Half a Decade of Blogging

Wow! I have passed HALF A DECADE of blogging. I launched my blog in May 2020 and have posted every week since. Today, I am reflecting back on what writing 277 posts over five years has taught me – and where I might go from here.

The discipline of persistent blogging has expanded my horizons, enabled me to develop my skills, and created a substantial body of work designed to help other startup leaders. As I reflect in May 2025, I am struck with a tinge of awe that I have reached this milestone!

My World in May 2020

Do you remember 2020? So many things have happened since then. When I think back, it seems like it was so long ago. Take a moment with me to remember what it was like in 2020.

A vaguely confusing and potentially threatening virus had emerged in China, but I was focused on moving my team into a new space and building my startup’s product. Then, suddenly, Covid-19 had fully burst onto the scene, cancelling massive healthcare conferences, sending many into lockdowns and social distancing, and taking my startup fully virtual in a matter of hours. It felt like a whirlwind of change in very short order!

All of a sudden, the ways I connected and shared with fellow entrepreneurs for decades became impossible. What had been a pattern of occasional coffees and conversations to encourage other startup leaders was blocked.

At the time, I listened to an interview with a famous software developer who said that when he got asked the same question more than once, he would write up a blog post on his answer so that the next time someone asked that question, he could just send a link with a little note. This was a way of scaling the distribution of his knowledge efficiently.  “Hmmm,” I thought, “That was an interesting way of solving the problem of answering the same question over and over again, a distinct pattern in my coffee connections.”

Shortly thereafter, I talked to two people I knew who had dipped their toes into the water and started blogging. “Hmmm,” I thought. “If they can do it, I could figure this out.”

Some questions remained as I ruminated on whether I really wanted to jump off the deep end and become a blogger:

• What would be the focus of my blog?
• Who was my target audience?
• Did I have enough content in mind to justify the launch costs and sustain the effort?
• Could I make it valuable to readers?
• Did I have the time to write every week?
• Did I want to do it?

As I mulled these questions over for a few weeks, one night at three in the morning, I found myself strangely wide awake with blogging on my brain. I finally went out to sit in a comfy chair, looked out at the stars, and started to think. Under the umbrella of what I had learned as a startup CEO, in thirty minutes or so, I brainstormed a list of over 100 potential topics. Then my adult daughter, who was also sleepless and living with us under COVID restrictions meandered in. I ran my emerging blog plan by her and asked if she thought I should do it? “Yes,” she said emphatically. Then she offered to figure out how to set up a WordPress blogsite for me.  Within a week, she had a site up and running, and I had started my first three blog posts. Together, we pulled the trigger, and www.StartupCEOReflections.com was born!

My World in May 2025

In a flash, it seems sometimes, a half-decade has passed. During this time, I accomplished many goals at the startup I was CEO of in 2020, was surprised by a neurosurgeon’s recommendation to have brain surgery in 2022, recovered wonderfully from that surgery, and moved into a new chapter with a portfolio of roles supporting first-time CEOs in high-impact companies. My best-friend husband and I invested in our children’s significant steps into full adulthood and set off on some spectacular globe-trotting adventures. I met and started working with some great new people. And I wrote and published 277 blog posts.

The informal feedback that folks like you have shared with me is that this work has been valuable. I have lost count of the number of people who have suggested that I write a book. Although I find the comment flattering, this suggestion always makes me laugh since the body of work in my blog post already exceeds the number of pages one might find in a book–and it is all available in bite-sized 700-to-2000-word chunks, tagged into topics on my site.  Also, it is freely available to whoever might find it useful.

Lessons Learned Along the Blog-Writing Journey

The discipline of weekly blog writing has taught me a great deal.

When I started, I would agonize over how to start, what to include, and would often get stuck when I bit off more than I could chew in a single blog post. Over time, I figured out the length balance and discovered that I needed to be more careful in scoping each topic. I perfected my ability to pick useful examples, pare down the number of examples I shared, and protect the identities of those I was using to illustrate my points. I found my style and my voice.

Undoubtedly, I am a better writer now than I was five years ago. Day-to-day life is an endless reminder of things I have learned and a generator of new topics and reasons to continue sharing. I find myself more aware of what it takes to succeed as a startup leader because I am constantly attending to what I should package up into a valuable nugget to share with other entrepreneurs. Codifying my learnings into text demands identifying what is essential, synthesizing the actionable takeaways, and figuring out how to succinctly illustrate my points. I have learned that sharing concrete examples, both good and bad, makes the ideas and stories come alive and yields that most treasured feedback that it sounds like what I write about is grounded in the real world, not some abstraction.

I discovered a few “no’s” along the way:

• No to those who want to write for me
• No to creating a paywall to monetize this work
• No to writing blog posts using generative AI tools that produce soft summaries lacking crisp examples, emotional resonance, and a tone that felt like my voice.

I also learned to leverage and sometimes reject tools. For example, I have learned the essentials of WordPress and website management, honed the complementary roles of author and copy editor, and delved deep into the strengths and weaknesses of Grammarly. I learned that having someone else read my draft before publishing it is essential to assuring quality (thank you to my husband!).

Finally, I learned how much I appreciate the occasional comments, whether in person, via text/email, or as a LinkedIn comment on what resonated for someone. I have felt encouraged when someone mentions sharing my blog with someone else who could benefit from it. Every one of those tidbits is a tiny dose of motivation to keep going.

A Couple of Key Reminders

Remember, especially if you read my blog on LinkedIn or Facebook posts, that there is a whole world of this content–practical advice from someone who has been there, done that–just sitting out there at www.StartupCEOReflections.com. All of it is intended to help you. No paywall or paid subscription. All of it is waiting to be scrolled through to find that nugget that resonates as something you are wrestling with right now.

Let me invite you to send me a note with a suggested topic or a question. Some of my most popular blogs had their genesis in a reader’s idea. If what you have in mind is something I can relate to and where I think I can articulate something that many might benefit from, I might well write about it.

Looking Ahead

My new career era spans multiple small companies building amazing things in parallel. I am blessed to be working with four first-time CEOs currently, and my interactions with them often remind me of what I have learned over time, and those reflections stimulate ideas for new topics to tackle. At the same time, I am growing and learning new perspectives and nuances in my roles as a board member of public, private, and non-profit boards. I am exploring the world of governance, CEO whispering, and empowering the CEOs I am privileged to support. Comparing and contrasting what is happening in the overlapping healthcare worlds of these organizations leads to new insights. Investing in my networks amongst healthcare executives and board members is a growth journey in itself.

Now that I have crossed five years of continuous weekly blogging (one of my original goals!), I might evolve this a bit. I am not sure how just yet. I might modulate my frequency, send out some “best sellers” into LinkedIn posts, and do a few more reflections on what it all means from one of my newer perspectives.

I am still motivated to encourage and teach individuals who decide to pursue an entrepreneurial dream. Perhaps I can ground those just starting to think about it and help bring valuable content to help others succeed.  I am still deeply “in the game,” with perhaps a more seasoned perspective as I progress through my second half-century. Regardless, I continue to love learning, honing my writing, and being able to devote substantial time and energy to contribute to high-impact ventures that make a difference in the world. Thank you for joining this journey with me! We shall see what the coming seasons become!