Two Years of Product Management IRL

Learning from sharing product management stories

Two years ago, I decided to write weekly about overcoming product management challenges. For the past 104 weeks, I've written a product management story every Tuesday.

Sharing what I've learned in the past week is a high point.  I have met many interesting people through this newsletter!

Who Reads Product Management IRL?

Here are some stats on you:

• You are a mix of product people, product developers, and entrepreneurs

• You are global

• 25% of you read product management newsletters from Lenny, Aakash, and Paweł

• 60% of you came from newsletter recommendations from David Pereira, Mustafa Kapadia, Jeff Matlow, and Andrew Clark

You like newsletters with practical tips on delivering great products!

Which Articles Did You Like the Most?

Nearly 50% of you read one article each month.  The types of articles that you read the most are:

Product Manager Life - stories about real-world product manager challenges.

• Sam Kawsarani on FinTech Product Management  This is the most-read article of the year!

• Product Manager Superpowers on the Job

• Trends in Product Management

• What Does It Look Like to Be a Senior Product Manager?

AI in Product Management - how AI is changing product management

• AI Use Cases

• AI Agents and Product Teams in the Future

Product Management Examples - case studies using product management

• Continuous Learning for Product Managers

• Adding Value to Your Product Team

• Customer Journey Map Case Study

• Solution Product Management

• Communicating Your Point of View

• Starting Your Product Strategy

Coincidentally, these were my favorite articles to write!  You want to know more about how product managers deal with challenges on the job. 

Many of you have commented that you deal with similar demands from stakeholders, and quirky coworkers and wondered if there are alternative ways to handle your product initiatives.

Behind the Scenes: Turning Challenges into Content

Step 1: The Inspiration

Inspiration for an article comes from many different sources.  Here are a few of the oddest sources of article ideas:

• My daughter draws pictures of superheroes

• An engineering newsletter article on the characteristics of a Staff Engineer

• A coworker afraid of making enemies by being an assertive product manager

• Stakeholders that question doing something new

• Being frustrated by a coworker who wouldn't finish a deliverable

• Out of ideas for a new product strategy

• Mistakes on the job

• Feedback from my boss

Most of the time, my inspiration comes from the theme of the week from the past week.  Depending on the stage of my product - requirements, planning, testing, launching - I discuss how I handled an aspect of product management.

Step 2: The Writing Process

Each weekend I write the article.  If the topic made me angry then the writing goes fast. 

Often the topic is a problem that I'm struggling to solve on the job.  The writing is slow when I'm dealing with a problem.  Most articles take 3-6 hours to write.

The steps to go from an idea to a first draft are:

1. Chat with AI about my topic points

2. Throw out most of the suggestions from AI

3. Discuss a good hook for the topic with AI

4. Using the hook that sparks passion in me, I write the article

5. Create the high points of the article in PowerPoint

6. Prepare a template in Google Docs for any frameworks mentioned in the article

7. Copy graphics from PowerPoint to the article

8. Proofread the article many times

9. Post the article to Substack

10. Let people know about the article on social media

Wednesdays are the high point of the week because I get feedback from you!

Step 3: Lessons Learned - Growing Through Writing

One of the most unexpected benefits of writing weekly has been the way it deepens my understanding of product management. Each article starts with a challenge or question from my work, and the process of researching, reflecting, and writing often leads to surprising insights.

Here are a few key lessons I’ve learned along the way:

• Collaboration builds better products: Researching examples and frameworks has shown me how working closely with stakeholders leads to more successful outcomes.

• Helping others sharpens leadership skills: Writing about mentoring and supporting teammates has helped me recognize how these actions develop leadership.

• New tools, like AI, unlock efficiency: Testing and writing about AI tools has made me more effective at tackling routine tasks.

• No one has all the answers: Exploring diverse perspectives in the writing process has reminded me that I need to meet people for the best insights.

By pausing to research and write about tough situations, I’ve discovered alternative approaches that reduce stress and improve results. Writing has become a way to learn in public, and that pushes me to think deeper and act smarter.

Look Ahead: The Future of Product Management IRL

What's ahead for the third year?  As I take on more complex product initiatives on the job, I'll keep sharing what I learn each week.  The themes that are ahead are:

• Trends in product management

• Using AI in product management

• Product manager life

• Dealing with the emotional side of product leadership

I plan to continue doing guest posts and share insightful guest articles here.  Here is a recent paid subscriber article about what I learned from guest posting Better Product Management from Guest Posts (paywall is removed for a limited time).

I'm having way too much fun connecting with readers and following product manager newsletters to do much beyond the weekly newsletter.

Conclusion - Celebrating 2 Years of Weekly Articles

Two years ago, I started sharing weekly stories about overcoming product management challenges.  I've learned so much and connected with a global community of product people, developers, and entrepreneurs.

Readers enjoy articles on:

• Product Manager Life: Real-world challenges and success stories

• AI in Product Management: The impact of AI on PM roles

• Product Management Examples: Practical case studies

Inspiration comes from everyday challenges - quirky coworkers, stakeholder demands, or mistakes on the job.  My writing goes from brainstorming, discussing with AI, drawing pictures, and then getting the word out.

Writing the newsletter has taught me:

• Collaboration strengthens outcomes

• Leadership emerges from helping others

• Tools like AI can streamline workflows

Looking ahead I'll dive deeper into trends, the role of AI, emotional resilience and product manager life.  Plus more guest posts and fresh insights from real-world experiences.

Thank you for two incredible years!🙏

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Last week’s backstory for paid subscribers was a humbling experience as a product manager. Working on The Product Team Exit Strategy

Connect to Amy on LinkedIn, Threads, Instagram and Bluesky.

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