If you’ve ever felt stuck with a big decision you have to make, a project you’re not sure you should take on, or any kind of life or work transition, it helps to have people in your life to help you process that stuff. You need a boss lady friend.


I’ve been in Chicago for a few days with my girl, Shannan Martin. It’s this thing we stumbled into a few years ago when I was writing Simply Tuesday. I needed to go back to my hometown roots in Indiana to soak around in my history and find some words that couldn’t be found anywhere else.

Shannan lives in Indiana so I figured it would be fun to meet up with her and so we did. We ended up spending a few days in Indianapolis to connect but also to write and talk about writing-related stuff. That was in 2014.


We ended up doing something similar in 2015 and then again this week. It has officially become a thing.

We each get our own hotel room because if we shared one we would never work. But then after hours of writing alone, we join up over some nachos, chat it up about all the things, walk around long enough to feel city-like, and then run back to our rooms and write for hours until it’s time to eat again.

As it turns out, I’m an internal processor who needs to externally process with people I trust. But here’s something I didn’t know for a long time – those people don’t just show up like magic processing faeries, waiting on your doorstep to ask you curious questions and offer you sound advice.

Those relationships have to be cultivated, sought out, and reciprocated.

If you’re reading this right now thinking that you need that kind of friend, or if you already have a friend you would like to do this kind of intentional time with, it doesn’t have to be as fancy as flying to Chicago and staying in hotels.

My friend Kendra and I do this on the regular. She lives a few blocks away from me and every now and then, we’ll text each other with these words “Okay, boss lady question:” and then we’ll launch into our non-urgent but completely-making-us-crazy question, thought, or idea.

Boss Lady

Sometimes, when the situation calls for it, we even plan a day-long meeting for serious boss lady conversation. In fact, about a year and a half ago when I was feeling overwhelmed with my writing and didn’t know how to be a person, I called on Kendra and she helped me learn to become a sane writer again.

We talk all about that meeting and what happened as a result on this week’s episode of The Hope*Writers Podcast: “Overwhelmed? How to Save Your Writing Life.

The point isn’t where you go, what you eat, or how long you stay. The point is that you have a friend who gets you, a friend who knows how to listen and ask good questions, and who understands the delicate balance of never rolling her eyes at you but also calling you out when you’re acting like a crazy person.
chicago rain

If you’re thinking you could use a boss lady friend but you’re not sure what you’re looking for, here’s a few things to get you started.

Here’s what you’re looking for in a boss lady friend.

She must be:

  • a good listener
  • not judgey about your twisty, weird, insecure fears about the work you’re doing
  • not take herself too seriously
  • take you just seriously enough

And you must also be all of those things for her.

You have to ask her.

If someone comes to mind, tell her to read this post and then ask her if she will be your boss lady friend. Make sure she knows why you are asking her this and what you hope for from the boss lady conversations.

If no one comes to mind, start paying attention. Pray for a friend like this. If there isn’t anyone in your hometown, consider friends you’ve met online who do similar work you do or who might have similar struggles.

Remember it isn’t just about you getting support, it’s also about you offering support to her. Frame it that way when you ask her and chances are she’ll jump at the chance to connect.

Plan a boss lady meeting.

Once you have your boss lady friend, look at your calendar and find a stretch of anywhere from 3 hours to 3 days. You can start small at first if you have tiny humans living in your house and cannot leave overnight or if you are a normal person with a job and a life.

Choose a place to meet where you can stay for a while. You may even want to meet at one of your houses, but wait until the house is empty. You can’t have a boss lady meeting in the Chic-fil-a playground area is what I’m saying. If you meet in public, choose a booth or a table in the back, as sometimes boss lady meetings include tears and snorting.

Have a loose agenda.

Before you meet, know what you’re going to need feedback on. Be prepared to ask her real opinion about things you’re doing (but only if you really want to hear what she has to say which of course you do because she’s your boss lady friend). Come with both your best and worst ideas. Be open.

Don’t hide the ugly stuff.

The most important part is you must be willing to let her see the underbelly of your work. Share your idiot moves and don’t laugh when she shares hers.

boss lady

Remember, boss lady friendship doesn’t have to be only about work. You and your boss lady friend might meet to talk about schooling options for your kids, meal planning, or church stuff.

The idea is to have a friend you can trust who is willing to go deep with you to listen, offer feedback, and help you either solve a problem or feel better about the fact that the problem is unsolvable so let’s just eat a cookie.

Here are some more resources for you and your boss lady friend:

Now go forth and rock that boss lady meeting! And if you don’t have your person yet, keep your eyes open. Now that you know what you’re looking for, she might come along sooner than you think.