December 23, 2025

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Speed is often touted as the startup’s superpower. Thus, speed was my goal.

If a client complained, I refunded them instantly. If an employee slipped up, I fixed it myself.

I won’t lie, it felt great. It felt productive. I solved real problems all day.

But the bill always arrives. The quick refund taught clients to push boundaries. Fixing mistakes trained employees that they didn’t have to be as mindful. I optimized for immediate relief (and ego). In doing so, I was blissfully ignoring future consequences.

Facebook’s old saying was “move fast and break things.” Not even they think the consequences are worth it anymore. For solopreneurs and small teams, the price is even higher. 

The thing you usually break is… well, your own future.

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Weekly Insight

Investor Howard Marks coined the terms “first-level” and “second-level” thinking to explain why most people lose money.

First-order thinking feels good. Second-order thinking feels like work.

The tech industry proves, again and again, exactly why doing this work matters.

The most recent time tech lost its collective mind was 2023.

ChatGPT launched, triggering what became known as the “AI arms race.” Companies rushed to ship half-baked chatbots to pump their stock prices. CEOs panicked. Investors demanded immediate answers.

They did a whole lot of first-order thinking.

But not Apple. They refused to play, and the public chastised them for it. Critics claimed it was “all over” for the company — especially when seeing how much other companies were spending in this race.

Now, finally, the market seems to be coming around to their decision. 

While rivals fought to build the best chatbot, Apple built the infrastructure to run all of them. They released a framework that allows developers to run AI models directly on Apple devices. 

They paused, leaned into second-order thinking, and now benefit greatly from it.

We face these same kinds of choices every week.

It looks like a client demanding a scope change. A competitor lowering their prices.

First-order thinking says “fix the pain now.” Second-order thinking asks if the “fix” destroys your profitability next year.

​​Related Reading 📚

Intent to Action

This whole topic is, in a way, pretty annoying. Like having someone tell you that going to the gym is good for you. Of course it is, but that doesn’t make going any easier.

So, rather than lecture you, I want to invite you into a little exercise. (no pun intended)

Look at each decision you make as a trade. You are trading today’s annoyance for tomorrow’s consequence. The goal isn't to be some perfect decision-maker. Rather, it's to make sure you actually want the new problem more than the old one.

Before you make any policy change, agreement, or new offer, run a simple test:

1. Current pain 

What’s annoying you right now? 

(i.e., “Answering the same client questions via email all day.”)

2. Proposed fix 

What’s your immediate (first-order) solution? 

(“Build an FAQ page and refuse to answer questions that are on it.”)

3. New pain 

If this works perfectly, what is the new annoyance? 

(“Clients will feel ignored. I lose the high-touch relationship that justifies my premium prices.”)

4. Verdict 

Do you prefer the new pain over the old pain?

How this looks in practice 

Take a consultant friend of mine. She wanted to switch from retainers to project-based pricing to stop scope creep.

She made the change… then found out just how painful the second-order consequence was. She realized — in her accidental trial by fire — that she hated selling more than she hated scope creep. It took time, but she’s back to the retainer model with a new cohort of customers.

Toolbox 🧰