I don’t believe in time blocking

People love timeblocking, and I get it. It seems like a great way to plan your day and make sure everything fits in.

Unfortunately, the thought of planning my days so rigidly makes my palms sweat and my chest feel tight.

On the other hand, I know some structure in my schedule is beneficial for my productivity. 

I learned this the hard way.

When I first started working for myself, I went all in on rejecting the trappings of traditional employment. I had no boss, obviously. I had basically no schedule. I kept track of deadlines in my head. I worked whenever I felt like it.

And for a while, everything was great! I was living the self-employment dream of freedom and flexibility! But as I got busier, I also got…stressier. 

I remember crying during a session with my therapist, lamenting about my stress and fear of falling back into familiar patterns of overwork and burnout. I thought being a freelancer would feel more free.

Her suggestion? Buy a planner.

😂

It’s so obvious now, but it literally had not occurred to me. I was so intent on enjoying my newfound freedom that I didn’t know what to do when the pendulum swung way too far in the opposite direction — away from the confines of structure, yes, but into complete chaos.

After much research, my new planner arrived in the mail. (It was Cambridge WorkStyle planner, fyi. I’m on my third one now.)

Since I was still a little structure-shy, I hesitated to write directly on it. Instead, I wrote my tasks on little sticky note tabs. That way, if I didn’t finish a task, I could simply move it to another day! 

It worked brilliantly, satisfying my need for structure with my desire for flexibility. 

Three years later, I still use this method to plan my work and my schedule. I even color-code my sticky notes to differentiate between tasks, meetings/errands, and non-client work (like this newsletter!).

I also love that this approach reflects the reality of my finite schedule. I only have so much time every day. Having a maximum of four “slots” for bigger tasks, errands, and meetings is perfect for me. Most days, I try to limit myself to 2-3 things. 

Smaller tasks, like emails, admin tasks, project revisions, etc. fit around these few priorities. I often split larger tasks, like long blog posts and articles, into two or more stickies (see “article start” and “article finish” on separate days, above).

As I started “getting organized,” I realized structure was never the enemy. I wanted autonomy, not anarchy. After doing the brave and essential work of stripping away the trappings of traditional ways of working, I needed to rebuild something that worked for me. And I ended up inventing a pretty great system!

Remember: Productivity gurus claim to have all the answers, but there are no right answers or silver bullets.

Don’t feel bad if the latest time-blocking-pomodoro-habit-stacking-inbox-zero hack doesn’t work for you. 

Take what feels good and leave the rest.

And if you aren’t finding anything that feels right, make something up. 😉 

See you next week,

Kara

Kara Detwiller is a writer and creative based in small-town Saskatchewan. She specializes in long-form content writing for enterprise SaaS, cybersecurity, and manufacturing clients. She is also working on her first novel, among other creative pursuits. To connect, reply to this email or find Kara on LinkedIn or Bluesky. To support her work on Wishful Working, share this email with someone or buy her a “coffee.”

Why Wishful Working? I write this newsletter because I want to see more people enjoy a life not centered around work. For some, the path to freedom and flexibility is through self-employment, but we also need to challenge cultural norms and champion healthier working conditions and work/life balance for all types of workers.