15 lessons learned from 15 years of freelance web design

Observations on business, design, and process.

22 min readJul 23, 2016


This is a transcript of my presentation at #nzgather
Auckland, New Zealand — 23 July 2016.

Hi, my name is Benek Lisefski. I learned HTML in a middle school elective class when I was about 15, back in the day when CSS wasn’t even really a thing yet. I was intoxicated by the power anyone could have to design and publish their own website to the world for free. Back then we used a free host called Geocities and all layouts were built in nested tables.

I was into art and design from a young age so I quickly jumped into Photoshop and immediately fell in love with designing graphics for the web. The power to both design and build your creation — to be the artist and the scientist — was magical. I’ve always considered myself existing in both the design and technical realms, but more and more these days I’m focusing on design.

I started doing part-time freelance web design as a university student back in 2001. After I graduated the natural thing for me to do was grow that into a full-time business.

Fast forward 15 years, and here I am now. I’ve worked with some big brands on interesting projects, and been head-hunted by some of NZ’s biggest tech and design-led companies, but I’ve always chosen to remain in my own business as my own boss.

So here are some things I’ve learned over those past 15 years. Most of these are general lessons about business and design process that will apply to a variety of creative roles. Near the end there are some points more specific to web and interface design.

1. Freelancing isn’t easy

Successful people are simply those with successful habits.
— Brian Tracy

I don’t like the word “freelancer”. In fact I never use it to describe myself! So I’m not sure why I titled this presentation the way I did except it’s a commonly understood term.

I consider myself a consultant. A small business owner. A business partner and digital strategist, whose skill happens to be in design. And maybe that’s part of the key to being a good freelancer. It’s all about how you position yourself and your perceived value to your clients. More on this later.

As a freelancer you have to be a business owner, strategist, project manager, marketer, accountant, etc. You can’t clock off at 5pm and leave work behind.

And you have to do it all yourself — it can easily get lonely.

It’s funny that people often joke about freelancers “not having a real job”, when in fact any freelancer will tell you it’s far more demanding than most “real jobs”.

The truth is, not everyone is cut out to run their own business. It takes a lot of discipline and self-motivation. You don’t choose it because it seems “easy”. However, having the experience of running your own business gives you better insight into understanding your client’s business challenges.

So run your business well — hire an accountant, register your company, pay your taxes, track your expenses, chase up invoices, use a contract, write good estimates and proposals. Treat your own business development with respect and that professionalism will reflect on everything else you do.

2. Professionalism, communication, reliability win every time

Being on par in terms of price and quality only gets you into the game. Service wins the game. — Tony Allesandra

This is what your clients will remember you for more than the work you do. This is also the reason client will leave you in a hurry. Focus on customer service as much as you focus on being good at your craft.

I get comments from clients all the time about stuff that seems normal to me or I take it for granted. They say “you’re the most professional contractor we’ve ever worked with”, or “We loved how you communicated the process to us and we knew what to expect at every step of the way”. Sometimes I’m shocked to hear those comments because it feels like this is the way everyone should be conducting their business, but clearly it’s not!

Don’t underestimate how comforting it is for clients to know they are with someone who’s extremely reliable and keeps them well informed.

3. Set expectations early and often

Overcommunicate and overcommunicate and then communicate some more.

Some clients need more hand-holding than others, but all of them without exception need to feel reassured they understand the process of working with you what to expect at every phase.

Communicate frequently and continue to set expectation for budget, timeframes, design and feedback process, how to provide useful feedback, budget, timeframes, what are the next steps, what will I need from you to complete those next steps, budget, timeframes…

End every phone call or email with an outline of what your client can expect next, and what, if anything, you need from them to do that.

Every part of your client relationship will run more smoothly if you’ve set the right expectation up front. And if you find yourself continuously working with “difficult” clients, take a step back and consider whether you’re doing a good enough job preparing them for the process you’re taking them through. Remember, most of them have never done this before. They need you to tell them how the process works.

4. Know your worth

The minute you settle for less than you deserve, you get even less than you settled for. — Maureen Dowd

Don’t be afraid you’ll suddenly stop getting work because you raise your rates. Raise your rates tomorrow. You’ll never regret you did.

Remember that as you gain experience you’re getting more efficient at what you do. Which means you’ll earn less than you did a year ago for the same job because you’ve done it faster — assuming you’re charging for your time at an hourly rate. Your rate needs to increase at least as fast as your efficiency so you’re always charging for the value your client get’s from your time.

Never negotiate price. Negotiate scope. If I client comes back to you after you quote them and says they can’t quite afford it, look for ways to modify the scope of the project to reduce its complexity and price. You can only justify a decrease in cost if you’re decreasing the amount of work.

