10 things I learned in my first six months freelancing full-time

May 15, 2014

Freelancing is nothing new to me. Back when I was a college student, I earned extra money with layout and graphics work on the side. And throughout my two decades in professional design, I’ve done occasional freelance work.

But even in recent years when freelance projects started to add up to 20% of my annual income, it was still only a complement to my salary as a designer and art director. Going 100% freelance sounded reckless. A little extra cash was one thing, but could it be enough to support a family of four and our big yellow dog? It seemed like a foolish decision I might immediately regret.

But last December, I stepped to the edge of the board and took the leap. The water was warm and invigorating. I’ve been busy with client work ever since. It’s been a rewarding, satisfying change.

And through some ups and downs, I’ve learned a lot along the way. So for those considering a similar move, or for others freelancing full-time but still trying to figure it all out, here are ten things I’ve learned in the first six months of running my own full-time freelance business:

1. There won’t be a “perfect time” to make the leap; you just have to do it

There is never going to be a 100% safe, risk-free moment to step into the freelance world. Your savings account may never be deep enough; the economy may never seem strong enough; you may feel like there’s a lot you don’t know how to do yet. Doubts are free and plentiful.

And here’s another challenge: it is almost impossible to have enough freelance work lined up before you quit your regular job. You face a classic chicken-and-egg problem: it’s risky to make the jump until you have enough clients to replace your current job’s salary, but you can’t take on that much freelance work while you’re holding down a full-time job. There are only so many hours in the day and caffeine can only do so much to fight off sleep.

The sober, sensible, and responsible rule-of-thumb is that you should save up six-month’s salary before you quit your job and go out on your own. That’s sound financial advice, no doubt, but I suspect that’s unrealistic or impossible for 90% of designers. If I waited until I had half a year of salary in savings, I’d never have made the change. I was influenced and inspired in part by The Freelance Web podcast hosts Sean Johnson and Liz Elcoate, who both shared their experiences of making the switch to freelancing, despite a) having kids and b) having no six-month nest egg to rest on. Their circumstances had been similar to mine in many ways, and helped convince me that my plan wasn’t madness.

Once I had three or four solid clients to start with, I felt as ready as I could be. I had enough to start with, but a lot of uncertainty about where I might be three months later. But I was willing to take a leap of faith. Two weeks later, I landed another big new client and I was on my way.

Bottom line: if you feel like you’ve got the skills, experience, and ability to make a freelance business work, you still need to take a risk. It’s always going to be a gamble. Many people, whether they tell you or not, will think it’s a horrible idea. But sometimes you just have to bet on yourself and go all-in.

2. You probably already know enough

yodaOne of my favorite moments in the original Star Wars trilogy is when Luke Skywalker, after a harrowing ordeal against the Empire and Darth Vader, returns to Yoda to finish his Jedi training. Yoda surprises Luke by telling him “No more training do you require. Already know you, that which you need.” Luke was ready; he didn’t know it yet.

Full-time freelancing isn’t for everyone: I wouldn’t recommend it to someone who is just starting out their career, or to someone who lacks self-control or discipline. But if you’ve been a professional, experienced designer for a few years or more, you may already have the skills that you need.

I’m not talking here about the technical, “hard” skills: any teenager can learn to master Photoshop, HTML, or CSS. You need to be good at what Leslie Jensen-Inman calls the “soft” skills: presenting, facilitating, critiquing, storytelling, sketching, and leadership.

You learn these skills over time when you work for other people. When you’ve navigated hundreds of meetings and calls on dozens of major projects, you learn how to work with clients and collaborators. You learn how to listen and ask good questions. You learn how to professionally and respectfully disagree with someone and present a different idea or solution. You learn how to take feedback constructively and use to improve the work and make a client happier. You learn how to meet deadlines and take responsibility for what you deliver.

When you go out on your own, you take those skills with you, and they are the things that can set you apart from the competition.

