Why I Almost Left My Software Engineering Career


Issue 28

July 9, 2024

Welcome to DW News

I’m David Weiss, an engineering leader and a solopreneur. I started this newsletter for one reason — to help people like you.

I share insights on leadership and entrepreneurship. Thanks for reading and making your growth a priority.

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Why I Almost Left My Software Engineering Career

In 2023, I nearly ended my 16-year career in software engineering.

My career was plummeting. And so was my mental health. It took everything I had to keep going.

I want to tell you the story behind the most difficult period in my career and what I learned from it. This isn't easy to share, but sometimes we must do hard things. If my story inspires someone, it's worth the momentary feeling of discomfort.

The story

I spent months trying to become a manager. I asked for more responsibilities and promotions where I worked. I applied and interviewed for manager roles.

In 2021, I finally got hired as a first-time manager. And then it all came crashing down ten months later when I got fired.

I lost the job (and title) I wanted more than anything.

  • How could this happen?
  • What did I do wrong?
  • Will I ever get another software engineering job?
  • What am I going to tell my wife and kids?

These were some of the questions that ran through my mind.

I didn't realize it then, but I was about to enter the darkest chapter in my career.

I was unemployed for eight months. I applied to almost 600 jobs and had close to 200 interviews.

After getting fired and failing to get a job, I was on the verge of giving up.

I switched careers before. Was it time for me to switch again?

I decided to keep going. I didn't give up on myself or my career. I still believed in my skills as a software engineer and leader. A month later, I got a job.

Since then, I've served in a Team Lead role and built several impactful features with my team. I'm surrounded by some of the smartest and kindest co-workers I've ever worked with. And I'm happy to call them my teammates.

Your life can completely change in a matter of months. If you're going through a challenging phase in your career like I did, don't give up. Dig deep and find the strength to keep going. You'll be glad you did someday.

The lessons

Businesses make business decisions

Getting fired hurts. So does getting laid off. But at the end of the day, it's a business decision.

Companies decide where to invest their time, energy, and money daily. The fact that a company no longer wants to invest in you is hard to swallow. You don't have to like their decision, but you do have to accept it.

Don't let one job or company define you. Your career is much more than that.

You don’t need a job title to lead

I learned more about being a leader in six months as a Team Lead than in ten months as a manager.

I used to think my job title had to include words like Lead, Manager, or Director to lead. The truth is actions make leaders, not titles.

If you want to manage someday, focus on being a leader first. The good news is you can start leading today regardless of your experience. For more leadership tips, check out the lessons I learned as a Team Lead.

I'm stronger than I thought

They say you learn more about yourself in failure than success. I couldn't agree more.

There were many days I wanted to give up while unemployed. Applying for jobs and preparing for interviews was exhausting. So were the countless job application rejections.

One thing motivated me more than anything – my family. I wanted to keep providing for my wife and two children. And I knew that meant finding a job no matter how hard it was.

Now I can look back on that time and be grateful. I'm glad I went through hell and survived. I learned how strong and resilient I am. And if I ever face a similar obstacle, I know I'll get through it.


Career growth isn't always up and to the right. It doesn't always go as planned. And there's nothing wrong with that.

It's hard to keep going when your career descends. But you've traveled down into valleys and up over peaks before. You will reach new heights.

Your journey is not defined by one valley or peak. Keep walking, one step at a time. If I can do it, you can too.

Thanks for reading this week. See you next week! 👋

David Weiss

Founder • Made by DW

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DW News

I help over 80 software engineers lead in their day jobs and build SaaS on the side. I’m a full-time Senior Developer and part-time solopreneur. Join DW News, my weekly newsletter, for insights on leadership and entrepreneurship.

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