December 13, 2020

You can’t do it all: How outsourcing keeps my side hustles running


I’ve been working on side-projects for well over a decade now. First it was a t-shirt company, then a little bit of freelancing, and now it’s creating things to help designers get better at their craft. Over the past ten years when I’ve spoken to people about these side hustles there’s always one question I can guarantee being asked: “How do you do it all?”. 

And just as the projects that I spend my time outside of work on have changed over the years, so has my answer to this question. I’ve been through many phases of routines and disciplines to get things done (including a spell where I woke up at 5am to edit videos before beginning my commute in London) and learned time and time again, usually the hard way, that these routines need to grow and change as you do. 

I was recently promoted to Creative Director at ConvertKit; a role that gives me added responsibility and a lot of exciting challenges. But it’s also a role that’s taking up a lot more brain space and energy. My job is important to me, but so are the side hustles I’ve been building for years. I knew I’d have to make a change in order to do them both well. I needed help to keep everything running. So, I hired an assistant (actually, two of them–more on that later). 

As an independent creator outsourcing can actually be kind of scary. You’re hiring someone to do something you are technically capable of doing yourself; likely something you have been doing yourself for a while. You have a certain way you like things. Will the person you hire be able to do them as well as you? Is it worth the cost to hire? Or do you just need to get better at time management? How do you even find the right person? What should you even outsource?

I want to share with you how I answered these questions for myself, and how I’ve ended up with a part time team of five people helping me run my business.

Step one: Realising you need help

The assistant(s) I hired recently aren’t the first I’ve outsourced work to. The first person I started working with on a regular basis is my wonderful video editor, Nancy.

In 2019, having been uploading videos to my YouTube channel for more than 5 years, I was starting to burn out. My uploads were getting more and more sporadic and I’d stopped enjoying the process of making a video. I’d film something and the footage would sit on the memory card for a few weeks until I could bring myself to open Premiere. I used to love the creativity of editing, but now I just wanted to get it done as fast as possible so I could get to the part I loved most: sharing the video and seeing responses from people in the comments.

I knew other YouTubers had editors helping them, but I felt silly considering it for myself. I mean, I wasn’t a big famous YouTuber with a busy life. I had the skills to edit myself. I just needed to be more disciplined and get it done.

Needless to say though, that wasn’t a sustainable approach. I got over myself and decided to try outsourcing my editing. Because if you have the means to, outsourcing the parts of your process you don’t enjoy is what will allow you to keep the passion for your projects alive. That was certainly the case for me. It still makes me so happy to receive an edit for review from Nancy, knowing that someone much more talented than me took the raw footage I filmed and shaped it into something that is engaging and drives the points home. I love that I can end up with a video I love without having to cut a single clip myself. It’s what has kept my Youtube channel going as I start my 8th year on the platform. 

Just a few months ago, I went through a similar internal struggle in deciding to hire an assistant. Who did I think I was, considering hiring someone to manage my emails or the publishing side of my content? Assistants are for fancy important people, right? I just needed to be more disciplined and get it done. 

Sounds familiar. 

Like with the decision to hire an editor, I realised that if I wanted to keep my business running while also freeing up the mental capacity needed to do my new job well, I should outsource the things that are draining me so that I have more time to spend on the parts I love. In trying to balance life, work and side hustles; time is precious. Why was I spending time doing something mundane or – in the case of my email inbox – living with overwhelm when I could hire someone to help make sure the time I spend on my business is on things that move it forward?

There’s nothing wrong with needing help. Sure I could have kept editing and emailing all on my own, but it would greatly reduce my capacity to create. I’d have less time and energy to act on ideas, and I’d be limiting the potential of my business.

Step two: Deciding what you need help with 

As a creator with a personal brand, something I worried about with outsourcing was losing the heart of my content. If I wasn’t making the decision of what clips to keep in a video edit, if I wasn't designing an Instagram story post myself, was the content still me? Was it still authentic? 

My personal connection to my audience is incredibly important to me, so as I decided what parts of my process I could outsource I asked myself these questions:

  • What do I love doing most? 
  • What things can only be done by me?
  • What would be inauthentic if it were done by someone else?

Here’s what I came up with:

  • Making/designing
  • Writing
  • Speaking
  • Planning what topics I want to make content about
  • Communicating with my audience

The list was shorter than I expected honestly. I realised that as long as it was my ideas or experience that was being shared, as long as it was my words forming the content, as long as I’m proud of the finished product; the content would be authentically me. It didn’t matter if someone else had put the pieces in place for me in the form of editing a video or uploading and sharing the content. Because at the end of the day I'm still in control of how it gets edited and shared.

These are the things I now outsource:

  • All video editing
  • Podcast editing
  • Video uploading (including ordering captions, getting correct links in the description, setting up end screens and card links)
  • Content promotion (including the layout of posts and stories for Instagram, caption drafting, adding links to my social media bio and website)
  • Newsletter layout and sending 
  • Email inbox management (sorting, starring, and declining any sponsorships I’m not interested in)
  • Paying invoices
  • Bookkeeping
  • Miscellaneous information gathering/research tasks

Having someone else take care of these things has freed up my time to write, to dream, to plan, to create things purely for the fun of it (like my new Twitch channel!) and most importantly, to stress less and take better care of myself. I’m still in the early days of working with my assistants, but already I feel the reduction in overwhelm. It's freeing. 

