Going Freelance: The Pros & Cons With “Top Web Designers”

Making the choice to go freelance (or independent as I prefer to call it) is a tough choice, I wish I had more knowledge about the pros vs cons when I made the decision to work independently.

Many of us are big fans of top web designers and their work. Throughout the years these guys published many tutorials, websites, and scripts to help designers and developers improve their skills. Today, we will sit down with them and get to know their experience about going freelance.

Let’s take a look at a large group interview with top web designers about the pros & cons of going freelance.

For this interview each participant was asked the same set of questions. Below you will see the questions listed with the corresponding responses from each person.

Thank you to all of the contributors who were so gracious in taking their time to answer my questions. If you have any additional questions, leave a comment and - just maybe - they might respond. No promises :)

1. What is the one thing you like and hate most about working "independently" as opposed to working "in-house"?

Elliot Jay Stocks of ElliotJayStocks

The absolute best thing about working independently is that I get to decide how, when, and where to do things. I've got to stick to client deadlines, but if I'm sensible about planning, I can swap projects around to suit me, and I can take time out whenever I want if I need to do something non work-related. I can work on the road, which allows me to do a lot of travelling, and I can do a variety of things - designing, illustrating, writing, speaking - all under the umbrella of work. And if I want to take a few weeks off to record a new album or design myself a new personal site, I can. It's brilliant!
The downside of independent working is that you're solely responsible for the way a project turns out, and it can often be hard to juggle the actual design work with things like project managing, client liasing, and all of the other stuff that comes with being self-employed. Plus it can sometimes be lonely; I miss the banter I had when I was working in-house with a bunch of other people. But these are small things; for me, the benefits far outweigh the drawbacks. I can't see myself going back to full-time employment any time soon.

Liam McKay of WeFunction

I think the thing that I prefer most, is that I certainly feel more valued, you get a lot more thanks, a lot more feedback and a more direct feel of responsibility for a good project. It’s not to say that there aren’t companies out there that don’t do a good job of making their employer feel valued. It’s just there’s definitely a bigger sense of value & appreciation attached to work when you are working directly for yourself and you have more of an involvement in the project.

What I like least about working independently is definitely the whole organization side of business. Answering emails, sending invoices, keeping track of payments etc isn’t really where I thrive. It’s not that it’s too difficult, there are a lot of tools to help speed up loads of these tasks, it’s just easy to go into freelancing thinking that all you’re going to be doing is designing, and forget about the things that go with it behind the scenes. But having said that I’ve realized now how important that side of work is, and am doing a lot better than I was.

Steve Snell of VandelayDesign

All of my experience in web design has come from learning on my own through books and tutorials, personal projects, work for friends and family, and working independently for clients. I've never worked for a design firm so it's hard for me to compare the two. However, I have had several years of employment in other industries, and I think in many situations the frustrations are similar. I prefer working independently because I can choose what I want to do and who I want to work with (provided I have the right opportunities and the income potential to make it work). If I'm talking to a potential client and I don't think it is the right fit, I can just be up front and recommend someone else to them. It saves me headaches, allows me to spend time in more effecient ways, and hopefully helps the client too. Likewise, if there is a client that I really want to work with, I have the flexibility to try and make that happen. There's no boss to tell me what I have to charge and what clients I have to work with.

On the other hand, I'd say the negative is that I'm limited to what I'm able to accomplish on my own. There's no team of people with different and complementary sets of skills. Outsourcing is always an option, but without the right relationship and organization it's not really comparable to a strong team of employees from the same company.

Chris Coyier of CSS-Tricks

I don't actually work "independently" per se, but I do work from home. The lifestyle is the best part. Not having a commute saves loads of time, stress, and gas money! I like intertwining the daily chores of life with my workday as a way to take a break and refresh. Office folks need to dedicate so much of their precious spare time to things like laundry and dishes, where I can take care of that stuff while getting up to stretch my legs. The time this saves is amazing and adds up to loads of truly "free" time.

