---
title: '#1 Biggest Regret as a Software Engineer'
source: 'https://youtube.com/watch?v=LEUD9zeCgs4'
video_id: 'LEUD9zeCgs4'
date: 2026-08-02
duration_sec: 240
---

# #1 Biggest Regret as a Software Engineer

> Source: [#1 Biggest Regret as a Software Engineer](https://youtube.com/watch?v=LEUD9zeCgs4)

## Summary

The video discusses the speaker's biggest career regret as a software engineer: staying too long in a comfortable job where they stopped learning. They emphasize the importance of continuous learning and switching jobs when growth stagnates, sharing personal anecdotes and advice for developers.

### Key Points

- **The Regret** [00:01] — The speaker's biggest regret is staying at their first job for too long, where they stopped learning new technologies and became demotivated.
- **Early Career** [00:15] — Started at a university job working on a unit testing tool for C/C++, then moved to a client site for an internet bank project in C# which they learned quickly.
- **Stagnation** [00:42] — Stayed at the same tech stack for two more years, doing the same work, and realized they had stagnated but took two years to notice.
- **The Change** [01:11] — Moved to a startup in London where they learned something new daily, grew skills and salary, and wished they had made the jump sooner.
- **Learning as a Metric** [01:23] — Now never stays in a position for more than two years, and asks 'am I still learning?' to decide when to move on.
- **Expert Trap** [01:37] — Being the go-to expert on a topic often means you're not learning anything new; you don't want to be the smartest person in the room.
- **Interview Insight** [02:04] — Candidates with 10 years at the same company on the same stack often lack experience with new technologies like .NET Core, AWS, and microservices.
- **Real-World Experience** [02:17] — Personal projects help, but nothing beats using a technology in a real-world setting ('in anger').
- **The 20 Years Quote** [02:29] — Quote from 'Six Months to Six Figures': 'I have 20 years experience' often means one year of experience repeated 20 times.
- **Loyalty Myth** [02:42] — Job loyalty doesn't count for much; recent layoffs at Microsoft show that loyalty doesn't protect you.
- **Layoffs and Comfort** [03:09] — Some laid-off developers may have gotten too comfortable, not contributing or learning; loyalty shouldn't factor into decisions.
- **Invest in Yourself** [03:35] — If you aren't a good investment, you'll be let go; invest in your skills to be beneficial when changing jobs.

### Conclusion

The speaker's key takeaway is to prioritize continuous learning and not stay in a role where you stagnate, as loyalty doesn't guarantee job security. Invest in your skills to remain valuable.

## Transcript

so today I want to talk about regret I don't have many regrets in my career as that really sticks out and I think a lot of developers probably have this regret too at least in hindsight on my first job at University I was working on a
unit testing tool for C and C plus plus it was interesting work I was learning about testing I was learning about embedded devices and how computers work a client site to work on their internet Bank the project was all in c-sharp
which at the time I didn't actually know but I was able to learn quickly and soon I was finishing tickets and adding features to the product over the next features Sprint after Sprint then I was
exactly the same Tech stack and there I stayed for another two years doing the same thing as time went on I got more and more demotivated I knew C sharp and be enough to do everything I needed to do in my job it wasn't that I knew
everything but I knew enough to do the work that I was required I had to do and seem to know much more than I did either for those last two years at that company technologies that I'd learned on one hand I'd basically stagnated but it took
me two years to realize this I changed jobs to an exciting startup in London and I was learning something new every day the work was challenging but I was growing and so was my salary if only I'd made that jump sooner I wouldn't have
learning anything new I'm now a lot better at switching jobs I never stay in one position for more than two years in some cases I might move internally at something new but other times I just have to change to a different job every
year I ask myself the question am I still learning I see developers all the the expert they like being the go-to person for any particular topic the anyone else on a particular subject you're probably not learning anything
new on a regular basis you don't really want to be the smartest person in the room I've interviewed lots of candidates before that have 10 years experience but when you look at their CV they've spent those 10 years at the same company on
the same Tech stack in the job that I was interviewing for we were using.net core AWS and microservices and of course these candidates had no experience in used these Technologies in their own personal projects then that does go in
their favor but there's nothing quite like using a technology in anger in a real world setting there's a quote in the book six months to six figures that comes to mind you often hear people say I have 20 years experience I should get
paid more but in actual fact they only have one year of experience repeated 20 times if after a year on your job you still aren't learning something new at consider looking for a different position in those are not used to
they're probably thinking doesn't job loyalty count for anything isn't it good to show that you've been at one company for 10 years well actually no it doesn't it means diddly squat if you look at the recent layoffs in software engineering
from highly profitable companies like Microsoft you'll see that loyalty really developers that have recently let go at Microsoft have been at the company for technologies that you use every single day clearly loyalty should never be a
factor in your decision-making process Microsoft may have laid people off at random based on their salary and nothing else but chances are there's probably a some of these developers at Microsoft got a little bit too comfortable in
people but they weren't necessarily contributing or learning anything new on a regular basis of course I don't know this for sure Microsoft could have just pulled their names out of a hat either way loyalty didn't come into the
you around if you aren't a good investment anymore you need to make sure that you're investing in yourself and you're investing in your skill set and will be really beneficial when you do come to change your job which probably
you like this video then you might like this one on the worst things about being watching and I'll hopefully see you in the next video