3. You need an accountant

Turbotax is fine for a basic tax return. I used it for years to handle my personal taxes, including my part-time freelance work. But once you make your freelance business your full-time job, you need to deal with things like incorporating your business, handling expenses, processing payroll, and reporting everything properly to the IRS. Amateur hour is over: it’s time to find a good accountant to handle this and let you focus on everything else.

4. Design is only half the job

Burke teaches "ABC: Always Be Closing"In many ways, work as full time freelancer isn’t that different than working for a company: the tasks, the techniques, and the process are essentially the same. But that’s the catch: design work is only part of what you need to do. You’re no longer just a designer or a creative director; you’re also an entrepreneur, a marketer, and a project manager. You’re not just the guy who meets the deadline with creative solutions; you’re also the one who finds clients, handles invoices, and promotes the business. You no longer have the luxury of focusing on one big project; you also have to be planning ahead for after that project is complete and working to make sure another one is on tap for the following month.

Most designers — myself included — haven’t spent much time learning how to manage and run a business. I’ve done design for so long, it’s second nature: but thinking like an entrepreneur is new. Running a freelance design business means you need to get outside your comfort zone and learn how to sell and promote your services.

5. The sofa is not your friend

A "no sofa" symbolNo, you can’t just stretch out there “for a bit.” Working there for “a change in scenery” is a horrible idea. Taking a break on the couch to “read for a little while” is a lie and you know it.

The sofa exists only for one purpose: to drain away every productive impulse in your mind and soul.

The sofa wants you to fail. Don’t trust it.

6. “Business Hours” don’t exist (unless you enforce them)

It’s always seemed strange to me that the American workplace is still structured around the eight-hour work day and 40-hour week that was established in the 1930s. And once I started freelancing full time, the antiquated notion that work happens between 9am and 6pm started to seem increasingly arbitrary. Some days I might work four hours, other days 12.

When you freelance full time, you’re the boss. You have all the flexibility in the world: take the kids to school, or pick them up early; go on long walks, bike rides, or dog walks during the day; take naps; go to the see Godzilla while everyone else is sitting in offices across town.

The bad news? Flexibility is a huge perk of being a freelancer, but it has its price. The work still needs to get done, especially if you spent daytime hours away from your desk. So this means you may need to work at night, before dawn, or on the weekends. When this becomes the norm, you’ve got a problem. As the notion of “work hours” blurs, it can feel like your business is never closed. You’re never off the clock.

It’s essential to establish boundaries on your time. Maintaining a sane work/life balance is important. There has to be a time when, most days, you are off the clock and can stop checking email. Just because your schedule is fluid and flexible, it’s not a good idea to run your business 24/7.

7. Distractions are your enemy

Fairy Angelina jumping on a bedYour freelance business is work, even though it may not feel like a job. You need to establish a quiet, focused workspace, free from interruptions. One of the hardest things to handle when you freelance from home is defending yourself from distractions, the two biggest being people and stuff.


Keeping your workplace distraction-free is often very hard, especially if you have kids. I’ve struggled with countless distractions and interruptions when trying to work in my home office: everything from stubbed toes to outfit checks to fairy fashion shows. You don’t want to be a nasty 1950’s dad who slams the door on his daughter’s face when she wants to show you her new princess outfit, but sometimes you need to lock the door and make sure everyone understands that you’re at work. I wish I had the answer for how to manage this better (comment below with any helpful tips and suggestions). It remains one of the biggest challenges. I love my wife and family, but when they are all home at the same time I’m working, it can be tough to shut them out and focus.


When you’re working at home alone, there are still endless things to distract you and feed the procrastination beast: laundry, your bike, ice cream, Hulu, PlayStation, a full trash bin, dishes in the sink, a dog who wants to play, and a new episode of Marvel’s Agents of S.H.I.E.L.D.. None of these things exist in a regular workplace, but at home, they’re everywhere and they beckon constantly. It takes a good deal of focus and discipline to ignore the hundreds of other things that vie for your attention.