Danny Outlaw of OutLawDesignBlog

The one thing I like most about working from home has to be the ability to work my own hours. If I want to stay up until 5 in the morning playing Halo 3 online, it's not a big deal. If I want to leave work in the middle of the day and go work at the coffee shop via laptop, I can do that.
On the flip side, the thing I dislike the most of working from home, is working from home. Sometimes its easy to get cabin fever from working from home all day everyday.

Niki Brown of Design-O-Blog

The thing I enjoy the most about working independently or freelancing is - the freedom. I can work really early in the morning or really late at night. I can work anywhere that has an internet connection. This freedom is alluring to a lot of people thinking about making the freelance jump - but it also has its drawbacks. Working independently can get lonely and feedback can be hard to come by. This is why having a network of designers around you (via twitter) is a helpful thing.

Brian Hoff of TheDesignCubicle

Working as an independent designer I have always enjoyed interacting with the clients head on, instead of getting the details and clients vision from another source ("the higher ups"). I also enjoy the ability to work with clients that I feel comfortable with and projects I feel excited about. There's nothing worse than designing a project you don't feel positive towards. Trust me, the end results will show it. On the flip side of things, I have always disliked doing the 'paperwork' part of freelancing – preparing contracts, invoicing, client management, etc. But someone's got to do the dirty work, right?

Walter Apai’ of WebDesignerDepot

Working as a freelancer is great. I set my own schedules and I don't have a boss to report to. I certainly feel free to express myself and take my business in any direction that I want to. I don't feel any creative constraints and the sky is truly the limit. As a negative, I guess social interaction is what suffers the most from freelancing, unless you take clear steps to address this.

Garth Humbert of IAmGarth

I really enjoy the flexibility. From your work schedule, to type of projects, to workload, to where you work - you get to make the decisions.

The toughest part for me is the business side. These are generally non-billable, non-creative tasks that are necessary to run a business: Accounting, Generating Estimates/Proposals, Taxes, going to the Post Office, etc.

Liz Andrade of CMDshiftDesign

The thing that I find to be the biggest benefit to being on my own is that I have control over the time I work and the money I bring in. This is a plus on a multitude of levels! In my former in-house position, I had a set salary and really no cap on the amount of hours I would need to put in everyday. Being independent, I now set the price for the work I do and because of this allow myself the freedom to have early afternoons if I need them, move my work schedule to fit other obligations and to budget time for learning news skills and improving my existing ones. It seems like my in-house position was always working at full force, never a break, never a moment to look back or forward, and always 2 steps behind. My days now are much calmer (even when insanely busy) and because of this I'm producing better work and am much happier!

Maybe no one will believe me, but I seriously don't have anything I like more. Sure, it is nice to know for certain what your paycheck will be every week - but I am happy to trade that in for having greater earning power and more control over my career! I guess I miss getting those free fancy dinners at year end holidays? ...but, that a real stretch.

Calvin Lee of MayhemStudios

What I like most about working independently is no boss/supervisor micro-managing me; I’m in control of the project and the decisions are made by me. I’m able to work faster and more efficiently, with no interruptions. Working in-house, it’s hard taking direction or respecting someone with less quality work than you.

The least favorite thing about being independent is the business side of design. It’s very time consuming, takes time away from designing. These include: getting the proper licenses, permits, taxes, business forms, dealing with clients, self-promotion, finding clients: bringing in work, networking, dealing with client/vendors, bookkeeping, managing/tracking projects, contracts and getting paid.

2. What advice would you give someone who is currently thinking about, or beginning to make the switch to the working independently (freelance)?

Liam McKay of WeFunction

If you're currently in a business which does something similar to the kind of work you will be doing independently take an interest in what other people are doing, and how the business is run. How does your company approach clients, what strategies to they have in place and how many techniques can you bring over into your own work. If you have a good understanding of how all aspects of business work then it's not going to be too much of a shock when you're out there doing it on your own.
I'm talking in really simple terms here, simple observations about the day to day tasks that everybody in the office takes care of, don't take it too far and get yourself in trouble looking at things you shouldn't!

