Years of Overthinking

How I finally chose a direction, and why I landed on AI.

Note to Self #001

Step 1: Choose your direction.
An industry or role. Generalist or specialist.
(Doesn’t mean you can’t change your mind later.)

Choosing what to focus on felt like the most important decision I couldn’t make.

I kept hearing the almost cliche advice:

“You’ll fail multiple times. Just don’t give up, failure only happens when you quit.”

I understood that. But I also noticed something else:
In most entrepreneurial stories, the failures aren’t random, they build on each other.

People fail within the same domain, which allows them to keep building on top of that with more knowledge, skills, and confidence.

So the real question became:

If I’m going to fail (which is probably inevitable), I want to fail in a direction where the failure actually teaches me something I can carry into the next step. So what balances my strengths, experiences, curiosity, and growth?

Everything felt downstream from that decision. The decision to choose a domain focus.

Though I’ve learned that just starting (anything) makes the answer clearer. Inaction is often worse than picking the “wrong” thing.

There will never be a moment where you have perfect information so make the best possible informed decision you can in that moment.

I took some time and asked myself:
What are my interests, experiences, and “Unfair Advantages” right now?

So I looked back…

  • 2013–2016: Discovered photography and filmmaking in middle school

  • 2017–2021: Occasional freelancing through high school and early college

  • 2021: Pivoted from creative work to focus on scalable business ideas that didn’t require my physical attendance

  • 2021–2023: Joined a college consulting org to build business and strategy skills

  • 2023: Started my full-time job in financial services/risk management and moved to North Carolina

  • 2022–2024: Experimented with launching a creative/digital agency, got one client for a small project, then stopped

  • Early 2025: Realized I didn’t feel aligned with creative/digital marketing and that I need to experiment and iterate quicker. Decided to focus on building high-leverage skills, landed on AI-powered automation

I’ve explored creative work, finance, data, tech, consulting, etc. That doesn’t even cover half of my interests, but one started to stand out: AI.

Recently there has been a lot of hype around the topic, but it also checks many of the boxes I seem to care about. To essentially free up time and do more of what matters to you through:

  • Efficiency

  • Systems thinking

  • Leverage

AI still has a lot of problems but it is clearly moving fast and will most likely affect all industries in some way so no matter what, everyone will have to adapt like we had to with the internet.

This is what I told myself in February 2025:

  • Focus on learning AI tools and automation

  • Document everything—experiments, workflows, and thoughts

  • Build systems, services, or products

Even if this direction changes, I believe this is a skill set that can help me fail forward to my next step (whatever that ends up being).

Thanks for following along. Real time updates coming soon.

— Ayan