Sometimes You Just Have to Ship
I’ve been in this software racket, depending on where you start counting, about 25 years now. I’ve been fortunate to work on a lot of different things in my career—embedded systems, custom hardware, shrinkwrap, web systems, software as a service, desktop, mobile, government contracts, government-adjacent contracts, startups, little companies, big companies, education, telecom, insurance, internal tools, external services, commercial, open-source, Microsoft-based, Apple-based, hosted onvarious unicies, big iron, you name it. I think the only major “genres” of software I don’t have road miles on are console game dev and anything requiring a security clearance. If you can name a major technology used to ship software in the 21st century, I’ve probably touched it.
I don’t bring this up to humblebrag—although it is a kick to occasionally step back and take in the view—I bring it up because I’ve shipped a lot of “version one” products, and a lot of different kinds of “version ones”. Every project is different, every company and team are different, but here’s one thing I do know: No one is ever happy with their first version of anything. But how you decide what to be unhappy about is everything.
Because, sometimes you just have to ship.
Let’s back up and talk about Venture Capital for a second.
Something a lot of people intellectually know, but don’t fully understand, is that the sentences “I raised some VC” and “I sold the company” are the same sentence. It’s really, really easy to trick yourself into believing that’s not true. Sure, you have a great relationship with your investors now, but if they need to, they will absolutely prove to you that they’re calling the shots.
The other important thing to understand about VC is that it’s gambling for a very specific kind of rich person. And, mostly, that’s a fact that doesn’t matter, except—what’s the worst outcome when you’re out gambling? Losing everything? No. Then you get to go home, yell “I lost my shirt!” everyone cheers, they buy you drinks.
No, the worse outcome is breaking even.
No one wants to break even when they go gambling, because what was the point of that? Just about everyone, if they’re in danger of ending the night with the same number of dollars they started with, will work hard to prevent that—bet it all on black, go all-in on a wacky hand, something. Losing everything is so much better than passing on a chance to hit it big.
VC is no different. If you take $5 million from investors, the absolutely last thing they want is that $5 million back. They either want nothing, or $50 million. Because they want the one that hits big, and a company that breaks even just looks like one that didn’t try hard enough. They’ve got that same $5 mil in ten places, they only need one to hit to make up for the other nine bottoming out.
And we’ve not been totally positive about VC here at Icecano, so I want to pause for a moment and say this isn’t necessarily a bad thing. If you went to go get that same $5 million as a loan from a bank, they’d want you to pay that back, with interest, on a schedule, and they’d want you to prove that you could do it. And a lot of the time, you can’t! And that’s okay. There’s a whole lot of successful outfits that needed that additional flexibility to get off the ground. Nothing wrong with using some rich people’s money to pay some salaries, build something new.
This only starts being a problem if you forget this. And it’s easy to forget. In my experience, depending on your founder’s charisma, you have somewhere between five and eight years. The investors will spend years ignoring you, but eventually they’ll show up, and want to know if this is a bust or a hit. And there’s only one real way to find out.
Because, sometimes you just have to ship.
This sounds obvious when you say it out loud, but to build something, you have to imagine it first. People get very precious around words like “vision” or “design intent”, but at the end of the day, there was something you were trying to do. Some problem to solve. This is why we’re all here. We’re gonna do this.
But this is never what goes out the door.
There’s always cut features, things that don’t work quite right, bugs wearing tuxedoes, things “coming soon”, abandoned dead-ends. From the inside, from the perspective of the people who built the thing, it always looks like a shadow of what you wanted to build. “We’ll get it next time,” you tell each other, “Microsoft never gets it right until version 3.”
The dangerous thing is, it’s really, really easy to only see the thing you built through the lens of what you wanted to build.
The less toxic way this manifests is to get really depressed. “This sucks,” you say, “if only we’d had more time.”
The really toxic way, though, is to forget that your customers don’t have the context you have. They didn’t see the pitch deck. They weren’t there for that whiteboard session where the lightbulbs all went on. They didn’t see the prototype that wasn’t ready to go just yet. They don’t know what you’re planning next. Critically—they didn’t buy in to the vision, they’re trying to decide if they’re going to buy the thing you actually shipped. And you assume that even though this version isn’t there yet, wherever “there” is, that they’ll buy it anyway because they know what’s coming. Spoiler: they don’t, and they won’t.
