Pros and Cons of Freelancing

A little backstory: I’m a freelance interaction designer, which means people hire me to design things on screens that people can tap or click on. I have a small private office in San Francisco, and mostly work alone, turning discussions into ideas and ideas into visuals, usually solving the problems with which people come to me for help. It’s interesting work, and I’ve been freelance for about three years now. Before freelancing I was one of the few and the proud to serve at the venerable KNI, where I was a general designer/developer/jack-of-all-trades for 12 years. I learned a lot about designing, building things, and business while at KNI, so I feel like I got a head start as I transitioned to freelance.

Not everyone has it so easy, though– if you’re curious about the freelance lifestyle, or already in it and finding it lacking the Ferraris, champagne and intrigue you were promised, take a step back. When it’s good, it’s great, but it’s also got downsides. So without further ado, here are a few — not all — pros and cons of freelancing, along with my take on how to mitigate the hurt of the cons.



It’s called freelance for a reason: A five-day work week need not apply. Now you can go out and about any day of the week, and avoid the weekend rush for everything! No projects booked? Take a long bike ride! In between deadlines? Take the whole day to catch up on whatever it is you’ve been meaning to. This is a major bonus of freelancing, one I savor whenever I’m able.

Diversity of Work

When a project ends, it usually really ends and a completely new one begins. You’re not stuck on a team or suffering the same kinds of work day in and and day out, or being forced to do stuff you are tired of doing. Unless of course you’re a very specific type of freelancer with a very specific style, in which case that’s your own fault, buddy.

Meeting New People

Like the diversity of work, you get a diversity of clientele. Individuals, companies, artists, businesspeople, any number and/or type of people can be encountered on a given day or project. This keeps it very interesting, as long as you like people.

Exposure to Processes and Spaces

Along with meeting new people and getting new projects, you actually get to see and try out different ways of working, in person. You get access to different workspaces, tools and techniques. It can really build your skill set to plug into different workflows and you can learn a lot from exposure to a multitude of ways of doing things.

Plenty of Focus Time

When you’re not out meeting people or doing an onsite, you have plenty of alone time to get things done. I have personal difficulty with open-plan offices and have a hard time focusing when there are frequent interruptions from coworkers — when you work alone, you can get into it. No headphones required.



“Will there be another project after this one?” is a common concern freelancers face. Even if you’re the hottest commodity in the dribbbbleverse, it’s not always easy to line up projects end-to-end-to-end, so there are moments of uncertainty, which can lead to fear and doubt.

Lack of Structure

If you’re the type of person who needs routine and a schedule, freelancing may not be your thing. From the moment you book work you’re expected to schedule out the project, manage your own time and keep track of invoicing, billing, and following through on delivery. What you do during a day is up to you, and unfortunately nobody else is going to tell you what to do or when to do it.

Lots of Admin/Busywork

There are no secretaries or billing departments in our world. You answer emails, you negotiate terms, you chase down overdue invoices, you phone call, conference call, Hangout, Skype, WebEx, BlueJeans, coffee meet, and sometimes lunch. Only in the downtime can you do the actual design work.

No Freebies

Health insurance? Paid vacation? Coffee breaks? Computer equipment? Gym membership? Office supplies? You have to cover all that, and it adds up quickly. No wonder contractors have a bad rap for being expensive.


The flip side of the ‘plenty of time to focus’ coin is that it can be a lonely game. Too many days by yourself can lead to a kind of cracky hermetic existence. If you thrive on social contact, brace yourself for a dry spell (unless you’re one of those people that runs an office out of a café).

There is hope: How to Alleviate the Cons


Try to line work up out in front as long as possible. Typically this maxes out at a couple months, and even still prospective clients can and will cancel or fudge dates around. Get verbal agreements when you can, learn what ‘kill fees’ are. The only real strategy for dealing with unpredictability is to accept it: meditate, exercise, medicinal herbs, scream therapy — however you want to deal with it is how you deal with it. If you’re good at what you do, and make a decent effort at getting your name out there, something will come along.

Lack of Structure

The best way to solve a lack of structure is to create your own structure. Yep, just as if someone else was blocking out your day, you have to get out the calendar, look at due dates, and start pinning down deadlines. Even if they’re arbitrary, deadlines can frame your time in manageable pieces, as well as allow you to plan for downtime. You can get as granular as you need to, I sometimes have single days sliced up into pieces dedicated to different projects, even down to lunch and exercise time. To monitor progress in retrospect you can self-assess every week, or do a monthly inventory of what you’ve been up to. Did you hit your marks? Are you keeping your head above water? Another solution is to set the same schedule for every day. Start work by X time, stop for 15 minutes at Y time, and so on. This kind of stuff helps form habits that can save your skin once you have a bunch of emails flying in and everyone asking for everything immediately.

Lots of admin/sales work

Emails and phone calls are part of this balance. The design (fun) part is about half, and communication (necessary) is the other half. Schedule time to take care of emails, say 30 minutes or an hour in the morning, and another 30 minutes in the afternoon. Don’t answer everything immediately, but also don’t sit on an email for more than a day or so. This ties into making your own structure and giving designated time for the admin stuff. If you give it a time slot, you can use the other slots freely without worrying that the admin stuff is slipping.

No freebies

Unfortunately, there’s no way to magically get free stuff. You have to set aside a percentage of every check — about 30% for taxes (in the US, at least), and then more for whatever else you want to factor in. Office rent if you decide to rent an office, health insurance, any business expenses like recurring software licenses, gym membership, dining budget if you’re that organized, etc. It’s surprising how much this can cut a decent paycheck down into a basic living wage, and makes asking for what seems like a high rate much more justifiable.


Get active about social life. Schedule lunches with colleagues, and talk about your work. Bring your work to someone else’s office once in a while (assuming they’re friendly with visitors). Find some industry-related events in your area and go to them (they often have snacks and free beer). Join a coworking space if you’re tired of working solo. There are many ways to mitigate the loneliness, but like the admin work and the scheduling, it just takes a bit of proactive effort.

Hopefully this helps you or someone you know out. If you do have a job, make sure to thank the people who do all the company stuff that you don’t have to do- sales calls, billing, payroll, HR, even the boss (maybe). Also remember to invite a freelancer friend to your company lunch once in a while. For business purposes, of course.