Two girlfriends on laptop making a purchase

The dire warnings against mingling money with friendship date back to Shakespeare, when Polonius, the chief counselor to King Claudius in Hamlet, says, “Neither a borrower nor a lender be, for a loan often loses both itself and friend.” They didn’t have electricity or equal rights during the 1500’s, but they were still enlightened enough to understand a thing or two about money: it often brings out the worst in people; a loan to the wrong friend could cost both the cash and the relationship.

I got a stiff reminder of this lesson a couple of years ago (my bad, Polonius), when a “mom friend” of mine, Ally, asked to borrow $500, stat. She had an urgent need for seed funding, and I am generally the type who will help a frog cross the road if need be, so I obliged. No interest, no strict payment terms, just goodwill. “Pay me back when you are financially comfortable to do so,” I said. “Don’t worry about the timing.”

You can guess how that turned out.

I am without the money I lent, and without the friendship I thought I had. We’d been close friends since our kids met in first grade, and she ghosted me after I did her a favor.

Despite my friendship-induced PTSD from this incident, I believe money and friendship can mix… with the right person. For me, that person is Jody.

I met Jody in kindergarten, and we immediately bonded over our shared first and middle names (Jodi Lyn and Jody Lynn, respectively). During 40 plus years of friendship, we survived a duel for the same boy in elementary school, high school cliques, double-dating two boys named Jimmy, 80s hair, playing the same varsity sports, attending different colleges, being roommates in our early twenties, multiple moves, marriages, divorce, trips abroad, health scares, pregnancies, motherhood, and my mother’s death.

(She never once asked me for money during all of these years of friendship, by the way.)

After my mom’s funeral, I became fixated on fulfilling her dream of writing a children’s book. I spent countless hours brainstorming and researching possible topics, and sketching out copy. When my son finally gave me the winning idea by innocently asking, “Mom, what was it like when I lived in your belly?” I devoted every minute of my free time to answering his question.

Multiple drafts and rewrites ensued at various coffee shops, between nursery school drop offs, pick ups, and freelance projects. Once I got the book to a place where I felt others could read it, I called her. Jody is not only an incredibly talented illustrator, she is a mom extraordinaire. I knew she would be a perfect second read, and she would see my vision better than anyone else.

I didn’t have any money to offer her at that point. I didn’t have anyone backing me or believing in me. I had no guarantee the book would ever be published. All I had was my word—a mutual trust earned through decades of friendship—and that was good enough for her.

It took five years to get it done, but, now, our book baby, When You Lived in My Belly, is available for pre-sale and will be out on August 6th. We effectively worked together despite multiple obstacles, differences of opinion, zero funding, countless roadblocks, and almost daily tests of patience, perseverance, and emotional fortitude to bring this book to market. There was a little strain and push and pull but, mostly, there was synergy, shared commitment, and resolve to see it through.

If you’re considering mixing money with friendship, how do you avoid an Ally? Here are five ways to pick a Jody:

  1. Assess the friendship. Women have a way of disarming each other and connecting on a deep level rather quickly. Close friendships can be formed during in-depth conversations at kids’ sporting events, school functions, or at the gym. Suddenly, someone who was never in your circle is at the center of it—but do you really know her?
  2. Take a hard look at the history of your friendship. Have you had a conflict before? If so, how did you resolve it? Differences of opinion are inevitable when dealing with money and business partnerships. Is your friendship strong enough to overcome challenges and weather storms while remaining intact? Do you really trust her or are you taking a leap of faith?
  3. Get to know her professional persona. Does she have expertise that will complement or clash with yours? Many friendships are based on similarities and not differences, but diverse skill-sets and perspectives make partnerships thrive. What’s her work style? Have you spoken to people who have done business with her in the past? Does she share your work ethic? You need to consider every positive and negative attribute before you take a leap.
  4. Take the rose-colored glasses off. According to the Bureau of Labor Statistics, the average American spends 8.5 hours a day at work, but entrepreneurs clock much more time than that. While it may be tempting to believe that spending 50-plus hours per week with your bestie is your version of a professional utopia, consider the alternative. Does she have quirks or issues that already grate on your nerves? Have you built enough friendship equity to spend more time with each other than you do with your families?
  5. Have an honest conversation about the structure of your business. Make sure you have transparent and thorough conversations about hierarchy, titles, hiring practices, goal-setting, financial investments, and work expectations. Better yet, capture the conversation in writing when it comes to anything involving money.
  6. Prepare for the worst, and hope for the best. The Small Business Administration states that while nearly 80% of small businesses survive their first year, only 50% last five years or longer. You’re about to embark on a partnership that has more chances of failing than succeeding. That’s the reality of starting any business, without the extra layer of complication a friendship can bring. Make sure you pick the right friend.

This article originally appeared on SWAAY, a website dedicated to changing the narrative by sharing the stories of women who are challenging the norms and giving them a platform to participate in more meaningful conversations.