A System to Stop Worrying (for founders)

As a founder, your greatest opposition isn’t the market or a competitor - it’s your own worry and anxiety.

It has the potential to crush you, and your family.

And it makes sense. We’re playing high-stakes games. On our best days, we’re on our way to being wealthier than all our friends and retired soon.

On our worst days, it’s all going to 0 and we’re losing our house and destroy our marriages.

I played this game fast and loose in my mid-20’s when I was freshly married with a newborn at home. I didn’t know how to control my emotions or anxiety. I brought every work-problem home and each evening and weekend my brain was solving business issues even if my body was giving my baby a bath.

At 35 (going on 36) with a large mortgage and 3 kids (6, 8 and 10 yrs old) I can’t do that.

Moreover, operating out of anxiety is bad business. Anxious founders:

  • Make bad decisions
  • Operating from a scarcity mindset
  • Are poor leaders
  • Are unhealthy
  • Are a**holes to their team (and families)

Still, sh*t happens. Here’s my system for deal with it (complete with a Notion template, as always).

How to Handle Anxiety When It Arises

Most of how I deal with anxiety can be summed up in 2 resources:

  • This video from Tim Ferris on “Fear Casting”.
  • The book, How to Stop Worrying and Start Living by Dale Carnegie
    • (Yes, the title is cheesy, but it was written in 1948)
    • (Yes, the same Dale Carnegie that wrote “How to Win Friends and Influence People”)

In essence these 2 resources can be summarized by this stoic sentence:

Anxiety it arises from focusing on what we can't control, and peace comes from accepting reality, living in the present, and using reason to confront fears.

Lately, when I get anxious about sometime (like, I cannot sleep anxious) I write a new entry in my “Problem Journal” (in Notion - here’s a template for you).

It follows these steps (more detail below):

  1. Define the Problem
  2. Analyze the Problem
  3. Apply Carnegies Principles
  4. Take Action
  5. Let Go and Accept
  6. Reflect

1. Define the Problem

Start by clearly identifying what’s bothering you. Ask yourself: “What exactly am I worried about?” Write it down in specific terms. This step brings clarity and cuts through the fog of vague, overwhelming worry. The act of naming the issue often reduces its power.

2. Analyze the Problem

Once the problem is defined, gather facts about it. What do you know for sure? What is speculation? Look at the situation objectively, as if you’re analyzing it for someone else. This step is about removing emotion and focusing on reality.

Ask yourself these 4 questions:

  • What are the facts?
  • What are my emotions about this situation?
  • What's the worst that could happen?
  • Can I improve on the worst?

3. Apply Carnegies Principles

  1. Ask yourself, "What’s the worst that can happen?"
    Accepting the worst-case scenario helps reduce fear. Once you’ve accepted it, you can focus on improving it.
  2. Prepare for the worst.
    Take reasonable steps to mitigate the worst-case scenario if it’s likely to happen.
  3. Focus on what you can do now.
    Shift your attention to practical actions instead of dwelling on the problem.

4. Take Action

After analyzing the problem and applying Carnegie’s principles, identify what you can do immediately. Anxiety thrives in inaction. Even small steps can give you a sense of progress and control, which quiets your mind.

5. Let Go and Accept

After you’ve done what you can, consciously let go of the problem. Remind yourself that worrying doesn’t change outcomes. Accept that some things are outside your control, and focus on the present moment instead of obsessing over hypothetical futures.

6. Reflect

Finally, revisit the situation later. Did your actions resolve the issue? Did the worst-case scenario happen? Reflecting helps you learn for the future and improves your ability to handle similar challenges. It’s also a good reminder that most fears are worse in your mind than in reality.

You’re not alone

Remember, anxiety is a natural part of being a founder, but it shouldn't control your life or business decisions. By following this systematic approach, you can:

  • Transform vague worries into concrete problems you can solve
  • Make better decisions based on facts rather than fears
  • Maintain better work-life boundaries
  • Lead your team with clarity and confidence
  • Be more present with your family and loved ones

The key is to make this process a habit. Each time you face a worry that keeps you up at night, open your Problem Journal and work through these steps. Over time, you'll find yourself naturally approaching challenges with more rationality and less anxiety.

And remember - you're not alone in this. Every founder faces these challenges. What sets successful founders apart isn't the absence of worry, but how they handle it.