It’s been about two months since I returned to freelance after two years of working with Chartbeat, and these last two months have been, well, hard.
I’ve done full-time freelance before, but it wasn’t nearly this much of a struggle. Back then I was 25, and I didn’t care very much about building a long term sustainable business. I was mostly motivated by working in sweatpants, and telling myself I was so liberated because I didn’t have a “real job,” and hey no one can tie ME down! It also probably helped that the other times I’ve freelanced I’ve been lucky enough to work with incredible agencies such as Happy Cog, SimpleBits, or MetaLab, so I always had a big group of better people backing me up and cushioning me from the realities of running a design business.
This time around things are more of a struggle, and the stakes feel higher. I’ve had to ask myself daily why I need run my own small humble little business when it’s so much easier not to. At Chartbeat life was GOOD you guys. I had cool opportunities to work on fun products I believed in. I loved my coworkers – some of the best smartest weirdest funniest people I’ve ever met are there. I had a flexible schedule, unlimited vacation, unlimited coffee, and creative freedom. (Oh god, why DID I leave again? By the way, Chartbeat is hiring, if any of this sounds appealing to you!)
As I have to remind myself sometimes hourly, I left because I want to build something myself, even if it is just a tiny little one woman plus one cat design studio. I had to move on so I could keep learning, so I could keep being uncomfortable and growing as a result. I had to, as Cheryl Strayed says, “walk into the darkest woods without a stick.” It’s a thing we all have to do sometimes, and it was time for me to do it.
In keeping with the dark woods metaphor for a bit – I have already tripped, and been bitten by hostile animals, and gotten lost once or twice. But every day I learn my way a little better, and it gets a little easier.
I’ve been thinking about the mistakes I’ve made so far, and what I can take away from them, and how I could be better than I am. So tonight I sat down with a glass of wine (or three) and wrote down the output of that thinking. Initially I didn’t intend to publish this, but since my last post on this site was “hey, I got a job at Chartbeat!”, I thought perhaps it was time for an update. And maybe the things I’m learning about carving out a path here in the scary world of freelance life will help other people trying to make their way.
So. Here are a few guidelines I’ve learned so far; the things I believe but struggle to live and therefore feel compelled to write down.
Yet another heap of words about client communication
Clients really really want someone that’s going to talk to them. Even if the news is bad: deadlines have slipped a little, I have ideas that are unfinished and I don’t feel great about yet, I don’t agree with their choices; I have to talk to them about it. Like, way more than feels natural to me. I have to send updates morning and night, or anytime I have a productive thought about the project. For the record, this is the hardest thing for me. Rather than admitting I’m struggling to find a solution, or asking a dumb question, or saying “I think you’re wrong,” I’d really prefer to resolve the issue myself, or avoid the question, or just prove they’re wrong with my stellar designs that blow their dumb criticisms out of the water (this never, ever works).
When I DO talk about a pain point, or ask a lot of questions, or disagree, clients are usually PUMPED. Because most of the time, just knowing that I’m getting worked up about their ideas and their needs is enough to make them happy. They are usually suffering for their work, and they want to know I’m suffering right along with them – that I give a lot of shits about how their thing turns out.
As an aside, some clients aren’t really suffering over HOW their project turns out, just when. I’ve had people tell me I don’t have to make it THAT good, and I don’t have to really love the work, I just have to get it done quickly. That’s fair, but these are not really the projects I want to work on. I want to feel proud of the work, not proud of how quickly we rushed something out the door. Part of the assumption in hiring someone with my skills and experience is that I can work fast, but I care way more about doing thoughtful work than cranking out a ton of projects back to back, even if it means less cash coming in.
But I still have to work as fast as I can
Having said that, working as efficiently as possible is obviously an important thing which I will struggle to be better at forever. What I’ve learned so far is that working efficiently has a lot to do with NOT trying to create stellar designs that will blow them out of the water. Working efficiently often means just sitting with your fingers on the keys and compelling them to start making terrible ideas and having faith that with more communication and more terrible ideas, it will become something good.
It has so much to do with those impossible calls and emails and meetings where I ask every dumb question and listen hard to every annoying bit of input. It has something to do with setting a timer and telling myself, “in 20 minutes, I will have made one part of this, regardless of how terrible it is.” And doing that about 20 more times. And then checking in with the client.
