The Perfect Freelance Client Does Exist

Hi there. I am a freelance UX designer. This means I sell my expertise—hourly or daily—to whoever needs it.

Freelancing isn’t easy, but it’s worth it. It means I can go to museums and beaches when they are least crowded. It means I don’t have to cram all my life-living into weekends. It means I have time for side projects and learning.

The engine of the freelancer lifestyle is the client-freelancer relationship, but a good one can be hard to find. In the Orbital community, discussions rage now and again about the stumbling awkwardness of it all. There’s anxiety over setting your rate. There’s hand-wringing about how to shut down a project gone awry. Lurking throughout all of this is the subtext of probable dry spells—those periods where you can’t even pay the rent.

Despite all the difficulties, one thing gives me hope: the perfect client does, in fact, exist. I am lucky to have found one this year with Assess+RE, a budding real estate technology startup in New York City.

The operative word here is “lucky.” I’ve been freelancing for years, and only now have I met a client that has demonstrated what a truly effective collaboration looks like. Good clients are still rare. But fear not—even though our lives are ruled by luck, knowing what to look for can up your success factor. After that, it’s just a matter of getting really really ridiculously good at what you do. (Fortunately, that’s not up to chance.)

So, what do you look for?

1. They trust your expertise

So you’ve entered into a new client engagement. The first few phone calls go really well—everyone is excited to work with you! They gush about how fortunate they are to finally find someone with your skills. They can’t wait to see the first designs.

So you send them over, and before long, they start to question you. They question your experience. They question your expertise. They even question the colors you chose, because their mom said it was “not their favorite.”

At which point we are apt to rage to the nearest wall, “Well does your mom have 15 years of design experience?”

Assess+RE is the first client I’ve worked with that has trusted their moms over me a grand total of never. Which is great for my ego because for the first time in my life, I’m free of Imposter Syndrome! (Hooray!) More saliently, it’s about the productivity. Ours at Assess+RE has been so high it may have broken several laws of physics.

When I deliver a design to the team, I receive the usual round of reactions and feedback, which I listen to keenly and take to heart. But then once we’ve spent a reasonable amount of time iterating on the problem, I explain the reasoning behind my choices, and stand firm. At that point the unthinkable happens: everyone trusts my decision and moves on.

Did I mention our insane productivity? We executed a full product redesign—on the live product, no less—in mere weeks instead of months.

Of course, I had to earn this trust. I asked the founder and CEO, Min Suh, what led him to trust me, and he had this to say:

From the start, you were able to walk me through the process and high-level steps of our first smaller project. It was clear that you were passionate about your work, had perspective, actively listened, and clearly communicated why something should be structured one way or another. After working together progressively I felt as though your stewardship, process, and viewpoint were clearly coming from a place of experience and good judgment. I think with any working relationship you have to start with some level of trust. Doubt really creates a poor collaborative process.

It’s a fundamental human joy to be the recipient of such trust. If you can find a client willing to give you that trust early on, that’s a very, very good sign.

2. They respect your time

One thing that’s always bugged me about some clients is their tendency to either try and get more out of you, or to keep you around forever.

The vast majority of freelancers enter into a contract not because they’re eager to partake in a lifelong commitment. (And if that’s what it is, both parties deserve to know that from the beginning.) Freelancers choose the freelance life, and its entourage of troubles, because it affords them something they can’t get with a traditional salaried position—the right to decide what to do with their own time.

By pressuring a freelancer to take on more work than they originally signed on for (or, worse: to try and increase the scope of a project without increasing the budget), you send the message that you don’t respect the freelancer’s time. It’s also just, you know, a tad irresponsible—it’s shifting the burden of fulfilling the company/project’s needs onto an employed agent, rather than owning the problem of how to square the company’s needs with the facts of reality.

(Of course, the freelancer has a responsibility to deliver the work she set out to do. But I’m mostly referring here to pressures placed outside of her contractual obligations.)

A long time ago, a younger and much more naïve version of me sat at her desk crying into a phone, begging for forgiveness. It wasn’t because I had done a bad job and let my client down—it was because I had done too good of a job and he didn’t want me to leave the firm. The client spun a convincing tale, casting me as the traitor and him as the hapless victim. The company would tank and it would be my fault. I stuck with my plans to leave, but spent days afterwards suffocating in guilt.

Needless to say, I could have spared myself the emotional anguish. Ensuring the survival of his company was never my problem to solve.

Assess+RE made it clear from day one that they would respect my time, so much so that it seems almost unfair to them. I straight-up had to ask Min, “Do you ever wish you had more more of my time?”

To which he responded:

This is where I differ from most. What I look for, whether its working with a publicist or you or Tim or anyone, is first: what does the other person want? And if its 2–3 days and no more, that’s a clearly defined line. So I have to think “Can I achieve what I want to achieve out of those boundaries? And is this still the most effective?”
It boils down to mutual respect for people… I have no monopoly on your time. It's your time, and you choose how to spend it.

Life advice: avoid clients (or people, for that matter) who don’t understand that last point above.

3. Their needs fit yours, and vice versa

Lest you start to think my client is somehow a saint, I should mention that the first thing anyone looks for in a relationship is whether it’s mutually beneficial.

I asked Min why he decided to work with contractors in the first place, and this is what he said:

The way I see it, I need to find the best people possible to get our product off the ground, fast and cheap. Whats the best configuration? I can work with people who I know or who were referred that are available and very talented and can execute. Or I can take the risk and go out there, trying to convince someone (which can take 6 months, 1 year) [to join full-time]. Ultimately I just decided I wanted to find the best people I can, regardless of the structure.