When you do work for a discounted rate (for a friend, family, charity, etc.) bill your full rate and then clearly mark the discount so they know the deal they are getting.

Another pricing option is to charge based on the value you’re providing your client, not directly on how much time you spend. Figuring out how to price projects like that (and how to justify that price!) can be very challenging and could be a topic for its own presentation. Just know that there are alternative to trading time for money, and it’s well worth exploring those options.

Also know that no matter how successful you get, there will still be some jobs you do more for the paycheck, and some more for passion. As you get more experienced that ratio get’s better.

5. Know your strengths

If you spend your life trying to be good at everything, you will never be great at anything. — Tom Rath

Should you be a generalist or a specialist? There’s a lot of value in both.

Small business and startups find generalists very valuable. They don’t have the time, budget, or resources to hire many specialists for their diverse design needs. If they can find a single person to handle all of their design requirements — branding, product design, web design, advertising, etc., that’s a huge win for them.

Generalists can have better and broader critical design thinking ability as their solutions are having to work across multiple medium and channels. They also have constant opportunity to grow as they are undoubtedly being pushed to go out of their comfort zone frequently.

Larger businesses and agencies see more value in specialists. They have resources and budget to hire a number of different specialists and help them work together to achieve their goals. They may have in-house generalists already but need help in more specific areas. Being a specialist can be perceived as being higher value and has the potential to make more money from the right kind of clients. Only call yourself a specialist when you’re truly special at what you do.

Don’t be afraid that finding a niche will cut out too many potential clients.

I try to be “T” shaped. Be the best of both a generalist and specialist. Be a master of a few skills, but proficient in a wide range of other supporting skills. Regardless of whether you’re a generalist or specialist, I highly recommend you have the attitude that you need to constantly learn and grow. You’re doing yourself a disservice if you’re not adding new skills and techniques that compliment and enhance your core offering. However, never lose sight of what work you’re really chasing. Focus on your bread and butter.

Let your strengths and passions guide your creative flow. (imagine said in Yoda voice!)

If you’re banging your head against a wall stuck on a design that won’t balance or a piece of code that won’t work, do something else! Leave it alone for a while and switch to something that requires a different kind of thinking or simply what you feel like working on the most at that time. This will jumpstart your creativity and then when you go back to that previous challenge your be in a better head-space to solve it.

6. Learn to say “NO”

Every time you say no, it allows you to say one more yes. Every time you say yes, it forces you to say one more no. — Daniel (my osteopath)

Honestly this is one of the biggest lessons for a freelancer. Even for experienced professionals the biggest fear in freelancing is that you won’t have enough work, and you may feel regret from turning down any work opportunity. However there are things that are more important for your long term business grown and personal happiness than being as busy as possible all the time.

Say “no” often!

Say “no” to the wrong clients — recognise those red flags for clients who will end up being nightmares to work with, or simply industries or jobs that don’t interest you.

Say no (most of the time) to the following:

  • Tire kickers or those asking for any kind of spec work.
  • Micromanagers.
  • Poor communicators or clients never available.
  • Mr. “won’t this take 5 minutes?” — doesn’t understand or respect your time.
  • Groups / committee decisions (even worse when they can’t agree on things amongst themselves).
  • Vague clients “I’ll know it when I see it”.
  • Clients who put personal taste over business goals.
  • Band-aid or rescue jobs when client’s have just rebounded from a bad previous experience.

However some of these clients can turn into good clients if you understand the complexities they add to a project and learn how to manage them.

Say “no” to things you don’t want to support. It’s OK to make ethical choices when it comes to your clients. You don’t have to work with gambling companies, or liquor companies, or design Donald Trump’s website if he asks you too. In fact, your moral or ethical client choices can become part of your differentiation and sales pitch.

Lastly, say no to bad design ideas. This leads to…

7. Challenge your clients

My greatest strength as a consultant is to be ignorant and ask a few questions. — Peter Drucker

As a designer, our job is to:

  1. Understand our client’s business, its goals and challenges
  2. Design solutions to overcome those challenges and help users achieve those goals

If a client’s expectations or preconceived ideas are not the best design solution for those challenges, don’t blindly accept them! You’re hired for your expertise — use it.

Question everything.

When met with a poor demand from a client, design exactly what they ask for (or as close to it as you can while still respecting yourself) and then show them an alternative design solution that is better. Learn to articulate your design decisions well so you can convince them why one solution is better than another using plain language.

Your design may not sell itself. You need to present it as the best solution. If you have to, find data to back you up. Find a usability or UX study, or get a second opinion from another reputable pro.

