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Can You Hire Friends In Your Business & Not Fall Out?

There’s so much advice about hiring friends in your business.

OMG don’t do it, it’s a disaster!

OMG, you’ll LOVE it, best thing I ever did!

To be clear I’m talking about hiring your friend in a freelance self employed capacity here. Although a lot of the same principles apply to employed, when your friend depends on you for a job, that’s a whole ‘nother level altogether.

I haven’t hired any friends to work with me but I do work for my other half on live streaming and video gigs during the year.

Instead, I asked my lovely virtual assistant (VA) Lizzie to interview her friend, Carla Watkins, the photographer at my upcoming Demystifying Limited Companies day retreat.

Take it away Lizzie…


Can You Hire Friends In Your Business & Not Fall Out?

To answer this question I had a chat with the lovely Carla Watkins (yes, there was tea and cake involved).

Carla is a writer, photographer and dreamer who believes in magic, unicorns and the gorgeous rebellion of making your life absolutely your own.

This is Carla…….



Right, time to brush away the crumbs and get down and get down to business!


Who are you currently working with that you have a personal relationship with?


  • Annastasia, who’s one of my best friends and the other half of my business Ink Drops
  • Louise, who’s one of my best friends and my business accountability buddy/lifesaver/stylist
  • Lizzie, we are now each other’s clients now.

A sizeable number of my clients for another of my businesses, Unfurling, and for websites have been friends first.

My main business mastermind started off as business relationships and they’ve now become close personal friends. 


How do you meet and how did the business relationship evolve?

Almost a perfect 50:50 split between being friends first, and having a business relationship first that the friendship came from.
For the friendships, it was a natural flow – Annastasia and I had very similar ideas (but very different strengths) and Louise and Lizzie keep me sane in the madder moments of self-employment alongside a day job!
The business relationships that evolved into friendships were usually word of mouth clients, and during the first few business calls we clicked, so began to talk about other things too.


Do you have any rules that you follow to separate the business and pleasure?

Nope, because none of my businesses feel like work, so our conversations and meetups flow seamlessly between work and play focus.


The best bits about working with a friend?

  • Someone to bounce things off
  • The ability to do things so much better than you might on your own
  • Being able to be completely blunt and not having to sugarcoat their lack of techie ability
  • Excuses to spend more time with people you really like who make you happy


The worse bits about working with a friend?

Having to ‘fess up’ when you’ve ballsed up or missed a deadline. None of them ever shout at me, but I feel far worse than I ever do for clients I don’t know.


What does a typical working hour look like for you and your friend?

For Ink Drops and my business accountability/mastermind friends, its a scheduled two-hour Skype or in-person meeting.


It’s sometimes accompanied by wine, and always with a notebook and Google Drive open so we can work collaboratively on anything from tweets to customers to a new book to a combined crowdfunding effort or planning the next trade show.

Sometimes there is structure and sometimes we just meander, making sure that we cover everything we need with a simple list.

With my clients, a coaching-style conversation is sandwiched between personal catch ups – for websites this gives me insight into what they really want (as opposed to what they say they want), and for the alter ego work I do, getting to know people personally is the best way to help them unlock their best selves.


Would you recommend mixing business and personal relationships and why?


The work I do brings me into contact with the most amazing range of like minded people who I’d never have otherwise met, and it seems a great shame not to follow through on those potential friendships if there is interest and enthusiasm on both sides.

I’ve also had great success stories working with friends and the relationship becoming more business focused for a period of time, it is good to have a testbed for new products and services now those relationships are already established.


Do you work with friends in your business?

How was it for you?

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Do you need support becoming unstuck so you feel free to grow your business? (working with a friend optional)

Explore my retreats, have a look at my sole trader and limited company coaching packages or contact me.

If you want easy to understand courses and guides with a sense of humour and mentions of cake, have a look in my shop.

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