A big part of what makes this relationship work is that I happened to be who they needed, at exactly the right time. My particular mix of skills and my ability to execute fast was worth more to them than my availability 9–5, five days a week.

I almost didn’t include this one, because this whole idea of “fit” seems largely outside of anyone’s control. You just have to be lucky, right? Well, not quite. Fit can’t be forced, but you can absolutely use it as a lens through which to examine new opportunities. Here’s a litmus test: if you find yourself bending over backwards and distorting reality to work with someone, or vice versa, it’s a sign that the fit may not be there. In those cases, it’s often best be honest with yourself and just walk away.

4. Your abilities complement that of the team

There is another aspect to “fit,” which occurs at the team level. This is where your abilities, and those of your team, augment one another instead of fighting for dominance.

I freelanced once for a company that had overstaffed for their design role. There were simply too many decision makers, and rather than cut me loose, they decided to keep me on as an adjunct designer. I remember being bored, under-challenged, and depressed by the fact that despite all of my accrued experience and talent, I was essentially designing t-shirts all day.

Sometimes, you just have to take a job to make up for a dry spell. But there are few things more soul-crushing than letting your brain languish in a puddle of menial tasks.

Assess+RE’s team, on the other hand, has been challenging, stimulating, and even fun. They understand what I want to do, what I’m good at, and how to support me in doing it. Min, the CEO and resident domain expert, will clue me in on how real-estate financial analysts think and work, but otherwise he trusts me to figure out all the design details. Tim, the CTO, works with me daily to implement the final designs. If I ever hit a roadblock in my understanding of the code, he guides me through it or simply asks me to assign him a ticket—no questions asked. Meanwhile, the other teammates voluntarily take on the roles of creating marketing materials, collecting customer feedback, and generating content so I don’t have to do. This is one of my favorite clients for the simple reason that I never have to beg them for website text—it’s already provided.

Oftentimes—and this doesn’t just apply to startups—roles can be hazily defined and abilities poorly matched. After serving as countless clients’ recycling bin for work that no one else feels like doing, I’m deeply grateful for the symbiosis at play in Assess+RE’s team. It’s not just a group of people—it’s an ecosystem.

5. They are transparent and inclusive

Sometimes, working with a client feels like a series of diplomatic missions to Mars. There’s the usual amount of second-guessing, of reading between the lines of terse email prose. But then sometimes, there’s even intentional barriers: the client may keep you in the dark about internal workings, blindside you with “higher-level” changes, or otherwise hold you at arm’s length.

Fortunately at Assess+RE, I was given access to everything I needed to know to do my job right, and then some. I had a full understanding of the company’s product roll-out plan, I had access to the full transcript of every support case since launch, I even had weekly insight into the CEO’s fundraising progress. A lot of this owes itself to the naturally open nature of an early-stage startup, but size doesn’t necessarily mean opacity. All it takes is a willingness to trust the other party.

This transparency carries over to how we communicate about the uncertain future. I can be unusually honest with Min about my plans because I know he’ll keep his emotions in check. I even straight-up asked him how he’d feel if I left one day. This was his response:

There’s always that [disappointment], but it’s your time, your life, and you get to work on what you want to work on. Of course there’s always the hope that I’d get a heads up… [but] I just accept everything for the way it is, and I operate within that reality every day.

That kind of honesty, not to mention equanimity, is a breath of fresh air. And ironically, it makes me want to stay.

(By the way, they even include me in the weekly Friday Team Lunch. As far as freelancing goes, there is absolutely no expectation that my client will buy me lunch on a weekly basis, but there it is. Is shared pizza the ultimate sign of team inclusiveness? More at 11.)

This client sounds great. Now what?

There are several more things I could talk about, but I’d rather not go on forever. (I did have an interesting thought while writing this: these five points don’t just apply to freelancing—they apply to pretty much any human relationship.)

At this present moment in history, freelancing is still a fraught lifestyle choice. Decent clients are hard to find. Not all of them will perform as meritoriously as my current one. But then again, why shouldn’t we expect them to?

Today’s dominant model of single-employer salaried tenure will not last forever. Society is still working out how best to balance the twin goals of productivity and happiness. So far we’ve built an employment system great at extracting productivity through entrenched hierarchies and economies of scale. But what about the individual’s happiness? Psychologists say human happiness hinges on being able to experience three things: competence, connection, and autonomy. From my experience, it’s very hard to achieve the last of the three when the vast majority of your waking hours, in the best years of your life, are ruled by the priorities of an organization.

These days, “independent” creators are carving out lives for themselves on networks like YouTube and Kickstarter. It’s also rare to see members the Millennial generation stay at a job for longer than 3 years. The overall trend appears to be towards a system of looser, shorter-term engagements that give the individual more power over their own lives.

Perhaps it’s time we started working collectively towards a new set of cultural norms for freelancing, whereby clients treat us not like mercenaries, but as valuable, contributing, and respectable members of their organization. As freelancers, we can start by being intentional about who we choose to work with. It won’t be easy at first—you’ll have to put in the time and work building up your network, your reputation and, yes, the courage to say no—but it will be worth it in terms of freedom and happiness gained.

For a longer discussion of how to hire and work with the right freelance designer, see Mike Monteiro’s You’re My Favorite Client.