• Starting in freelancing is tough, and mistakes can easily put you under.
• These successful freelancers overcame their mistakes, but advise that you avoid them from the beginning.
• Avoid giving too much of your time away for free and always specify a contract, they said.
• They also recommended vetting your clients to ensure that you would be a good match and constantly selling yourself.
• Click here for more BI Prime stories.

Making rookie mistakes in your freelance business can doom your enterprise to failure before you've even had time to gain traction. But even veteran freelancers are not immune to the occasional slip-up or setback that can lead to the loss of clients or steady income.

"It's not that surprising that so many freelance businesses go under, when many freelancers don't think about staying afloat," wrote freelance writer Rajiv Sighamony in a 2017 blog post. "They set out to seek their fortune, giving no thought to the fact that they've set sail in a colander."

As an alternative to the leaky-boat approach, Business Insider interviewed several freelancers on the biggest mistakes that they've made while practicing their trade, with their rear-view insights on how you can avoid a similar fate.

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1. Sharing too much expertise for free

Freelance virtual assistant and blogger Phyllis Pometta confessed that the biggest mistake she's made as a freelancer has been giving away too much billable information to prospects without getting paid for her time and expertise.

Pometta recalled times when potential clients had arranged for a discovery call with her - presumably to explore her services - and ended up picking her brain and extracting valuable information that was part of what she was supposed to be selling.

"I would often provide information - sometimes detailed - as to what I could do and would do during our 30-minute discussion," said Pometta. "However, I'd also give some tips/advice that should have been paid for. I like to show my kindness as well as my knowledge, but sometimes that can be taken advantage of."

As a result of this error in judgment, the freelancer found out more than once after sending a proposal that the prospect was hiring another virtual assistant because they charged less - and most likely took Pometta's trade secrets to her competitor.

Because of this experience, Pometta no longer offers her expertise for free as part of exploratory calls, and she recommended that other freelancers follow her lead.

Now, she "sticks to the script," not offering any additional information until she has a signed contract in hand. By doing this, the freelancer has controlled her time and avoided being taken advantage of, and works only with people who value her worth and skills.

"Previously, as I was talking to potential clients, I would brainstorm while I was on the call," Pometta explained. "Their 30-minute consult then turned into an hour conversation on what they could do. Now, I stick to what they specifically asked for in their discovery interview and don't go into so much depth right off the bat."

To help keep these conversations focused, she aims to keep the discussion within the scheduled 30-minute time slot without running over. She does like to give prospects one key take away from that initial conversation that makes them think, "I never thought of that ..." and encourages them to hire her.

2. Working without a contract

Marc Andre currently does some part-time work as a freelance writer for Vital Dollar and previously was a freelance web designer as a sole proprietor. He remembered that several years ago, when he first started freelancing, he made the mistake of working with clients without a contract.

"I knew that I should be using a contract to protect myself, but I was just starting out and I felt like I wasn't good enough or experienced enough to use a contract," Andre admitted. "I felt insecure being a beginner and thought that if I asked clients to sign a contract, they would think I was overstepping."

Andre recognized that this mistake hurt him in two specific situations. In one case, he had started working with a client, putting time into her assignments, but she disappeared and stopped communicating with him mid-project without paying him. Since the client hadn't signed any contract with Andre, he had no definitive recourse to take action and recover his pay.

In the second situation, Andre was working with a client that had some unrealistic expectations about the scope of work for the project. Since he didn't have a contract that specified the work, the project kept growing and took much longer than anticipated.

Andre now advises other freelancers to use a contract with each and every one of their clients, whether they are first starting out or have been in the game for a while. He said that based on his experience, there is no reason to dread talking about contracts with a client - especially because, assuming the contract is fair and balanced, having it protects both parties, so most clients will probably prefer to sign one to have some protection as well.

"I think my fears [of using a contract] were unjustified, and once I started using contracts, clients seemed to view me as being more professional," he said. "That client probably deals with contracts whenever they hire other contractors or freelancers."

In terms of how and when to introduce a contract into the conversation, Andre suggested talking about the contract whenever you're discussing the terms, timeline, and payment schedule of the project.

"You'll probably estimate the amount of time that you'll need in order to complete the project, and you'll present them with a proposal or a quote," he said. "Your proposal should lay out the timeline and order of events. If the total price of the project is $3,000 and you want to get 50% up front, the proposal or quote should cover those details."

