Navigating Weekly Planning As A Solopreneur
Updated: Jul 17
Transforming Remote Work Chaos into Order with Effective Planning - One Week At A Time
Ever find your attention wandering during work, drawn to a quick coffee break, or a social media update? It's not easy to stay on task with distractions all around us.
But what are you getting distracted from? Do you have a plan for your day? Making a plan can feel just as difficult for your job. It feels easy to work on urgent tasks and stay busy.
Planning often feels like solving a complex puzzle. How to make a plan for your week or day? How to stick to it?
Now, imagine handling all this on your own, as a solopreneur.
I wish I could say this article is here to share deep secrets of planning and focus. It is not.
But, I will share 4 weekly planning approaches I tried. These approaches brought order to my work weeks as a business owner. What worked and didn’t work for me? What helped plan and focus in the absence of managerial oversight?
To-Do Matrix Is My Plan
I used a 2-D to-do backlog as a full-time employee. So, I started my solopreneur time in 2022 with the same. Here is an example.
The matrix helped me because:
I did not need to remember a task. I could add it to the list.
It forced me to review each task’s urgency and importance.
I removed tasks that stayed on the list for a long time. It helped me prune my wish list.
My issues with the to-do matrix:
It forced me to review tasks I don’t need to do this or next week. Which tasks can or should I do several weeks in the future?
It did not have a time element. What should I do this week vs. next?
It did not have a scope element. How big is each of these bullet points? Does each of them take a similar amount of time? Can some take days and some minutes?
There was no visibility of progress. When I complete a task, it disappears from the list.
My Calendar Is My Plan
One problem with the to-do matrix was it did not have a time element. What should I do this week vs next?
I added a time element to my plan by using my calendar to plan my days and weeks. I also partially solved the scope element. Thanks to Blur photo editor for a blurred version of my calendar below.
I found the calendar helpful because:
I allocated most of the time in my week. It made me think of the urgency and importance of tasks.
I estimated the time for each task. I understood the feasibility of completing a task by a date.
I knew what to work on at any given time. I didn’t need to fumble through my list every hour.
But, my issues with a calendar approach for planning were:
It forced me to estimate the time to complete a task. As Nasim Taleb points out in Black Swan, we are terrible at estimations. I would explain the time block to do my current task every few hours.
Although the calendar added a time element of when to do what, it was an artificial time element most of the time. I could always choose to move things around. I moved other items around on my calendar if I had a new meeting. The tasks seemed like time blocks, but they were not blocking my time.
Sometimes, I would find a new business avenue, but all my time was already allocated. How do I create time to explore a new direction? Should I miss my plan for exploration or ignore exploration for my plan?
I noticed I had less motivation to handle deep work, like thinking. I had more motivation to handle time-bound tasks, such as meetings or the execution of earlier plans.
Calendar seemed to solve for the time element and scope element, but created problems on both those fronts.
Hand-Written Weekly Plan Of Business Functions
I found the calendar approach too tactical. I wanted some unstructured time to think about my week. I wanted an accountability partner to share my plan with. A calendar is hard to parse or summarize.
So, I wrote weekly plans every Monday and shared them with my spouse. I used OneNote and thought about each of my business functions. See more at Organizing and Scaling my business as a solopreneur.
Although my business may have several functions, I cannot do much on my own in a week. I heard a similar complaint from other solopreneurs. Here is a version of a weekly plan.
SIPL: website content review Distill: user metrics, chrome recos, priorities
Customer research plan. Oversee: CRM automations.
(legal) Marketing hiring. Marketing outreach. Oversee: Emilia video/slicing. Emilia writing. Chrome reco writing.
Create accounts on GLG, etc.
Lunchclub. Nitin V. John D.
Start w/ priorities. 1-liner priority. Pomodoro. workout. Diet.
HA Migration. Energy meter. Decide on a co-working space.
I will break down the “Habits” function, because it does not fit with the rest.
I start each day by first reviewing my weekly priorities and that day’s calendar. I want my daily calendar agenda to reflect my weekly priorities.
I keep one or two most important items to complete daily. The meat of the day. Rest everything is ancillary. Like salad dressing. I write this focus on my Chrome new tab in Momentum.
I follow the Pomodoro technique. I work in 25 mins work and 5 mins break sprints.
I work out every morning. I follow a measured diet of whole foods. More about being a Fitness Fanatic here.
Each day I update my table with goals vs accomplishments. By the end of the week, it gets filled. Here is a version at the end of the week, from another week
SIPL: website content review, M1 start
SIPL: website content reviewed. started M1.
Suraj-resume. Maven explore peers.
Suraj-resume. Maven explored peers.
