In my recent conversations with fellow freelancers in the Creative Lounge at the Hub, one of the questions that eventually comes up is how to best to gather and visualize the ever-expanding set responsibilities, projects and aspirations that we carry as solo business owners.

While growing my digital studio, Methods, I've experimented with and (mostly) abandoned a decent number of task management systems, reminder lists and flashy new apps that promise more intentional daily organization.

You've likely been through a similar song and dance cycling through various forms of structured planning and rituals to get your most important work accomplished. Personally, I eventually arrived at a place of being honest with myself that my work as a freelancer will always be a bit messy and improvised regardless of how hard I try to mold it into a singular system.

So it was with this perspective that I came upon a refreshingly unconventional approach to building a daily practice with an app named Sunsama. In only a few short months of use, my relationship with daily organization has been reinvigorated.

Sunsama is an extremely accessible daily planner that enables me to articulate, anticipate and assemble all of the building blocks that shape my work.

Whenever I tried implementing a new task management app in the past, there would always be that one thing that felt like it was missing. Now I've come to realize it wasn't one more inventive feature that I needed, but a tool like Sunsama that overhauled the entire dynamic — acting as my collaborator — to encourage me to have a consistent open dialogue and feedback loop with myself.

As a freelancer who works primarily remote, I've had to develop my own unique working rhythms, generate activation energy and coach myself through the dips in motivation that inevitably come along during my day. In the early weeks of settling into Sunsama, I observed that I was suddenly having a realistic conversation about my workload and began to better appreciate the iterative progress I was making in the small things day-to-day.

If you've ever used a kanban-style (visual board) app before such as Trello, Asana or Notion, you'll feel at home with the Sunsama interface. Beyond this brilliant structure to visualize your week — the unexpected relief of having an automated co-pilot guide your planning and reflection at the beginning and end of your day with thoughtful suggestions is its most delightful feature.

At this point, I'd highly recommend you pause reading and set up your Sunsama. Experiencing Sunsama's calm and mindful daily practice will be the best 15 minutes you can gift yourself today.

Get 30 days of Sunsama for free as a member of the Freelancer's Union.

A brief guide to getting started with Sunsama

Welcome back! Now that you're in the flow with Sunsama, here’s a handful of features that have come to shape my relationship with time management and progress as a freelancer:

Daily Planning & Shutdown

At first, I felt the automatic settings to plan and reflect on my daily tasks, events and weekly objectives was a bit heavy handed. But within a few days, it became obvious that this was quickly becoming an essential ritual to help me acknowledge the purpose and priority of my daily work. As I adapted to estimating and tracking the actual time I contributed to tasks, I noticed my ability to anticipate the effort necessary to accomplish bigger objectives becoming a lot  more accurate.

Time Blocking & Focus

Every time I settle into a new task in Sunsama, I instinctively start the timer and enter Focus mode. With the desktop app installed, you can use the handy Focus bar that hovers on your screen as you work. I use Focus constantly as a mechanism to notify my brain it's time to concentrate on a singular objective. Rather than feel self-critical when I don't fully achieve my goal in the time I blocked, I've began to proactively add bite-sized subtasks and track subsequent focus sessions to see a single task though to completion.

Channels with Context

Rather than having to manage endless tags and folders for projects, using the concept of "adding context" for each of my tasks and events with #channels makes identifying and narrowing down responsibilities much more intuitive as I move through my day.

Connect External Sources

This deserves an entire separate post, but by having direct access to the most common  task creation sources outside of Sunsama gives me a far more tangible sense of what I have to take care of. One of the topics I mentor fellow freelancers on is how to overcome the magnetism of using email as a checklist. By connecting Sunsama with your Gmail or Outlook, you can mindfully stay out of your inbox during the day and selectively action important messages without being caught up in a whirlpool of distraction.

Auto Archive & Backlog

As a new user of Sunsama, this feature was invisible to me for the first week. But as I got   in the rhythm of using Daily Planning & Shutdown, I realized that rather than endlessly guilt me for unfinished tasks, Sunsama began to intelligently auto-archive or recommend that I adjust priorities to future days or the backlog. This small feature reflects the realities of life in a way that I’ve seen few apps ever take into consideration.

Conclusion

The longer you use Sunsama, the collaborative perspective it provides will only continue to grow with you. This is my favorite type of app, one that adapts to the realities of life while gently encouraging you to develop new rituals and clarity along the way.

If you want to explore Sunsama or other topics related to embracing creative tools & techniques in your freelance journey, come meet with me in-person at the next Creative Lounge & Tech Bar at the Freelancers Hub.

Can't make it in person? I offer dynamic 1:1 creative sessions for freelancers in my virtual studio at Methods. Have questions or feedback about this guide? Drop me a personal email at josiah@methods.nyc.