Time management: Are you a time-blocker, or a box-ticker?

I’ve had a few requests for this topic, so let’s address it! Readers have asked me for ideas on “getting it all done,” how to organize your day, calendaring techniques, and just (waves hand in air) “all of that” in general, so let’s take a look.

First, a few resources:

• Cal Newport’s recent episode of his podcast Deep Questions, How I’m organizing my life this fall. He’s a computer science professor (not what we do) and an expert on deep work and how to give yourself time to think about important topics (what we do), and I really liked this episode. 
• Amelia Hruby’s book, Your Attention is Sacred (Except on social media). I don’t want to quit social media, but I really like Amelia’s podcast, articles, and book, about reclaiming your time and attention from The Scroll. Her viewpoint reminds me of a quote from Cal Newport that I liked so much, I wrote it on a Post-It note above my desk: “If you aren’t intentional about how you spend your time, technology will do the choosing for you.” 
• Todoist, the to-do app that I use. I find the free version sufficient, and I love being able to pre-schedule things on a recurring schedule. Remind me to do X task every Monday, every weekday, the first day of every month, etc. etc. 
• Toggl, the time-tracking app that I’ve grudgingly started using, but gotten a lot of benefit from. 
• Pomofocus, a simple timer that prompts you to work in 25-minute blocks, then take a break. 

First, what does a typical day look like for you?

I know, there are no typical days as a freelancer. But I get asked this a lot, so here’s an overview. 

I usually go to bed around 10:30 or 11:00 PM and get up around 7:00. My husband works from home and I work at a co-working office (more on that below), so we usually have breakfast together, then I take the bus or ride my bike to my office and get there between 8:00 and 9:00. I typically work until around 4 or 4:30 PM, taking regular breaks throughout the day to move around (stretch, do a little strength workout in my office, take a 10-minute walk, etc.).

After work I often go to a yoga class, have dinner between 7 and 8 PM and then lift weights and/or practice one of my musical instruments. That’s a typical day, but of course there are variations: picking up and dropping off our foster cats, having dinner with my parents who live near us, getting together with a friend for a walk or dinner, etc. etc. 

One thing you’ll notice: at this point in my life, I have close to zero caregiving responsibilities. For years and years (18 years, in fact!) my daughter’s schedule was the main driver of my schedule, and I nearly always stopped working around 2 PM, then picked back up for a few hours after dinner. If you have a massive factor like this in your life: aging parents, kids, someone else who needs you, your own health/energy level issues, give yourself grace and wiggle room when scheduling your work.

Here’s the first question: how many external demands/scheduled appointments do you typically have in a day, because I think that may dictate whether you’re more of a time-blocker or more of a checklist person. I’m more of a checklist person, because I tend to have a lot of scheduled appointments during the day. Here’s a look at this week: 

Monday
8-10 AM remote court interpreting assignment 
1-2 PM meet with ATA mentee
3-3:30 PM consultation with graphic designer about my new website 
3:45 leave work to meet a friend for early dinner 

Tuesday
8-10 AM remote court interpreting assignment 
11-11:30 online coffee chat with someone from my advanced freelancers’ group
2:45-3:45 get my hair cut 

Wednesday
10-11 T4T alumni question and answer session 
12:30-2:00 remote court interpreting assignment 
2-3 attend a webinar on SEO
4:30 leave work to pick up new foster cats 

Thursday
8-8:30 meeting with a consulting client 
10-11:30 T4T ghostwriting class
1:30-3:30 remote court interpreting assignment 

Friday
10-12 remote court interpreting assignment 
1:30-2:00 weekly meeting with a client 

It’s actually pretty rare that I have a day with no scheduled appointments or meetings. Writing this prompted me to look at my calendar, and the next day when I have absolutely nothing scheduled is October 13, almost a month in the future. Thus, I’m scheduling “everything else” (translation and writing work, all things Training for Translators, my own marketing and administrative work) around these pre-scheduled appointments. 

Time-blocking, or task-oriented planning?

When you’re thinking about how to organize your time, I think this is question #1: should you use time-blocking (single-tasking for a designated part of your day or week), or what Cal Newport calls “A, B, C time management,” where A is what you have to get done, B is what you’d like to get done, and C is what you do if you have time after you’ve completed all the A and B tasks. 

Personally, I like the idea of time blocking, but I just don’t have enough time for it to work (insert gales of laughter at that bad joke!). It’s just so rare that I have a whole day as a blank slate, and honestly I like it that way. I’m impatient and easily bored, and I’m an Upholder, so I love a list of things to check off, I’m pretty disciplined even about things I hate doing (Upholders gonna uphold, right?) and if something has to get done, I get it done. Time-blocking is promoted as “stop constantly switching from one task to another,” and just between you and me, I love switching from one task to another. The checklist productivity method works for me! 

I also incorporate the Pomodoro method. I recently, grudgingly, started time tracking in Toggl and I admit that it’s really helpful. First off, I’ve learned that I work a lot less than I think I do. But that’s a topic for another time! The topic here: I watch the Toggl timer, and when I’ve worked for about 25 minutes on one task, I take a break, so I use Toggle as a de facto Pomodoro timer and I find that helpful as well.

But maybe you’re the opposite: your days are completely yours to organize, you’re not an interpreter, you don’t have many meetings. Then maybe think about time-blocking. You could do this in a few ways:

• Divide the day into Pomodoros (25-minute periods of focused work). Aim for a certain number of Pomodoros in total, or a certain number where you do a certain thing, i.e. at least one marketing Pomodoro per day. 
• Create a one to two-hour Deep Work block at your most productive time of day, especially if you can do that at a time of day when you don’t have to regularly check e-mail (before or after your clients are in the office, depending on time zone). 
• Learn from other people. Here’s a freelancer who calls himself Captain Time, who has a really good video on time blocking with Google Calendar. And here’s an article by Austin Church (who runs the advanced freelancers’ community I’m in) on his time management method, which is much more time-block than task-oriented. 

Other factors 

Here’s a list of questions I find helpful, along with my answers in case they can help you:

• What time of day are you most productive? What’s your worst nightmare of a time of day to be working? Me: I maintain that I’m neither a morning person nor a night person, I just love to sleep. But I really, really dislike working at night and try to avoid it. 
• Where (physical location) are you the most productive? Me: Not at home. The rest of the world dreams of working from home; I end up with really clean closets and that’s about it. I moved to a co-working office in 2012 and (with the exception of six highly unproductive months at the start of COVID) have never worked at home since then. 
• Are you more of a time-block person or more of a checklist person? Me: Checklist all the way. 
• Scale of 1-10, how avoidant are you about tasks that you hate? Me: Probably a 6, but I’ve found that if I force myself to do the unpleasant stuff first thing in the day, the feeling of satisfaction is so great that it outweighs the avoidance. For example right now I’d like to find a new content marketing client, so I do the outreach for that before I even answer my e-mail. 
• How chaotic is your work life? How often are you missing deadlines, finishing projects at the last minute, pulling an all-nighter, logging on after an interpreting assignment has begun, etc. etc. I ask this because if these things are happening, I think you need to look at the bigger picture, not just time management. Do you dislike your work? Do you have neuropsychological factors at play (ADHD, depression)? Do you feel overwhelmed in life in general? Did you last take a day off in 2018 and you’re just totally burned out? Me: I’m OK on these, but I know they are issues for a lot of people and I have a lot of empathy for that. I feel fortunate to have the time and money to take regular vacations and days off so that I don’t burn out, and I know that’s not the reality for everyone. 

I hope these tips are helpful if you’re trying to organize your time this Fall! Talk to you next week!