Chris Coyier of CSS-Tricks

I'm not quite sure, I've never taken that plunge myself. I know just how people in this position feel though. They are thinking how nice it could be to be your own boss. Potentially make more money. Work on projects of your choosing. Sounds great, but then you worry about finding enough work, losing insurance, losing retirement, etc. The big thing for me is how stressful freelance can be. There is no buffer zone between you and clients when you freelance like there is when you are just an employee of a larger entity. And we call know how clients can be. Hair-pulling at best, hostile at worst. Not to mention all the billing and complicated tax stuff...

Danny Outlaw of OutLawDesignBlog

Like I said before, being good at networking can go a long way to bring you more work, save you money, and make you more money. Focus on networking and develop a brand for yourself. The rest will fall into place.

Elliot Jay Stocks of ElliotJayStocks

Independent working isn't for everyone, so try and get a feel for it before you make the leap. The switch isn't as hard as you think, but make sure you've got plenty of freelancing experience. For me, that meant doing freelance projects during evenings and weekends, and I did that pretty much the entire time I was working full-time (4 years), on and off. It allowed me to build up my portfolio, got me doing projects I wouldn't usually have encountered in my day jobs, and taught me how to be self-disciplined and deal with clients. Fortunately, I also had the chance to work from home for the majority of the week when I was working for Carsonified, so that gave me a good taste of home-working life without any of the risks.

Also, get an accountant. They're surprisingly cheap and will save you absolutely loads of time, effort, and money.

Niki Brown of Design-O-Blog

I would suggest that you save up as much money as you can before making the jump. This will help you have something to fall back on in case all hell breaks loose. :)

Brian Hoff of TheDesignCubicle

Make sure the time is right and you have all ends covered. Prior to taking the freelance plunge get yourself and your business organized! When I started freelancing more and was working my way towards full time freelance, I wanted to create invoice templates, contracts, etc. that way I could spend more time on things of more importance, such as marketing, networking and, of course, designing.

Walter Apai’ of WebDesignerDepot

You need to have a strong discipline to be a freelancer. Set your work times and stick to them. It's easy to let work overflow into your daily life and work shouldn't become your life. Make a clear cut separation between your career and your personal life. Also, be proactive and stay on top of your game by constantly learning new things and evolving. Finally, sit down and think really hard if this is what you really want and what your reasons are for this. Are they valid, do they make sense and are they achievable?

Steve Snell of VandelayDesign

My advice would be to start part-time while working a full-time job if at all possible. That way you'll be able to get a good feel for what freelancing is like and if it's something that you really want to do full-time. There's much less risk involved because you can start to build up a client base before making the plunge so by the time you go full-time it won't be so hard to stay busy. Another piece of advice is to save everything that you're making from freelancing part-time. If you have a full-time job you can most likely live on that income. If you can save all of your profit from part-time freelancing it will be a safety cushion for when you go full-time. If it takes a few months to find much work it won't be a big deal if you have that extra money. Plus, you won't get used to living on an income that consists of a full-time job and part-time freelancing. That income will be difficult to replace for a while, so avoid getting comfortable on that income. Another thing that helped me was to diversify your income. Things like freelance writing for design blogs or managing your own websites can provide other income that supplements what you make on client work.

Garth Humbert of IAmGarth

Before you take the plunge, make sure you've got some clients and projects lined up. It's a big step and depending on what you need to make, you're gonna need to buckle down and work hard. The other thing that's been really helpful for me is surrounding myself with other designers. Twitter has been amazing at providing a steady stream of links, resources, witty comments, inspiration, and is a great sounding board.

