Eryka Peskin, a friend of mine, recently asked me to look over the language of a webinar she was putting together for her life-coaching business because I am a freelance writer and editor. A few text exchanges soon turned into a lengthy phone call. Mid-conversation, Eryka asked, “Should I be paying you for this?”

I paused. “Probably,” I said with a laugh. But I didn’t press the issue. After we hung up, I replayed the conversation. I had hired Eryka, who is 49, for her coaching four years ago, so we had exchanged money for services before. And if I want to succeed as a freelancer, I can’t always provide free work. Yet when Eryka suggested the possibility that we move from friendly favor to negotiating a payment, I demurred. Why?

“If you’re a freelancer, and you’re good at what you do, your friends are going to want to ask you for your help,” said Blair Glaser, 54, an executive leadership coach in Los Angeles. “And then if you’re a generous person, and it’s natural for you to give, you’re going to want to give it to them. So what happens in the free work is that the roles start to get confused.”

Somewhere in my chat with Eryka, we had transitioned from a friendly collaboration to a more formal edit of her work. But I wasn’t prepared to have a conversation about money.

I enjoy working with friends and wanted to learn how to navigate the boundaries between doing work as a favor and charging a fee. I spoke to various people who have worked with friends — personal trainers, graphic designers, real estate agents and consultants — as well as some of their client friends. Overall, they agreed that working together could be fruitful to both parties as long as the parameters were clear.

Bottom line, “there has to be a healthy reciprocity,” Ms. Glaser said. “Otherwise, there will be some kind of resentment that leads to some kerfuffle in the work or the friendship.”

When to Have the Conversation

“The biggest cue that this conversation needs to be had is when the issue comes up, there’s a moment of panic,” said Kavita Pandit, 66, an executive coach in Athens, Ga. She recommends drafting and practicing scripts, something she has had to do with friends this year after retiring from Georgia State University and setting up her own business.

When a friend calls asking for career advice, Ms. Pandit explains that she offers structured sessions at a fixed minimum rate and is willing to negotiate pricing. “Your ace in the pocket is you have that language to initiate that conversation,” she said.

Nafasi Ferrell, founder and principal consultant of Narratives Unbound, an education and consulting company, said pausing and reframing the conversation was one of the most powerful tools for broaching the topic of money with a friend. As an instructor of the Trauma of Money course, an online financial literacy program, Ms. Ferrell, 32, approaches wealth from a trauma-informed perspective, which includes recognizing when topics like money trigger deep physiological and emotional responses.

“Just take a moment with yourself,” she said.

Many of the entrepreneurs I spoke to said they would pause to reframe a casual, friendly chat between friends if they found themselves asking the type of questions or offering the type of advice they did in client sessions. Ms. Glaser, for instance, will tell friends that she’s happy to explore a topic more deeply in a coaching relationship but will otherwise just listen. If she and a friend decide to work together, she will use language like “I’m speaking to you as your coach right now” anytime she feels the need to make a point outside a scheduled session.

What to Charge

Nearly every person I spoke to charges less for friends and family. Ms. Glaser offers a 20 percent discount. Others negotiate on a case-by-case basis, depending on things like the closeness of the friendship and the friend’s financial situation.

Ms. Pandit has even given coaching sessions to friends as gifts, or asked them to donate to a charity of their choice instead of paying her. “It’s not like you have to have an exchange of money for it to be official,” she said.

My friend Eryka negotiates with every potential client, including friends. She advises people to come up with “an amount that feels significant enough that you’ll take your investment seriously, while not being unfeasible.”

Sometimes, friends will insist on paying full price, something that has happened to Justin Miller, 42, a nutrition and lifestyle coach at Nerd Fitness who also offers personal training. When he asks friends to choose between a full-price 12-week coaching contract or a looser verbal agreement, they tend to pick the contract because they want more accountability built into the relationship.

