A Freelancer Who Actually Takes Time Off? Meet Penny H.

Before we dive in, we wanted to thank you for the response we received for our first interview with Jordi Pages. We loved hearing that you found it helpful and inspiring - that’s exactly what we hope to achieve with every one of these blog posts. 


So let’s get to the next one! Introducing Penny H.

Interview by Bernard / Blog written by Teri

September 2, 2021

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Penny on the zoom call with Bernard

Tell us a bit about yourself. 


I’m a freelance designer specialising in packaging and illustration.

I’m from Denmark, but I was always drawn to England. When I was 18 I realised I wasn’t ready for Uni yet, so I took a gap year working in a pub in London!

I headed back home to get my bachelors in Visual Communication. It was a bit of everything - half advertising, half design. In a three year course we had only two weeks dedicated to packaging, but there was something about it that I loved - the 3D element, the fact that it’s a real product. And I like paper - there’s no way I was going to do digital. 

To finish the course we had to do a three month internship somewhere, so my packaging teacher told me: “You need to go to London. London is the packaging hub for Europe, or probably the whole world.” 

So I came back! I found an internship at Creative Leap, which was not really my style, but it was the only paid internship I could find and it was a pretty good deal. 


How did you land your first job out of Uni?

After the internship, I wanted to stay in London. I landed a one week internship at an agency called Big Fish, which they then extended to two weeks. They were happy to have me but I felt I wasn’t making much progress, so mid-week I told them: “Sorry guys, I gotta go. I’m looking for a job and I don’t feel like I’ll find one here.” 

I’m not sure how people would react to an intern saying that nowadays, but it worked out pretty well for me then. That Friday I got an email asking for my phone number, and I got a call that Monday morning, 7am. It was the boss, asking me what I wanted - what kind of job, what kind of package. I was caught off guard but we ended up agreeing on a low but decent figure for a junior.

Some of Penny's visuals for Big Fish


I started the next day. Everyone still thought I was the intern, obviously, but I ended up staying there for three years.

I was working with big brands there - Dorset Cereals, Gü, Kallo. Very British and quite illustrative. It was 2005, and it was all about Facebook and Twitter content at the time, so I got to spend two days a week focusing on illustrations for social media.

Three years in - what happened next?

Big Fish was a small agency - I was one of 10 designers when I left. I learned a lot during my time there, but I wanted to experience work in a bigger team. 

An agent reached out to me and I got an interview at Design Bridge, which is a giant. The design team is 100 people in London alone. I worked there for five years and learned so much: working with global brands, training in New York, the works. It really balanced out what I had learned from the smaller agency - the two jobs were a good combination.


Packaging design @ Design Bridge

Was that when you decided to go freelance?


Honestly at that point I was a little bit burned out. In giant agencies, when things get too much, it’s easy to hide away. I was also dealing with some personal things at the time too, so with everything happening at once, I didn’t really care any more. I lost my passion. 

At the time, my good friend had moved to New Zealand. Perfect timing. I quit my job and booked a six-week visit. I planned to take my laptop with me and sort out my portfolio while there, but that didn’t really happen. I just enjoyed the break. One of the perks of working in a large agency is the number of contacts you make, so I felt that the portfolio could wait.  


Penny in New Zealand

Sure enough, my first client was actually a contact I had made while working full time, and my second client was one of the owners who used to work my first job. We never overlapped while there, but I reached out to her on LinkedIn and we still work together today.

Since then it’s all been through word of mouth and recommendations. I don’t actually have my website up yet because I’ve been so busy with work (but it’s coming soon!)


Was LinkedIn useful in finding clients?

Yes! I just went through my LinkedIn connections which I had made over the years. I took note of anyone who was working in an agency that I would like to work with, and I just sent them a message. That’s how I got my biggest client.


You juggle packaging design and illustration - Where do you find inspiration?

When introduced to a brand, I start off by researching the visual elements and how it could be represented in different styles. My main inspiration websites are Behance, Pinterest and Designspiration but my favourite blog for vintage illustration inspiration is theanimalarium.blogspot.com which gives you something very different from the typical design blogs.

