The Ultimate Guide to Goal Setting for Your Startup Job Search

The Importance of Goal Setting 

Research has shown that people who write down their goals are 42% more likely to achieve their goals than people who do not write their goals down.

Why is goal setting so effective? It forces you to clarify what you want, motivates you to take action, provides a filter to evaluate opportunities, helps you overcome resistance, and enables you to track your progress.

Goal setting is arguably the most important component of a startup job search, but it is also the most commonly overlooked. Setting clearly defined goals will create a strong foundation for your startup job search and will help you avoid burnout down the line.

If goal setting is so effective, why do so many people skip it? The simplest answer is that goal setting is really hard work. As you’ll see, it forces you to sit down and confront big questions about what you truly want out of life, which can be uncomfortable.

The Five Steps to Goal Setting for Your Startup Job Search 

In this post, we’ll give you a comprehensive five-step framework that you can use to develop well-thought-out, detailed goals for your startup job search. We’ll provide you with prompts that will challenge you to think deeply about what you really want out of your career.

The five steps to goal setting for your startup job search are: 

  1. Step 1: Brainstorm through self-reflection
  2. Step 2: Define your long-term career objectives 
  3. Step 3: Identify short-term milestones 
  4. Step 4: Be SMART 
  5. Step 5: Develop a target company list 

Let's get into it! 

Step 1: Brainstorm Through Self-Reflection 

The first step is self-reflection through the process of brainstorming, so be prepared to put pen to pad (or fingers to keyboard.)

Understanding yourself is the foundation for setting goals that align with your personal and professional aspirations. Your responses to the prompts below should feel like a brain dump, so write down anything that comes to mind. Write down as much as possible and be as specific as you can. You can always go back through later to clean up and reorganize your thoughts.

Assess the Current State of Your Career 

Start by reflecting on the current state of your career. You must understand where you’re at before you can clearly articulate where you want to go.

Use the following questions to think through the current state of your career: 

Am I happy with the industry I'm in? (e.g., Saas, cryptocurrency, artificial intelligence, etc.) 

  • If so, do I want to stay in that industry? 
  • If not, which industries would I prefer to work in? 

Do I want to continue working within my current function? (e.g., engineer, marketing, finance, etc.) 

  • If so, what are the things I like most about working in this function? What are some other roles that I’d consider within this function? 
  • If not, what makes me dislike working in this function? What other functions would I prefer?

Am I passionate about my work? Do I wake up excited to tackle the day's challenges? 

  • If so, what do I find most exciting about my work? Be as specific as possible. 
  • If not, what would need to change in order for me to find my work more exciting? 

Do I feel challenged by my work? 

  • If so, what challenges do I find most engaging and intellectually stimulating about my work? 
  • If not, what about my current role is holding me back from feeling challenged and engaged? What changes would you make in order to feel more challenged? 

Is there room for growth in my current role and/or on my current trajectory? 

  • If so, what are the opportunities for advancement in my current position? How long would it take to advance? What would change if I were promoted?
  • If not, what are the specific reasons that I don’t feel like there is room for growth? Is there anything I can do to open up a path for growth within my current company?

Am I happy with my current compensation and benefits? 

  • If so, what are the reasons I feel adequately compensated for my skills and contributions?
  • If not, what level of compensation would I be happy with? What do I need to change to get to my desired compensation level?

How would I rate my job satisfaction on a scale of 1 to 10? 

  • What factors contribute to this rating? 
  • What would need to change about the factors that brought down my satisfaction score to get those factors to a score of 10? 

Reflect on Your Skills & Preferences 

What interests me? 

  • "What feels like play to me, but looks like work to others?” Naval Ravikant
  • When I have free time, how do I usually choose to spend it? 
  • What topics or subjects do I find myself reading about or researching for pleasure? 

What are my current skills? 

  • What skills do I possess that I am most proud of?
  • What are my hard skills? Write out as many as you can think of.
  • What are my soft skills? Write out as many as you can think of.
  • What skills do I wish I had that I don’t currently have?

What kind of personality do I have? 

  • Do I enjoy working with people, or do I prefer tasks that allow for more solitude? 
  • Are there specific personalities or types of people that I work best with? That I generally like to avoid? 

Step 2: Define Your Long-Term Career Objectives 

Now that we’ve thoroughly gone through our self-reflection exercises, we need to set clear long-term career objectives. Defining our career objectives will be like a compass that will guide us through the rest of our goal-setting process.

Think through the following prompts based on where you would like to see yourself in the medium-to-long-term future (five to ten years). 