Contacts cleanup. Customer research plan. Oversee: contacts cleanup, CRM automations
Oversaw: contacts cleanup, CRM automations
(legal) Marketing intern hiring.
Emilia video/slicing. Andrew social media post.
A - ContactOut. email scale ireland about SCT discount.
(legal) marketing intern hiring.
Emilia video/slicing. Andrew social media post.
Althea - ContactOut. Email Scale Ireland.
Lunchclub. Pita Donut Valerian. Founders meetup. Bhanu UCLA. PITA social.
Pita Donut Valerian. Pita social. Founders meetup. Bhanu UCLA.
Start w/ priorities. Momentum 1-liner. Pomodoro. workout. Diet.
HA Migration testing. Energy meter. Decide on a co-working space.
Tax_22 docs. Energy meter. Co-working think. HA migration testing.
I found the writing of a weekly plan helpful.
I would start each day by looking at my plan. Does my day align with our priorities for the week? How did I do on my habits yesterday?
How much did my execution align with my plan? What functions had the most scope creep?
How much seems reasonable to plan for this week?
I knew the priority order for the functions because I had kept consulting at the top, followed by coaching.
But, a weekly plan table still had shortcomings.
I want to do a task soon. But it won’t fit in this week. Where do I store it?
I have some tasks in progress. How do I mark it as the week goes on?
How do I align my weekly planning table with my content backlog and resume parser backlog?
Using Project Management Software
I was using Asana for my content calendar and Zoho projects for my resume parser backlog. Anytime I had an idea for my business, I used to add it to the calendar at a random date in the future. Or I would immediately work on it the same day by pushing out my plan.
I realized I should neither add every idea to this week nor the coming week’s plan. I should not add an idea to my calendar at some random date. It should go into my business planning backlog.
I knew Jira and was almost going to use it. I heard great things about Linear.app from product communities, so I decided to try its free version. I was skeptical. What’s the value of keyboard shortcuts? What’s the point of using a project management software that is not as feature-rich as Jira? Yet, I tried it out. I was floored. It worked great for my simple needs. After using Linear, I try keyboard shortcuts in every other enterprise software.
I realized I did not want to track my habits or non-business activities in Linear. I also wanted to review my week's progress and goals at a summary level. So, I integrated Linear with google sheets. I used slicers and pivots. I extracted the output and pasted a table into my email. Linear helps me create weekly sprints of focused work. Here is an example email and process.
I could create sub-tasks for a task. Creating sub-tasks helped me track incremental progress. It helped me feel fulfilled. It sped up my progress.
I could close off a research-style task and create the next task for it. I could schedule it for the next week.
The most significant benefit for me was having a backlog of ideas. I prioritized the backlog (backlog grooming). I assigned some tasks to week N in the future.
Now, my calendar is free in the coming weeks. Only meetings showed up on my calendar.
I found these challenges when using project management software.
I sometimes stare at the board. Then pick up a low-priority task. How do I beat procrastination?
I don’t estimate the effort of the tasks. I feel sad when I work for hours on one task on the board, but it isn’t yet complete.
It doesn’t make sense to track daily habits on a weekly sprint board. So, where do I track those?
I am on my laptop all day. It is easy for me to get distracted while planning if my plan is also on my laptop.
I use RescueTime to track my productivity. I noticed I have 65-70% productivity. Not 100%. RescueTime helps me track my time spent. It alerts me when I spend too much time on Slack, Email, Videos, or other distractions. But it doesn’t help me plan my time.
I use monthly accountability calls to share my progress with a mentor and get feedback. But that does not help me plan my day-to-day.
I do a weekly check-in with my spouse. Some of our check-in is around our work. It helps me retrospect. It helps me plan for the next few months. But not the next day.
I use the deprocrastination chrome extension. It helps me not deviate. But, it does not help me plan the week or execute high-priority tasks.
Am I At Peak Productivity Process? How Do I Reach There?
I liked the benefits of a board view for tasks over a calendar or task lists. I moved my house tasks to a Kanban board in Zoho Projects. I moved my content calendar from the free trial on Asana to my existing paid plan in Zoho Projects. I like using Linear for my weekly plan.
Using project management software is not the ideal approach for me. What is the best approach? I have an approach, but it is not perfect.
I could change when I plan the week. Should I do it on Friday afternoons instead of Monday mornings?
I could merge my backlog from the content calendar, resume parser product, and home tasks to the weekly planning in Linear. But each board goes through different steps.
I could start a backlog grooming process. That will soothe my worry about missing items from the backlog.
I could think of other day-to-day productivity approaches while keeping the weekly as-is. Should I take the most challenging item as the day's first task? Should I write for 30 minutes first thing daily? Should I take up the smallest item as the first task each day?