I always struggled with double-entry accounting, even after I got an MBA. I could do it and mostly memorized my way through a lot of the jargon, but it wasn’t until I took a systems view to accounting that I really understood the mechanics of how things worked. I figured I’d share some thoughts about that.

Stocks vs. Flows

A common theme in systems thinking is the idea of stock vs. flow. In accounting, everything looks like numbers, but in reality, some of those numbers are stocks, and some are flows, and understanding that distinction is critical.

So — more generally — what…

I’m listening to what you’re saying. I’m sorry if it feels like I’m not. It’s just that my mind is racing. My mind is racing most of the time. It races harder when I try to stop it from racing.

It’s not an “inner monologue”. Inner monologues, I presume, are coherent and single-threaded. This is more like random chatter. On one hand, it’s somewhat abstract because it’s not really words or sentences, but on the other, it’s laden with all sorts of emotions.

It’s not “voices in my head” either. Not hallucinations. Not things I can listen to and have…

Originally published on somehowmanage.com, I’m publishing it here for posterity. There’s also a fun comment section on HackerNews around this article.

It’s a common narrative in tech to design products with the assumption that users are stupid and lazy. I think that is both disrespectful and wrong.

The idea is rooted in a lot of research around product usability, but it has been bastardized. Thing of it as a perversion of the Don’t Make Me Think thesis.

Don’t Make Me Think, the seminal web usability book by Steve Krug, tells us that products should be as simple as possible for…

@nickmorrison via unsplash

I often write design documents even if no one will read them.

There are a lot of resources out there on how to write good design documents. There are also many different ways to define what constitutes a design doc — what it includes, how long it is, how formal it is, etc.

For my purposes, a design doc is any document that you write before you begin the actual implementation. It can be long or short, formal or informal, etc. The point is it’s something you do independently of the implementation—and before.

Most of the known benefits of writing…

@reidzura via Unsplashed

I see a common pattern with startups and teams I’ve advised or been a part of. I call it the Software Over-specification Death Spiral, or SODS for short.

It looks like this:

  1. Product Manager (or CEO, Engineering Manager, etc) drafts up some sort of specifications or requirements for a new feature or product.
  2. Product Manager (or CEO, Engineering Manager, etc) drafts up some sort of specifications or requirements for a new feature or product.
  3. The requirements are handed over to the engineering team to implement.
  4. The engineering team “implements” it, but gets some things wrong. One bucket of things that…


On many teams I’ve advised or been a part of, code is generally viewed as an asset. Only some code, the “bad code”, is considered technical debt. The highest-performing teams, however, viewed things differently. For them, all code is technical debt on some level.

Programming vs. Software Engineering

Software requires two broad classes of effort. There is the immediate effort to write the software, and then future effort to maintain it. (Titus Winters of Google would call the former simply “programming”, and the sum total of both as “software engineering”).

Software engineering is programming integrated over time. Engineering is what happens when things need…

One Question

Learn how to tell who is a great worker, and which of your workers can be great leaders

Illustrations: Thomas Hedger

Growing teams need managers, and who better to manage a team than someone who is already part of one? While that may be true, picking the right person to become a team manager can be a lot harder than it looks. While this piece will focus on engineers, the lessons within are applicable to all kinds of worker-to-leader transitions.

There’s some pretty great literature on making that transition, on being successful in a new managerial role, and on avoiding common mistakes. There are even some great reads on transitioning back and forth between engineering and management. Having advised startups on…

Credit: @hannynaibaho, Unsplashed

Over the past few weeks, after joining Monarch, I started writing code again. For context, save for a few side projects here and there, I haven’t written much code in the past two years (focusing instead on management, writing, and product).

The first thing that stood out: I am somewhat rusty. The second: I had forgotten how fun and engaging writing software is. I feel like I’ve discovered an old addiction. Granted, after code reviews, recruiting, and other tasks, I’ve only got 20–30% of my time left over for coding (and unlike in the past, I can’t expand that time…

I left Quora about 5 months ago. Last week, I joined Monarch Money. I’d like to talk about why I made those decisions, and I hope this will be useful for others who are thinking through their careers.

Leaving Quora

Last year, my wife and I had a baby (little Ahmed Osman Ahmed Osman Ahmed Osman—true story), and something clicked. I felt like suddenly, the opportunity cost of my time had increased dramatically. Any time not spent with my wife and baby had better damn well be worth it. …

Photo Credit: Bruno Nascimento on Unsplash

If you are a founder or manager, one of the highest-leverage activities you can conduct is hiring. And in our competitive market, it’s just not something you can afford to screw up.

A common model for recruiting processes is the recruiting funnel. From a company’s perspective, if you look at how candidates progress through the recruiting process, things resemble a funnel. At the (wide) top of the funnel are candidates that have just applied or that you have reached out to. At the (narrow) bottom of the funnel are the candidates you hire. …

Osman (Ozzie) Osman

Co-founder, Monarch Money. Ex-Quora, Google.

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