What is your ultimate career goal or aspiration? 

  • What skills are required to reach my ultimate career goal? 

What does my dream role look like? 

  • Which function does my dream role fit into? 
  • What is the title of my role? 
  • Which level am I (e.g., staff, senior, manager, director, etc.) 

What specific achievements and accomplishments do I want to achieve at the pinnacle of my career? 

  • What kind of impact do I want to make on my industry or field? 
  • Are there specific causes, projects, or initiatives I want to champion? 

How heavily am I considering my values and priorities? 

  • What values do I consider non-negotiable in a workplace?
  • What boundaries are I firm on, pertaining to work-life balance?
  • What am I willing to give up in my personal life for better career opportunities?
  • How can I ensure that my career objectives support a healthy and sustainable work-life balance?
  • Are there any other people whos quality of life will be affected by the career decisions and tradeoffs I make (e.g., spouse, children, etc.) 

Step 3: Identify & Develop Short-Term Milestones

In Step 3, we will break down our long-term objective into manageable short-term milestones. Breaking down your long-term goals into short-term milestones is the bridge between aspiration and achievement. 

What skills do I need to acquire? 

  • Do I need certain qualifications? 
  • Are there any courses, degrees, or certifications that I should consider? 
  • How can I most efficiently fill any skill gaps I currently have? 
  • How much time will it take for me to acquire any necessary skills? 

What experience do I need to be a qualified candidate for my dream role? 

  • What is the next step that I can take to move toward gaining the necessary experience?

What connections should I make? 

  • Are there any pre-existing networks that I can plug into that would allow me to easily interact with people who can help me achieve my goals? 
  • Would I benefit from a mentor? If so, what is the first step I can take toward finding a mentor? 

Make a timeline. 

  • Develop a timeline that outlines when you should aim to achieve each of your short-term milestones and how they relate to your long-term career goals. 

Step 4: Be SMART 

You've probably heard of the SMART acronym for goal setting before. It's popular because it's a great framework. SMART refers to goals that are: 

  • Specific 
  • Measurable 
  • Actionable 
  • Relevant 
  • Time-Bound 

As you turn your short-term milestones into full-fledged startup career goals, make sure you are meeting the SMART criteria. 


Always aim for a specific, concrete area for your goals. The more specific you are about your goals, the more equipped you’ll be to accomplish them. Always be as specific as possible when you write out your goals and never be afraid to be too specific.


Once you’ve made your goals as specific as possible, you’ll want to make sure they’re measurable. Measurable goals allow you to track your progress and evaluate success or failure. 

Measurable goals relate to how you know when a goal is accomplished and should answer questions like:

  • How much? 
  • How many? 
  • How quickly? 
  • When? 


Although you want to be as ambitious as possible when setting your goals, overly ambitious goals will result in frustration and demotivation. Achievable goals will be challenging yet realistic. A great strategy for making your goals more achievable is to set actionable short-term goals that move you toward your long-term goal.


Your goals should align with your broader aspirations and core values. A relevant goal is one that really matters to you and is aligned with your desired end result. We’ll often break long-term goals into smaller short-term goals. Relevant short-term goals will always move you closer to your long-term goals.


All goals need to have a time frame. A goal without a deadline is just a wish. Time-bound deadlines give your goals structure and create a sense of urgency. You will always want to set an exact date for when you plan to achieve your goals. Whenever you’re dealing with a longer-term goal, break it down into multiple short-term goals, each with clear deadlines.

Step 5: Develop a Target Company List

Hopefully we uncovered some valuable information by answering the questions posed to us during the previous steps in the process. Now, we’re ready to use our thoughts to develop a target company list of at least 40 startups that align with our values, career objectives, and work preferences.

If you have more than 40 startups you’d like to add to your target company list, go for it! We’d recommend keeping it between 40 and 100 startups – you can always add more companies later. The 2-Hour Job Search by Steve Dalton has some really great advice for compiling a target company list.

Steve recommends starting with your “dream employers” – companies you’ve always aspired to work for. Once your “dream companies” are added, determine common traits shared by your dream employers, systematically look up the startup’s peers, and also add them to your spreadsheet.

If you’ve thoroughly explored the questions we asked in the “brainstorming” step, you should have at least 40 startups on your target company list in no time!

In Conclusion

Setting goals for your startup job search is a pivotal step in building a career that aligns with your passions and aspirations. Goal setting will help you take actions that are truly aligned with your core values and avoid burnout when the startup job search becomes difficult.

Remember that goal setting is hard work, but each step you take brings you closer to your dream startup job!

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