Coaching is something you should consider outsourcing as a freelancer – yes, really!

As freelancers, the idea of outsourcing can seem like a really big expense. It can feel – and often is – a big spend to pay someone else to do something we anticipate we could do ourselves. From podcast editing and website updates, to tax returns and social media, we often end up doing everything ourselves because it feels cheaper, and perhaps we want to learn, too.


Outsourcing is also usually a practical thing. As well as the examples above, there’s VA work, bookkeeping, perhaps even things like tech or writing your blog content.

They’re all tangible. You outsource, you pay, and you get something you can see progress with in return.

Think of coaching, and it probably doesn’t seem like something you’d categorise as an outsourcing expense. I certainly used to feel like that. The idea of paying to talk about things I felt I could ‘sort out’ for myself felt indulgent and even a waste of money. And, as a freelance writer, I didn’t have a lot of spare money! Through my experience of training as a coach as well as being coached, I have begun to change my mind, and I’m sharing this to get you to wonder if you might do the same.

For me, hiring a coach to help with your freelance business is as valuable an ‘outsource’ as an accountant, IT support or VA.

Coaching is hugely beneficial to freelancers, in my opinion, for myriad reasons. There is a whole world of people we can bounce ideas off in the self-employed community, from close friends and former colleagues to groups such as IPSE and Freelance Heroes. All worthy places. However, asking a friend what you should do will bring their opinion. It will also bring their wants and needs, even subconsciously. While they may have your best interests at heart, they will also be advising you to do something that might not, deep down, be the right thing for you.

That’s where a coach comes in. Talking to a coach – especially one who specialises in working with freelancers – is a process whereby you come to the conclusions. There is no ‘kind advice’, just questions which will lead you to making your own realisations and decisions. It’s not easy – it means you have to dig deep for your own answer and to make your own goals.

Essentially, you are outsourcing your mental to-do list, your hopes and dreams and your goals and plans to someone who doesn’t have the bias to say ‘go for it!’ when it’s not the right thing. You see, a coach won’t tell you what to do, whether to make a leap or go for it with a new client. They’ll help you reach those decisions. You brief them in the same way you would to any other outsourcer – for example, you set the agenda for the session, or sessions, you choose whether to stay on the topic. A coach doesn’t tell you what the theme of the session is, so that’s in your control.

Just like an IT wizard might help sort out your computer issues, a coach can help sort out your ‘what now/next?’ issues.

So how do you end up seeing that tangible result that we all love with outsourcing? After all, if you are going to invest in coaching, you want to see some kind of results, right? I agree.

First of all, there’s the way it will feel – clarity, confidence, decision making that’s all in your control.

But then there are other things – the choice to raise your prices after a session about it, and that leading to higher income, perhaps a decision to launch a new project leading to new clients. You might work through your confidence with networking thanks to coaching, and find yourself attending more events, building your network and growing your business as well as your confidence.

The scope is, arguably, endless – once you have experienced coaching you will find you can apply it to your freelance life, thinking ‘what would my coach say right now?’ rather than ‘what would my well-meaning friend ask?’.

Investment in outsourcing will always feel like a ‘treat’ or an extra expense to me, but through my freelance career I can say whenever I have, I haven’t regretted it. I hope this post would help you to consider how coaching is another on the outsourcing list, rather than something you don’t feel you have the budget for.

IPSE member Jenny Stallard is a freelance writer, podcaster and coach. Her wellbeing platform, Freelance Feels, supports the self-employed with community and coaching. www.freelancefeels.com 

We’re always on the lookout for ways where we can promote member-driven content so if you would be interested in contributing a blog for the IPSE site, please contact [email protected].

Meet the author

Jenny Stallard