Pushed and challenged

All of us want to feel like we’re making progress in our careers. Now more than ever, there’s a pressing need to keep building skills and make yourself more marketable with everything you do. The gig economy, the side hustles, and the industry connections don’t magically happen. It’s fueled by people constantly trying to grow and expand their skillsets in new ways, often at the cost of personal time and energy.

This is something I’ve been struggling with during my entire time in the working world. Every time I start a new job and get into a flow of doing the work, it feels good. I get comfortable with the problem, get into a smooth state of producing results and then repeat the process for the next project. It feel accomplished and productive. But there’s always a nagging feeling at the back of my mind that I’m not really growing my skills. If I’m doing the same thing over and over, where’s the learnings? Sure, I can make minor improvements here and there, but how is the work improving my design skills?

I then get into a state of mind where I need to feel like I’m being pushed and challenged with my design work. I want to work on complex and interesting problems that re-frame the way I think about the solution space. I want to test and validate long held assumptions and want to push the boundaries of the constraints I’m working within. These are the times when I feel most excited to be a designer and when I feel like I’m truly solving problems instead of just shipping interface solutions for a feature the product needed.

But there’s a catch. Every single time I’ve had the opportunity to work on stuff like this in my design career so far, it’s always been an intensely stressful and hectic experience. There was always a looming deadline that seemed unrealistic. The deliverables were always something ridiculous like a fully interactive functional prototype with beautiful transitions and animations. And the team working on it was a mixed bag of designers, product strategists, product managers, and user experience researchers who all had a very different idea of what the design should be. At the end of the day, I was not just trying to come up with a design solution to the proposed problem, but was also trying to plan out how it would all fit together in a high-fidelity prototype that told a coherent story of the user journey, while also managing the expectations and visions of everyone working on the problem with me.

To make matters worse, the problem is almost always never stated clearly from the get go. Usually, I’m given a very task-oriented direction, like “figure out how to make it easier for users to manage their list of tasks” or “make it easier for people to connect with each other from the social link screen.” This doesn’t state the root problem at all. Why does our system force users to manage tasks manually in the first place? What are people looking to get out of connections in the first place? What’s in it for them? How does it help them and us?

A better problem statement would be “users are finding it tedious to manage their list of tasks” or “the core value of our product is in social link connections, and 60% of our users don’t have a single connection”. Starting from this problem statement leads to vastly different solutions than the directional ones, and not enough product managers realize this. Just give your designers a problem statement, don’t tell them what solution to design. The results will speak for themselves. We might end up learning that our task statuses update way too frequently, which requires manual user input to update the task state from their end too often. So a solution could be to either update the task statuses from our end less frequently, or automate the user’s job of manually updating the tasks. In the connections case, we could learn that the 40% of users who do have connections were referred by someone onto the product and automatically see the value of the product through the one connection, or that the home screen doesn’t do a very good job of honing in one on the value prop of the product. Again, different solutions for both cases, one dealing with the referral flow and another with onboarding or first-time user experience improvements.

So naturally, I tend to spend a lot of time drilling down to the real problem and trying to figure out what exactly we’re trying to get to the bottom of, because it’s very easy to design the right solution for the wrong problem. Let’s say the deadline for the deliverable is in a week. I’d personally rather spend 5 days getting clarity on the problem and spend 2 days designing the solution, but in reality, the opposite happens. The product strategist wants to start whiteboarding with me right away and the product manager starts putting together a timeline roadmap of what we want to have done by the end of each day. The rest of the team is throwing out all sorts of ideas in some document but no consensus is being reached. I’ve found that the only time people start getting on the same page is when they see their ideas visually represented in the UI. So it’s only when I’ve made mockups and start showing people what it’s beginning to look like do they start pointing out the flaws. The user experience researcher chips in with all the things that make no sense based on who the users are. The product strategist mentions how the right features aren’t being highlighted properly. The product managers keeps saying we’re behind on schedule and that the client wants to see some progress. Meanwhile, I have four more rounds of iterations and revisions to do before meeting with the rest of the team the next day to figure out the story we want to tell in the prototype. And then I have to actually create the prototype. And I still don’t have clarity on what the problem we’re solving actually is.

As you can tell by now, the combination of all these things makes the situation extremely stressful. Don’t get me wrong. I actually love going through this and working through the challenges step-by-step. This is by far my favorite part of the design process. I get to ideate, innovate, brainstorm, and create all in a very short timespan. I frantically fill up sketchbooks with design ideas and scrap all but one or two of them. I try out twenty different interface treatments before landing on a couple I want to share with the team. My brain feels like it’s firing on all cylinders when working on this stuff and balancing user experience with product clarity, user journey with monetization strategy, and user workflows with proper interaction design. The end result is a compromise between product, UX, and design that solves the problem for users while also building a foundation for generating revenue as a standalone product.

But this entire time, I’m stressing out. I’m working almost 24×7, constantly spending evenings and nights working on this thing. I’m spending the whole weekend worrying and working about it, wanting the deliverable to be as good as possible. And worst of all, the whole time, I’m constantly thinking that we might be solving the wrong problem. This is an unhealthy amount of stress and can seriously lead to burnout or design fatigue if not handled properly. I’ve managed to get through it every time and come out the other end as a designer who has learned incredibly valuable lessons from the experience on many fronts, but every single time, I find myself wishing it didn’t have to happen in such a high pressure and high stakes situation.

What I find myself straddling is this fine line between wanting to be pushed and challenged in my design career, but also only wanting it to happen during business hours so that I’m not losing my personal time and energy to it. I realize how unrealistic that sounds due to the nature of the design process in general, but there’s been many times where I’ve wondered if this lifestyle is sustainable. I love tackling hard problems, but I still need to figure out a balance between that and actually just taking some downtime for myself. It’s tough when you care so much about the thing and want it to be good, and you know that it will be 10% better if you go to bed two hours late just for one night. That balance is really hard for me to find. How much of my mental energy and stress levels am I willing to expend to make my professional work X% better? Where’s the line? Is this even the right way of looking at this tradeoff?

So at the end of the day, it’s just me wishing that there was a more obvious and straightforward way to balance these things. I’m sure there is and that I just haven’t found it yet. Or I know for a fact that I’ll find it soon. One thing I’ve definitely noticed myself getting better at over the years is just being more self-confident with design decisions. I remember a time when I wouldn’t override the decision of a product strategist, but I now find myself engaging in spirited debate about why a solution they suggested won’t work due to an interaction design problem with how users navigate through the UI. As I get better at this, it’s only natural that I get more comfortable with the process. So it’s just a matter of time. Meanwhile, if you do have any tips of how you deal with this situation of wanting to be pushed and challenged but not wanting it to happen at the expense of your personal time and mental energy, do let me know! Would love to hear any thoughts on this, as I haven’t seen a lot of writing or discussion about it online.