3 Goal-Setting Mistakes I Made (And How I Fixed Them)


Issue 34

August 23, 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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3 Goal-Setting Mistakes I Made (And How I Fixed Them)

We’ve made it to part three of my series on major mistakes in my career. Last week I wrote about why you should keep learning. This week I want to share the importance of goal setting.

This is a four-part series about the biggest mistakes I made in my software engineering career:

Part 1: Ask for what you want

Part 2: Learn new tech

Part 3: Set goals

Part 4: Create boundaries

What I did wrong

Goal setting isn’t something you’re naturally born with. You have to learn through trial and error. And you need to seek out resources and people to help you along the way. I didn’t put much thought into creating goals at the beginning of my career. I also thought I could do it on my own.

I didn’t set measurable goals

I used to set goals like this:

  • Learn TypeScript
  • Learn GitHub Workflows
  • Learn AWS Lambda

It’s hard to measure and achieve goals like that. Learning a new programming language or framework can take months. And without some way of demonstrating what you’ve learned, it’s hard to see your progress.

The hardest part about learning something new is getting started. The second hardest part is being consistent. Without a measurable goal and a plan to reach it, the odds are against you.

I didn’t ask for help with my goals

When I look back on my career, I set goals without asking for help. In the world of video games, this is skipping beginner mode and going straight to hard mode. I made things harder for myself from the start.

I didn’t set long-term goals

When it comes to professional development, quarterly and yearly goals get most of the attention. It’s admirable to think about what you can do right now to improve your skills. But your long-term career goals should also be considered.

Early in my career, I failed to think about what I wanted to be doing in 3-5 years. I was so focused on what I could learn this month or this year. And that delayed my overall growth as a software engineer and leader.

What you can do right

Goal setting does get easier over time. It takes strategy, help from leaders, and thinking big.

Create SMART goals

You’ve probably heard of SMART goals before. SMART is an acronym that stands for:

  • S: Specific
  • M: Measurable
  • A: Achievable
  • R: Relevant
  • T: Time-bound

With this in mind, you can create very focused and attainable goals. And this will help you reach those goals by being clear about what you’re trying to do. Here’s an example of how to do this.

Bad: I want to learn JavaScript.

Good: I want to learn JavaScript promises and use them in 3 functions I write this month.

This goal describes what will be learned, how it will be measured, and the timeframe. You might still have a bigger goal of learning JavaScript and that’s fine. Your SMART goal will help you make progress on your bigger goal.

Share your goals with leaders

Ask anyone, who’s reached a challenging health or fitness goal, how they did it. They will tell you they got help. They used an app, worked with a coach, or had an accountability partner. They didn’t reach their goals alone.

If you want to set yourself up for success, share your goals with people who can help you. This includes your manager, department leaders, and others in the company who can provide mentorship.

Communicating your goals with others is beneficial for several reasons. It can help you create better goals. It holds you and your goals accountable to someone else. And it gives you someone to celebrate with when you do reach your goals.

Think big

If you haven’t read The ONE Thing by Gary Keller yet, go read it. It’s one of the best productivity and self-help books I’ve ever read. I reflect on the book’s lessons often.

In the book, the author talks about setting someday goals. From there, you can work your way back to set weekly and daily goals. When you do this, your present goals are intertwined with your future goals. They transcend the smallness of today and are anchored to a better version of yourself.

You might want to become a Principal Engineer, Manager, or CTO in the future. You might want to transition to a completely different career in 10 years. You might even want to start your own business someday.

Don’t think big in three or five years. Start today. Use your goals this year to help you get closer to your someday goals.


A healthy and successful career is built on strategic goal setting. You can’t learn everything in a day. And you can’t achieve a big goal in a week. Growth takes time. And that’s okay.

Make goal setting a recurring agenda item in your 1:1s with your manager. Seek out mentors to help you move forward with your goals. And dedicate time every few months to reflect on your goals, progress, and growth.

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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