Many of my most satisfied clients are ones where I was involved at an early strategic phase of the product or project’s development and had the opportunity to question and challenge anything and everything that didn’t make 100% sense from a UX perspective. While they didn’t necessarily anticipate my involvement at that level, that critical design thinking turned out to be the one aspect of my job that they appreciated the most.

8. Become more valuable

Always deliver more than expected. — Larry Page

To become a more valuable designer you need to create value for your clients. Clients can get more or less the same value from a number of different designers that have the same level of skill and experience as you do — so why pick you over someone else?

You can be more valuable than your competitors if you’re adding value in other ways beyond just your technical ability. Technical ability is at most 50% of the job — you have to be technically great at design but just as important are things like: process, communication, project management, empathy in design, business acumen, problem solving, conviction, etc.

Always look for ways to increase your value to clients by improving those fringe parts of the job that overlap between design and business. Most often the highest value is in strategic design thinking, rather than the more concrete tasks like visual design. Anything that delivers tangible business benefits to your clients is a huge value add.

9. Be proactive & never stop marketing

Brand yourself for the career you want, not the job you have.

Market yourself even when you’re busy. Especially when you’re busy! Because you always stop being busy. And you might appreciate a little slow patch to recharge after a big project has ended, but not for long!

Show your work on Dribbble, Behance, or other sites to get genuine feedback or simply self-promotion. Don’t be afraid to toot your own horn when you’ve finished a project you’re really proud of. As a freelancer your reputation is everything, so you have to take every opportunity to build that reputation. But also stay humble.

Make new connections all the time. Force yourself to meet colleagues. Look for opportunities to collaborate. One new connection could completely transform your career.

I’ve made an effort this year to get myself out there and create a lot of new relationships with colleagues, web development shops, and design agencies, and it’s already paying off with many new exciting projects that I would have never had the opportunity to be involved with before.

Nothing is more valuable than a good long-term relationship that continues to bring you repeat business. Getting more business from existing agencies or clients is always easier than getting brand new clients. So seek out, build, and nurture those relationships all the time.

Define the industries and types of jobs you love the most and chase the clients you want. Be proactive. Don’t be satisfied with letting work come to you and accepting what falls into your lap.

Do the type of work you want more of. Good work will lead to more similar work. Even if that means start small. Just get a foot in the door of where you want to go.

10. Look after yourself

Don’t confuse having a career with having a life. — Hillary Clinton

Don’t be fooled into thinking anyone who cares about their career needs to work long hours. Balance is key in everything including your work.

I don’t like the term “work / life balance” because that assumes that work and life are separate or that work is inferior to life. If you believe that to be true, start looking for another line of work right now!

The point is: maintain a healthy life whatever you do. Your work is just one part of that. Stay balanced; practice moderation. Stay close to your family, your partner or husband or wife. Have fun with your kids. Follow what brings you joy.

  • Look after your health.
  • Practice good posture.
  • Get a height adjustable sit/stand desk — honestly it changed my life.
    (I got a Herman Miller Riser desk from Unison workspaces Parnell)
  • See an osteopath or chiropractor every now and then.
  • Exercise as often as you can. I run every weekday morning along my local beach.
  • Eat well.
  • Meditate (seriously it’s the bomb come talk to me if you want to know more about Transcendental Meditation, which I’ve been practicing since I was 10 years old).

11. Ignore trends

There is a cool/tool spectrum and we always want to be more tool than cool. Being a tool means you’re useful. Being cool means you’re ephemeral. — Yancey Strickler, Co-founder Kickstarter

Trends come and go in cycles and usually by the time you’ve mastered emulating a trend you’ve seen, it’s already dated. Never impose a particular style on any project — let your client’s needs and customers dictate that style.

I consider my ability to be style-agnostic a strong selling point as a designer. That means clients are coming to be because they value my design process and problem solving ability rather than being impressed by a fleeting trendy case study.

However having your own signature style, can be of great value too. If people recognise your work before knowing it’s yours, you’re establishing an incredibly strong personal brand.

Understand why trends exist and what they were/are achieving. For example, skeuomorphism helped people learn touch interfaces before they were common. Once that need was gone, the trend quickly died. If you’re reproducing any trend, ask what it’s original purpose was, and are you using it for the right reasons? Or any reasons other than trying to be cool?

Daily UI challenges? Don’t even get me started. To be honest I never even look at other people’s “work” online if it’s not real client work, solving real-world business problems and design challenges is what it should be all about. Which brings me to…

12. Look for inspiration outside of the web

Look at books, magazines, posters, furniture, architecture, nature. You can easily get stuck in a vacuum or echo chamber if all you see are popular dribble shots and fancy Behance presentations.

