How I Tackled the Biggest Project of My Professional Career While Crushing My 9-to-5 Workload
By the time you’re reading this, my final InDesign files will have been buttoned up and sent off to my book publisher, and the layout of the The Financial Diet: A Total Beginner’s Guide to Getting Good with Money will have been completed. *SCREAMS WITH JOY INTO THE WIND!*
You see, I’m a co-founder of a multichannel personal-finance media platform for young millennial women called The Financial Diet, and overseeing the design of the brand’s first-ever book was the biggest undertaking of my entire professional life. Laying out and designing my first-ever published book was an enormous milestone in my career as a designer, and while the prospect of tackling such a large project was exciting, it was also intimidating. It was the first time I had been tasked with designing something so massive — it’s a 205-page book, with charts, infographics, illustrations, and recipes — and I doubted whether I could handle the workload while simultaneously helping run a company.
Because while handling this project, I still had my day-to-day responsibilities as a co-founder of TFD and as the designer for all our website, video, and sales assets. That means I have to wear a couple different “designer hats” and juggle working in different mediums, which can be daunting. I’ve always struggled with multitasking, and it can be difficult for me to keep track of multiple projects progressing alongside one another at the same time: Deadlines and internal milestones get mixed up, and goals I’ve intended to hit always sneak up on me. But I know I’m not the only person who struggles with this, and for this project, I had to work what felt like 10 times harder to make sure I stayed organized and kept the project moving along on time.
So, with some extra effort and focus, I pulled through, and by the end of the project, I felt confident that I came out with my wits still intact. That was largely a result of having drawn up five strategies to keep in mind throughout the process.They covered everything from the way I structured my actual workflow to how I addressed my worst impulses to make sure I didn’t pay for it later on. Here’s what I did — take a look!
1. I Improved My Workflow
At the start of this project, I broke the entire scope of what I had to do into chunks. This prevented scope creep since I was setting out my workload and everything that it entailed from the get-go, and it helped me create internal deadlines for myself to help stay on track. (I use Trello for task management.) For example, when you use a productivity app that lets you move elements of a project timeline into “done” buckets, it allows you to easily measure how far you’ve come. I find this to be super-helpful, because you can track progress in a measurable way. Personally, it keeps me motivated. Seeing visual cues and reminders for when I’ve hit and moved past a milestone made me feel excited to continue and almost tricked my brain into seeing it as a “reward.” I’ve found that positive reinforcement is key to making it through a marathon-length creative project and is something I now try to start at the beginning of every new one.
Another thing I did when designing the TFD book was go through the manuscript and set time limits on each chunk of the project to keep myself moving. This way, I didn’t risk getting caught in one stage for too long, obsessing over details that would be better off if I just called it at a certain point and moved on. Having failed at projects in the past, I’ve done postmortems on them to understand exactly what went wrong and how I could fix it in the future. Again and again, I realized that my inability to cut myself off from obsessing over certain elements meant that I blew past initial estimates for how long something would take me. When teams were lean and there was no supervisor checking in frequently, I let myself get caught in the weeds of design problems, which backed up the work.
Now setting time limits in apps and workflow platforms is something I can’t live without—it checks my worst impulses to overthink problems. I like that I feel accountable to it and that it reminds me to keep moving. You’re forced to get creative with solutions when you don’t have a traditional work environment. Learning to embrace stuff like productivity-based apps and platforms was one of the most integral parts of helping myself manage this project.
Finally, to keep work flowing smoothly, I took care of each day’s small, tedious tasks first thing in the morning, like finding and editing stock photos for our articles and working through my inbox. I worked efficiently, pruned overlong processes, and plowed through what I needed to do. This left me with several hour-long time slots to work on the project uninterrupted. It’s terribly hard to keep myself on track if there are small tasks I know I need to complete buzzing around in the back of my mind or minor interruptions/distractions popping up. (Even hunger poses a problem, because I can’t work if I have hunger pains — keep granola bars handy if you suffer similarly!) Overall, I noticed stuff that once took hours suddenly took a fraction of the time because I wasn’t pushing them off and procrastinating. I had bigger fish to fry. *insert sunglass-wearing emoji*
2. I Stepped Up my Organization
This should go without saying, but organization is so, so crucial. If you don’t have the essentials of your main file set up and organized from the get-go, you’ll end up producing something sloppy and create a lot more work for yourself in the end. And that doesn’t just go for designers. It rings true for nearly every job in every industry. It’s one of the biggest takeaways and lessons I’ve learned in my years working as a creative professional. Even though I’m well aware of effects of being disorganized (you can read up on it in this really insightful article), I didn’t avoid this pitfall entirely.
One mistake I initially made while designing this book was not taking the time up front to set up all the copy with character and paragraph styles. I just figured, “Eh, I’ll deal with it later.” Well, deal with it I did. Because I didn’t take time to address styles at the outset, one global change from our publisher meant that I had to revisit every. single. page. of the 205-page document to edit something that could have taken a fraction of the time. I wanted to kick myself, because I knew better but convinced myself it was a smarter idea to save time at the beginning. (?!?!) WRONG.