The trick is to know all this ahead of time. Know that you won’t ship everything, know that you have to pick a slice you actually do, given the time, or money, or other constraints.
The trick is to know the difference between things you know and things you hope. And you gotta flush those out as fast as you can, before the VCs start knocking. And the only people who can tell you are your customers, the actual customers, the ones who are deciding if they’re gonna hand over a credit card. All the interviews, and research, and prototypes, and pitch sessions, and investor demos let you hope. Real people with real money is how you know. As fast as you can, as often as you can.
The longer you wait, the more you refine, or “pivot”, or do another round of ethnography, is just finding new ways to hope, is just wasting resources you could have used once you actually learned something.
Times up. Pencils down. Show your work.
Because, sometimes you just have to ship.
Reviews are a gift.
People spending money, or not, is a signal, but it’s a noisy one. Amazon doesn’t have a box where they can tell you “why.” Reviews are people who are actually paid to think about what you did, but without the bias of having worked on it, or the bias of spending their own money. They’re not perfect, but they’re incredibly valuable.
They’re not always fun. I’ve had work I’ve done written up on the real big-boy tech review sites, and it’s slightly dissociating to read something written by someone you’ve never met about something you worked on complaining about a problem you couldn’t fix.
Here’s the thing, though: they should never be a surprise. The amount that the reviews are a surprise are how you know how well you did keeping the bias, the vision, the hope, under control. The next time I ship a version one, I’m going to have the team write fake techblog reviews six months ahead of time, and then see how we feel about them, use that to fuel the last batch of duct tape.
What you don’t do is argue with them. You don’t talk about how disappointing it was, or how hard it was, or how the reviewers were wrong, how it wasn’t for them, that it’s immoral to write a bad review because think of the poor shareholders.
Instead, you do the actual hard work. Which you should have done already. Where you choose what to work on, what to cut. Where you put the effort into imaging how your customers are really going to react. What parts of the vision you have to leave behind to build the product you found, not the one you hoped for.
The best time to do that was a year ago. The second best time is now. So you get back to work, you stop tweeting, you read the reviews again, you look at how much money is left. You put a new plan together.
Because, sometimes you just have to ship.
“And Then My Reward Was More Crunch”
For reasons that are probably contextually obvious, I spent the weekend diving into Tim Cain’s YouTube Channel. Tim Cain is still probably best known as “the guy who did the first Fallout,” but he spent decades working on phenominal games. He’s semi-retired these days, and rather than write memoirs, he’s got a “stories from the old days” YouTube channel, and it’s fantastic.
Fallout is one of those bits of art that seems to accrete urban legends. One of the joys of his channel has been having one of the people who was really there say “let me tell you what really happened.”
One of the more infamous beats around Fallout was that Cain and the other leads of the first Fallout left partway through development of Fallout 2 and founded Troika Games. What happened there? Fallout was a hit, and it’s from the outside it’s always been baffling that Interplay just let the people who made it… walk out the door?
I’m late to this particular party, but a couple months ago Cain went on the record with what happened:
and a key postscript:
Listening To My Stories With Nuance
…And oh man, did that hit me where I live, because something very similar happened to me once.
Several lifetimes ago. I was the lead on one of those strange projects that happen in corporate America where it absolutely had to happen, but it wasn’t considered important enough to actually put people or resources on it. We had to completely retool a legacy system by a hard deadline or lose a pretty substantial revenue stream, but it wasn’t one of the big sexy projects, so my tiny team basically got told to figure it out and left alone for the better part of two years.
Theoretically the lack of “adult supervision” gaves us a bunch of flexibility, but in practice it was a hige impediment every time we needed help or resources or infrastructure. It came down to the wire, but we pulled it off, mostly by sheer willpower. It was one of those miracles you can sometimes manage to pull off; we hit the date, stayed in budget, produced a higher-quality system with more features that was easier to maintain and build on. Not only that, but transition from the old system to the new went off with barely a ripple, and we replaced a system that was constantly falling over with one that last I heard was still running on years of 100% uptime. The end was nearly a year-long sprint, barely getting it over the finish line. We were all exhausted, I was about ready to die.