Ms. Ferrell usually charges her friends full price for her financial coaching, but may give them a discount if she knows their finances are tight. However, she pointed out that women of color, like her, often needed to resist the urge to discount their services.

“The one thing I hear all the time is I can’t charge more because I’m stealing from my community,” she said. “Women of color, we give all the time. That practice of receiving is one that we actually have to practice.”

Amy Weitzman, a real estate agent in Massachusetts, always asks herself why a friend might want a discount before she agrees to give them one. “I really try not to give from a disempowered position,” she said.

She has often dealt with perceptions that she’s just handing out brochures and hosting open houses — not, as she explained, researching markets and negotiating deals.

“I deserve financial stability,” Ms. Weitzman, 47, said. “So I don’t want to make any choices that undermine that, even if someone wants me to because they know me as a friend.”

Bartering is a popular method among many entrepreneurs, especially if they are just starting out and have less disposable income. However, multiple people I spoke to noted that in-kind payments can be far more complicated and prone to situations that create resentment. One graphic designer who charged $30 per hour decided not to barter again after a masseuse who charged $90 per hour told her that she owed three hours of design work for one 60-minute massage.

How to Navigate Conflict

Ricardo Tejeda, owner and operator of Show and Tale Creative, a creative agency in Asheville, N.C., used to do informal verbal agreements, but not anymore. “Everything is a contract now,” he said.

As a former musician, he has helped many friends in the industry with their promotional materials. “I was a broke artist who needed all the work done and didn’t have the budget. So I understand that,” he said.

Even so, he was ready to pause and have a conversation with a good friend who had received a “supreme discount” when he noticed scope creep, the term for when work on a project begins to exceed the agreed-upon parameters. “I had to remind him of the agreement,” Mr. Tejeda, 39, said.

Alissa Ballestrin, a communication and conflict navigation coach and consultant, recently had to chase down a friend for payment. Ms. Ballestrin, 40, initially felt a contract wasn’t necessary, but then months passed without payment. Given her line of work, she had the skills to broach the subject.

“They didn’t feel like there would be any consequences if they made me wait until I was like: ‘Yes, there will be consequences. And that will be that I will never work with you again, and it might affect our relationship,’” Ms. Ballestrin said. The friend agreed to pay with a credit card.

Ms. Ballestrin is also waiting for a payment from her friend Kaitlyn Lynch for coaching her through a conflict with a mutual friend, but she does not have the same worries. For one, Ms. Lynch, who is 39, has reached out multiple times asking which payment method to use — something they had not agreed upon earlier because no contract was involved. Ms. Lynch has a 9-month-old, so “I can only do things in, like, two steps, max,” she said.

The Joy of Working With Friends

There’s an adage that friends and money don’t mix, but the reality is that money touches all of our relationships, and working with friends can have benefits.

First, the trust and shared experiences between friends can make the collaboration more fruitful. For Ms. Lynch, working with Ms. Ballestrin on a conflict they had between a mutual friend was an easy decision, partly because Ms. Ballestrin understood how to appeal to their friend to preserve the relationship. Moreover, Ms. Ballestrin could be flexible about when the sessions occurred and their length, working around Ms. Lynch’s unpredictable schedule as the mother of a newborn.

I chose to work with Eryka in part because, as friends, we had already had conversations around many of the issues that came up in our coaching sessions.

For Mr. Tejeda, working with friends whose values and perspectives he respects gives him confidence. “Morally, you’re going to be aligned,” he said. He also noted how important friends could be for referrals.

Plus, there’s a joy that comes with helping a friend. Eryka reached out because she respected my talents, a validation I appreciate. Why wouldn’t I want to share my gifts with my friends? And if I can figure out a way to “invite the question of money into the space in a way that is nurturing, loving and caring,” as Ms. Ferrell encourages, why not also get paid for it?

“All of us are just building new dreams in the world. So who do you want to be a part of that dream?” Ms. Ferrell asked. “That doesn’t have to be a stranger; that can be your best friend.”