You all know that Kathleen and I started as business besties—gabbing about all manner of life and work via Skype for years. Over time, that morphed into being each others’ clients, doing collaboration projects for clients, and then into starting Being Boss, an actual business partnership. Now, most of our chats are more about our next launch cycle together and less about how the other would handle a sticky client situation. (Phew! ::wiping brow::)

But even now, we still have business bestie conversations—convos where we’re not talking about Being Boss (though that certainly does usually come up), but where we try to put that aside and go back to talking about what we used to talk about, as friends hustling it out. We discuss our businesses (Braid Creative and Almanac Supply Co), work/life balance, and more.

But, to tell the truth, Kathleen isn’t my only business bestie. I have several cool, creative cats in my corner who are rocking an online business and who I like to meet up with on the regular to chat life, business, and the fun and weird gray space in-between. All of these relationships are important to me because they’re imperative to the development of, well… me, but also to my business.

In this week’s episode, we talked about how those business bestie relationships begin, and it’s usually a simple email or sharing social media comments that get’s it all started. But, how do you grow that first interaction into something more? Here’s a look behind the curtain:


All of my best business relationships happen because one or both of us have a routine of emailing occasionally. Usually once a month, or at least once a quarter, it hits one of us that we haven’t chatted with the other in a while. So, we craft a quick email to set up a meeting, usually something like, “Hey, I miss your face. Let’s chat.” Quick and easy.

But, insider secret: I use Contactually to manage most of my contact reminders. Nothing like a handy tool to help you manage all the things that are in your head.


Business bestie meetings are just as important as any other meeting or appointment in my life, meaning they make it onto my calendar. We schedule a time and it goes into my Google Calendar, and that’s it. It’s a thing that I’ll attend, come hell or high water. (Eh, maybe not, but you get the picture.)

For more insight into how I actually do this, be sure to check out Episode #66 // Managing Your Calendar with Gavin Zuchlinski from Acuity Scheduling.


Then, I show up—easy as that. One of my favorite things about being so active on the web is that I can be really good friends with someone literally half-way around the world. So why wouldn’t I have a Skype lunch date with my pal in Portland? Or an after-work cocktail with my girl in Australia? Talk about a rich life!


Business besties can’t be shy about the details. Talk about your struggles. Share your wins. Share numbers and details and the lessons you learned. Dive deep into your experiences. These are not relationships where being shy is going to behoove you.

Then listen. Be a really good listener and learn to ask good questions. Help your bestie dive deep, and they’ll do the same for you.


The best business bestie relationships have a basis of reciprocal assistance. You help each other.

  • Hey, tell me about that new platform your using – should I use it too?
  • What’s your biggest struggle right now?
  • What’s your next step forward?
  • How can I support you?

Use your business bestie relationship to help you move further in your business. Be each others’ sounding board and accountability partner. Brainstorm and plan together.

NOTE: If you’re asking for your business bestie to do time-consuming work that’s based on their expertise, either do an even trade of goods or services (talk to your accountant) or pay them. Business besties don’t just trade tips, sometimes they trade work for money. Don’t burden your relationship by assuming you get work for free.


Once you know what you’ll both be doing next, do the thing. Take action. No one wants a dead weight business bestie. You work to inspire each other.

And then you start it all over.

– – – –

My business besties are my people. Even if they’re on another continent, these are creative folks living their dream by doing business in the online world. I hold these relationships with as much weight as my “real life” friendships, and in many ways, these people understand my wins and my struggles more so than my family or friends who don’t operate online businesses that are juggled with a family.

These people are my community of equals—bosses who are rocking it out in their own right, and who share as much insight with me as I do with them. They support me and my growth and vice versa. They’re relationships that are worth beginning and nurturing and carry potential for great outcomes that I know I don’t even see yet.

I mean, look at Kathleen and me. Who knew we’d be here all those years ago. Thank heavens we made our relationship a priority. Amen.

Emily is the co-host of Being Boss Podcast, helping creative entrepreneurs learn how to run their own creative business with the tough love they need to hear to do the work. She also owns Almanac Supply Co., a maker and retail business focused on creating and curating items to help you live closely with nature, based in Chattanooga, Tennessee.