Andre added that you should tell the client that the project will begin when both parties have signed the contract and the initial payment has been made. That way, the client will know that they should expect to receive a contract, and if they have any questions about it you can work out those details together before moving forward.

3. Ignoring your intuition and red flags

Digital marketing consultant Michael LaLonde has been a freelancer and operated his own small agency, LDM, for almost a decade. LaLonde pointed to failing to listen to his own instincts during initial conversations with potential clients as his biggest mistake as a freelancer.

"Those initial calls are crucial for understanding the kind of businessperson you're working with and whether or not you'll get along," LaLonde said. "There are a lot of different styles, approaches, and philosophies when it comes to not only the projects themselves, but the kinds of relationships that form between the company and you as a freelancer.

LaLonde explained that being aware of this reality - and recognizing relationships that will work and those that won't - are key to doing good work, as well as just keeping your sanity as an independent worker. Long-term relationships are vital to freelancing successfully without constantly selling, which many freelancers would prefer to avoid. So figuring out how to effectively evaluate potential relationships during initial calls, looking for red flags, and honestly evaluating whether a client is the right fit for you are key to establishing a long and happy freelancing career.

LaLonde recalled several times when he ignored his instincts to abandon a new client and regretted it. In his case, red-flag clients included people who thought they knew more than he did about his specialty, were more focused on learning what he was doing than working together, or who vented a long list of complaints about previous providers.

"Some freelancers are happy to babysit clients like that, but I'm not one of them," LaLonde stated. "Sooner or later, things will come to a head, and you'll part ways not on the best of terms due to these incompatibilities."

To help other freelancers avoid his own mistakes, LaLonde suggested evaluating yourself and how you work best, as that allows you to recognize clients who are compatible with your working style - as well as those who are a poor fit.

"If you can afford to, don't compromise it," LaLonde said. "Stick to your strengths, and look for those great matches."

4. Only marketing yourself when you need work

Cyrus Vanover, founder of the Frugal Budgeter and freelance copywriter, told Business Insider that he still struggles with his biggest freelance mistake: stopping his marketing efforts when he is fully booked, rather than continuing to search for new business.

Vanover shared a recent example of making this error. Last spring, he landed a writing project with a company that offers online courses. His job was to go through each chapter of a textbook and create PowerPoint slides, write study questions, and also create a bank of test questions for the chapter and final exams.

It was a three-month project to complete the course, and the client indicated that he was pleased with Vanover's work, assuring the freelancer that he had "many more courses that needed to be developed" after this one was completed.

"Thinking I had hit the freelancing jackpot, I completely stopped marketing my services," Vanover confessed. "I thought I had enough work to keep me busy full-time through the end of the year, and possibly longer."

After completing the first course, however, the company made the decision to pause the development of new courses for the foreseeable future.

"And just like that, I was out of work," Vanover said. "I then had to start marketing my services again to land more work. In some ways, the experience felt like starting my freelancing business all over again."

He added, "It's easy to become complacent as a freelancer when you have more work than you can handle and think the good times are going to continue without marketing your services. But it rarely works that way."

To put an end to the "feast or famine" cycle of freelancing, Vanover said to constantly market your services, even during periods when you have work coming out of your ears.

He suggested that there are many different ways that freelancers can effectively market their services, including the popular method of cold emailing.

"In a cold email, you both introduce yourself and offer your services," he explained. "A variation of this is the warm email where a connection is first made with a client (to warm them up), and then you offer your services."

His own marketing strategy involves the use of LinkedIn rather than email.

"People on LinkedIn are much more receptive to pitches than with email," Vanover said. "LinkedIn is for business, after all. It's expected. After connecting with a marketing manager on LinkedIn, a freelancer can then initiate a conversation to make an introduction and pitch his or her services."

He added that after optimizing his LinkedIn profile with keywords that people are searching for (for example, "freelance financial writer"), he does occasionally have people contact him about his services.

"Like Google, LinkedIn is a search engine," Vanover said. "The main difference is instead of getting links to websites when you do a search, you get people's profiles."

Vanover concluded that marketing is so important that it should be the first thing you do in the morning before starting work on any freelance projects.

"This doesn't guarantee you will always have freelance work, of course, but it can go a long way in stabilizing your income," Vanover said.