The other other hardest thing is being vulnerable; I have to show unfinished work and continue to ask probing questions about the product and be receptive to feedback and new ideas. It’s about communication, but it’s also about humility. I won’t get it right the first time, and I’ll always need input and productive conversations to get there. I have to talk to clients about my ideas and my progress and the things that I don’t know yet, even if my ego-fueled desire to only show perfect work or have all the answers makes that so hard.
The opposite side of this coin is having the confidence to disagree, to make a case for the more useable approach, to care enough and be brave enough to compel everyone involved to do it right. I can’t be be afraid of seeming rude or disagreeable just because I think there’s a better solution than the one the client is proposing. This is the thing they hired me for. But when I disagree, I must do so with a spirit of humility, and with the knowledge that everyone wants to make the best thing for their users. Unless I discover they don’t want to make the best thing, or simply can’t. Then sometimes I have to fire them, but I try to do so with kindness.
I have to think about communication and efficiency and humility and confidence all the time. Thinking about and enacting these qualities is harder than any other work I do, but it’s also the most rewarding.
Estimates and deadlines and expectations and disappointments
One of the hardest things for me is knowing how long a project is going to take. Or that’s not true, I know how long a project will take because it will always take at least 1.2 times longer than the absolute most amount of time I can imagine spending on it (thank you, Jackie Balzer, for this very helpful guideline.)
Why do deadlines slip? Why do I often feel rushed? Sometimes it’s because the right solution requires an excruciating amount of work and garbage and meetings before it comes along, and in the early optimistic proposal phase I assume it will just happen naturally because I am a gifted genius. Then when I sit down to do the work, I am reminded again that I am not a gifted genius. None of the work comes as easy as I hope it will, it is always going to be a struggle.
There are days when things take longer than I want because I’m flawed and hungover or scared of failing or really into Mad Men right now, and this makes me feel worse until it’s all I can do to just open Photoshop and start dragging shapes around until something emerges.
Sometimes projects take longer than I want because I didn’t listen to my instincts when they told me this project wasn’t a good fit for me. How do I find out if a project is a good fit for me? How do I get better at estimating the time something will take? I ask a lot of questions before putting together an estimate, but I can’t really ask the questions that will REALLY determine how long a project will take, such as:
- Do you have a secret crazy boss that you’re going to unleash on me later in the process when it’s too late to get out, who will derail everything we’ve made and force us to start over?
- Do you think you know what you want, but once you see what you thought you wanted, will you realize it’s not right, not at all, and will this send us on a long, tedious path to redesigning the same pages for weeks on end? Will this make me cry and think it’s my fault I can’t give you this vague amorphous “feels right” thing?
- Do you harbor secret dreams of being a designer, and actually see me as a prop to execute your inner design diva wishes because your dumb manager wouldn’t let you just design it yourself and also you don’t really know Photoshop?
- Will you tell me you want “simple, lightweight” interactions, but really mean you want an animated exploding map that draws itself and then scatters across the page like smoke that slowly clears to reveal your restaurant hours?
- Are you really just hiring me because you want someone to sit on the phone and listen to you talk about how creative you are, and what your company could be doing if only people listened to you? Are you hiring me to be your work girlfriend because you’re lonely and bored and do I think I have to listen to you because you’re paying me hourly?
These things can and have happened to some degree, and they’ve derailed deadlines and caused me to shove my computer under the couch cushion and walk away from it because even thinking about what’s waiting when I open the lid makes me feel crazy.
One of the most important thing I’ve learned is I have to get better at saying no. No to 5th or 6th round of revisions. No to bending the terms laid out in my contract. No to people who send ideas they made in Sketch and just want me to “clean up a bit.” No to the unproductive calls that go on for hours.
I think it’s especially hard for a woman to say “no” in this industry / society / existence. I should just be grateful to be here, right? Who am I to say what’s acceptable? I have to constantly remind myself I deserve to say no, and I don’t have to always be “nice.” I do have to communicate and try my hardest, but I don’t have to run myself ragged in an effort to do anything other than tell a client no.
The truth is, being a freelancer means being thrown into a crazy shitstorm that I have little understanding of until I’m in it. Every team and every project has its own internal bizarre issues and infighting and expectations that don’t come up in the initial getting-to-know-you meetings. I have to figure out how to navigate these strange waters I’m thrown into with each new project. Sometimes that takes awhile. Usually about 1.2 times longer than I thought it would.
