Planning Your Next Step as a Freelancer

Apr 4, 2018 · 11 min read

If you’re lucky, you’ll wake up one morning — or finish a project, or have a shower moment — and realize that you’re ready to move into the next phase of your career. More likely, though, is that it won’t be obvious — because it will be gradual, like having a harder time waking up in the morning, opening VACATION 2018 boards on Pinterest, buying a WORK SUCKS, GO SURFING sticker for your bike.

Maybe it’s burnout or maybe it’s boredom, but either way, it’s time to make a change.

After three years of freelance writing, I was over it. Completely. Everything I wrote started to sound the same, and every day I woke up more certain than ever that everyone was going to find me out. That my best days were behind me.

I moved to the desert, but that didn’t help. I stopped eating sugar, but that didn’t help. I turned off my phone on weekends — nothing.

The change had to come from my work.

I was working on 389358 things, 389354 of which felt very not me. It’s not that I didn’t like them — they just weren’t what I signed up to do. They felt like the next step of someone else’s career.

So I sat down with my notebooks from year 1 of freelancing and got back into what I liked, what I loved, and what I missed.

It would be fun if I told you figuring out what I wanted was easy, or actually doing it was easy — but those would both be lies. What I can do is give you my action plan for getting back into what you love — based on real life experience.

👼 Step 1. Get back to your roots 👩‍👩‍👧‍👦

Do you remember your first few months of freelancing?

Whether you’re a gold-star forever freelancer or you got here from an office job, I know it’s a cliche but those few months are about freedom: going to the gym in the middle of the day, working in your underwear, taking projects for the love of web design (or copy, or whatever you’re A+ at).

However, those months will pass, and with experience and time the nature of your projects will change — and sometimes after a few years you realize that the web designer you are now has nothing in common with the web designer you used to be.

It’s a sign of growth, but with growth comes stretch marks. And growing pains.

How do you keep the romance alive? Let’s start getting back to your roots.

Action item: List and reminisce

If you’re like me, you write everything down in a journal, but if not, you’re going to have to rely on your memory. Head back into the memory bank for those first few months, and remember what made you become a web designer in the first place.

Write it down*

* Seriously, write it down! You’ll be surprised about the weird connections your brain makes when you put things on paper.

  • What was your first dream project? By putting your finger on what you originally excited you about web design, you’ll be able to get in touch with the push that got you motivated to freelance in the first place. This works especially well if it’s something you haven’t gotten the chance to do — like experimenting with code. Pretty soon we’ll be talking about the importance of your original wants from your freelance career, and how that can — and should — help you develop your passion project.
  • How is that different from what you’re doing today? Whether for the love or for the money (or for the love of money), what are you doing now that wasn’t in your dream plan? Are you happy doing what you’re doing, or would you want to head back to that plan — or are you exactly where you thought you would be?
  • What’s changed about your industry? Web design changes all the time. Have you changed up your tools since you started designing? Are you still with Photoshop, or have you moved on to Sketch? How was learning responsive design?

👯 Step 2. Get to know the right people 👨‍❤️‍👨

No man is an island, right? John Donne made a good point: we all need to feed from other people’s energies. We don’t mean crunchy granola-style energy cycles; it’s more in the sense that our ideas expand with our conversations, we learn from people around us and apply others’ experiences to our own lives.

As a freelance web designer, it’s easy to disappear into your own world. We fall into self-contained entities of home offices and client work, and the outside becomes a scary trap of noise, small talk, and pants that button.

Interacting with brains that aren’t ours, though, pushes us to create new neural connections, to think faster, and to challenge our own thoughts.

That’s why we read books, watch movies, and most importantly, build relationships.

Action items: Roll with your homies

Between us, the best way to meet people is the internet. The challenge is to know where to go, and how to sort between 9Gag black holes and actual people producing actual work.

