The Beginning of Business Besties

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.

A Business Bestie Is The Best Investment

The life of a solopreneuer or small business owner can get lonely. That doesn’t mean you need to commit to a team or a business partner. You can find the support you need in other small business owners, entrepreneurs or in a community.

This connection is truly a critical ingredient in your recipe to success as an entrepreneur and has many benefits.

Support From A Boss That Gets It

If you missed, this episode on :10 to Being Boss, I shared that my secret weapon for making decisions in my business are my boss friends.

After I have looked at my data, checked in with my values, and done all my homework, my boss friends are there to support me in any tough decision making.

Because of our relationships, they understand my business and I understand theirs. This goes beyond surface level and allows us to tap into each others experience and insights. This means that they will ask questions I haven’t thought of yet.

And most importantly another boss can lend a diverse perspective to any opportunity or challenge to make sure I am making the best decision I can.

A Source Of Honest Feedback

When it comes to taking feedback, I think it is important to know whose opinion matters. Your business pals will likely be included on the short list of people you’ll go to first when looking for feedback.

When you have a true business bestie, they’ll be a source of honest feedback for you and your business. Because of that deeper level of understanding of your business and goals, their feedback will most often times be in alignment and should be applied.

The other plus side to this is that if you have a really strong business bestie relationship, they should also be comfortable telling your the truth and calling you on your crap, from self-limiting beliefs to needing to do the work.

Motivation and Accountability

The journey through business is not always an easy one. Sometimes the goals you set or the moves you need to make feel big and scary.

Having a relationship that can be not only a source of motivation but also one of accountability can be critical to your long term success. Motivation and accountability can look different for everyone, so finding someone that aligns with you will be key!

Fueling Your Business Bestie Relationship

In Episode 87// Mixing Friends and Business with Shayna Haider and Gala Darling, 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.


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 Zoom 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 you’re 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.

What Having A Business Bestie Means To Me

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.

Three business besties at a NOLA Retreat

Finding Your Business Besties

When you work for yourself, connecting with other business owners takes work and can sometimes feel difficult. To make sure you are connecting with the right people, it’s important to understand what type of relationship you want to have with any potential boss connections.

Consider the type of support you need in your business, what contribution or strengths you can bring to the relationship and maybe most importantly how you like to have fun and unwind.

Attend Conferences + Retreats

Many small business owners budget to attend creative or business events each year. An obvious reason for attending these events is to educate yourself, learning tips, trick, and strategies from experts.

However, attending a creative or business conference or retreat is the perfect way to meet like-minded people or even find opportunities to collaborate. These events bring together diverse groups of business owners that already have a lot of things in common.

You can hear how Nikki Nash and I connected at Alt Summit in Episode 265 // Market Your Genius with Nikki Nash.

Join In-Person or Virtual Coworking

Coworking is the perfect way to meet other entrepreneurs and get some work done! Both in-persona and virtual coworking have their benefits.

There is better accessibility with virtual coworking. That means you don’t have to leave the house and you might meet a much more diverse crowd of business owners.

With in-person coworking spaces, you get the change of scenery. You’ll be able to make in-persons connections and you might also get the added benefit of access to additional events and networking opportunities.

You can try out virtual coworking in the Being Boss Community for free!

Connect + Engage on Social Media

Social media is a great way to find fellow bosses you want to get to know. You can start a genuine connection by interacting with their content and starting conversations.

You can also send a DM letting that boss know you want to connect for a deeper convo!

Join A Community

Here at Being Boss, we want you to be surround by other smart, creative bosses! Because when you connect and interact with other small business owners – magic happens.

You’ll be inspired to show up, get motivated to set goals, and be held accountable to do the work!

So why not surround yourself with people you look up to or that have already accomplished the things you aspire to?

That is why we built the Community, a place where you can connect to other bosses who understand where you are and what you’re going through in your business journey.

Community is an important part in our overall success and it’s a great shortcut to finding your business besties! Our Community tier is completely FREE! Join us today and get connected with other business owners, creatives and entrepreneurs!

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.