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.
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.
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.
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:
- Lady Boss Mastermind Meet-up Questions from my sister
- How to Bullet Journal: The Absolute Ultimate Guide from Kendra at The Lazy Genius Collective
- The Accidental Creative: How to Be Brilliant at a Moment’s Notice by Todd Henry
- Overwhelmed? How to Save Your Writing Life – Kendra and I talk about one of our boss lady meetings on The Hope*Writers Podcast
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.
After listening to the Hopewriters podcast yesterday, it was like lightbulbs bursting in my head! Unintentionally, my friend Abby and I have done this for years. But we seem to feel like our extended talks on all our “stuff” is a luxury. You have named something that needed naming in my life and I am so grateful. I look forward to meeting up for our first official “boss lady” meeting soon! So glad you also wrote about it too. Brilliant.
You will be such an awesome Boss Lady, Kelli!
WOW! This so good! I have had a freind like this before, but because of life moving and changing She is no longer in my life.. With that comes a regained fear of finding another person to be vulnerable with again. So I have and am looking for someone like this for such a long time, I have pretty much just given up.. However this encourages me to keep looking.. Thank you!
You are the smartest. Will be praying for some boss lady friends ASAP!
Boss Lady is a good way to say it. I like the part about “not taking herself too seriously, but taking you seriously enough”. (smile)
We do have to hop on a plane sometimes. Last summer I met one of my Boss Lady friends at her family cabin in Red River, NM. I finally got to see so much of her history and take it home with me. Now when I think of her, I have a red Jeep, a family cabin and all those hummingbirds in my memories.
You have inspired me to make it a thing.
Keep writing Emily!
Oh I do love my boss lady friends. I just never called them that before.
But they’re gonna just love it when I share this with them …
Love this so much. Thank you, Boss Lady Mentor Extraordinaire. You rock. xo
Love this! Just listened to the podcast earlier this morning on Hopewriters and took lots of notes. This post is better. 🙂 Praying for bosslady friends!
I meant this post is better than the notes I took…just wanted to clarify, because the podcast was super helpful too. 🙂
Thanks for writing this, Emily! This type of accountability and encouragement is so needed for our joy and sanity, huh?
Wanted to chime in for those of you who are on your search for boss lady friends. It’ll happen. You will find her/them. Several years ago I was longing for this type of connection with boss ladies. I prayed a lot –and in a FB group shyly asked if anyone wanted to chat spiritual things and business with me. Three ladies responded and we tested the waters with an initial video chat. We’re all from different states, different time zones. We became fast friends, strong supporters of one another, and have been meeting virtually every other week for several years now. Can’t even begin tell you the amount of business/life progress and growth we’ve experienced together.
So — I’m praying for *you*. The ones searching for boss lady friends. Be encouraged. It’ll happen.
Kaylie Hodges is my boss lady friend. I’ve been telling her we need a writing getaway for a while. So fun to see how productive and enjoyable your trip was!
This is so good, Emily, and something I need. If we want to go anywhere good in life we need to do it with others. I have one person in mind as I write and will be thinking more about this.
I love this! It kind of makes me feel like you’ve been reading my journal though, because it’s like you wrote about everything I’m currently looking for.
Hmmm. I need to think and pray about this one.
I think I have at least one, but I’m not sure how the title will sit with our almost fifty and slightly over fifty brains. I like it; it’s just that when I use certain “in” lingo around my older teenager and young adult sons, they think I’m weird. It’s hard to strike a balance between trying to be understood by the millennials that surround me (and are more and more my pastor, doctors, teachers, etc.) and sounding like the grey-haired (thank God for hair color!), wise women we are.
Thanks for the wise advice. 🙂
A friend and I have taken a girls retreat for the past couple of years. You have inspired me to make sure we keep doing this. I’ll have to share this with her and start calling her my boss lady friend. I think we do that for each other a lot anyway. We met as teachers 24 years ago and have been friends ever since. Great advice as always, Emily. Thank you.
Oh, this is so good! I have been praying for a friend like this for awhile now. I’m still waiting for the right person, but even in the midst of waiting, I’m also trying to BE a friend. I don’t think it will just happen, so I’m working to find the balance of pursuing a relationship like this without being some kind of weirdo, and also allowing God to provide in His timing. So thankful for you that you have these two women in your life.
This is fabulous advice. I actually like to cultivate a number of friends who wisely and happily boss me around when I ask them to. I call them my cabinet. https://goetschblog.wordpress.com/2015/04/22/how-im-like-the-president/
I’ve put it into the universe! Excited for the possibly of a bosslady friend/book husband/ writing partner. I know God will provide.
Mmm, I don’t even know anyone else who tries to write. I have only recently started writing after not doing so for about 40 years. It is difficult getting started, however I feel God’s leading to do so. He is telling me to be His voice. It does take a lot of prayer and listening for what He wants me to say. I will begin to pray for someone to help with accountability in my writing.