Lessons after 6 weeks on Substack

Giving thanks and reflecting.

Skye, in meaningful reflection.

This weekend was Canadian Thanksgiving—we celebrate six weeks earlier (and with way less football or shopping) than American Thanksgiving. In another six weeks, I will hopefully be celebrating the completion of my Portfolio and many other amazing things outlined in this post (…Perhaps with football and shopping?).

Here's what I've learned after my first six weeks on Substack:

Lesson #1

Writing takes longer than I think it will (but it's worth it). I'm embarrassed to admit that I didn't know writing would take me as long as it does. One post a week would surely be a breeze, right? Wrong. What seems like a simple idea often turns into a time-consuming process of organizing, refining, and editing. I'm learning to respect the craft and take myself more seriously as a writer.

Lesson #2

Public accountability drives faster (and better) results. I started writing on Substack mainly to create an accountability mechanism for myself. I thought that writing in public would help me stay on track toward my goals by holding myself accountable for weekly progress updates. So far, it has worked, which leads me to the third lesson… 

Lesson #3

Working in public has a flywheel effect. Sharing my goals and deadlines publicly has helped me move through ideas and unknowns significantly faster than working alone in private. I've made greater strides in these last six weeks than in the previous six months. I have also fostered numerous connections, which have led to new opportunities and perspectives.

Lesson #4

Making internet friends is fun. I live on a small, rural island with only 3,000 people, where the median age is 61.6. While it has its positives, not many people are career-oriented. It has been fun to connect with many kind, cool and ambitious people. From casual exchanges in a comment thread to direct messages and ad hoc video chats, they have felt effortless and special. Thank you!

Lesson #5

Jump off the cliff (before you are ready) and trust the process. Leaping into the unknown of Substack forced me out of my comfort zone. It pushed me to confront my fears of being seen and possibly unliked, criticized, or not welcome. While it still feels scary each time I post, I am learning to trust myself a little more, love myself a little more, and discover parts of myself that I didn't know existed, which makes it worth it.

Peaking back and looking forward

Goals review

Five weeks ago, in my ‘Action Plan and Execution’ post, I outlined my goals for the third and final act of 2024, focusing on the first six weeks from September 2nd to October 13th.

The theme of this period is "Experiment! Experiment! Experiment!."

I set up three main experiments with a handful of measurable deliverables each.

To move quicker and more effectively, I had three key assumptions:

• 1st assumption (a.k.a. 'Content' Experiment): Sharing my goals in public and documenting my journey will create accountability, which will, in turn, help me make progress faster.

• 2nd assumption (a.k.a. 'Portfolio' Experiment): Creating a work portfolio and revamping my professional identity will help me gain confidence and clarity for my portfolio career. Following a program will help me achieve this faster than if I went it alone.   

• 3rd assumption (a.k.a. Project X): Taking a consulting-style approach to a new project with my current employer will help me understand whether I want consulting in my Portfolio and provide a more recent/relevant case study.

The good news is that I completed all my deliverables for the ‘Content Experiment’ and ‘Project X.’ The bad news is that the Portfolio is proving to be quite challenging.

What went well?

• 300 subscribers in 6 weeks (But now it's crickets).

• I had a couple of personal breakthroughs regarding who I am professionally and where I want to take my career.

• I'm pleased with the overall headway I'm making—even if sometimes I doubt myself.

What went poorly?

• Case studies are taking longer and are hard. I am struggling.

• I fell behind on fitness, nutrition, and housekeeping. I don’t like how I feel when these are out of sync.

• Negative self-talk is loud. The gremlin voice in my head has been loud, saying:

  • You are moving too slowly

  • You are a terrible writer

  • This is pointless

Stop/Start/Continue

Stop

• I will only add something new to my calendar for the remainder of this year if I remove something else. The next few months are busy. Look at what I can subtract.

• I decided not to start my PocketCOO Substack for now and instead focus on this publication and the things on my 'Start' list.

• Getting hung up on numbers. Focus on delivering something of value instead.

Start

• Getting to know my subscribers. I want to say hi, get to know you, learn why you subscribed, and discover how I might help you with your goals.

• I created an assessment to help me understand where I am currently with my portfolio career and where I want to go. I want to test it out on people and get feedback to see if it can be helpful.

• I was asked to create a workshop on leveraging the 80/20 Principle for solopreneurs and teams of one. This feels like a great opportunity and a topic I love.

Continue

• Keep writing weekly posts. Improve writing skills, style and voice. Get clearer on purpose.

• Daily (weekday) notes. 

• Getting to know Substack friends.

Maybe

• Start using Notion—for planning notes and posts.

• Rewrite the Substack welcome email. I haven't touched this. 

• Rename the publication. The more I explore the topic, the more I see this as a place to experiment with my dream portfolio career mix rather than document my journey.

Sprint 2 Plan

Here is the updated canvas with my goals from the last sprint and revised goals for this next sprint:

Looks like I have my wok cut out for me. See you next week!