There’s also Instagram of course. If you had to look at the accounts I follow on there you’d find that it’s probably 50% illustrators and 20% design - and then 20% memes and 10% friends!



Talk us through a typical job - who are you working with, and for how long?

I mostly work with agencies who bring in freelancers to work with their team for a short while. I’ll typically stay with that team for a week, or up to a month or two. 

Sometimes I’ll be asked to work on a project from scratch, and I’ll be there from the start. It’s nice to be with the same team for a longer time - you actually get to work on the different stages of the project instead of only dipping in and out.

This sort of project work is closer to permalancing than freelancing. I never really intended to do that, but it feels good to be a part of a team on a longer booking, especially during the pandemic.


Is there anything you miss about being a full-timer?

At first I missed my lunch breaks with my friends. When you’re a freelancer no one speaks to you or asks you out for lunch. You won’t be working there for long, so they don’t make an effort. I understand sinceI was the same when I was permanent. Sometimes you sit with other freelancers and there’s more chat, or I get deep into an audiobook instead.

After a while though, I decided I was going to be the social one. I cannot not talk to people when working.

Besides, there’s the hiring aspect to consider. Of course, your talent is important. But if they don’t like you as a person, they won’t book you. Attitude matters more than you think. So many people know what they’re doing as designers, but their social skills are lacking. If you think about it, agencies want to hire freelancers that they’ll enjoy working with. 

What do you hate the most about freelancing?

The Pencil system in London. Agencies “pencil you in” for bookings, but it is not a final booking. It can be difficult to balance bookings and pencils without disappointing someone. It’s frustrating when you have to deal with a last minute cancelation but it is also part of the freelance deal. As frustrating as it is, I do understand and try to stay positive, no agency wants to deal with an angry freelancer.

Character & style development @ The Adorned

And what do you love the most?

I’m aware that this isn’t the case for many people, but I like the freedom. I have been really good at taking time off, and I schedule buffer weeks in between jobs to give myself a break.

A lot of new people are scared of saying no to work, thinking they’ll be forgotten and won’t have jobs down the line. The risk of no guaranteed work is always there. But I realised that I’m currently paid more than I was while working full time, so I can actually make time for everything now.


Could you break that down for us? 

I split my month up like this: In the first two weeks, I make enough money to cover the home. I put the third week towards pension and holiday pay, which leaves me with the last week that’s a bonus! So if I get a cancellation and I don’t have any work for a week here and there, that’s ok. It was always going to be a bonus. That fourth week is where I take my breaks. 


Penny's freelance monthly plan!

Personal project when working @ Design Bridge NYC

Of course you gather them up and spread them out depending on the jobs and circumstances. When the pandemic hit I didn’t have work for a whole month, but that was ok because I had already banked the bonus weeks from previous months. 


Tell us more about getting through the pandemic.

I was super lucky - the week before it hit, I accepted a three-month booking with a tiny agency, which I’ve never done before. Even when it hit, they kept the booking and I ended up staying there for a year. Eventually they ran out of work, which is normal when working with small agencies.

I was sure to invoice every 2 weeks, because I didn’t want to get caught out if the company had to close. Of course some agencies want you to invoice every month, so it’s not always possible.


Packaging design @ This Way Up

Are you invoicing as a Limited Company, or as Self Employed?

I set up a Limited Company straight away. I’d heard that a lot of big agencies will only work with Limited Companies, so I took the advice of a friend of mine who had used Accounts Studio and told me to start there. That’s how I got my company stuff sorted.

Did you go for that one recommendation straight away, or did you shop around?

I’m in this Whatsapp group of freelancers who were talking about the different rates they pay their accountants, so I knew what was out there before deciding. It’s not just about pricing though - there’s also the relationship to consider. A friend of mine had a terrible accountant and actually got in trouble for it. 

I’d heard about horror stories out there, and I didn’t want to get into that. I had 2 good recommendations from friends for Accounts Studio and the process seemed smooth, so I chose them. I liked that it wasn’t some big agency you’re dealing with. You’re not just part of a big machine.


🙏 Thanks for chatting with us, Penny!

Check out more of Penny’s work and get in touch with her over Instagram or Behance

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