One of the things that happens when you leave the corporate world is that you suddenly have time to think about what you actually did with the last thirty years.
Now that I have this time, one realization keeps surfacing: some of what I remember as the hardest decisions of my life were not hard at all. They were instant. They only look difficult in the retelling.
The reason is that I already knew what my priorities were, whether or not I could have written them down at the time. The decision may have been important or heavy or pressured, but it didn’t actually challenge my priorities. There was nothing to think about or deliberate on. The decision was obvious.
After those decisions were made, however, their importance or the pressure I felt at the time made me file them away in my emotional memory as “tough decisions,” even if the decisions themselves weren’t tough at all.
In all of the examples I am thinking of, anyone who knew me well would have predicted every one of those calls. “Of course Dave will do that. It’s who he is.”
That is a comforting sentence when the decision was a good one. It is considerably less comforting when the thing I did without hesitating was unwise.
Here is the flattering example.
My mother was dying of cancer. I took a few months under FMLA to be with her.
I was a son who loved his mother, and there was nothing to decide. There was never a question. The decision was easy.
Now here is the unflattering one.
At Amazon, I owned the Appstore backend services. We depended on another team’s entitlement system, and we were building around its inadequacies rather than getting them fixed. My team was absorbing work that, architecturally and from an ownership standpoint, belonged somewhere else. We were on a tight timeline.
It was not fair. So I pushed.
I was told no by the senior manager. So I went to his director, who also told me no. So I went to his VP, who told me no as well.
Three levels of the same answer, but I kept going because I knew I was right.
I will be honest with you: I still think I was right. The architecture argument holds up. The ownership argument holds up. If you put the design on a whiteboard today, I would make the same case.
But this pushing cost me. It cost weeks I did not have on a timeline I could not move. More expensively, it cost relationships with three people I would need later, and rebuilding those took considerably longer than it took my persistence to destroy them.
Here is what I could not see at the time: that team was not being unreasonable. They had their own priorities, their own timeline, and their own leadership telling them what mattered. From inside their world, my urgent problem was someone else’s roadmap request.
And underneath that was something larger. Amazon ran on an ownership model where every team builds what it needs. I never fully accepted it, and I still have reservations, because it collided with priorities I had spent twenty years building as a software architect: Reuse. Clear boundaries. Do not make ten teams solve the same problem badly.
I was not fighting the entitlement team. I was fighting the operating model, one senior manager at a time, without ever quite admitting that was what I was doing.
Both of those decisions were instinctive; instant.
The pull toward my mother and the pull toward the fair architecture came from the same place, arrived at the same speed, and felt identical from the inside. Certain. Obvious. Not really decisions at all.
They are not two different traits. They are one trait, pointed at different targets.
Sometimes, it is a trait I am glad to have. Other times, it has cost me time, credibility, and momentum. The uncomfortable part is that in the moment, I could not tell them apart. Both felt like integrity.
If you want to know why some decisions are easy, the mechanism is not complicated.
A decision is easy when your values are already ranked, and the situation only touches one of them. There is nothing to weigh, because nothing is competing.
A decision is genuinely hard when two things you actually value collide, and you have never before had to find out which one sits higher.
This is why difficulty and stakes are almost uncorrelated. Not many agonize about whether to be with a dying parent, but many people agonize for weeks over whether to cut a project someone loves, whether to tell a strong performer they have plateaued, or whether to say the thing in the meeting that everyone is already thinking. Those look small from the outside and feel enormous from the inside, because two real values are grinding against each other.
When you are stuck on a decision like that, the instinct is to gather more information. More data, another conversation, one more week of thinking. It almost never helps, and now I understand why: the problem was never information. You are being asked to publicly demote something you value, and in a way that has real impact.
That is why it hurts, and why the deliberation loop can run indefinitely without producing anything. You are not analyzing. You are refusing to rank.
I do not think there is a clean way through that. I have never found one. But knowing what the stall actually is has, at minimum, stopped me from mistaking endless deliberation for diligence.
There is a specific version of this that every senior leader eventually meets. My entitlement fight was mine.
At some point, your personal hierarchy will collide with the one your organization rewards.
Mine ranked architectural integrity and fairness across teams near the top, while Amazon ranked ownership and delivering results. Neither ranking is wrong. They are simply different, and I spent an embarrassing amount of energy treating a difference in priorities as a failure of reasoning that the right argument could fix.
It could not. You cannot argue an organization out of its ranking, because the ranking is not an opinion. It is whatever the promotion committee rewards, and it has years of momentum behind it.
What you can do is know your own priorities well enough to see the collision coming, and then choose deliberately: adapt, absorb the cost, or leave. All three are legitimate. What is not legitimate, or at least not effective, is the approach I used at Amazon: continuously escalating in the belief that someone would surely see it my way.
This brings me back to that decision I opened with, taking time off to be with my mother.
Taking those months off cost me. Not “officially,” of course. Amazon followed the letter of the law, and I am not accusing anyone of anything.
But culture and policy are two different things. In a culture that prioritizes delivering results, a person who steps away for a few months to sit with their mother has, in the only language that system reads fluently, stopped delivering results. That shows up later. It showed up for me. It slowed down my career progress at Amazon.
Was that fair?
Maybe. Maybe not.
But the cost was real. However, I would make the same call again and again without hesitation. That is what happens when your priority ranking is already settled.
One more thing, because otherwise this sounds more fixed than it is.
Priorities shift. Mine have. The ones I hold at fifty-nine are not identical to the ones I held at thirty-five. Some of that is growth, while some of it is simply that circumstances changed and different things rose to the top.
What has not changed is that testing priorities clarifies them. Every time a decision arrives and you watch yourself answer it instantly, you learn something true about your own hierarchy that no amount of abstract reflection would have told you. Those moments do work that introspection cannot.
The question I would leave with you:
Think of a decision you made instantly that other people would (or did) describe as hard.
Then think of a fight you picked instantly that other people thought you should have let go.
Both of those came from the same place. What is it?
Answer honestly and you will know something about your own priorities that most people never bother to check. You will also start to see it in the people around you. Everyone has priorities, and they become visible in the moments they act without deliberating.
Then look at the decision actually sitting in front of you this week. If it has been too hard for too long, you are probably not missing information.
You are refusing to rank two things you care about.
If you don’t rank them intentionally, someone else will rank them for you.
