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  • Writer's pictureHarshal

Navigating Weekly Planning As A Solopreneur

Updated: Jul 17, 2023

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.

To-Do Matrix


​Very important

​Important

​Less important

​Very urgent


  1. Sipl - Write Qs for partnerships research

  2. Hire freelancer for competitive research as per skeleton

  1. Create v0 list of services. Possible service is design thinking workshops.


  1. Embed poll in substack

Urgent


  1. Synthesize B2B Chats

  2. Split PM resume checker to separate website

  1. Create sub pages for consulting (portfolio) and coaching (job hunt tips) in Wix

  2. Create account to see government Tenders

  1. market size of chrome extensions

Not urgent


  1. define input/output metrics for my business.

  2. Register on GLG, etc.


  1. revamp linkedin cover photo

  2. Find a writing coach

  1. Add pricing example to website

  2. split large CX posts into individual posts

  3. run internal link opportunities on my blog

The matrix helped me because:

  1. I did not need to remember a task. I could add it to the list.

  2. It forced me to review each task’s urgency and importance.

  3. 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:

  1. 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?

  2. It did not have a time element. What should I do this week vs. next?

  3. 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?

  4. 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.

blurred screenshot of color-coded calendar planned from 8 am to 9 pm, Mon-Sun.
blurred screenshot of color-coded calendar planned from 8 am to 9 pm, Mon-Sun.

I found the calendar helpful because:

  1. I allocated most of the time in my week. It made me think of the urgency and importance of tasks.

  2. I estimated the time for each task. I understood the feasibility of completing a task by a date.

  3. 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:

  1. 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.

  2. 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.

  3. 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?

  4. 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.

​Function

Goal

​Consulting

​SIPL: website content review Distill: user metrics, chrome recos, priorities

Coaching

​Resume-checker publish.

Customer Research

Customer research plan. Oversee: CRM automations.

​Marketing

​(legal) Marketing hiring. Marketing outreach. Oversee: Emilia video/slicing. Emilia writing. Chrome reco writing.

Sales

​Create accounts on GLG, etc.

​People

​Lunchclub. Nitin V. John D.

Habits

Start w/ priorities. 1-liner priority. Pomodoro. workout. Diet.

Other

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.

  1. 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.

  2. 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.

  3. I follow the Pomodoro technique. I work in 25 mins work and 5 mins break sprints.

  4. 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

Function

Goal

Accomplished

Consulting

SIPL: website content review, M1 start

SIPL: website content reviewed. started M1.

​Coaching

Suraj-resume. Maven explore peers.

Suraj-resume. Maven explored peers.

Customer Research

Contacts cleanup. Customer research plan. Oversee: contacts cleanup, CRM automations

​Contacts cleaned-up.

Oversaw: contacts cleanup, CRM automations

Marketing

(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.

Sales

-

-

People

Lunchclub. Pita Donut Valerian. Founders meetup. Bhanu UCLA. PITA social.

Pita Donut Valerian. Pita social. Founders meetup. Bhanu UCLA.

Habits

​Start w/ priorities. Momentum 1-liner. Pomodoro. workout. Diet.

✔✔✔✔✔❌🌓

Other

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.

  1. 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?

  2. How much did my execution align with my plan? What functions had the most scope creep?

  3. How much seems reasonable to plan for this week?

  4. 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.

  1. I want to do a task soon. But it won’t fit in this week. Where do I store it?

  2. I have some tasks in progress. How do I mark it as the week goes on?

  3. 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.

Current cycle in Linear for product solo consultancy.
Current cycle in Linear for product solo consultancy.

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.

Summarizing a weekly plan using Linear and Google Sheets.
Summarizing a weekly plan using Linear and Google Sheets.

Benefits

  1. 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.

  2. I could close off a research-style task and create the next task for it. I could schedule it for the next week.

  3. 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.

  4. 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.

  1. I sometimes stare at the board. Then pick up a low-priority task. How do I beat procrastination?

  2. 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.

  3. It doesn’t make sense to track daily habits on a weekly sprint board. So, where do I track those?

  4. 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.


Alternatives

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?


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