Pain is when truth is staring you in the face

3 macro lessons from building and failing many times

Est reading time = 7 min

source: stable diffusion - prompt: life lesson in watercolor

Today at a glance:

• Do not play short-term games with people if you are in it for the long-term.

• Stand for something. Fight for it and speak your truth. It will all work out.

• You will be misunderstood. Expect it and it will be easier to manage.

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Most people do not change after a TED talk or medium article - they have to experience it. I feel the same.

For my brain to be rewired I have to live through it and suffer the consequences. For example, I ignored all advice regarding warming up before exercise. An accident, 2 surgeries, and 9 months of crutches later I now believe in warming up. Turns out I am not invincible and smart people suggesting I warm up had a point. An extreme story, but you get it.

This logic (advice is useless without an independent experience) makes this newsletter obsolete. Fully aware of this. Without action these are just words on a page. More hustle/advice porn on the internet! That’s true, but I’ll still write for # of reasons and I hope it helps someone.

So for today let me share 3 macro lessons on building out of ~30+ that I’ve got written down. The common theme behind each lesson is that it hurt before I understood. There was pain and consequence before it became a lesson. Often, I fucked up many times before I understood. I was fortunate to have had supportive teammates who were patient with me as I learned.

Do not play short-term games with people if you are in it for the long-term.

There are countless examples of how decisions that optimize for the short-term hurt us later. From tech debt to relationships to product. For a change let me share a brief negotiation story.

Story: We were negotiating with partner A on a deal. I’ve mapped out all the scenarios for how I thought this negotiation would play out. I also had reason to believe that A needed this more than us. Skipping a lot of the negotiation prep, our final proposal was a multi-layered offer that embellished a lot of our deliverables and anchored at a high “price”. It was aggressive and one-sided in our favor. Throughout the negotiation I did a # of things to ensure that we do not move far from our initial offer. We closed on terms favorable to us. It felt like a win for our team, but in time the deal fell apart. The terms made A look bad internally. And it got harder for us to justify our worth. It would have been smarter to leave more on the table for A and ensure that it’s a sustainable partnership. Solid popular book that further shaped my thinking on this is Finite and Infinite Games.

Lesson: In long-term games with people avoid optimizing for the short-term and if you do, be prepared to pay. Maybe you won’t pay, but your successors will - someone will pay.

Word choice here is deliberate.

I think it’s fine to take shortcuts to win, but I try to avoid taking shortcuts in long-term games that involve people. Emphasis on people. For example, 9/10 times I'd take a shortcut to ship quickly and accrue code debt. But when it comes to people - I think we need to draw the line. What falls under people? To me its users of our products, its our teams (internal), and its our counter-parties (external). This stuff always come back so it’s better to do the hard things early and to be kind.

Stand for something. Fight for it and speak your truth. It will all work out.

I’ve been trying to figure out how to share a quick story around a belief that I hold and how I fought for it. Many of my beliefs are around strategy/ops, product, or around team dynamics. These are very specific stories. They are difficult to share in writing publicly so I’ve landed on a simpler story. My hope is that this anecdote is more relatable because most of us have been in these situations.

Story: One of my truths is that most meetings suck. I also believe that it is someone’s job (often mine) to protect the builders. Folks from other teams would ask for meetings with me or with the team that I am supporting. Often these things can be solved in writing. Sometimes these meeting would come in the form of a straight-up calendar invite with zero context. No explanation - just an outright claim on people’s time. And so I would reach out to the person setting the meeting and share our philosophy on meetings and on building products. I would propose we handle this in writing, ask for an agenda, and a desired outcome of the call. This seems like a small thing, but it mattered to me because it was counter-culture that I was trying to foster.

Sometimes certain people in meetings would be on their phones or laptops - not paying much attention to the presentation. Rude to the team that put in the work and counterproductive, right? And so I worked up the courage to share my beliefs over email and in person, asking attendees to be present. Then it happened again and I asked the person who was disengaged to leave the meeting unless they can focus on the presentation.

Nobody loved that, but..

“If X% of powerful people do not find you arrogant, you are doing something wrong” - Taleb

Both instances got me in trouble. One time I was chewed out for something similar. Another time someone found me “difficult”. Another time it was implied that I “shouldn’t be part of exec meetings” until I get some coaching. You get the idea.

It took a lot out of me to stand up in both instances and I felt beaten down after. I worried (a lot) that the teams I was supporting would suffer indirectly and that I’d need to do more work to build social capital back. But in my mind it was trading short-term pain/discomfort, for long-term protection of an ideal and that was worth it.

Lesson: You should have a few things that you believe in and you should fight for them. Beliefs without a fight is like awareness without courage to act - not worth much.

Stand for something and be prepared to die on that hill. I would be selective (i.e. not every hill is worth dying on) and I would put a lot of thought into how I approach these situations, but I would push.

Figure it out. Will it to existence. This is often a product, but it can be anything like a cultural value. This mentality should shape the day. When I am not reacting to the world, I am using all of my energy to advance my highest convictions. I worry that if someone doesn’t have a few select convictions - they are just along for the ride.

The following sequence served me well: have convictions→ do not tolerate problems that stand between me and my convictions/goals → systematically analyze my journey and each problem (some will be blockers and some will learnings and feedback) → come up with solutions → get there. I believe that this mindset applies to everything from product to teams to 3rd party relationships to culture.

If you stand for something - put in the hours and thought cycles. Get a few bruises along the way, but that’s part of the process. Get it done or fail, but at least we went for it, right?

You will be misunderstood. Expect it and it will be easier to manage.

Story: Drawing a blank here. So far I’d give story-telling in this email a C+.

A few instances come to mind where I felt alone, but they are difficult to convey plus I don’t want pity. Other instances come to mind where I believed in direction X, nobody did, then I went for it anyways. It was the right call, we made millions, and everyone lived happily ever after. This feels like a gloating LinkedIn post so that’s a pass.

There are many ways in which you may experience this feeling of being misunderstood.

There are beraucrats and empty critics. There are people whose entire professional identity is built on taking others down. They will ask questions that put others on the spot, make themselves appear smarter, and never offer solutions. Only takedowns.

Sometimes people will have the best intentions, but won’t understand the vision because they see the world differently. Sometimes they just won’t engage at a deep level with you. You won’t get support, but you also won’t get a clear “no” or actionable feedback. I found this to be common.

Lesson: All of us will feel misunderstood at some point. All builders and artists experience loneliness and loss.

The stronger your convictions and the more long-term you think - the more it may hurt. The larger your bets - the more it may hurt. I’ve found that 3 things help: (1) prepare my mind “this will happen”, (2) re-anchor myself in my values, (3) have someone who can tell me whether something has promise or is nonsense.

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Tying this back to the start- this is just words on a page without action. Think the #1 thing is to make moves and to have these experiences (some will hurt and that’s okay). You can observe the pain, let it pass, and with time something positive will displace the discomfort.