When I need to fill out the crew, these are my go-tos:

  • Start with Pinterest. Pinterest is a down-low creative mecca for whatever inspiration you’re looking for. Search keywords and start pinning; the Pinterest algorithm will point you in the right direction. (That’s from personal experience.) * If Pinterest isn’t your thing, any other content aggregator will do.
  • Change up your reading list. Find some websites, blogs, magazines with content that you get down on. I’m not talking work resources or personal development — something purely creative, whose added value is making your brain work extra. Personally, I go for Dazed, Broadly, and Pudding.

Choose 3 online spots you enjoy and commit to checking them out every day, whether it’s in the AM or when you need an afternoon kick. Figure out if there’s a common theme between the content you dig: if it’s video blogs, designing for accessibility, or something else you could enjoy doing.

  • Make Twitter lists. Twitter has a cool feature called Lists, where you can build subject-specific public or private lists with your favorite Tweeters in a specific field. Not only will this help out your algorithm (if you can’t beat ’em, join ‘em), but it will also help you keep an eye on trends and creativity without the fuzz of your sorority sister’s engagement photos.

The best part of finding peeps and resources on the internet is making those creepy algorithms work for you. Once you’ve identified an inspirational person or two, you’ll start seeing more of the same on your feed — and the more in-depth you go, the stronger your results will be.

🎨 Step 3. Find your thing 🖌

Let me tell you about my thing.

What I knew was that writing is the only thing I want to do — the only thing I like to do, and probably the only thing I can do — and I know helping people by doing that makes me feel damn good.

When I first started freelancing, I wasn’t very picky; I just wanted to write.

My first projects weren’t my dream clients, but they helped me chase the dream of being a freelance writer.

That dream, though, was based on the career crush I still have on Beth McColl, more commonly known as @imteddybless. What I love about her work is how much she gives of herself to people who think they’re the only ones to ever feel anything.

Because what she brings out of other people is what I want as well. And where she uses Twitter and her advice column in Dazed, I work with the web design community that I met through my work in tech.

I love my community, I’m super bossy, and I love helping people out. So, it was simple: I was going to write an advice column for designers.

Writing for, and with, web designers gives me a weird, unexpected opportunity to connect emotionally with people in a space that isn’t traditionally emotional, whether it’s UX writing or feelings-heavy blog posts.

Action items: Defining the dream

Put the paper and pen to work again. You’re still freelancing, so something’s got to be going right. Now we’re going to figure out how to combine what you like about what you’ve learned how to do with what your fantasy career looks like.

  • List your top 3 favorite people in web design. Take what you learned from Step 2’s activity and make a top-3 list: for example, the top 3 best writers in web design. Once you’ve got this down, you’ll be able to identify what they have in common — and what they’re working on that you would be happy to take on too.
  • List the 3 things you most enjoy doing about your job. Hopefully there’s things you’re working on now that excite you, whether it’s writing design documentation, conducting user interviews, or giving client presentations. What you’re doing now isn’t far from your first dream — it’s a sign of evolution.
  • Put it all together. Once you have those two lists, answer these questions to figure out how everything fits together. You don’t have to give up on what you’re working on now to do something new, and I don’t think you should; rather, think about what you’ve learned and who you’ve met and how you can combine all that into a new, fun goal.

Keep in mind:

  • What skills have you picked up since you started freelancing that make your job more fun?
  • Is there anything you’ve learned how to do that surprised you?
  • Have you picked up anything while working that you want to explore more deeply?

🔨 Step 4: Build a plan 🔩

With your skills, your likes, and your wants written down, the next step is putting together an action plan.

So with these things I knew about myself, it all came together: like Teddybless, I was going to write an advice column!

Which is dope, but I didn’t want to write it for myself and my dogs, so I needed to figure out my next move. Which came with, you guessed it, actionable goals!!! Because, seriously, without these action items my brain turns into scrambled eggs and nothing gets done.

Keeping track of steps helps me divide my time and resources so i can make actual progress.

Writing an advice column meant two big things: write good content, and get those words to some eyes. For the content part, I gave myself a goal of three columns in a month, both to see if I liked what I was writing and also if I could keep up with the pace.

3 posts, 4 weeks. Not a bad starting goal.

