
What stories have you never finished?
That’s it, I’m shipping these unfinished thoughts.
I’ve started and failed to finish so many blog posts over the last two years. 83 stalled drafts, and only 7 published.
Anyone who’s ever tried to write knows there are many reasons why you give up on a story. Mid-way through, you feel it’s boring, or you lose inspiration, or it becomes hard to make your thoughts coherent, and you give up.
After looking at my Medium drafts last week, I was shamed into googling up my first ever book on writing and found a gem. It’s called Writing Down to the Bones, and it’s incredible.
All those feelings I’ve had writing: the dishonesty, the fear of judgement, the moments where I’ve gotten completely blocked — to hear them all eloquently articulated by another writer, and even recognized as patterns that every writer faces, was incredibly powerful and reassuring.
I clearly remember when I started writing. It was 7 years ago, when I started writing notes on Facebook. My first post was something about how to churn credit cards (lifetime 500k aeroplan points, what-up). I don’t remember why I did it, maybe it was to sound smart to my network, maybe I simply wanted to share something helpful, maybe I just wanted to solidify my own thinking — maybe it was all those things.
After posting, I got some likes, a few comments, and some general interest from those around me. Someone even said “start a blog bro”.
I’d be lying if I said those little nuggets — the drug of social approval- didn’t compel me to write more. Maybe that’s why I still write. Maybe that’s why I’m writing this post right now. Maybe that’s the wrong reason to write. Maybe it doesn’t even matter.
Regardless of why, this book and my general inability to ‘finish’ has made me realize something — I may not be a bad writer, but I’m bad at writing. What I’m really bad at is the creative process of writing, and evolving mine into one that works and is repeatable.

7 published posts and 83 forgotten drafts means I have a 7.7% completion rate.
That is just weak-sauce, and with this post I’m committing to changing my ways.
To commemorate turning the tide, I’ve decided to share some unfinished, unedited stories that I spent countless hours hammering through to no avail. These are truly raw posts, in some cases nothing more than streams of consciousness, but I’m sharing them to both free myself of the feeling of wasted work, and of course in the hope that they have something valuable to say. Wherever possible, I try to “explain” why I never finished.
The stories I never finished…
(tap titles to read the drafts)
“That time I got into a war with a bitcoin trading bot”
Progress: 1235 words || Coherence of narrative: 7/10 || Reason for stopping: “Who gives a shit about this?”
One-liner: How trying to make some side money on bitcoin led to an interesting project
Gist: I built some simple programs (“bots”) to help me trade bitcoin for profit. I thought no one else would be doing it but I soon realized there was another bot taking away my opportunity. Here’s some stories of weird battles I got into with it, and how I learned to kick its ass.
“Nope. No Way. Never. Nada.”
Progress: 438 words || Coherence of narrative: 3/10 || Reason for stopping: Couldn’t find a good narrative.
One-liner: If you don’t say “no” a lot, you don’t know what you’re doing.
Gist: Saying no is the most powerful mechanism I have in my work. When the world is asking you for a yes, saying no shows that you have a vision and know how to prioritize, whether for yourself or for your team.
“A Framework For: Time”
Progress: 1550 words || Coherence of narrative: 6/10 || Reason for stopping: Couldn’t find a good narrative.
One-liner: How to value your time, over time.
Gist: All these on-demand products (uber, homejoy, etc.) are essentially trading money for more time and convenience. They’re wonderful, but they beg the question — do you know the value of your own time? Time is fixed in life, and therefore the most important thing to optimize for. Everyone should know the value of their time and know how it changes as their wealth grows, or their time starts running out.
“Zero to 100,000 — Real Quick”
Progress: 1537 words || Coherence of narrative: 8/10 || Reason for stopping: Thought it was unoriginal
One-liner: Scaling companies
Gist: I’ve worked at companies ranging from 2 to 100,000+ people. I’ve also seen growth from two to nine people at Tunezy, and from 100 to 200 people at FreshBooks. From those experiences, here’s how I understand organizational scaling problems and where I think companies should focus when improving them.
“Five surprising things that happened when I switched careers”
Progress: 930 words || Coherence of narrative: 7/10 || Reason for stopping: “I am not BuzzFeed why am I writing this”
One-liner: Switching careers is hard but not as hard as you think
Gist: Going from a career finance to technology was like entering a new world. I knew nothing, and had no business being there. But 5 years later here I am, and I realized that I didn’t waste those first 4 years in finance: here are the skills I was able to transfer.
“Collars be damned. We’re all screwed.”
Progress: 730 words || Coherence of narrative: 2/10 || Reason for stopping: I felt I had no credibility writing about this and people would roll their eyes.
One-liner: Technology is reforming the world and eating all the jobs — here’s how I think it’ll play out.
Gist: There’s an ongoing debate that basically boils down to “they took our jaaabbs!”. Let’s take a look at three different outcomes: Pitchforks, Abundance, Innovate.
Why Write
Reading Writing Down to the Bones has evolved my thinking on why I’m compelled to write. In order of importance, I’ve come to realize that:
- Writing helps me solidify my own thoughts
- It makes me feel like I’m affecting change in the world (no matter how small)
- It’s a creative outlet, and a safe space for my mind (until I publish, then I’m 100% aware of being judged/typecast, but that’s OK and I’ll get over it.)
From here on in, I’m going to learn to write with more voracity, consistency, and most importantly — honesty. Opinions are my own.
What stories have you never finished?
Share them with me: Twitter & Medium