Career-Limiting Advice

Saying goodbye to an old friend that you finally realize might have never been a friend. And what makes it even sadder is knowing that they’re wasting real potential.

Trust isn’t dying. It’s just being rerouted from tired institutions to TikTok teens and the new class of billionaires. If you have to pick one, invest in the teens.

AWS is the buffet. Azure’s your friendly dad at a BBQ. GCP’s quiet luxury. And they either want to sell you crack, fries, or a magic muffler.

How should we build companies going forward? Trust, autonomy, and actually paying people for impact instead of their meeting stamina.

Super simple guide to navigating around corporate seniors: less heroics, fewer firefights, more alliances… and know when to nod, smile, and duck.

Culture is what we do; the spirit in the machine; the secular, business equivalent to a soul.  It’s pivotal to every company’s success.

Tired of average engineering output? Empower engineers. Not with capes. But with some Batman-grade, Alfred-supported self-awareness.

Low-code/no-code is a noble goal because its intent-- like our greatest ambitions-- is to serve the underserved. But it’s just a magic stone.  

Your success in the corporate world is tied 100% to how well you hoard good managers— those rare “net exporters of talent.”

Better word: integrate! Because a buy is just a build in disguise— a focus on data that needs your builders and can’t be bought.

The title says it all.

Originally published in 2013 in Information Week… anonymously. There are definitely times when anonymity is a great idea.

If you’re looking for a future-forward side hustle, let me suggest “AI journalism” — quotes intentional and dipped deeply in spicy sarcasm sauce.

Stop using spaghetti as your work complexity metaphor at work. We all deserve to keep our carbs and chaos separate. Instead, try icebergs.

AI will definitely come for your busywork! Let me play futurist and tell you the result: same meetings, same deadlines, same timeframes. You’re welcome.

Want to achieve Dad-level, epic comedy glory? Super simple. Use the heart emoticon in Teams waaaay more than you should.

Remember when doors just opened? Someday, the bots will break and a Whole Foods line will form. Bring snacks.

No one at work needs to know that you’re playing improv games. Just find a someone as twisted as you and, well… keep twisting. Make work joyful again.

At some point— 25 years from now— this younger generation with their “healthy” sense of “purpose” and “balance”– will be in charge. God help us all.

If you need to change up your OOO message, feel free to steal mine. It served me well for some 25 years.

Innovation requires some demolition, the occasional tearing down of a wall. For sunlight. For play. For profit. So bring your hammer and a snack.

Gutenberg— by today’s standards— was unsuccessful. His printing press flopped because buyers couldn’t read. Human history: still getting dumberer.

Software needs joy and surprise. Maybe even the occastional clown nose. Because boring apps are just sad little formal shoes to fill.

Human brains— like companies— love reruns. Like new consultants, same mistakes. Your “mistake pathways” aren’t just nostalgia. They’re on repeat for a reason.

Why must every tech gadget scream its brand? Give me an Hermès vibe, not some “drunk uncle” logo. Differentiate on design. Make life more beautiful.

Mandates don’t work. And memos don’t get read. Adoption needs early fans with ice cream cones they really, really, really want to share. Social capital, yo!

Three universal thruths: 1) Peanut butter cups are medicine. 2) PoC is theater. 3) PoA is survival.

AWS is the buffet. Azure’s your friendly dad at a BBQ. GCP’s quiet luxury. And they either want to sell you crack, fries, or a magic muffler.

“No Meeting Fridays” are for people who haven’t mastered “no.” It’s old school paternalistic bs, unapologetic and proud.

“Fake it till you make it” works a little too well. And you don’t want to hear this but fitting in (and success on “their terms”) is just not worth the sacrifice.

Mentorship is a nice walk. Sponsorship is a bridge. If you want real growth… sweat together… build together. No shortcuts. No TED Talk wisdom required.

The engineering jobs you worry AI will kill… never existed. But be worried if you’re in commercial art, copywriting, marketing, banking ops.

Banks spend billions on data. They hire data scientists who don’t understand their core businesses and then act shocked with their lack of insights (and speed).

Your direct reports will work hard on everything, including making you feel like everything is going well. Just remember that real growth happens when you sweat the small stuff together.

I don’t know who needs to hear this but there’s no reason for capitalism to have a hard edge.  It can and should reflect who we are and who we aspire to be. Softer. Kinder. Less toxicity.

I wrote this journal entry when ChatGPT first released their product to the public. I spent a lot of time in my man cave, playing with it.

Coaching in the corporate world is fundamentally broken.  Same goes for mentoring and sponsorship.  My answer? Build a side-hustle. Lose the armor.

Engineers are rarely treated like the artists they are. Until we market coding as a creative class—expect more caves, less light and escalating threats about being replaced by AI.

Laid off? Google says: Network! Brand! Network some more! I say: dance with your fears. Take long walks. Practice faith. Serve others. Dancing is good for the soul.

Achieving diversity as hard enough without the political backlash. It’s harder now than ever— an uphill climb— a mountain with more mountains behind it.

Every org is filled with dogs, cats, and rats. Most dogs just want to be liked. They bark at the cats but they don’t bite. Which usually means the cats ignore them and the rats take over.

Moonlighting isn’t some moral failure on the employee’s part. It’s a management problem. The answer is to fix how we measure output and value.

There are only two times when I turn my camera off during meetings.  The first is the obvious one— you do *not* want to see me eating.  I was clearly raised by ramen-lovin’ wolves.

Next purchase for my kids: a gene splicing kit.  I don’t care if their room is a mess but somewhere in there, they better be growing something cool.  On purpose. 

If any one of us wants to lead from home, every one of us has to change how we lead. Seven new leader archetypes. Infinite ways to Zoom different.

Getting to a fully-automated Ops future means ditching the hallowed static mindset and embracing both radical iteration and end-to-end thinking.

The word promotion has come to mean doing a larger job, sitting in a larger seat.  It does not mean doing the same job (better) for more money.

Before the Edmund Pettus Bridge became a symbol of courage and hope, it was just a bridge.  If you think about it, your office— right now— is just an office.

Monolithic products strip teams of autonomy. They rob good engineers of agency. The real case for building micro-products is that small plus simple equals empowering.

Why are stories about Bezos so much more compelling and prone to be retold than stories about Zuckerberg?  What holes in our souls do they fill?