Surviving 26 years as a freelancer with sanity intact – with Shawn Hesketh [Q&A]

It’s sometimes difficult to consider how we’ll still be around in 26 hours as a freelancer, let alone 26 years.  So it was a pleasure to host my latest guest on the Freelancelift Q&A call, Shawn Hesketh.

A freelancer of considerable experience who has grown beyond day-to-day project work to establish, a 22,000+ user strong WordPress training community.  From maximizing customer lifetime value, to productizing your freelance service and running projects more efficiently Shawn had some great insights to unveil.

Learn how NOT to do things, and never stop learning

Shawn advocates the approach of constantly embracing new technology but doing so in a way that doesn’t just implement new for the sake of new.

Indeed trial and error, learning how not to do things will be your guiding light long term, so work with new platforms, keep learning but just ensure this within the frame of constantly getting better, or evolution as I like to call it.

Move away from the ‘project mindset’

In my book ‘Stop thinking like a freelancer’ I talk about the difference between the partner and the labourer.  The labourer takes instruction from a client while the partner becomes an asset to the client’s business.

Shawn recommends investing in time deeply understanding a client’s business.  Their market, their competition, their problems.  In doing so you’ll put yourself in a position to be able to offer suggestions for how to improve their situation for the long term.  Ultimately, this is directly linked to the longevity of your relationship with that client and when longevity = ongoing income it pays to get this right.

Provide concise, clear communication at every step

I have no issue with project management systems, however when administration of communication comes at the expense of client clarity they can be more of a distraction than a supporting mechanism.

Shawn discussed a simple roadmap feature he developed. Maybe if I twist his arm once this is live we can update the post with a link to an example!  Give us a shout in the comments if you’d like to see that.

“Ensuring everyone is on the same page is critical to a successful partnership. Effective communication begins with careful listening with intent. How well are you communicating with your clients?”

Avoid disruptions

I enjoyed what Shawn had to say in and around minimizing disruptions.  Its your responsibility to ensure you are connecting with clients in the most efficient way, if client phone calls are disrupting your flow put boundaries in place for handling such communication.

If you’re pulling time out of the project to handle calls and the alternative is email (which doesn’t attract any subtraction of time) your client will almost always choose email.

Exceed expectations

You can maximise the lifetime value of a client by building over-delivery into your projects.  At Tone we’ve achieved a 60% repeat customer rate, with each one of these spending an average 115% on top of their initial order over an 18 month period.

That’s huge for the predictability of my business.   This only happens as we’re consistently delivering far more than what the client expected.  Moreover, they see us as an asset and partner rather than a supplier.

Shawn highlights this is as one of his defining ‘mindset shift moments’.

Side note:  If you’re a designer or developer, Shawn offers a white labeled version of WP101 (a plugin) which you can just add into client sites to overcome the email to-and-fro that comes with teaching your clients WordPress basics.

Head to for a 25% discount. I’m not affiliated with the product, just a good old fashioned friendly gesture!

Leverage productized services

Shawn has built a six-figure business around a minor element of his job (as a designer) which he productized.  Once you launch a site as a designer, there is the ‘client bedding in’ period once you hand over the keys to the admin panel.

The ‘pain’ at this point for Shawn’s client was a complete lack of understanding as to what WordPress could do.  This ended up in pain for Shawn too, as clients were calling and emailing to ask simple questions.   So he built out a series of video training screencasts which developed into WP101 as it is, in its current state.

To investigate whether you can productize any element of what you do, take a look through your inbox, which questions keep popping up and how could you answer them with a book, video, guide or PDF.

Could you sell that?   This is the mental track you need to start down.  I built a full course for freelancers looking to productize their skills over at be sure to check that out.

If you want me to dig deeper into any of the topics above in future episodes be sure to let me know in the comments.   You can find more about Shawn at or

Learn anything? Please share

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  • Shawn Hesketh

    So enjoyed this Q&A, Liam, and thanks again for the opportunity.

    At your request, here’s an example project roadmap from one of my actual client projects:

    As you can see, it’s very simple and just makes use of basic HTML/CSS. But it provides a beautifully simple, “at-a-glance” overview of every step in the project, resulting in crystal-clear expectations on both sides.

    Unlike full-blown online project management tools like Basecamp, a roadmap like this requires no special learning on the part of your client, no need to set up a user account, or subscribe to a 3rd party service. We should never burden our clients with learning a new system just to communicate with us.

    My clients loved this tool because it helped create a smooth workflow that translated into better communication and greater efficiency. But tools like this also help differentiate you from the competition, and that translates into higher earnings.

    Hope this helps!

  • Kerri

    Some very helpful tips here. Thanks for posting.

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