How I juggle wildly different freelance projects and don’t lose my mind
My hybrid system for staying on top of things
Freelancing is a game of self-imposed chaos. At first, things were simple, one big client at a time. But after sending out multiple pitches, I hit the jackpot: three new clients, all at once. The catch was that I had to work on all their projects simultaneously. What followed was a total collapse of structure.
I’d wake up at 6AM already behind, frantically bouncing between emails and trying to decipher my own half-written notes. One client needed revisions on a strategy doc, another was waiting on a pitch, and somewhere in between, I had to make sense of a last-minute brief I had completely forgotten about.
My immediate solution was task blocking in my Google Cal, but it quickly started looking like a losing game of Tetris, as tasks overran, interruptions took place and quickly everything became a big mess of overscheduling and subsequent rescheduling.
I started questioning myself: How are other people managing this? We all have the same 24 hours in a day — isn’t that what Kim K said? Maybe I just don’t wanna work. Had I taken on too much, or was I just terrible at time management?
The reality check
I know from experience that whenever you want to change something in your life, the first step is to be brutally honest with yourself. You need to ask: How much do I really spend each month? How much do I actually work out? Only then can you figure out why you’re not saving any money or seeing the fitness results you want.
It hadn’t occurred to me to apply this same level of honesty to my time. But once I did, the results were a real slap in the face. The amount of hours I thought I was working versus the actual time spent on deep work was actually embarrassing. Hours spent “working” were padded out with answering quick messages, checking X every 10 minutes and completing small insignificant tasks. Yes, I am distracted and avoidant.
I cleared everything from my Google Cal and stared hard at the blank Week View. The hours were there and I needed to understand how so many of them were going unaccounted for, if I were ever going to succeed in working for more than one client. I started to wonder if this was more about managing my own delusion about time than time itself.
Tracking my time and restructuring my days
To figure out where my time was going, I started backtracking everything in my calendar. I tracked every time I sat down to work, went to the kitchen, took a shower, and left the house for a few hours. The gaps were eye-opening — I spent more time on everything else than work itself. I told you, avoidant.
I read Cal Newport’s Deep Work, which helped me understand that I was filling so much of my time with shallow tasks and not getting to the important “deep” stuff. Day after day, I was filling my mornings with busywork, putting off deep work until the afternoon and then not having sufficient energy to do it.
I took some time to wallow reflect on what was happening and tapped into something I already knew about myself. I have the highest level of concentration in the early morning, so if I want to get anything meaningful done, I have to capitalize on those morning hours. The rest of the day, I could give away to shallow (but necessary) tasks.
The perk of freelancing of course is that you can plan around what works best for you. For me:
Early mornings → Deep work (writing, strategy)
Afternoons → Study, admin, light tasks
Evenings → Offline time, no screens
Getting organized
From my experience, any vague sense of organization starts with a list. I love lists — shopping lists, movies to watch, books to read, to-do lists. They work great on paper for some things and better on a computer, where you can edit and remove items for others. So, whenever I’ve got multiple tasks on-the-go, a list is typically involved.
I’ve also spent a lot of time playing around with Kanban boards; there’s something satisfying about dragging tasks from To Do to Doing to Done. But when I’m managing multiple projects with shifting deadlines, I’m still having to put in the time to manually shuffle everything around. This led me to trying AI scheduling tools but I never went further than the free trial because there was too much manual setup to get it exactly how I wanted it — all time taken away from actually working.
Each time I started to feel overwhelmed by these tools, I’d default back to old-school list writing in Obsidian, then keying in deadlines and meetings to my Google Cal. I knew things could be more efficient but they work fine-ish like this.
So, it went like this for a while:
Prepare my list in Obsidian the evening before.
Get up early, complete the most important “deep” work and not touch any of the “shallow” stuff or social media until the afternoon – which still to this day takes a lot of discipline.
Prepare a new list for the next day. This was a crucial step — spending time figuring out what I’d be doing the next morning — so I could dive straight into it.
My current hybrid system
I’ve now created a system that works even better than this. I don’t need to spend time each evening figuring out what to do the next day anymore. I plan the upcoming week on Friday — and that’s it.
I’m still using Google Cal but I’m also using an app called Nestful. Google Cal is predominately where I put my fixed meetings and block out time where I know I will be sitting at my desk. I use Nestful alongside this — it’s basically a dynamic to-list, so it orders your tasks based on deadlines and tells you what you need to work on as soon as you sit down to work.
Here’s how it works: I add all the events that need to happen at specific times and places to my calendar. This often fills up further in advance than a week, but Friday is where I do my regular calendar check-up, so I know what’s coming up. Next week, I’ve got a couple of client check-ins, a few deadlines to keep an eye on and some on-site filming events — these all need to happen at specific times. The rest of the time, when I know I’ll be sitting at home at my desk, I block out with “Spontaneous work.” This is where I will go into Nestful and complete whatever it tells me is due next.
Instead of “Spontaneous work,” why not add the tasks to the calendar directly? Let’s revisit my Tetris point. Life is too unpredictable. A client requests something urgently, the dog pukes on the nice rug, mother calls for a chat — each of these derails the task-blocked calendar instantly. Maintaining the calendar becomes a task in itself and, as you’ll already have noted, I have too many tasks as it is.
Now, onto Nestful. I drop in all the tasks I need to do into its homepage. Each task can nest smaller tasks, so I give the main task the client’s name and then nest all the tasks required and due dates within it.
Here’s what it looks like within my client task:
I’ve done the same thing for my two other clients, adding in all of the tasks and due dates. Now, when I go to the Nestful homepage, it looks like this:
I can see exactly what is due today and get a holistic view of all my tasks coming up. Once today’s tasks are completed and checked off, they get archived. Tomorrow when I open Nestful, the Tomorrow column will have shifted to Today.
Nestful shifts the focus away from time allocation and scheduling to getting things done. All I need to know is that I have a two-hour window of concentrated work scheduled in my calendar, and then Nestful does the work of telling me exactly what to focus on next. There’s no need to schedule and reschedule tasks because they’re just there, waiting to be completed.
If you’re a freelancer struggling to keep up, I recommend trying this. The combination of structured flexibility is the only thing that’s actually worked for me so far.
This system keeps me sane. No decision fatigue. No wasted minutes debating priorities. Just work getting done.