These are simple things that don’t seem like a waste of time until they are. And it’s not only your workflow that will suffer. When you don’t have a clear method of organizing your work, others suffer too. You’re at risk of bringing down other team members if you hold up timelines because you can’t execute tasks effectively.
Instead of beating myself up during times when I might have failed, I’ve learned to shift my perspective outward and think about the people whose work lives are made smoother and easier by my good habits.
Staying organized makes me feel confident and clearheaded, and I found that a clean and tidy environment actually strengthens, not inhibits, my creativity. Simply setting aside a few minutes at the end of each workday to clean your desktop and organize files properly before closing up shop is a must. I would recommend using consistent and proper methods to name files, set alerts on your phone, and put Post-its on your desk reminding you of essential to-dos. I found that when I had a small reminder for organizational “housekeeping” items, they started becoming habitual and easier to remember.
3. I Improved My Ability to Set Boundaries
While I was juggling an intense project alongside other work and deadlines, I learned that I had to be ruthless about eliminating distractions. I had to be very clear about what my boundaries were and what I could and could not commit to. Everyone hates saying no to doing something or going somewhere, but believe me, you’ll hate yourself a lot more when your heart is racing at 3 a.m. and you’re trying to finish something that’s due in six hours because you’ve stretched yourself too thin. During the long chunks of time I set aside for myself to work on the book project, I let team members know in advance that I would be largely out of reach unless there was an emergency. It was important to set strict boundaries and do what I needed to get done, and then pop into the work chat earlier than everyone expected to say “hi!” and ask if they needed anything.
4. I Faced Problem Areas Head-On and Avoided My Tendency to Ignore Them
Know yourself. Take a hard look in the mirror. During this project, I learned the way I worked best — what tripped me up and what would build me up—and I was a lot more capable of facing large projects with confidence because I created an environment for myself where it was easier to succeed.
I used to struggle with putting things off. We all have our reasons for procrastinating, but I got a lot better when I faced exactly what was scaring me and delaying a project. So often, I put enormous pressure on myself to make things perfect the first go-around (and I know plenty of other designers who are this way). There’s such a strong desire to produce flawlessly executed and technically sound work from the get-go that it becomes a handicap. For me, I fear that if I work loosely, I’m failing. I lose sight of the benefits of just getting work down and fine-tuning later. I used to think my best stuff would come from working super-slow, nailing my design ideas at the start of the project and immediately carrying them through for consistency. But that tendency toward perfectionism only made me procrastinate more.
Now I strive to work in looser design “rounds.” I think of round one as the skeleton of the project, and then I build up the “meat” and “ornaments” later on. This allows me to try a lot of different things and produces higher-quality, well-considered work. Embracing this mentality of just getting the work out on paper and being unafraid to work loosely drastically cut my tendency to procrastinate. I no longer feel that internal pressure and am confident that building something up slowly in layers was the best possible environment to design the book.
5. I Learned to Avoid Burnout
This dovetails with the point number four. One of the absolute biggest hurdles tackling a project like this one is simply losing steam and knowing I can’t afford to slip up and get lazy because my timeline is so tight. So I set up a reward-based system where I treated myself when I hit a certain milestone. I knew this would keep the process fun and enjoyable! I was, after all, designing a book and wanted to make sure it still felt celebratory. I know myself well, and the past few times I’ve had a large project, I seriously struggled with burnout because I just push, push, push myself until I’m not even creating good work anymore. When I would revisit the work with fresh eyes the next morning after a session of burning the midnight oil, the work looked like garbage, and I’d think, “Who the hell was working on this?” and scrap most of what I did.
I talk to a lot of professionals who all have their version of this story. They treat themselves so they have something to look forward to at the end of each project milestone or something to force themselves to take well-deserved breaks. For example, one designer friend spent months working through a massive app redesign. He said that what helped enormously was treating himself at the end of each project leg to supplies that made his morning bike commute more enjoyable. Once a level of the project was complete, he upgraded his water canteen, then his biking sneakers, then his commuter backpack, and finally, he got nicer headphones to wear on his ride into work. It doesn’t have to be a system where you buy things to reward yourself—it can be anything. All you have to do is make sure you give yourself a break when needed, and listen to your body.
Now I force myself to take breaks, even when I think, “Just another five minutes!” Similar to the way my friend treated himself every time he hit the end of a chunk of work, you can create a system that works for you. Keep it simple if you want. I would walk to a favorite restaurant and order a fancy cocktail I’d been wanting to try and read for 30 minutes while I drank it, or I’d go take a yoga class or do something else totally offline to let my eyes rest and recoup. I enjoyed making my breaks active, because that’s what works best for me.
Of course, these tips are highly personal and have helped me hit my stride to work confidently and efficiently as a designer who can juggle substantial and varied work. You don’t need to be a creative professional to reap the benefits of these suggestions — knowing yourself, feeling unafraid to ask difficult questions, and being prepared are enormously valuable in this gig economy, where it seems everyone has five different projects on their plate at any given moment. You don’t have to be perfect at any one thing, you just have to be good at making it all work.