My Worst Career Decision Ever Made

We all make bad career decisions. But one usually stands out. Today, I’ll share my worst career decision ever made. Spoiler – it’s not technology related.

This blog post is the longer response to a question asked at

The question was: What’s the worst career decision you’ve ever made?.

As I was writing my response, I noticed the size of it. I decided to summarize it and write a separate blog post for the full blown story to share with you.

My worst career decision ever made is:

Not blogging/sharing content online

Story Time

Get your cookies and milk (or coffee). Or liquor. It’s 5pm somewhere, right? ?

Timeframe: 2004-05

My (professional) first job was a teacher assistant at a .NET 3-month boot-camp. Some duties included:

  • Grading projects. Looking at the code and suggesting best practice where applicable.
  • Interviewing (phone and face-to-face) developers who applied to the program.
  • 1 on 1 tutoring sessions with struggling students
  • Assist trainers during lab week. (This is where students would work on a full project assignment and apply everything they learn.)

(Note: 80% of students = developers with 5yrs to 15yrs of exp leveling up their skill set).

Most students had no or very little HTML knowledge and struggled on their ASP.NET Webforms project.

There was the random HTML/CSS unicorn who would create something really awesome, though! ?

After answering the same questions over and over, I created a thorough HTML/CSS tutorial. It had explicit details for anyone to follow. I made sure of that because there was always that one student who makes your day longer than what it needs to be.

The original idea was to give the instructor the document to hand it out to his students.

But one of the instructors (and later my mentor) asked me to present it to his class.

It’s your material. You should present it!

He said with a encouraging smile.

All in-house training staff attended (probably some big wigs too) to my first presentation.

I delivered.

It was a huge hit with the students, and so damn successful it became part of the school’s regular curriculum. ?

The school had something additional to offer (HTML/CSS). The students had a project to be proud of when presenting it to potential employers.

It was a win-win.

I presented my tutorial many times during my 2-year stay. I got good, really good, at presenting.

The same instructor, my mentor, encouraged me to create a blog and post it online. He also suggested I should pursue teaching as he said I had a natural gift for it and seemed to enjoy helping others.

But I was 22-23 with huge self-confidence issues.?

Who would read this? I’m not good enough. People will make fun of me and my tutorial.

I thought. And…

Me? Teach? Nah, I want to be left alone and code!

Nevertheless, my mentor asked for my blog URL every time he would come teach at the school. I tried to avoid him at all costs.

In Retrospect

Looking back, yeah. I should’ve started and continue blogging. Maybe not to the same level or detail as of that tutorial, but it would’ve kept me motivated and interested in technology. You know, sharpening the saw.

And honestly…I enjoyed (and still do!) helping others. Sharing knowledge and ideas. Collaborating with others for a common and greater good.

Now in 2017, over 10 years later, I believe it was possibly the worst career decision I’ve ever made.

My low self-confidence isn’t to blame here.


It was my belief, my perception inside my head, that others would make fun of me.

…and I never created that blog.

Imagine where I’d be today if I had follow my mentor’s advice and suggestion on starting a blog and sharing my content.

My experiences with my current blog have allowed me to meet awesome people, and expand my horizons by leaps and bounds. Best of all, share great content with your in form of stories.

I wish I had started/done this sooner.

You’re neither too early nor too late. We arrive somewhere when we’re meant to get there.

That’s advice from another mentor. But I’ll save that story for some other time.

Take away

If you got something, anything to share, put it up online and share it!

I’ve found out most people want you to succeed. Others will not care and move one. The very, very few will take their time to troll you (but hey at least you got someone’s attention!)

Ignore your negative thoughts.

Don’t make the same mistake that my 22-year-old self did. Your mid-30s self (and beyond) will thank you.

And you never too old to get started. Trust me.

So, get blogging/writing/sharing today! 🙂

  • Thank you for sharing your story. I’m 27 now and about to do the same.
    I struggled for years setting up my own website eventhough I had the experience and skills.

    • Go for it, man! You don’t even have to set up your own site. There’s plenty of sites ready for you to share your content like Medium or Dev.To. It doesn’t matter.

      Let me know when you have your site up and running to come and check it out 🙂

  • It’s hard to when you listen to that inner naysayer…there’s lots of regret there. I can certainly empathize.

    I have worked on lots of technologies in lots of spaces but I, like you, didn’t blog them or tell folks about them. I always rationalized it with “I can’t be the only one that knows this stuff.” While that it is factually correct, it’s good for us as tech professionals to share what we know because we have access to people that may want to know what we know and we may have to talent to share it with them in a way that’s actionable and palatable to them.

    Thank you for sharing this!

    • Yes, that internal judge is the same one who condemns you (at a later time) for nothing taking action (aka guilt).

      Yes, share, share, share. Someone will find it useful. It may not be new to you, but it will be new to someone else. We all learn from difference sources. Who knows maybe you turn to be great resource to learn from!