Published Mar 27, 2022
In late 2017, I quit full-time work to start freelancing. Designers tend to do this for a number of reasons. Sometimes it’s about freedom - to break free from office politics, set working hours or having to sit in an office all day. Some designers go freelance with an ideology, interested only in working with certain clients on particular projects that they see fit… like only tech startups or companies that work towards social good. Some designers are just tired of their dismal salary and want to find clients that will pay good money for their work.
While all of these are good reasons to leave the confines of traditional full-time employment, I chose to leave to discover a world outside of the industries I’m familiar with. I wanted put my skills to good use and design innovative products in emerging industries around the world and hopefully, figure out what I was truly passionate about in the process and eventually determine where I should work next. I figured this should only take a couple of months at most, so in the meantime I’d do some freelancing to keep my head above water financially. Plus, I’d hoped that freelancing would give me a moment of clarity between the fast-paced startup environments I was used to.
Starting an agency wasn’t entirely intentional. I was quite fortunate in the first few months of freelancing - picking up projects that required a lot more than just a single product designer… complete rebrands and product redesigns for companies that required a small team of designers and developers to execute. I always found it hard to say no to a client, not because I find it generally difficult, but because I loved the idea of helping them out as much as I could and seeing how far we could take the relationship.
Lacking the capacity to handle all these tangential creative requests myself, I ended up subcontracting a lot of work to folks I’d collaborated with in the past, either at previous roles or just friends. This ended up working really well until I noticed that pitching “Hayden and friends” wasn’t particularly clean, plus the demand was continuously rising. So, after about three months, I incorporated a design agency and moved towards handling creative direction and operations.
Moving from being a hands-on product designer to an agency director was a massive change, both in the type of work and mentality. But I guess, as Douglas Adams so eloquently put it, “I seldom end up where I wanted to go, but almost always end up where I need to be.”
The agency path was really cool as I got to meet lots of people, see how different industries worked, contribute to a lot of amazing products, brands, websites which is exactly what I wanted. Plus, with everyone having come from a startup background, we ended up filling a gap in the market for a reliable, end-to-end agency for startups that didn’t feel like you were working with an agency. We also spent a lot of time on our own brand and website. I'm a huge fan of showing rather than telling and creating a brand that sells itself. One of the last things we did was a rebrand for Jellypepper that led to some incredible results.
As fun as it was, there was always an underlying issue — the second-degree relationship we had to the client’s product. I like actually investing in the products I work on (literally and emotionally) but you can’t do that with an agency, not really. Even if you find a product you really like, there’s a hard start and end to your involvement in a project and you’re always limited by the budget. I come from a background of working directly on products, helping ideate, build, launch and grow them, so this was always a bit of an issue for me personally.
Eventually, seeing these great products come and go, I realised that I’d prefer to be working on a single product suite and brand, making them the best in the market. After 4 years, I figured if I don’t step away from things now, I likely never will. There’s no perfect time to change tacks, so it’s better to just get it done.
Anyway, here's some things that I learned along the way. Maybe they'll help you, but more likely me when I inevitably forget.
When Jellypepper started, the idea was to help our clients from start to finish with whatever they needed. This means that we took on any form of creative work as it meant being able to provide more value to our clients. But here’s the thing: just because you can do something, doesn’t mean you should. You should only offer what you’re exceedingly good at. Don’t worry - you’re not expected to know this upfront. It took us 9 months and a few project mishaps before we realised that taking on every problem at once is not a sustainable way to solve any of them.
Nowadays, we offer a whole range of things because we’ve created teams that are able to effectively fulfill those needs. We’ve written playbooks for our product design methodology that walk you through our process of using UX, UI, interaction and motion design principles to create the best solution for any given problem. If we need ad-hoc work done like videos or photography, we team up with some of the best freelancers in the world.
The hardest thing about managing multiple projects at once is context switching. It’s a popular term in agile team management that basically means jumping between various, unrelated tasks. It haemorrhages your productivity through constantly switching mindsets or, more commonly, the contexts of tasks.
I’m not a big fan of multitasking at all and much prefer the concepts of deep work - the ability to focus on a piece of cognitively-demanding piece of work without distraction. I think it’s a skill based on two important factors: your ability to work on a certain task for hours on end without being distracted; and your time-given opportunity to do so.
One of the biggest time-sucks is unnecessary meetings, so we don't run them. If we do need to meet, we talk about everything we need to with 5 minutes maximum each topic. It’s like Twitter - constraints enforce brevity, encourage creativity and promote getting to the damn point.
The reason I crave deep work is because it’s not always readily available - I can have between 10 and 15 client meetings a week and they really disrupt your workflow if you let them. I try to organise all my meetings back-to-back on certain days so that for 3 days a week, I can be in deep work mode.
