latter relies on someone else—implying a need for extrinsic motivation—to do their job to the best of their ability. Such is not the case for freelancers.

In freelancing, there is no one readily available to guide or motivate you other than yourself. This implies a need for intrinsic motivation, i.e., self-reliance. If you often find yourself struggling to do things on your own and need input from others, freelancing will trouble you.


Train yourself to reduce your reliance on external motivation. Take on small challenges and reward yourself whenever you achieve them. Remember to slowly increase the difficulty and track your progress over time. This will help build discipline and a work ethic.

6. You Have Trouble Managing Projects

An illustration of planning ahead

Project management ultimately comes down to three things: time, money, and effort. As a freelancer, you are expected to know how to manage multiple projects at once. No client wants to hear why you couldn’t complete their work because you were busy with some other client’s work.


Prioritize your projects based on three brackets: urgency, necessity, and scalability. Look at the overall value that you will get out of a certain project or a client relationship. It may sometimes be better to let go of a lucrative short-term opportunity for a reliable long-term one.

There are a ton of project management tools available that can help you organize projects, set priorities, visualize deadlines, and allocate resources. Depending on the kind of work you do, the best project management tool for you will vary.

Related: Free Project Plan Templates to Simplify Complex Tasks

Learn the Traits of Successful Freelancers

As great as freelancing is, it’s not for everyone. It requires you to learn the skills and tolerate the risks that you may not want to bother with. You may value stability more than control, and that’s fine.

As a suggestion, if you are considering freelance work as a career but feel you are not yet ready, try networking with freelancers within your network and asking them about their experiences.

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