I started coding in 1984. CTO, founder, exit survivor.
These 7 career mistakes cost me a decade, and most developers are still making them.

I’ve been a developer since 1984.
CTO. Founder. Exit survivor.

I’ve made money. I’ve lost it.
And if I had to start my career over, I wouldn’t change the tech—I’d change the career decisions.

In this video, I break down 7 career mistakes that keep smart developers stuck, invisible, and burned out:
• Playing the hero instead of the architect
• Being “helpful” instead of valuable
• Saying yes to everything
• Speaking tech instead of business
• Ignoring politics and influence
• Staying too long in bad companies
• Grinding skills instead of positioning

These aren’t motivational platitudes.
They’re career traps I lost years to.

If you’re a mid-senior developer, tech lead, or engineer aiming for Staff, EM, or CTO—and you feel stuck at the same level—this video is for you.

Leadership isn’t presence.
It’s judgment.

Good work doesn’t speak for itself.
And being great at coding is a tool, not a strategy.

👇 Resources & Next Steps
• Practical career frameworks (link below)
• Limited 1-on-1 career strategy calls (application required)

This is not for juniors.
Not for the comfortable.
It’s for developers who are done being invisible.

Your career is your responsibility.
Take it, or don’t.


 Chapters:

00:00 Why I’d Restart My Career Differently
00:39 Being Helpful Makes You Replaceable
01:05 Stop Playing the Hero
01:21 Say No and Create Leverage
01:31 Why Good Work Is Invisible
01:52 Speak Business or Be Ignored
02:16 Politics Is Influence (Not Fake Smiles)
02:44 When to Leave a Bad Company
03:10 Coding Is a Tool, Not a Strategy
03:36 Positioning Beats Grinding
03:56 The 7 Career Traps Summarized
04:07 Frameworks & 1-on-1 Strategy

Tags

#DeveloperCareer
#TechLeadership
#SoftwareEngineering
#CTOAdvice
#careerstrategy

Serious CTO's resource offers insights, tutorials, and resources for Chief Technology Officers (CTOs) and technology leaders. Readers can learn about technology strategy, team management, and leadership skills. With articles, interviews, and case studies, Serious CTO provides  guidance and expertise for leading technology organizations and driving innovation.

The Serious CTO

A CTO with 40 years of experience shares seven career mistakes to avoid: being too helpful instead of strategic, failing to document and communicate achievements, not speaking the language of business metrics, avoiding organizational politics, staying too long in toxic cultures, focusing solely on technical skills over positioning, and not building external credibility. The advice emphasizes that career advancement requires strategic thinking, visibility management, business acumen, and deliberate self-promotion rather than just technical excellence.

7 Career Mistakes I’d Avoid If I Started Coding Again (CTO Advice)

All very good points however ,
“avoiding organizational politics, staying too long in toxic cultures” a lot of times the politics itself is what can contribute to toxicity. Not all places but there are a good number of them.

It’s at the same time refreshing and downright depressing to know that we ALL go through the same things (Corp BS, politics, etc…) no matter the region/location/culture.
Great insight, totally agree.