Design agencies operate a service-based business model. Practically, this just means you can grow… but not really “scale”. Every new client you bring on means more people needed to complete the work. In the first few months, I would wake up every morning to a slew of Slack messages with urgent reminders, overdue tasks, people needing things. It was not fun at all.
Being good just isn’t enough. If you allow your agency to take over your life, it will… very easily. You need a framework around how you operate and learn to compartmentalise. While project work should never be rinse and repeat, you will have to implement a methodology for time’s sake. Create templates for your questionnaires, request for briefs and moodboards. Write a sales pitch and automate sending your proposals and agreements, adding a personal touch where possible.
This doesn’t just apply to design work either. Running a design agency means that sales is going to be part of your job. For traditionally-employed designers, being responsible for your own work, time, contacts and income can be a pretty big change of pace. The only way to manage this at scale is by creating a sales funnel with CRM and Sales software so you can track a client all the way from visiting your website to having a meeting, sending a proposal, paying you and receiving their work, then following up afterwards.
It took me months to implement processes and it was just in time too. Another week of manually typing up proposals for leads that didn’t pan out would have sent me over the edge. After turning all my tasks into processes, what I assumed was me finally losing my mind from falling behind on everything was just the overwhelming silence of being on top of everything.
Jellypepper went from being a small to a medium size studio way quicker than we should have. While this sounds like a fantastic problem to have if you’re small, the amount of work we were taking on started to affect our existing clients. I was receiving 60 new emails a day. I only had 30 minutes a day to handle them which wasn’t enough, so we took up to 3 weeks to reply to a client or lead. Fortunately they were patient people, but it wasn’t sustainable.
It’s not just project work either - running a business means you’ll need to handle accounting, taxes, BAS statements, salaries, superannuation and all sorts of fun legal stuff. Then there’s project management, resourcing and scheduling and making sure everyone’s got what they need to do a great job.
If you’re hell-bent on being the best designer in the world and designing everything yourself, hire people to manage your clients and run your business. If you’re ready to let go of your hands-on approach and run the business, you’ll need to grow a team, foster a good design culture and manage your clients directly to handle the workload.
Part of managing the business side of the studio means knowing the numbers inside and out… and not just the financials. You need to know your metrics. What’s your agency's NPS score? What percentage of clients do you lose… and for what reason? Did you meet your financial goals for this quarter? What’s your client retention like? Once you know these metrics, you’ll know when to circle back with lost leads and how to close more deals. If you choose to focus on one side of your business, the other will inevitably suffer and ruin you.
Determining and holding your values closely is the key to success as an agency. It’s what determines the work you say “no” to and how you interact with your clients. We inherently value a lot of things… people, design, good culture. We also value knowledge. We’re always reading, exploring and discovering to be the smartest we can be. There will be people who don’t vibe with our message and that’s okay - it means we won’t waste both of our time trying to make a relationship work that clearly won’t.
Your values tie in to how you operate as well. Since we value knowledge, it’s important to us that we deeply understand the company that we’re working with - not just their product and service offerings but their mission, goals and vision for the future of the company. Understanding the business takes time and energy, so we factor into our proposals. If we don’t do it, we won’t fully understand your business, we’ll make mistakes and miscommunicate. There’s a much higher chance the project will fail or not be what you want it to be, and we’ll both end up having wasted money and time.
If you’re going to handle sales as well, you need to figure out your sales strategy and how this aligns with your agency's values. There’s a lot of sales tactics out there, most of them rely on figuring out what drives your customer, what they fear, and digging into it. I’ve found that the strategy that works for me is simply being upfront about what you do and how you do it. I’ve found people generally want to work with you if you share the same attitudes and values, but are talented in things that they aren’t. If people vibe with you when you’re honest, they’ll be a fantastic client past the initial meeting.
When you make the shift from an office environment to an agency, co-working space or even your apartment, it’s easy to forget the things you take for granted, like a healthy social life with colleagues, a well-lit office and ergonomic desks. When you take the plunge, it’s easy to just lie on your bed with your banged-up 15" Macbook Pro and make do with what you have. It’s part of the romanticism of bootstrapping your own company.
For a while, I did exactly that. My old workspace was my bed, away from any decent light source which, combined with a 16+ hour work day led to a solid Vitamin D deficiency. It’s important to optimise your new workspace for productivity - there’s plenty of research around how light affects productivity and mood.
Lastly, remember to work smarter, not harder. It’s a cliche quote but it’s absolutely true. Schedule some time every day for your health. Your clients won’t expect you to take care of their product if you can’t take care of yourself. Plus, you won’t get very many sales if you’re sick or dead.
One last thing I wanted to mention is that there’s a fantastic book that helped me when I was about to throw in the towel early on. It’s called Run Studio Run, a book by Eli Altman that aims to help small creative studios build and grow their businesses. It helped me so I recommend you check it out if you’re looking for a bit of guidance, particularly in the early days.