Why is goal setting so difficult?

This is a guest post from Tiffany Jachja. Enjoy.

Dear Developer,

Many people will encourage you to set goals and find ways to share them for your career development. All of us have struggled with filling out templates, worksheets, and other forms of documentation to lead the conversation about what we hope to accomplish in the future. And your manager, mentor, and maybe coworkers will look at them once you’ve written them down and try to adjust them into a SMART goal: a goal that is specific, measurable, attainable, relevant, and time-bound.

One of the pitfalls in my career, and I’ve seen others struggle with this, is setting goals that matter. It’s common to hear that our goals are unrealistic, random, or unattainable. This feedback can be fair, and the SMART framework for goal setting can help with setting smarter, standalone, accomplishable goals. However, we can often lose the magic and inspirational aspects of pursuing goals that excite and animate us with SMART goals. When we’re asked deeper questions like what your ideal career looks like 3-5 years from now, it can be hard when we’re faced with constructive feedback. This letter is meant to discuss setting goals that matter to you in the context that this is a very difficult practice.

The Challenges of Goal Setting

Earlier in my career, I’ve been lucky to have managers and mentors ask me about my motivations, skills, preferences, goals, and ideals regarding work. These questions shaped my professional development as I would follow the career ladders and corporate structures meant to guide me on a path forward. This was all. It was just a path, not necessarily my path. And if I had stayed on it, I would certainly not be closer to the experiences and skills that make me a better engineer, developer, and leader.

After starting my engineering career, I started to pick up on patterns and pitfalls for career development conversations:

  • you reach these goals, and they don’t matter to you
  • you haven’t set goals that others can help you with / the goals aren’t aligned with the company’s top priorities for the year
  • you set goals for the sake of setting them, and they don’t get you out of your comfort zone

When we hear that our goals are too ambitious, bold, and unattainable, we’ll sometimes settle for more digestible, SMART, and safe goals that don’t matter to us but check social or career checkboxes.

The Lost Opportunity In Seeking Out “SMART” Goals

The challenges of goal setting outlined aren’t experiences that are unique to me. Now, as a manager, I hear engineers often talking about the opportunities that call out to them. Opportunities to give back, communicate, share, and become known or respected for their work. And often, these engineers put these goals or motivations aside to set goals around getting promoted or delivering their features and work.

What happens after the title change? Most people will find it difficult or intimidating to answer this question.

Did this bring you closer to your ideal professional, personal or social life? Did it advance you closer to the inner callings of a life filled with happiness, freedom, community, or any other core value you have? It can be scary to audit our goals and find that the answer is no. It doesn’t mean we don’t have a goal or meaning for work. We just don’t have the clarity to communicate or share them, and this letter will share some exercises to help with gaining career clarity.

It’s a wasted opportunity to set goals that are “safe” when you continue to talk about your actual goals as if it was nice to have or some distant fantasy. The alternative could have been for us to work together to set the milestones for achieving those goals. These milestones could be tied to the career ladder, which outlines skills needed to advance in the corporate paths.

A discussion around HARD Goals

There was an evolution in research around goal setting that sought to extend beyond SMART goal setting. Researchers developed a notion of HARD: heartfelt, animated, required, and difficult goals from exploring how goals could help us achieve meaningful outcomes and life satisfaction.

To outline some of the thought processes associated with HARD goals, questions like the following would be asked:

  • Why do you want this goal, intrinsic, personal, extrinsic
  • What are you doing, who are you working will, and what does your ideal day look like in the future?
  • What are the skills needed to achieve this goal? how will you develop these skills?
  • What can you do to accomplish this goal by the end of the next X months?

Gaining Career Clarity

Building a meaningful career plan means incorporating your strengths and passion to achieve your goals. Here’s my framework for helping developers gain career clarity by exploring who you are and what they want to accomplish. Themes and patterns should emerge by analyzing the responses across the exercises shared.

Step 1: Grounded in gratitude.

Write down some times you have in your life: career, social, and personal that you are proud to have. What were the things you wished or prayed for in the past?

I ask developers to find grace for themselves regarding goal setting. We all feel levels of imposter syndrome. The feeling that we need to do better, do more, or be more. There is a difference between the person making decisions from a mindset of “I don’t have enough” and “I am enough.” When setting HARD goals, you need the confidence that you’ll be able to pursue something meaningful and not necessarily easy to pursue. You may additionally notice some themes or stories around what you have and what you want to have started to emerge during this first step.

Step 2: Expressed through ideals.

Find three sheets of paper and 30 minutes to talk about what could happen in your life, if anything could happen? How will it feel, and what would your ideal life look like? Do this for three areas of your life.

  1. Professional: As it relates to your job, education, retirement, and income.
  2. Personal: As it relates to your skills/mastery, hobbies, location, personality, health, and other accomplishments.
  3. Social: As it relates to your social activities and relationships with friends and family.

This exercise is about no judgment, no limits, and no lies. I encourage people follow step 1, which looks at the past. This step encourages us to look into the future, and we do it from a place of gratitude and meaning.

Step 3: What’s this mean to you?

Now take some time to review your responses. What feels most meaningful to pursue, what makes you emotional, and how does it make you feel? These motivations stem from our core values and things that are important to us. For some people, it’s security or community; for others, it’s excellence; these are valid values.

Step 4: What can you do now?

List some thoughts you feel around what you should be doing and explain why you feel those feelings. Then list things that are nice to have but are things that you have not gotten to pursue because you are too busy with other tasks and goals.

Understanding our pressure points can be meaningful when it comes to balancing our current state with what could be. Sometimes developers feel as if two goals are conflicting but often realize by writing them down that they are tied to a personal or core value. Values are unifying and can be one way we tell a story when it comes to expressing and sharing our goals.

There are also 24 hours a day, so we can’t achieve everything all at once. Understanding priorities and auditing our activities can help us take goal-aligned actions.


I hope this letter gave you the courage and the tools to look deeper within to set goals that matter. I shared why goal setting is difficult but important and my framework for gaining career clarity. Nothing worth having is easy. Good luck to all you amazing technologists seeking betterment and joy in this lifetime.


Tiffany Jachja is a technologist, writer, speaker, and podcast host from the Baltimore-Washington D.C Metro Area whose aim is to help people reach their true potential in tech. She is currently a software engineering leader for a machine learning product team and enjoys sharing her experiences on platforms like Twitter and Twitch. You can find her at @TiffanyJachja
or on Twitch where she shares her experiences in software engineering to help others in the tech community.

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