3.25.2014

Making The Switch

When I was younger, I worked as a lifeguard at a summer camp, which was a relatively easy job. Campers would play in the designated swimming area and have a good time. In that swimming area, there was a raft, and on that raft was a “tower” the campers could jump off of. Generally, campers would ascend the ladder and jump off, screaming with glee while they did so. The tower was fun, and everyone knew it.


But there were always the kids who, as soon as they got to the top, would freeze up. They’d realize that even though they saw their friends jump off the ladder and emerge unscathed, they were going to be killed instantly by the fall. As the lifeguard, my job was to then talk them into jumping off. “It’s fun, you’ll be fine!” we’d shout. The braver ones would take a small amount of coaxing. Others would need more verbal poking and prodding before they’d finally jump. More often than not, after the initial fear was conquered, the campers would surface with cries of “Awesome!” or “I want to go again!”

Unsurprisingly, it’s not that far off from transitioning to full-time freelance work. There’s a lot of uneasiness, and a lot of poking and prodding by friends or “lifeguards,” those who have gone before you and know everything’s going to be ok. I thought of a few key points that will hopefully make the transition smoother for you as you make the switch to full time freelance work.

1. Get Reassured

Take some time and chat with those who have been freelancing for a while, and ask them about their experience. I chatted with countless friends who were freelancers, and I’m glad I did. When you have connections who have experienced exactly what you’re going through and made it out alright, why wouldn’t you chat with them? Make new friends, buy them a beer, and learn a thing or two.

2. Be Confident In Your Abilities

I feel like this goes unsaid in a lot of freelance advice articles, but I find this extremely important. If you’re going to be a freelancer, you need to know your stuff. This isn’t to say that you’ll have it all figured out when you begin freelancing, but you can’t expect to be successful if you’re still green in the field you’re freelancing in. Don’t know much about illustration? Probably best you don’t quit your day job to become an illustrator.

This may seem obvious, but I’ve read a lot of “pursue your passion” articles lately that completely disregard the fact that you need to be talented to be a successful freelancer. Years ago, when I first moved to Portland, I tried freelancing and failed. I was inexperienced, and potential clients smelled it a mile away. Knowing your craft doesn’t just make for good design, it also gives you a confidence that your clients can trust, and this is crucial to your success.

3. Calculate Your Expenses

This was a great bit of advice from my friend Jake Caputo: Calculate what you need every month to pay the bills, and you’ll have a good idea of what you’re going to need to make per week, etc. Before getting into the nuts and bolts of freelance, you don’t realize that there are real budgets and numbers that need to be met in order to succeed. It’s not all a pantless, “sleep-until-noon and make cool stuff” lifestyle.

4. Get Savings In Order

Again, this seems like a no-brainer, but it needs to be said. You can’t expect to go freelance and have nothing saved away. Sure, you may have your schedule booked for two months out as you start, but getting your billing schedule in order is another story. As a freelancer, expect to be invoicing folks once a month or in chunks according to milestones, not bi-weekly like your current gig.

I’ve read lots of articles about this topic, and have heard everything from 2-6 months worth of expenses saved away. I think 6 months is unrealistic; for the sake of transparency, I had a bit over 2 months of expenses in savings when I started. You’re not going to be getting paid for at least several weeks, so it’s best to plan ahead.

5. The Tax Man Cometh

As a freelancer, you’re going to get paid some decent checks, but remember: it’s gross income, so you’re going to have to pay your taxes. The best way to combat this is to make a budget and stick to it. Figure out all your bills, when they’re due, and how much extra funds you’re going to need to sock away for the tax man (try 35-40%). This is going to prevent you from the freight train of news that you owe the IRS 40% of the income you already spent. This happened to me, and I’m still paying it off. Don’t learn the hard way, budget your income and save your taxes.

6. Set Up a Work Space

Whether it’s in your spare room or in the corner of a bedroom, set up your workspace while you’re still at your agency job. This is a great exercise only because it helps the transition hit home a bit more. There’s nothing that says “Go time” like making a trip to IKEA or a vintage shop and getting a desk and some shelves for your office. Getting all your stuff set up helps your brain catch up with your plans. Yes, this is happening, and yes, it’s legitimate. Every office needs some rad artwork, so maybe buying a few prints from your favorite illustrators will help make the space your own.

7. Fill Your Time

When you start freelancing full time, it’s best to fill your time with work. In the months or weeks leading up to you switching, do your best to reach out to contacts and friends about booking time with you. If you find yourself in your first week of freelance with only 8 hours booked, no sweat. Use the extra time to email potential clients or work on that side project you’ve been wanting to pursue for a while.

As you begin freelancing, you’re going to need to learn how to work efficiently on your own, so make some office hours and stick to it. Nothing will set you up for failure more than working those 8 hours and playing video games the rest of the time. Freelancing gives great flexibility, but don’t be foolish.

8. Figure Out Your Schedule

If you read even a fraction of the articles on being a freelancer, you’ll run into a statement that goes something like this: “As a freelancer, prepare to work a lot more than at your current job, since you’re going to be wearing a lot more hats…” This is a harmful lie, and you shouldn’t buy into it for a second. Do you want to be the freelancer that works a 4 day work week? Be that freelancer. Do you want to work from 9-4 and no longer? Make it happen.

Whatever your strategy, you need to figure out how to earn what you need and still do good work. Your knowledge of your expenses and budget will help you know how much you need to work each week to meet your needs. Don’t let someone else tell you that you need to be a client’s whipping post just because you’re a freelancer. It's not right, and it’s certainly not professional. Why would anyone expect a colleague to answer an email at 3am or on a weekend?

Again, this is all within reason. I personally work from 9-6, with an hour for lunch each day. I find that I need to work these hours to allow for exploration and flexibility.

9. Enjoy Right Now

If you’re anything like me, reading this article won’t have answered all your questions. Most likely, you’re feeling more antsy than ever to get started, and wish you could keep reading or find out even more. If that sounds like you, just remember to enjoy the present. This excitement you feel is awesome, and you’ll find that once you start freelancing it’s going to look a lot like… work. It’s funny how quickly you adjust to being a freelancer, so for now just enjoy all the unknowns and try not to live in the future.