Welcome to your Career Roadmap. Let’s make this actionable. How are you actually going to move forward?

The process of creating your Career Roadmap is not about the inflexible approach of setting a goal and figuring out the linear path to accomplish it. This is an exercise to reflect on what matters to you, decide what success could be for you, and then commit to experiments that start you on the path forward.

  • Old version: Set a goal, get to that goal
  • New version: Create hypotheses and test them

Norms. Let’s set a few ground rules that will create a positive experience as you spend a little time designing your career.

1. This is a living document that will (and should) change over time.
2. You own your career. Not your manager. Not your mom. You can and should take charge. One of the only ways you can fail at this is if you only fill this out to appease your manager.
3. A bias towards action helps both in this exercise (when in doubt, start writing ideas) and in building your career.
4. An experimentation mindset takes away the pressure. Prototyping is how the best companies build products. The same can apply to your career. Don’t make big commitments without smaller experiments first.
5. It’s ok to ask for help. Just because you own your career doesn’t mean you can do it all yourself. One of the best ways to grow is to ask for ideas and help from others.


Two frameworks that we’ll use to create your lightweight roadmap:

Why • What • How

Now • Next • Later

Grab a piece of paper to write on or open a new document and let’s dive in:


    Why: Your Motivators

    What drives you?  

    List your motivators

    Bonus: Stacking is part of the richness of finding your motivators, write down important words from your stack as well. 

    B. Now let’s help you remember the exercise, the feeling, and conversation. Write down a
    single sentence that gives more context. Why do these words matter to you?


    Prompts that could help you right your single sentence:
    • I want a job where …
    • I’m most fulfilled when …
    • I’m at my best when …

    Want to go deeper? Check out the +journaling exercise. 

    What: Ideal State

    A. What does success look like?
    We’re going to start wide. List as many potential desired outcomes as you can. How do you want to grow? Write as many as you can in 7 minutes

    You don’t have to follow the traditional path. Don’t limit yourself—these could be anything from what you want next week to what you want when you’re 100. The focus of this roadmap is career, but feel free to go beyond career if you wish.

    These could be
    1. a skill you’d like to build
    2. a role you’d like to have
    3. a large project you’d like to work toward
    4. a characteristic you’d like to embody
    • Learn how to xyz.
    • Run point on my own project
    • Get promoted
    • Start my own business
    • Speak at a conference about javascript
    • Find a mentor
    • Write a book
    • Become a manager
    • Transition to a new department/role
    • Earn more money
    • Do more collaborative work with peers
    • Have more free time
    • Be healthier
    • Become the top sales rep in the North East
    • Become an industry influencer
    • Be the subject matter expert on our new product

    B. Prioritize your future possibilities


    Now that you’ve written your list, let’s identify the ideas you want to work towards first. Doesn’t mean they all can’t happen, but you have to start somewhere. Circle the top 5. Add clarifying details to those 5 if needed.

    How: Career Experiments

    Take your top 5 ideal state ideas and list them on the left column
    . Rewrite if needed.

    This is where most people get stuck. Going from idea to execution. Two major problems happen:


    1. We pursue ideas that aren’t good (they will be unfulfilling, ineffective, or impossible)
    2. We know an idea will be great, but we don’t know how to get started.

      The best way to avoid making major commitments that may not work, is to experiment. For instance, if you’re unsure about becoming a lawyer instead of “enroll in law school”, the first step could be “talk to 3 lawyers about their jobs”. Or prototype a product before you jump into building for months.

    The best way to get started is to find outside resources to help us move forward and get the right tools to do the job. 

    Let’s check each of your ideas to make sure you don’t get stuck.

    A. Vetting your career experiments


    Take each top ideal state idea and answer these 5 questions:
    • Do I know I’d enjoy this? If not, find ways to learn before you commit. (fulfillment)
    • Can I actually accomplish this? If not, find ways to adjust the desired state in ways that are feasible that could still get you what you want. (feasible)
    • Will this lead to an outcome I want? How do you know? If not or if you don’t know yet, prototype a small part, get feedback from others. (validation)
    • Do I know exactly how to proceed? If not, find a way to learn from someone who’s done it (read an article/book, talk to an expert, take a course, as a friend for help). (enabled)
    • Do I have what you need? If not, find what tools or skills will best help you and how to acquire them. (equipped, empowered)

    If there are issues at any step, think about what you could change or how you could get started. 


    B. How will you get there?

    Draw a table with your top ideas on the left side and columns for “now”, “next”, and “later” on the right side.
    List out actions that will help you make progress in the next month (now), quarter (next), and year (later). 

    in “Now” list out ways you could easily get started with an experiment and better know if this is something worth pursuing before you commit lots of time or money.

    You could list out resources you will use and people you will connect with to make meaningful progress.

    Don’t feel like you have to fill it all out perfectly. You’ll have more detail on the
    “Now” than the “Later” and that’s ok. It’s also ok if you only have one of Now/Next/Later filled out. You can revisit, adjust, and update later. 

    This is a living document that will change over time. Revisit often. Come back to meetgroove.com/getstarted for additional resources and ideas for making progress.


    Making It Stick

    Ok. You made it. You drafted v1 of your career roadmap. Now what? Well, some people put this on their desk or tuck it away somewhere and never think about it again. That’s not going to help you continue to grow and find more fulfillment in your career. 

    Schedule time on your calendar. Calendars are better than todo lists. Put time on your calendar to review this roadmap in 3 days. Take 15+ minutes to read it through, write additional thoughts, edit things that don’t quite feel right. Make a date with yourself  1 week, 1 month, and every 3 months after that to spend a few minutes reflecting on your career roadmap and adjusting your experiments.