A popular quote about insecurity from social media like Instagram is:

We compare our behind the scenes with everyone else’s highlight reel.

The same is true for any kind of design. Never feel insecure about your design abilities when comparing your work to others “highlight reel”.

Use inspiration as motivation to get better. Maybe that means challenge your clients to be more forward-thinking and push boundaries a bit. Maybe it means challenge yourself to be more detail oriented and really nail those subtle interactions that you’re impressed with. Or maybe it simply means work as hard as you can to satisfy your clients. Afterall that’s who you’re working for. “Likes” from peers doesn’t amount to much at all in the end. Never EVER design anything because you think it will be popular if that compromises the goals of your client or their users.

13. Use good tools

Efficiency is no longer an option but a necessity imposed on all human activity. — Jacques Ellul

Tools don’t make a designer or craftsman, but they can certainly help you along the way.

I don’t mean just design tools like Adobe or Sketch but efficiency-improving services and apps like:

  • Trello — make lists for everything. I manage almost all of my projects through trello cards and checklists. Sometimes I share these with the client for a collaborative process and sometimes it’s just for my internal notes and processes.
  • Toggl — a simple and easy time tracking app you can use in the browser or on your desktop and comes with good reporting for your invoices.
  • InVision — a fantastic web-based tool for presenting design prototypes of any kind and really helps streamline feedback and other design processes.
  • Cushion — a great app for freelancers to manage your workload and scheduling and forecast when you’re over or under booked.
  • Xero — to manage your accounts, expenses, invoices, GTS, taxes. Your accountant will thank you.

Don’t be afraid to pay for good tools. Anything that saves you time and makes you more efficient so you can focus on your design work is well worth its price.

14. Web design observations

What separates design from art is that design is meant to be… functional. – Cameron Moll

  • Don’t skip UX design if you can afford it. Understanding your users and working out how they’ll accomplish the goals you set out for them is hugely important to the success on any interface design. Sell the value of UX design to your clients so they make room in their budget to include it. If you absolutely can’t, fold some UX work into your hi-fi design phase but never leave it out completely and leave yourself reliant on quick assumptions — even more so if they’re the client’s assumption and not yours.
  • The fold, thank god, is well and truly dead. With touch devices taking over there is literally zero barrier to effortless scrolling. And when not on touch most people have at bare minimum a mouse with scroll wheel. Yet clients will still talk about it like it’s the gospel to keep important content above the fold. See “challenge your clients”.
    One caveat: users need to know to scroll. The common practice of a full-screen hero image often doesn’t give a clue that there’s more to discover below. And the band-aid of putting a “scroll down” arrow link (I’m guilty of it on my own site!) means there’s something wrong with your design. Consider having that hero image take up 80–90% of the height so more contents peeks up just above the fold indicating that there’s much more to see below.
    Second caveat: mobile, especially native apps, are still expected (on certain kinds of screens) to fit on a single page without scrolling. Know those expectations before you design.
  • Forget sliders — carousel, whatever you call them. People rarely see past the first slide. Back your design to convey what’s important in an instant even if the page is completely static. You don’t want your “hero” to say four different things anyway. Pick that single goal your page is trying to achieve and be content you’ve achieved it. You don’t have to say everything right up front. People explore. Invite them to explore.
  • Photography always has and always will make or break a project. Probably more today than ever before because everyone has a fast connection and they expect high-quality visuals. If you client doesn’t have good photography, encourage them to hire a photographer to produce that for them. If they can’t afford it, make very careful use of stock photos by avoiding the ones that look like stock photos! Sites like Unsplash can be great resources for more alternative imagery. Please don’t use that one smiling young asian lady that’s everywhere. Use good placeholder images in your designs to show your clients the type and quality of images you expect them to continue to use in the future.
  • Design with real content. If you can, demand it from your client. If they simply can’t have it ready in time, use real content from elsewhere. Pull something, anything, real from their existing website or marketing material. If you have to, pull content from a competitor’s website. Afterall the foundation of your job is designing content. If you don’t have the right content to work with, how can you be expected to do your job?

Content precedes design. Design in the absence of content is not design, it’s decoration. — Jeffrey Zeldman

  • Micro interactions are great. Animating everything is terrible. Be subtle.
  • Think responsively all the time. This doesn’t mean you have to design mobile first — most of the time I don’t. But know in the back of your mind how everything you design will work on tablets and phones so those views aren’t compromised when you design them later.
  • Design atomically. Design patterns, components, and layouts instead of designing pages. Create design systems that can grow with your client over time.
  • Don’t leave developers any guesswork. Define clear interaction style guides for navigation, links, buttons, form fields, error states, and anything else that might not be self-evident in your designs. If you leave those states to someone else, they will never turn out exactly as you expected.

