trust before depth
There's a conflict between the optics of reactivity and the delivery of value. And in most organizations—especially startups—optics wins.
I have a strong conviction that the most highly leveraged, valuable work requires depth. Flow state. Dedicated, uninterrupted time on a single task. Cal Newport, Stephen Covey, the deep work greats—these ideas aren't new. But they seem to be unintegrated into most organizational cultures. At least, not baked into the actual values.
My honest impression—and I'm open to having my mind changed—is that most orgs reward reactivity over depth. The short-term dopamine hit of getting a Slack message back immediately beats a well-crafted project that delivers real value. Reactivity satisfies many small needs quickly. It looks like effectiveness. Deep work, by contrast, is invisible until it's done, run, and felt over time.
Even if you carve out an hour here, a two-hour block there, it doesn't matter. If you're constantly needed for some meeting or some message, your focus stays fractured. You never go deep.
the incentive structure
Here's the frustrating part: most people would probably say, "Yeah, we'd love you to deliver that valuable thing that would uplift the entire team."
But they won't give you the time to do it.
Especially when your performance is assessed based on what other people say about you. If someone doesn't get a response from you within some timeframe they deem appropriate—even if it's not agreed upon—you get dinged. You'll see the incentive structure very quickly. You'll feel it in the performance evaluations.
I've been experimenting with this recently. After switching from my old mindset (deliver big-time value through focused, time-blocked work) to responding to people quickly, the company seems to receive me much more warmly. They trust me more when I'm reactive.
I know there are things that, if I spent a couple of days—maybe even a week—doing uninterrupted, I could deliver something genuinely valuable. But why would I do that when my performance is assessed by how much people like and trust me?
the validity of trust
And here's the thing: there's validity to that.
Having your teammates trust you. Earning that over time. Paying your dues. Showing, in a new organization, that you are reliable. That's all fair. It should not be discounted—it's real. There is a genuine social dynamic in organizations; it's part of what makes an org distinct from an individual working alone.
But it's a painful choice when you see opportunities that require deep work and can't get to them.
why "getting buy-in" doesn't work
You might think: Well, just ask your manager. Get buy-in for the deep work project.
But when the company's attention is constantly fractured—when every new shiny object calls us away, when everything is an emergency, when everything is important—there is no real buy-in.
You can get agreement. Someone will say, "Yes, that's valuable." But there's always a caveat. You might agree that 4–8 hours or 24 hours is a decent response time, but then certain customers require faster responses. And the evaluation criteria for which customers? Unclear. It's brand equity. Vibes.
If your client is Amazon versus some smaller name bringing in the same revenue, you're going to pay more attention to Amazon. Even if the smaller client pays more, the organization will prioritize the recognizable brand. You can agree on that dynamic, but you can't measure it. There's no clear rubric.
The choice between optics and value is real. And getting buy-in is a hurdle because it's incredibly difficult to gather people around a consensus of what something actually means. What's the measurable result? People don't have time—and often don't care—to come to that agreement.
the order of operations
I'm not trying to be doom and gloom here. I think there is a way to get to a point where your deep work can be honored.
My best guess, at least in the startup world, is that it's an order of operations issue.
You build trust with your team first. You show deliverable results in the tasks that require reactivity. You prove you're reliable. Then, once people aren't freaking out if you don't respond to their Slack message within five minutes, you can more easily get that buy-in—or just trust—to build a system or deliver something that uplifts the team.
Not a formal proposal. Not a plan with exact minutes or numbers. Just trust. Trust that you do good work. Trust that you have the best interests of the company in mind.
That's what opens the doors for deep work.
But there's an uncomfortable reality here: deep work may not be available to you until you've built trust through reactive work. Less a matter of defeat, more a strategic play. It's knowing the order of operations—and playing the game long enough to eventually play your game.