And the reward was: nothing. No recognition, no bonus, no time off, the promotion that kept getting talked about evaporated. Even the corp-standard “keep inflation at bay” raise was not only lower than I expected but lower than I was told it was going to be; when I asked about that, the answer was “oh, someone wrote the wrong number down the first time, don’t worry about it.”
I’m, uh, gonna worry about it a little bit, if that’s all the same to you, actually.
Morale was low, is what I’m saying.
But the real “lemon juice in the papercut” moment was the next project. We needed to do something similar to the next legacy system over, and now armed with the results of the past two years, I went in to talk about how that was going to go. I didn’t want to do that next one at all, and said so. I also thought maybe I had earned the right to move up to one of the projects that people did care about? But no, we really want you do run this one too. Okay, fine. It’s nice to be wanted, I guess?
It was, roughly, four times as much work as the previous, and it needed to get done in about the same amount of of time. Keeping in mind we barely made it the first time, I said, okay, here’s what we need to do to pull this off, here’s the support I need, the people, here’s my plan to land this thing. There’s aways more than one way to get something done, I either needed some more time, or more people, I had some underperformers on the team I needed rotated out. And got told, no, you can’t have any version of that. We have a hard deadline, you can’t have any more people, you have to keep the dead weight. Just find a way to get four times as much work done with what you have in less time. Maybe just keep working crazy hours? All with a tone that I can’t possibly know what I’m talking about.
And this is the part of Tim Cain’s story I really vibrated with. I had pulled off a miracle, and the only reward was more crunch. I remember sitting in my boss’s boss’s office, thinking to myself “why would I do this? Why would they even think I would say yes to this?”
Then, they had the unmitigated gall to be surprised when I took another job offer.
I wasn’t the only person that left. The punchline, and you can probably see this coming, is that it didn’t ship for years after that hard deadline and they had to throw way more people on it after all.
But, okay, other than general commiserating with an internet stranger about past jobs, why bring all this up? What’s the point?
Because this is exactly what I was talking about on Friday in Getting Less out of People. Because we didn’t get a whole lot of back story with Barry. What’s going on with that guy?
The focus was on getting Maria to be like Barry, but does does Barry want to be like Barry? Does he feel like he’s being taken advantage of? Is he expecting a reward and then a return to normal while you’re focusing on getting Maria to spend less time on her novel and more time on unpaid overtime? What’s he gonna do when he realizes that what he thinks is “crunch” is what you think is “higher performing”?
There’s a tendency to think of productivity like a ratchet; more story points, more velocity, more whatever. Number go up! But people will always find an equilibrium. The key to real success to to figure out how to provide that equilibrium to your people, because if you don’t, someone else will.
Getting Less out of People
Like a lot of us, I find myself subscribed to a whole lot of substack-style newsletter/blogs1 written by people I used to follow on twitter. One of these is The Beautiful Mess by John Cutler, which is about (mostly software) product management. I was doing a lot of this kind of work a couple of lifetimes back, but this one of the resources that has stayed in my feeds, because even when I disagree it’s at least usually thoughtful and interesting. For example, these two links I’ve had sitting in open tabs for a month (They’re a short read, but I’ll meet you on the other side of these links with a summary):
TBM 271: The Biggest Untapped Opportunity - by John Cutler
TBM 272: The Biggest Opportunity (Part 2) - by John Cutler
He makes a really interesting point that I completely disagree with. His thesis is that the biggest untapped opportunity for companies are people who are only doing good work, but give off the indications that they could be doing great work. “Skilled Pragmatists” he calls them—people who do good work, but aren’t motivated to go “above and beyond”, and are probably bored but are getting fulfillment outside of work. Not risk takers, not big on conflict, probably don’t say a lot in meetings. And most importantly, people who have decided to not step it all the way up, the’ve got agency, and deployed it.
In a truly world-class, olympic level of accidentally revealing gender bias, he posits two hypothetical workers, “Maria” who is the prototypical “Skilled Pragmatist” and by comparison, “Barry”, who takes a lot of big risks but gets a lot of big things done.
He then kicks around some reasons why Maria might do what she does, and proposes some frameworks for figuring out how to, bluntly, get more out of those people, how to “achieve more together”.
