Insights from Dana
The Grey Area Between Friendship And Doing Business With Your Friends

Ooh…this is a complicated one.

I’m not sure if there are enough shades of grey to cover all the nuances of this…

But I am going to try to cover this topic anyway…

By discussing two completely opposite situations happening in my life right now.

(And even though there are two…they aren’t black and white!)

One of my absolute favorite clients is one of my best friends.

She is a really high-powered, super successful real estate agent.

We have been friends since the month I moved to Portland.

I have lived in her house.

We have been in a book club for 17 years. (I think we have read more books than Oprah…)

I have been working with her for the past year and completely shifted her business.

Unlike most real estate agents, she takes 8 days off a month and a full 6 weeks in the summer.

And is making more than she ever has.

When we are working together we are all business and it hasn’t changed our friendship at all.


Because in a social context we don’t talk about business.

We can separate our two lives – and it works.

The other scenario is…not that way.

I have a second close friend who is a business coach.

We rely on each other for advice.

We talk through the down and dirty stuff of being in business (because it isn’t all roses).

We share the good stuff and the scary stuff.

While at the beginning of our relationship we did buy services from one another…

We have found it gets in the way.

So, in the last couple of months we have come promised to never sell to each other ever again.

Because (for us and in this case) it muddies the friendship.

As if like magic, this choice has taken all the tension out of the relationship.

It allows us to be truly transparent and intimate.

Without fear and without having to protect ourselves from being sold to.

And so, when it comes to that grey area, I’m sorry to say there is no perfect formula.

My best advice?

Feel it out for yourself in each situation and always have an open mind.

Whatever the outcome, if they are good enough friends they will understand.

Stay connected!


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