What I’ve learned by Working in the Divorce Business for 11 Years

By Jackie Pilossoph, M.A., Founder, Divorced Girl Smiling

When people ask me what I do, my reply is, “I’m in the divorce business.” This is usually followed by, “Oh, are you a divorce attorney?” to which I respond, “No, I have a media company called Divorced Girl Smiling that helps connect people getting divorced with trusted divorce professionals.”

In my heart, I feel great about the work I do, benefiting those facing what perhaps is going to turn out to be the hardest time in their lives. But let’s be honest, Divorced Girl Smiling is a business, and one of the reasons I’m in business is to financially support myself. Just like divorce attorneys, mediators, coaches, mortgage lenders, real estate agents, financial advisors, and other divorce professionals. But what we also all have in common is (at least I hope so) that we are passionate and dedicated to helping those who really, really need us.

It’s hard to believe I started Divorced Girl Smiling 11 years ago. As a former TV reporter and Chicago Tribune columnist who loves to write, Divorced Girl Smiling began as a blog in 2014; a chance for me to vent about my own divorce issues. It was an outlet. Nothing more. That year, a divorce attorney called and offered me $50 a month to advertise. She is the person who opened up the door to my realization that people getting divorced could greatly benefit from connecting with really good divorce professionals. 

Since then, Divorced Girl Smiling has added a podcast, a mobile app, a free consult for anyone facing divorce, and 42 trusted professional advertisers. Divorced Girl Smiling is a big business now, and I attribute that growth almost entirely to following my mission: This business first and foremost is about helping support people who are getting divorced. It’s pretty simple. Follow that path and everything else sort of falls into place.

For example, have you ever had one of those days or weeks when you just feel burned out? You’re overwhelmed, you feel like you’re at your desk 12 hours a day or more, and you feel unappreciated? You may even doubt why you’re in this business. We’ve all been there. Those are the times when I say to myself, “Follow the mission. Keep helping people.” Why? Because there is no better feeling and no better source of self-worth than feeling like you are giving back in a positive way and changing lives for the better. And that’s when the success comes. That’s when opportunities present themselves. But most importantly, that’s when fulfillment and purpose come. 

The divorce business is a massive industry. According to IBISWorld, the revenue of family law and divorce lawyers alone in 2023 was $12.8 billion. But make no mistake, in the divorce business, everyone knows everyone—or at least knows “of” each other. Each has a reputation and people talk. I’ve run across the best of the best, the worst of the worst, and everyone in between. That’s just my opinion, though. Maybe some in the industry think I’m the worst of the worst! I hope not.

Eleven years in the divorce business has taught me a few things:

  1. Your competition isn’t your enemy. In fact, you can learn from them. There’s enough business to go around and sometimes your competition is too busy, and if that person trusts you, he/she will pass along business to you. 
  2. Forget Even-Steven. In other words, if you do something for one of your colleagues, don’t expect something in return. Just do it to be nice and to help someone else who is working hard, just like you. Good karma will come back to you from a different person. For example, if you agree to do a podcast guest swap and you have the person on your podcast and then they never reciprocate, don’t sweat it. You did a good thing and your “payback” will come from somewhere else in the universe. 
  3. Don’t be cheap. Pay for the drinks or the lunch or the dinner, even if you don’t get the business in the end. People remember things like that. If you spend money on something that didn’t work, try to forget about it and move on. Plus, it’s tax write off! Having a business entails risks. The next thing you might spend money on might turn out great! All you can do is educate yourself and trust your gut.
  4. Try not to talk negatively about anyone else in the industry, no matter how frustrated you are feeling. It could come back to haunt you. Plus, talking negatively about someone just feels kind of icky. You’re better than that.
  5. Be friendly with others in the industry but set boundaries. In the end, this is business. That might sound cold, but it’s reality. Honestly, I have made many dear friends in the divorce business, and have actually lost a couple because it became too personal and hard to stay objective. 
  6. When you feel betrayed by a competitor, remember that for every one “bad guy,” there are 10 good guys! Focus on the good ones—your mentors, people you love learning from, people you know are rooting for you, and people who when you leave a lunch with them, leave you with a warm feeling and good self-esteem. Distance yourself from the ones who you feel don’t have the best intentions, who are jealous of you, and to put it bluntly, just annoy you! 
  7. When you’re feeling burned out, and thinking, ‘Maybe I need to change careers,’ follow your mission. Forget about everything else and remember the people you help with your wonderful work. They depend on you. 

The divorce business is tough. Think about where our clients are when we meet them: devastated, scared, irritable, stressed, sad, angry and bitter. It’s hard to have meetings all day long with people in this mindset. It can feel depressing and exhausting.

For me, I get emails and I have consultations with people like this every day. It’s important to remember to stick with the mission because after they work with you, the part you might not see is the person’s post-divorce life—the life they have months or years later, when they gain peace and acceptance, when they become empowered and independent, and when they fall in love again. I only know this because I sometimes get emails months and years later from men and women thanking me for Divorced Girl Smiling, telling me how much it helped them through the divorce, and expressing how much the divorce professionals from Divorced Girl Smiling helped them get to a good divorce settlement.

Like many other industries, the divorce business is highly competitive and can even feel cut-throat, at times. But it’s also an amazing industry because I’d say most people I’ve met are in it for the right reasons. The passion and dedication I’ve seen in so many of the professionals I know is heartwarming and inspiring. The things I’ve learned by knowing other divorce professionals is valuable. So next time someone asks you what you do, and you reply “I’m a divorce lawyer” (or your profession), say it with pride. Say it while remembering your wonderful, beautiful mission.

Jackie Pilossoph is Founder of DIVORCED GIRL SMILING, the company that connects people facing divorce with trusted, vetted divorce professionals. Divorced Girl Smiling (DGS) is also a podcast, website, mobile app, and well-known brand and community. DGS has a mission to empower, connect and inspire men and women before, during and after divorce. Pilossoph, who holds a Masters degree in Broadcast Journalism, is a former television news reporter and features reporter and writer for the Chicago Tribune. Her syndicated weekly column, LOVE ESSENTIALLY, was published in The Pioneer Press, The Chicago Tribune, and all Tribune Publishing editions for 6 1/2 years. Pilossoph was also a Huffington Post divorce blogger for five years.

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