Liz Andrade of CMDshiftDesign

I wrote a post about this a while back called "Ditching your 9to5 to be Freelance & Fancy Free", and that post was in response to the emails I get from those of you thinking about making the leap and asking for advise.

Calvin Lee of MayhemStudios

Learn the business side of running a business from your day job, before going on your own: contracts, invoicing, billing, estimates, working with print shops, preparing print ready files, working with clients and file management.
Networking and making connections within/outside of your industry before going solo is very important in finding work, clients and projects. It makes it a lot easier when you're on your own, since you’ve already built trust working with them on your day job.

Self-promotion is equally important. It doesn’t matter how talented you are. If nobody knows you’re out there and available for projects. Sign up for social networking websites like Twitter, Facebook, Linkedin, Bizik and the many portfolio sites to get your name and work out there. I’ve had the most success with Twitter as a way to network and connect with potential clients.

3. If you could change any one thing about working independently what would it be?

Liam McKay of WeFunction

It would probably be where I work, I definitely need to mix it up a little. I'm currently working from a desk in my room. But ideally I'd like to have my own office, and set myself some office hours, just to give myself some more structure and reality. Another thing I'm hoping to do is get a laptop and start working remotely, take my laptop somewhere nice when days in the office are getting a bit dull. I think as a freelancer you have a lot more freedom, but I feel at the moment i feel I'm not taking advantage of that.

Chris Coyier of CSS-Tricks

One thing I wish is that there was awesomly fast wireless internet that saturated the globe. One day I'd love to live in a remote Alaskan village, but I don't think I'll ever be able to live with out fast reliable internet =)

Elliot Jay Stocks of ElliotJayStocks

My plan is to do less client work and more 'product' work (i.e: things I can sell), so I guess that's something I'd like to change, and hopefully I'll achieve it. But in general, there's very little I'd change about my current freelance way of life.

Brian Hoff of TheDesignCubicle

I've always considered myself a people's person and enjoy interacting and socializing with people in a work environment, so if I could have some random people just sitting behind me while I work from home that would be fantastic! Any takers? I pay with good conversation and stories. :)

Walter Apai’ of WebDesignerDepot

Ease up on the pressure. Even though I don't have to report to anyone, self-pressure to excel and do well can be very taxing if not managed properly.

Garth Humbert of IAmGarth

Be available. Artists and designers have a notorious rap for being flaky. Surprise your clients by answering the phone, responding to emails quickly, and delivering on time. Take care of your clients and they'll take care of you.

Liz Andrade of CMDshiftDesign

If I could change one thing today, it would be to have a special room in my home for my office. Right now I work out of a nook in my living space but I dream of one day moving up to have a real room with a door! :)

Calvin Lee of MayhemStudios

The worst is the isolation working alone, independently with no real human contact, not able to bounce ideas off someone. Even though there is instant messenger and Twitter. It’s not the same as communicating with people “In Real Life.”

I don’t know if there is a solution for this. I guess that is just part of freelancing. That is why I try to get out to networking events/design meetups as much as possible, to reconnect.

How do you find the right balance between working independently, and making time for non-work related activities (i.e. family, friends, recreation) ?

Steve Snell of VandelayDesign

That's something that I still struggle with. My tendencany is to work as much as I can and the other stuff often takes a back seat. One of the things I've learned that really helps me is to have a set ending time for the day. If I don't know how long I'll be working for the day, I usually wind up working almost from the time I get up till the time I go to bed. But if I have a set time when I know my work day is over, it helps me to stay focused, get things done, and still have time for personal stuff.

So there you have it, a lot of great input from top web designers, If you found any of this info helpful or related to their answers drop them a line, and let them know.

Author: Aaron Irizarry

Aaron Irizarry is a Front End Web Development / User Interface Designer. He is passionate about User Experience, Front End Web Development, Experience Design, and writing about some of the practical aspects of these things on his blog.

Write for Us! We are looking for exciting and creative articles, if you want to contribute, just send us an email.