How Do You Measure Success?

"The thing is, Bob, it's not that I'm lazy, it's that I just don't care." - Peter Gibbons, Office Space

How Do You Measure Success?
i have pizza on the brain.

One of the more valuable habits I've been trying to do more frequently this year is to search randomly through my past journal entries to reflect a bit deeper on some random idea or post from a few years ago and tease my current thinking on some topic.

With that in mind, I came upon this wonderfully simple comic from The Oatmeal called "The Oracle."

Created from, of all things, a 'micro fiction' tweet of James Miller, it was a super simple and poignant post that had me doing quite a bit of self-reflection.

With that in mind, here's the question I posed: How do you define success?

That question is one that I've been asked several times, ironically most often in Q&A sessions, after I give one of my talks on what matters in having a career in technology.

I've been feeling more and more resound in the idea that each needs to create their definition of success. What's important to me is very different than what matters to you, and there's no magical fortune cookie to guide you to what success even is.

I've never really found any measure of success is quantified by the size of your team/organization or a particular title. Still, I know plenty who value and place emphasis on that. And, maybe that's the big challenge; it's an open-ended definition that requires each person to decide when you've been successful.

"Success in life could be defined as the continued expansion of happiness and the progressive realization of worthy goals" — Deepak Chopra

"Success is 1% inspiration, 99% perspiration." — Thomas Edison

"Try not to become a man of success. Rather become a man of value."  —  Albert Einstein

I wonder if some of these inspirational notions of success are too lofty. Judging your success is more about what completes you as a human. Something more ... personal.


  • success is brewing that perfect cup of coffee in the morning.
  • success is walking to the mailbox after a significant health incident, or success could be completing a marathon for the first time.
  • success is an amazing pizza.
  • success is an evening with close friends, laughing and sharing stories under the stars.

And that's what matters - whatever you achieve is your qualifier of success, not anyone else's. You need to define what, where, and how success looks like in your life.

For my own journey, Sir Richard Branson has the right the idea:

"Happiness isn't just how I measure my success; it's also the key to it. Life's too short to waste your time doing things that don't light your fire. If you don't enjoy what you're doing, or aren't having a lot of fun – despite the fact that you're making a lot of money or rubbing shoulders with the rich and famous – then it's time to move on to the something that does make you happy."

If you enjoy these posts, you can buy me a coffee ☕️, or if you'd rather just keep up with my daily ramblings, follow me via your favorite RSS reader, via Mastodon or keep reading my posts on this blog.

Slow Tech

If you're from Connecticut, you probably are already aware of the fantastic pizza from Frank Pepe Pizzeria Napoletana in New Haven. So I was shocked when I saw Netflix had a new series, Chef's Table: Pizza, in which episode 4 featured Franco Pepe.

It turns out I'm an idiot; Franco isn't Frank - they're both pizza masters, and from totally different worlds.

Franco's pizza is called, by some, the best pizza in the world, and what spoke to me was the process in which he makes the dough - no machines are involved. He views pizza as 'more than a vehicle to deliver sauce and cheese,' but as an expression of creativity.

Today, everyone wants to go the easy way.
No obstacles. No sacrifices.
But my father taught me that the pizza chef's
identity is passed through the dough.
And this dough, rises through the years.

Brain Dump

Here are a few articles and videos that resonated with me over the last week:

  • For frequent readers, you already know that I'm a huge fan of Do Lectures and the Do Book Co, so I was delighted to see that Russell Davies (of 'Everything I Know About Life I Learned From Powerpoint' fame) is writing his next one for them. I can't wait to see what he cooks up in Do Interesting — [via New Do who this?]
  • A wonderful read that was shared on Mastodon this week on coffee and why drinking 'bad coffee' is the author's latest obsession. It's more about the experiences and company he's shared with those terrible cups, but it was fun to read through. — [via The Case for Bad Coffee]
  • A reminder on how not to obsess too much about the tools but the process of constant iteration to craft something a bit better each time. — [via Thinking Too Hard About Starting]
  • Continuing from a deep dive into 'hacking' the thought process of Wordle and using grep to find permutations, it's a fun geeky read. — [via Wordle permutations]
  • The folks over at IA have a wonderful essay on the impact of generative AI (ChatGPT) and the importance of language being a bridge. 'If we disconnect one side of the bridge, the bridge falls. If one listener or speaker, writer, or reader stops feeling what is said, the bridge crumbles. Language without a body is senseless, meaningless, void.' — [via The End of Writing]
  • On the geek side - I agree with everything in this post. I want an 11" or 12" MacBook Air - not a larger one. Put MacOS on an iPad Pro M2 11," and I'm happy. — [via I like 11 better than 15]
  • A powerful post posits that we are all just "blabbing away" on the Internet. And it's not wrong, even this newsletter/blog - we're all just 'saying things' — [via We're All Just Saying Things on the Internet]
  • If you manage a team and struggle with internal communications, you'll appreciate this post. It provides some great practical examples of improving communications within your teams. — [via Internal comms for executives.]
  • Not something many want to think about, but I realize I need to do this - create a 'digital legacy.' It hit me hard when I was being wheeled into heart surgery a few years back that my wife didn't have the passwords to access most of my accounts, and it's an essential thing to think about in case of the worst — [via Digital legacy the homemade version]
  • Sure, the timeline is wrecked enough already; let's read from new Books of the Dead that have been recently discovered and bring some mummies back to life — [via Archaeologists discovered a new papyrus of Egyptian Book of the Dead]
  • Stumbled on this tribute website to the fantastic book Four Thousand Weeks. Rather than describe it, go experience it — [via Four Thousand Weeks]

This Weeks Mantra


The Yiddish word describes 'the art of trying to fix something only to make it far worse.'

Be well. ✌🏻