Once I did that, I put together a distribution plan: a top-5 blog list for publishing, and then a few more as a guest post kind of pitch. Until I made this, I couldn’t start writing.

Action item: Determine smart goals

  • Set goals: Real, smart, actionable goals. Not smart like, witty or funny, but like SMART: specific, measurable, attainable, relevant, time-bound. Something like this. It’s harsh, but think about it like this: You’re doing this for you. And if you can’t keep a promise to yourself, then who are you working for?
  • Create a process: Figure out what you have to do every day in order to actually hit these goals, even the long-term, is it Q2 already?! kind of goals. It might even be more important than the goals themselves. If you’re anything like me, you’ve set goals for yourself and planned your sleeping, eating, living schedule around them — and it never, ever works. Building a process will make you take a look at your scheduling and re-think that 3-hour cut to your sleep schedule.
  • Set up project management tools: Split up your tasks into actionable steps and track how long they take you to do by setting up a project management tool (I use Trello) and time tracker (I use Harvest). Starting off organized will help you stay on course.

Sorry about all the homework, but when you’re done with all this, the next step is way more fun.

Step 5: Do the damn thing

Action item: Get started.

That’s the whole thing. Get started.

🔬 Step 6: Evaluation station 🔭

You’re on your way to happy happy web designer time, but before you can officially upload your #careerbliss photo to Instagram, you have to figure out if what you’re doing works.

Once you’ve gotten started — but only once you’ve gotten started! — you’ll be able to check in to figure out whether the action you’ve chosen to do helps you meet your goal. This is a crucial step because goal-hitting is a huge part of goal-sticking.

Goal-setting is difficult, but what’s even harder is continuing on, especially if you’re not seeing success right away. Harder than all of that, though, is deciding to move on.

Think about all of this like a new, long-term job or client commitment. After you’ve been hired, you’re not expected to be able to run free without guidance; there’s usually scheduled check-ins to make sure you and your supervisor/client are satisfied, and the work is meeting expectations.

What you’ve chosen to do here isn’t very different — it’s a long-term project commitment, only you’re the client. As important as choosing your project is making sure it works — and if not, figuring out what you can learn from the experience.

Action item: Review and revise

  • Feel your feelings: To keep on keeping on with your refresher, you have to enjoy what you’re doing. Figuring out what engaged you and what you could imagine doing in the long-term will help you cut out the things that sap your energy and work with what you love.
  • What did you enjoy doing? What sucked?
  • What did you learn about yourself from the whole process? How did this change your perception of your job as a web designer?
  • Reevaluate your goals: You built a set of tasks to fit into your goals. In retrospect, you should be able to tell how well you broke down your goals, and what you could have done better or more efficiently.
  • Was your plan actionable? Were you able to complete your steps in the way they were planned? Even though you broke your plans and goals into actionable tasks, things come up and sometimes you get sick and — well, maybe you overscheduled yourself.
  • Did your goals change throughout the project? Sometimes our plans change while we’re working. Did you find the process changed your perception?

The goal of this is to understand how close the project you designed is to the project you’d like to be doing. Projects you do for yourself can be really difficult, and while challenge is good, something meant to fulfill your creative needs shouldn’t stress you out. This kind of check-in makes sure you’re not just working to work, but you’re doing something good for yourself.

💻 Freelance web design life ain’t easy 📓

We know how hard it is to stay focused, motivated, and creative all the time; that’s why we put together this guide for staying fresh and getting back in touch with yourself.

Anything we can do to keep our brains working is game, not only for us, but for the future of creativity. When AI takes over, creative jobs are the only ones that won’t get stolen by the robots — which is why we’re already starting to see designers and design tools working with AI to help get their work done better and faster.

Learn more about what we do >>>

*This post was also posted on The nuSchool’s blog

RapidUI Blog

Letting designers build websites that look, feel, and function exactly how you want them to look, feel, and function.


Written by


Managing Editor @ InVision. Not a designer yet, but who knows what my next life will bring.

RapidUI Blog

Letting designers build websites that look, feel, and function exactly how you want them to look, feel, and function.

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