Again, this just means I have to think hard every day about empathizing with clients and communicating clearly and listening better and managing expectations and being honest with myself and others. These are things I’d have to think about anyway to become a good human, but freelancing compels me to work harder at being good than I previously thought I could.
Subcontracting and seductive product managers and that time I realized I’m not really a front end developer
Here are some stories about subcontracting.
The first time I hired a subcontractor was because I took on a project with an unreasonable deadline. I knew it was unreasonable from the beginning, but I desperately wanted to do it anyway because it just sounded SO COOL. Here’s a tip: smooth talking Product Managers who spend all their time talking to investors are REALLY GOOD at making you believe their startup is going to be the NEW BEST THING that you’ll wish you’d gotten in on.
So, since I knew the workload was crazy from the beginning, I hired my awesome friend Andrew Witherspoon to pitch in with parts of it. He is an amazing designer and did a fantastic job producing great work, as he always does, but nothing either of us did was right for the client. There were so many stakeholders, and nobody could agree, and we did 9 revisions on the “about us” page, and after weeks of trying with only a few pages completed, I had to fire the client. Or they fired me. Or we had to agree that they weren’t ready to finish their project, and I wasn’t ready to provide them with infinite ideas for an indeterminate amount of time and no money.
I didn’t get paid for this project (except for the tiny initial deposit, which I let them negotiate down to almost nothing because I thought this project was SO COOL), but I still had to pay my friend who worked really hard on making great ideas. Had this been the right project, we would’ve seriously kicked some ass together.
So I ended up losing money in the end, and feeling like a pretty huge dummy. But I gained some pretty valuable insights into the importance of trusting my instincts, not getting seduced by seemingly glamorous work, and also asking better questions up front before blindly jumping into something. I also learned that under the right conditions, with the right person, subcontracting could theoretically be a great way to get things done.
So on another recent project, I tried working with a subcontractor again. I should back up a bit and talk about my skills and the things I think I am good at: I used to call myself a front-end developer because I can do some pretty awesome things with HTML and CSS, and I prefer designing in the browser, and reading about responsive design makes me giddy.
But the more actual front-end devs I work with, the more I realize the value of people who specialize in this type of work. I also finally accepted that I have no interest in being one of them. I am a designer who knows enough about markup to execute most of her ideas directly in the medium where they will live (the browser). But when you get down to building production ready, super optimized, crazy interactive, multi-device ready code, that is just not my jam.
I finally admitted this to myself on a recent project after spending two days trying to make a flawless complex touch activated responsive menu that ended with me weeping into some jQuery mobile documentation, with about 32 Stack Overflow tabs open in Chrome. The following day I was bemoaning my struggles to my friend Brian Mcallister, an ACTUAL front end dev, and he agreed to take some of this work off my plate.
Hot damn. I mean HOT DAMN you guys! He got the project into git, set up Sass, gave me a thorough tutorial on what I needed to know to work within his framework, rebuilt my crappy navigation, and knocked out every other somewhat daunting interactive element I needed in a day.
Why had I made myself miserable over work that I could not and did not want to do, and wasted so much of my own time and money (I’m working on a flat rate for this project, so every hour cuts into my net hourly rate), when I could just hire an expert to knock it out in no time? This probably sounds pretty obvious to most of you, but it was a crazy epiphany for me. THIS IS HOW BUSINESS WORKS. You can hire people to do the things you aren’t good at!
How business works
I don’t know a lot about how business works. It’s the hardest part for me after communicating enough and estimating the project scope accurately. Honestly, just about everything but making designs is hard for me, and even that is a struggle – it’s just the part of the struggle I really enjoy. I have 95% of an English Lit degree and 10 years of experience working in all kinds of situations, and I have an earnest desire to make good work and build a web design studio that’s known for integrity and ingenuity. I hope that and my commitment to consistently getting better is enough to make this work.
There’s so much more I’m thinking about and learning that I could and will share, but I’m already asking a lot of you if you’ve read this far. I also really want to hear from you, person who is maybe reading this. What have you learned about running your own freelance business? What are your favorite articles and tools and techniques for solving these problems we face? I realize this is a huge topic and most of what I’ve discussed here has already been written about ad infinitum, but I’m fine with that because it’s hard work and talking about it makes it easier for all of us. So talk to me.