Step three: Finding the right people

I’ve been lucky that I haven’t had to look to far to find the help I needed. I’m a big fan of hiring within my network or that of a friends rather than googling “video editors for hire” and browsing a dozen portfolio sites. It’s really important to be able to trust the people you bring on to your team, and I felt more comfortable hiring within my network rather than posting a job description and sorting through applications. 

This is my team and how they came to work for me:

  • Our podcast editor, Áine, was a listener of our show Design Life who reached out one day to offer her services (we took her up on it and outsourced podcast editing and show note writing to her when the show started making some income via our community membership).
  • My video editor, Nancy, was a viewer and member of my Patreon who offered to help when I started talking about how much I hated editing.
  • My other video editor, Belén, is the sister of a friend here in Valencia.
  • My admin VA, Katie, is a friend with an accounting background who reached out when I tweeted about wanting to hire a VA saying she’d love to help on the side of her day job.
  • And my content VA, Chloe, is the odd one out here as someone who wasn’t in my network previously. She contacted me through honestly the best cold email I’ve ever received and after chatting to her on a video call I knew we’d get along great.
How good is this cold email from Chloe? I'd tweeted that I as looking for a VA who worked with creatives and she made sure to explain how her experience lined up with that.

Why two video editors? I started working with Belén recently in order to increase capacity. Nancy has her own day job and like any other human needs to take breaks sometimes! So having two editors I can count on reduces the need for me to ever open Premiere Pro and edit a video myself. They both do fantastic work, take my feedback really well and adapt their edits to suit, and also bring their own ideas in to the edits which overall makes my videos so much more special than the ‘get this done as quickly as possible’ approach I was taking previously. Hiring for this has elevated my content and helped me to continue to enjoy producing videos.

Why two virtual assistants? Because each one has their own specialty. Katie is incredibly organised, and with her accounting background was keen to take over reconciling my bank transactions in FreeAgent and making sure everyone gets paid. Plus, because she’s a friend, I knew I could fully trust her with my financial information. Chloe doesn’t offer a bookkeeping service to her clients, but she specialises in helping creatives. As well as being organised and reliable she’s got design chops of her own which have definitely come in handy, and she also brings her own ideas to the table. I’m someone who just doesn’t think about content cross-promotion, so to have Chloe upload a video for me then take the initiative to send through a beautiful graphic in my brand colors suggesting we post it to Instagram has been wonderful!

In all cases, I’ve found help by first voicing that it’s something that I need. If you need help in your business, talk to people about it. Bring it up in conversation, tweet about it, let it be known that you’re interested bin hiring someone and see who comes out of the woodwork. Do a few test projects, and if it doesn’t work out with that person–keep looking. Oh, and always make sure you have a contract in place. 

Step four: Figuring out a process

In order for outsourcing to actually help decrease your workload, you need to stop doing the work yourself. I know that's may sound obvious, but letting go of things can be really difficult. When you’re an independent creator used to doing everything your way, it can be hard to let someone else take over – even if it’s a task you hate doing!

If you hire help and find yourself micromanaging every single thing it could be for a few reasons:

  • You haven’t shifted your mindset to your new role in your business–you’re there to lead and work in your zone of genius, you’re not a one-woman show anymore.
  • You didn’t set your contractors up for success by giving the information they needed to do their job well.
  • Or maybe, you haven’t hired the right people.

Transferring your knowledge to someone when it’s a task or process you’ve previously been doing yourself can be tricky, but it’s worth persevering with. Document things and make requests for the way you’d like something to be done, but be open to their ideas too. After all, you’ve hopefully outsourced to someone who specialises in the thing you need so by allowing them to bring their own ideas to the table you’ll likely end up with a higher quality finished result.

With my content editors I found I had a lot of feedback the first few times they made something, but they quickly picked up on what I liked and didn’t. So if you outsource something and don’t feel initially like it saved you a lot of time, stick with it a while and it should get faster the more you both ease in to the process (and if it doesn’t, maybe it’s time to try someone else).

As far as tools go in my process of outsourcing, I set up a Slack channel that I use to communicate with my VA’s (one of the things I needed help with was email overwhelm so I certainly didn’t want to add to that for our communication!). And with my video editors I simply sharing a Dropbox folder with the footage and any notes I have about the video whenever there’s a new one ready for them to edit. I’ve been using Notion for my newsletter content so Chloe always knows where to grab it from when a new issue is ready.

I’m sure my process will evolve over time, but for now this is working out well for me.

Investing in the future of my side hustles

I’d be remiss if I didn’t touch on one last (important) factor involved in a decision to hire help: the cost. There’s no doubt that hiring the help of five people is cutting into the profits of my side hustles. Last year my income from side projects was around £20,000, or around £1666 per month, and I’m easily spending over £1000 a month on my contractors now. But as long as I’m not going into the red on this, I’m okay with it. 

I believe that the expense of hiring help is actually an investment into the potential of earning more income from these projects in the future. A bet which seems to be paying off as only 6 months into my accounting year I’m at over £19k for side hustle income already. Hiring help has freed up my time to focus on the big picture, but also to just do things purely for the fun of it too (like streaming on Twitch!). I’m confident the investment is worth it for me.

So, that’s how I’ve been outsourcing help to keep my side hustles running alongside my full time job as Creative Director at ConvertKit. I’m grateful to have found these wonderful people who are aiding me in bringing my ideas and plans to life.

My answer to the “How do I do it all?” question is different now: “I don’t. I have help.”