15. Yes, you need to code

Front-end code (just HTML and CSS; let’s forget Javascript for now) is intrinsically linked to the design process. It’s a design tool just as much as Photoshop. — Elliot Jay Stocks

The age old question: Should web designer know how to code?

I’m firmly in the “Yes” camp.

You have to intimately understand your medium and there’s no way to do that without direct experience. But you don’t have to do it all the time. You just need to know how to do it. Just enough to stay current with limitations and possibilities of the technology.

  • Don’t CSS like a caveman — use CSS pre-processors and post-processors wisely. I use Sass and Autoprefixer as my main CSS tools but I don’t want to get into a discussion about all the pre-processing options now. The important points being: know your craft and don’t use these tools as a crutch, but take advantage of anything that will make you more efficient and code easier to work with.
  • Prepros is a great app for managing Sass and Autoprefixer in an easy to use GUI instead of using the command line. It also has some great tools to help preview your work in different browsers and devices through a local server.
  • Don’t fall into the “frameworks are quick and easy” trap. I’ve coded some really complex front-ends and I’ve never used a framework like Bootstrap. Frameworks can be great for prototyping or if you’re coding a site with a very generic design. But if you do bespoke work like I do, the bloated code and fight against default styles will not be worth the benefit. Frameworks can also be dangerous if, like pre- or post-processors, they make you too insulated from the fundamental code you’re working with. Don’t use anything until you fully understand what it’s doing behind the scenes. Plan well, and create just what you need. Frameworks like Bootstrap are also partly responsible for the boring vanilla web design that is so prevalent on the web today. They are not, and never should have been considered a design shortcut.
  • Even if no one else will see you code, write it like they will. Who knows how much you’ll remember two years later when your client asked for an edit. Name things well. Structure it well. Write comments. Follow best practices all the time and create those good habits even for the smallest jobs. And of course if you’re working with a team this is 10 times more important.

It’s OK to suck at freelancing

An essential aspect of creativity is not being afraid to fail. — Edwin Land

It’s OK to fail at freelancing. It doesn’t make you a bad designer. It’s awesome for some kinds of people, and simply not right for others. You may thrive in that environment, or you may be longing for a normal 9–5. If you crave constant social interaction you’ll probably struggle freelancing. If you’re not disciplined, easily distracted, or get bogged down in all the “non-design” stuff that comes along with running your own business, freelancing may not right for you.

But if it is, it’s magical.

I love it because:

  • I like being in control of my own business — its successes and failures are my own.
  • Choosing my clients and projects that I’m passionate about working on.
  • Making my own schedule, and breaking it if I want to. Flexibility to craft my schedule around all of my life — not just work — needs. That means better family time, and more focused work time.
  • Variety. In clients, in project, in processes, in challenges. It’s easier to be creative (and maintain interest and focus) when you’re stretched with new challenges or pushed to work in new mediums or styles with each new project.
  • Work from home, or wherever else I want. Commuting is not worth it!
  • Working super efficiently. Very little wasted time in meetings. No bureaucracy, no politics, no egos to work with. Just you and your work, however you do it best.

Some people use freelancing as a short-term solution between jobs. Some people start out freelancing because they think it’s easy and then end up pursuing a more traditional full-time position. Some people spend half a lifetime at an agency and then burn out and turn to freelancing as a rebirth for their career. And others, like me, will probably be freelancers for life.

Tasman + Pacific

Are you freelance branding expert, designer, developer, marketer, strategist, or any other digital professional at the top of your game looking for something a little different?

I’m starting Tasman + Pacific — a remote full-service design collective consisting of the most talented creative professionals across New Zealand.

For members, it will be reinventing a collaborative design culture for New Zealand creatives to thrive in. A hybrid between the best of freelance life and design agency culture.

For clients, it will revolutionise the way they interact with creative professionals and the design process. Delivering results better than a traditional agency in a more honest, efficient, and transparent process.

If you think you have what it takes to be a member, please get in touch with me. I’m wide open to any feedback on the concept and want to discuss this with anyone interested.

Thanks for listening.

I hope at least one of my points today resonated with you or inspired you to improve your freelance design business, or maybe to start freelancing for the first time.

Any questions?

Please 👏 clap if you found this valuable, and 👉 follow me for more writing like this, as I unfold 17 years of freelance business knowledge 🔥

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I’m a UX/UI designer from Auckland, New Zealand. Writing about freelancing & business for indie designers & creatives at https://solowork.co