Let's make it a little less vague: my biggest regret in hindsight is not writing.

By writing I mean writing more documentation for my team members, blogging when I had an errant thought I wanted to pursue, and writing down more case studies and articles about my work as I was living the work.

But honestly? I wish I had done more writing of all kinds - even stuff like creative writing, journaling, etc. I just wish I had indexed more heavily on writing my entire life and career.

What's the point of writing more?

This is a fair question and I think is the bulk of what I want this article to cover.

Writing everything and anything achieves a few core things:

• Leaving a record for people

• Leaving a record for myself

• Having content for people who want to read about my work and thoughts

e.g. I've been saying for years I want to blog regularly, but I never have because I get distracted by XYZ ABC. While I've always been busy, I've let that constantly become an excuse when I could've found a few hours here/there to write down some notes - not everything needs to be a well-written well-edited blog article!

Leaving a record for people

At the core of this regret is the feeling I could've done a better job in my career to communicate and empower my team to see behind the scenes with my work and thinking. I feel like I've been seen as mysterious because of how I communicated and approached my work in some previous roles. It was fine when you directly talked to me and I explained things, but I didn't index enough on async-accessible documentation.

This "record for others" also would've enabled me to create historical context for my team after I left, enabling smoother transitions out of my roles. I don't think enough product teams document their work in a way that makes it understandable for future generations of the team. How much of the past team decisions are questioned without context?

Leaving a record for myself

The most important thing for me in this feeling of "loss" is that I could've been able to reflect inward, looking at my life and experience in a meaningful way, using the writing I didn't end up doing.

I know I've lost a lot of the insights I could've gleaned from my past decisions and way I lived by not documenting my life more proactively. Journaling, looking back on past/work decisions, and taking notes about how I've felt/thought in the moment - these are things I could've done that would've opened up a world for me to look back at. Instead all I have is blurry memories and a few stickynotes.

Having content for people who want to read about my work and thoughts

The last piece here is more practical: having content to be able to adapt for my portfolio, public-facing blog, etc. Being able to make my journey and story accessible to the people around me would be a game-changer for me today.

While not all of the content I would've written should've been published, I could've written content (or adapted content I wrote) for public sharing. Even if I adapted it now, I'd still be referencing and going off the notes of the me at that time - which is better than the blur that is the last 8 years of my career.

If this is a regret, what can be done now to resolve it?

Honestly, there's only one thing I can do to walk back from this regret and feel like I'm meaningfully changing my future: writing more now.

Making sure I write more now and in the future, and writing what I remember from the past, puts a freeze on this problem. I can document everything moving forward and build the repository of knowledge I wish I had built over the years. I'm still young, this regret is not something I'm coming to terms with at the end of my career - I have time and change begins today.

It's also really important that I write down what I remember about the past now, because that puts a freeze on forgetting, on it blurring more, on losing this history. It's not as good as if I had documented it before, but it's something. I can't live just regretting this forever.

Why publish this as a blog article?

First of all, I want to write more - so why not write this and share it with the world? Even if it's a shorter article, it's philosophical and insightful to me. I want to share my perspective and help people understand what I think about when it's 2am and I'm staring at my phone.

I also am writing this as a call-to-action for you to join me. Even if writing isn't your strong suit, just take bulletpoint notes every day of what you did and what you felt. If something resonates with you throughout the day, jot down a note of it.

What matters is that you create a history - but the shape and look of that history depends on you. Do you write full journals every day? a collection of bullet points? weekly blog articles on a private blog? etc.

Imagine yourself in 2 years thanking yourself for writing that case study about the major project you did at work that's now sitting on your public-facing blog. Anyone in the world can read that and feel inspired to talk to you, learn from you, hire you.

Obviously when things are NDA'd this gets harder, but most of us have jobs we can talk about to some degree. Write it for yourself, find the boundaries on what you can share publicly, and adapt the internal memo into something shareable. If you're not sure how to do this, just message me on Twitter and I'll help you.

Conclusion

My greatest regret in my career is not writing more, so let's change that. Who wants to join me? 😉

I'm Raven and this is my blog, follow or subscribe and read along if you want more content like this - I'm on a mission to write here at least twice a month. We'll see if I can write more than that, but no promises!

Thanks for reading, I hope this was insightful!