Working from home can be liberating and empowering, but the people and stuff around you can easily suck away your time and energy. Sometimes I’m incredibility efficient in my home office, but other times, the buzz of distractions is just too much. When that happens, it’s worth packing up the laptop and heading over to a coffee shop or a co-working spot where distractions can be minimized.

Sometimes, the best way to work from home is to flee it.

8. The time you’re not billing matters, too

Early on, I felt uncomfortable any time I was doing stuff at my desk that I wasn’t billing. If I wasn’t on the clock doing client work, it seemed like I was wasting time and losing money.

Over time, though, I’ve learned that (see #2 above) design is just part of the job, and a lot of other things matter, too. If I’m researching new techniques or tools, that’s work. If I’m watching a video on Treehouse or Lynda.com, that’s work. If I’m getting my inbox down to zero to help me stay focused and in control of my priorities, that’s work. If I’m networking or engaging with other designers, that’s work. If I’m reading a book on CSS or content strategy or animation, that’s work. Writing this blog post is work. Anything that potentially builds your business or makes you a better designer is part of the job. When you do a lot of things like this at a traditional workplace, the twisted perspective of management or coworkers is often that you’re wasting company time. But as a freelancer, you can shrug off outdated definitions of work and tackle your role with a more balanced, holistic approach.

9. Freelancing can be isolating

I’ve always considered myself a bit of an introvert, so I often looked forward to a day when I didn’t share my workspace with anyone else. And generally speaking, I don’t miss the office environment much: I love the quiet, relaxed environment. That said, while the freelance life is great, it can be isolating.

When you work (mostly) from home, it can feel like your world is shrinking around you. Your interactions with others outside your family become less frequent and you can easily pick up cabin fever. I miss random conversations with coworkers about the last night’s NBA playoff game or the developments in the latest episode of Mad Men. Those little exchanges turn out to matter: they connect you with others, even over the dumbest stuff.

What’s the antidote? I’m still looking for a good answer to this, but many of the things I’ve mentioned—co-working and meetups—can help. But you also need a break from other designers and freelancers as well. Poker night, anyone?

10. Other freelancers can teach you a lot

It’s been tremendously useful for me to tap into the experiences and ideas of other freelancers. It also really helps to realize that you’re not alone in the ups and downs of the business. Here are my five favorite places to learn and get ideas about creative freelancing:

Home Work. Part of the 5by5 network of podcasts, this weekly show is “for people who work from home, whether freelancer or telecommuter.” It’s 110 episodes deep as of the time I’m writing this piece, and it tackles everything from time tracking and management, handling contracts, tools and services for freelancers, the “impostor syndrome,” and a ton of other topics. Hosts Aaron Mahnke and Dave Caolo keep it fun while delivering a wealth of ideas for freelancers.

The Freelance Web Podcast. This British podcast is a lighthearted, smart, and useful show “for freelancers working on the web, discussing the everyday ups and downs of freelancing”. The hosts, Sean Johnson and Liz Elcoate, have an enjoyable rapport and don’t take themselves too seriously. As noted above, this podcast helped give me a little extra motivation to make the jump to full time freelancing. It’s a great listen.

The Deeply Graphic Designcast. Another excellent podcast. Hosts Wes McDowell and Mikelle Morrison, joined by a few other co-hosts, mix self-deprecating humor with very practical discussions about the freelancing life.

The Freelancers Union. First off, if you’re a freelancer, you should join the union. In addition to building a nationwide network of independent workers, it engages in advocacy, education, and delivers services to freelancers. Those services include insurance and retirement plans, along with help creating contracts. For me, the Freelancers Union blog is its best offering: a steady flow of useful articles on all aspects of the freelance business.

Meetup.com. Maybe this one is obvious, but in my area, I’ve met and and shared ideas with lots of local freelancers at meetups. Podcasts and websites are great, but person-to-person meetings are especially valuable when you spend a lot of time on your own. Find a local meetup and check it out.

So that’s it: the ten biggest freelancing lessons so far; many more to come, I’m sure.

Artwork by Max Griboedov (Shutterstock)

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