Not to use too much tech industry jargon here, but my response to this is:
HAHAHAHA, Fuck You, man.
Because let’s back way the hell up. The hypothetical situation here is that things are going well. Things are getting done on time, the project isn’t in trouble, the company isn’t in trouble, there aren’t performance problems of any kind. There’s no promotion in the wings, no career goals that aren’t being achieved. Just a well-preforming, non-problematic employee who gets her job done and goes home on time. And for some reason, this is a problem?
Because, I’ll tell you what, I’ll take a team of Marias over a team of Barrys any day.
Barry is going to burn out. Or he’s going to get mad he isn’t already in charge of the place and quit. Or get into one too many fights with a VP with a lot of political juice. Or just, you know, meet someone outside of work. Have a kid. Adopt a pet. That’s a fragile situation.
Maria is dependable, reliable. She’s getting the job done! She’s not going to burn out, or get pissed and leave because the corporate strategy changed and suddenly the thing she’s getting her entire sense of self-worth from has been cancelled. She’s not working late? She’s taking her kids to sports, or spending time with her wife, or writing a novel. She’s balanced.
The issue is not how do we get Maria to act more like Barry, it’s the other way around—how do we get Barry to find some balance and act more like Maria?
I’ve been in the software development racket for a long time now, and I’ve had a lot of conversations with people I was either directly managing, implicitly managing, or mentoring, and I can tell you I’ve had a lot more conversations that boiled down to “you’re working too hard” than I’ve had “you need to step it up.”
Maybe the single most toxic trait of tech industry culture is to treat anything less than “over-performing” as “under-performing”. There are underperformers out there, and I’ve met a few. But I’ve met a whole lot more overperformers who are all headed for a cliff at full speed. In my experience, the real gems are the solid performers with a good sense of balance. They’ve got hobbies, families, whatever.
Overperformers are the sort of people who volunteer to monitor the application logs over the weekend to make sure nothing goes wrong. Balanced performers are the ones that build a system where you don’t have to. They’re doing something with the kids this weekend, so they engineer up something that doesn’t need that much care and feeding.
I suspect a lot of this is based on the financialization of everything—line go up is good! More story points, more features, ship more, more quickly. It’s the root mindset that settled on every two weeks being named a “sprint” instead of an “increment.” Must go faster! Faster, programmer! Kill, Kill!
And as always, that works for a while. It doesn’t last, though. Sure, we could ship that in June instead of September. But you’re also going to have to hire a whole new team afterwards, because everyone is going to have quit after what we had to do to get it out in June. No one ever thinks about the opportunity costs of burning out the team and needing a new one when they’re trying to shave a few weeks off the schedule.
Is it actually going to matter if we ship in August?
Because, most of the time, most places, it’s not a sprint, and never will be. It’s a marathon, a long drive, a garden. Imagine what we could be building if everyone was still here five, ten, fifteen years from now! If we didn’t burn everyone out trying to “achieve more”.
Because, here’s the secret. Those overperformers? They’re going to get tired. Maybe not today, maybe not tomorrow. But eventually. And sooner than you think. And they’re going to realize that no one at the end of their life looks back and thinks, “thank goodness we landed those extra story points!” Those underperformers? They actually wont get better. Not for you. It’s rude, but true.
The only people who you’re still going to have are the balanced people, the “skilled pragmatists”, the Marias. They’ve figured out how to operate for the long haul. Let’s figure out how to get more people to act like them. And they want to work in a place that values going home on time.
Let’s figure out how to get less out of people.
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I feel like we need a better name for these, since substack went and turned itself into the “nazi bar”. It’s funny to me that as the social medias started imploding, “email newsletters” were the new hotness everyone seemed to land on. But they’re just blogs? Blogs that email themselves to you when they publish? I mean, substack and its ilk also have RSS feeds, I read all the ones I’m subscribed to in NetNewsWire, not my email client.
Of course, the big innovation was “blog with out-of-the-box support for subscriptions and a configurable paywall” which is nothing to sneeze at, but I don’t get why email was the thing everyone swarmed around?
Did google reader really crater so hard that we’ve settled on reading our favorite websites as emails? What?