Embrace Your Self-Taught Journey

failing forward and learning my first mental model

I’ve been thinking about writing more recently and have been inspired by others on substack like

Jordan Cutler

Sergio Visinoni

. My self-taught engineering idol is Sebastián Ramírez (Tianglo), the FastApi Python library creator.
So, in the spirit of learning publicly, my first writing is about embracing your self-learning journey and some of the things I think about and practice.

1. Own Your Background: In interviews, I rarely disclose that I'm self-taught unless prompted. My unique path from being homeschooled to being Director of Data Engineering in a New York City startup highlights my ability to keep learning without traditional schooling. Using every part of your personal story to highlight your strengths is essential. I learned this while taking the altMBA that Seth Godin and Wes Kao created ( if you get a chance, you should take it - it will push you to ship stuff and not idolize perfection)

2. Seek Inspiration from Trailblazers: Identify and study non-traditional leaders who resonate with your aspirations. For instance, Tadao Ando, a self-taught Japanese architect, inspired me with his unconventional use of concrete. His journey bolstered my confidence in forging my path. Find your Tadao Ando; we all need someone who inspires us.

3. Confront Self-Doubt Head-On: Self-doubt is common among self-taught individuals. I counter this by maintaining a log of completed projects and successes and, more importantly, failures. Each entry is a testament to my growth and capability. Start a success log today; it will serve as your anchor in moments of uncertainty. I like to use the mental model of Identity → Process → Outcome.

[Identity] I am a software engineer.

[Process] I will write code for 30 minutes every day. Showing up is 90% of the work.

[Outcome] I will create a working piece of software to show X.

4. Implement Identity-Based Habits: Transition from aspiring to being by acting the part. I started my engineering career not by landing a big job at first but by building a simple website for a friend. It didn’t matter that the project was small; what mattered was it paid, and that payment symbolized my professional value. Take on small projects that reinforce your professional identity; volunteer, but find someone or thing that holds you accountable. We all have projects that could be a thing, but we get stuck or fail once we hit our first or even second roadblock. Failure is part of learning.

5. Document and Reflect Regularly: Every week, I write down my accomplishments, no matter how small, and review them over coffee. I recently told my wife and kids what I feel most proud about: things I have learned or failed to understand. This is even more important as I get older—not to brag, but to learn to celebrate. This routine helps keep my progress and goals in focus.

Make it a habit to document and think about your achievements often. For example, this is the first post on my substack. I have nothing to teach or offer, but I'm sure that's my lizard brain—it's time to set up my new mental model.

Identity writer.

6. Curate a Learning Toolbox: Equip yourself with resources that enhance your learning. Here are a few I’ve found invaluable:

• Farnam Street's Mental Models
  I used this as a reference point as Shane Parrish, frequently writes and talks about mental models.

• Decision by Design by Farnam Street
  I did this course over a year ago, and I loved how sometimes weird or hard-to-follow mental models made sense with practice and trying to apply to your life.

• Ness Labs on Mental Models
  Good reference and other thinking on mental models

• James Clear on Mental Models
  Changing your habits, one small step at a time

Take Action: Identity → Process → Outcome

This approach isn’t just theoretical; it’s a practical blueprint for continuous improvement and success. Start with your identity, engage in processes that reinforce this identity, and achieve outcomes that reflect your growth.

Embrace this cycle, refine it, and watch how it transforms your landscape.