Building For The Future

Sep 15, 2025

Jon Sabados, a seasoned staff software engineer at The New York Times, shares insights on building sustainable software systems that can evolve over time. He discusses the importance of long-term planning to avoid technical debt and the delicate balance between speed, cost, and quality in development. The conversation delves into the challenges engineers face, the journey from legacy systems to modern solutions, and even a skeptical take on AI's future role. Get ready to rethink your approach to software development!

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INSIGHT

Future-Ready Work Protects Velocity

Building for the future preserves delivery velocity when priorities shift.
Without it, ad hoc firefighting creates tangled systems that slow development.

ADVICE

Make Trade-Offs With Stakeholders

Balance speed, quality, and cost with product and engineering stakeholders.
Revisit decisions continually as new facts and timelines emerge.

ADVICE

Begin With Problem Discovery

Start discovery by understanding the user's actual problem, not requested UI changes.
Ship a minimal, usable solution early and learn from real feedback.

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We've all experienced the dreaded rewrite. A system that was promised to last for years has grown so full of technical debt and cruft that we feel we need to throw it out and start over again. How can we avoid this? In this episode, Angelica and Matt are joined by Jon Sabados, where they discuss how to build software that can last long into the future.

This week's episode does not have a companion break episode, but check out our backlog if you haven't watched them already! Watch it on YouTube or listen with your favorite podcasting app! Learn more by going to https://break.show.

This week's episode features a bonus chapter for supporters! Not a supporter yet? You can fix that by heading over to https://fallthrough.fm/subscribe where you'll get not only extra content but also higher quality audio. Sign up today!

Thanks for tuning in and happy listening!

Table of Contents:

Prologue (00:00:00)
Chapter 1: Why Should We Build For The Future? (00:03:13)
Chapter 2: Business Value & Future Planning (00:10:18)
Chapter 3: Where Do You Start? (00:13:21)
Chapter 4: How To Make Decisions Effectively (00:27:35)
Chapter 5: Crafting A Solution (00:39:55)
Chapter 6: What Does It Actually Mean To Build For The Future? [Supporter Only] (00:47:50)
Chapter 7: A Case Study (00:49:57)
Chapter 8: Incorporating New Technologies (01:05:07)
Chapter 9: Building For The Future Outage (01:08:19)
Chapter 10: Final Advice (01:16:34)
Appendix UNPOP: Unpopular Opinions (01:20:03)
Epilogue (01:35:12)

Hosts

Matthew Sanabria - Host
Angelica Hill - Producer
Kris Brandow - Producer
Jon Sabados - Guest

Socials:

(00:00) - Prologue
(03:13) - Chapter 1: Why Should We Build For The Future?
(10:18) - Chapter 2: Business Value & Future Planning
(13:21) - Chapter 3: Where Do You Start?
(27:35) - Chapter 4: How To Make Decisions Effectively
(39:55) - Chapter 5: Crafting A Solution
(47:50) - Chapter 6: What Does It Actually Mean To Build For The Future? [Supporter Only]
(49:57) - Chapter 7: A Case Study
(01:05:07) - Chapter 8: Incorporating New Technologies
(01:08:19) - Chapter 9: Building For The Future Outage
(01:16:34) - Chapter 10: Final Advice
(01:20:03) - Appendix UNPOP: Unpopular Opinions
(01:35:12) - Epilogue