How to Curate a Career Roadmap

Career Roadmap

Life is full of unexpected events, and it’s the same for your career path. Career paths don’t always follow a straight line, and you can pivot at any time based on your needs and experiences. However, every individual is ultimately responsible for their career and the best way to achieve success in anything is to control the variables that you can control. Benjamin Franklin once said, ‘If you fail to plan, you are planning to fail”. Thus, this article looks at one of the planning methods that could help you to create your dream career. Your career roadmap is a personalized strategic guide to the milestones, achievements, and progressions you wish to make on your career journey including switching fields, gaining financial freedom, or landing that big promotion. It is a plan for the decisions you need to make, and the paths you need to take to learn and develop and position yourself for a successful career. If you want to know how you can increase your chances of landing that C-suite role, keep reading.

Of course, not everyone has a clear path or knows what they want to do for each stage of their life, and that’s okay. Whether you know what you want the next ten years of your life to look like or are keenly embracing your becoming, you can still create milestones to guide you along the way. When curating a career roadmap, there are four main steps to follow: Self-Assessment, Exploration, Decision-Making, and Milestone and Goal Setting. Let’s dive in!

Self Assessment

The first step to creating a career roadmap is to get to know yourself. This step is especially important if you haven’t explored the possibilities outside your current position or you are just entering the working world. Many individuals simply go with the flow and end up in a job that goes nowhere or only has a hefty paycheck. In order to have a fulfilling life, it is best to find the career or role that best fits you, encourages you, and makes you feel like you are making a difference by adding value to your life and others or satisfying your inner purpose. To start your self-assessment, consider the type of person you are, the life you want to live, and the values that would make your life more fulfilling. To do this, write down a list of values that are important to you and that you want your career to enable. 

  • Are you someone who loves autonomy? Maybe freelancing, a management role or a flat company culture would fit you best. 
  • Do you want a career that provides security and benefits?
  • Are you adventurous, risk-taking, or creative?

These are all examples of important questions you should ask during self-assessment. You can even take personality tests to learn more about yourself. One popular and trusted personality test is the Myers-Briggs personality test, which categorizes you into one of sixteen archetypes.


The next step is to explore all the options you have in your current or prospective career paths. Growing up you may only be familiar with the occupations of the persons around you but the actual range of career options available is bound to be a much larger pool once you start venturing beyond your current environment. Now that you have done your self-assessment, you can begin drilling down into all the roles and fields that you have been exposed to. Here are a few ways you can do this:

  • Attend job fairs and seminars. These events provide you with the means to meet and engage with professionals and ask them about their experiences. 
  • Read, read, read. You can also learn about different career options by reading online articles, blogs, and academic texts, or taking courses within your field. 
  • Attend online conferences. Now that many conferences are being held online, the barrier of access to industry experts and creative professionals is far greater. 

At the baseline, the more information you expose yourself to, the greater your options become. This will not only increase your awareness but also help you to make a better decision about what you want to do.


Having learned about yourself and explored different options, it is now time to merge the knowledge gained from the two. Think about how the roles and career options you know fit into your interests, skills, and values. Are there any options that allow you to do something you are good at while enjoying yourself? Which options would allow you to feel fulfilled? Which options do not serve you or do not align with your life values or goals? Once you can identify the answers to these questions, you can then select a role or set of roles to pursue. At this stage, it is important to note that though you must make a decision in order to plan, your decision is not engraved in stone. As you grow and change, your life circumstances, interests, skills, wants, needs and career will also change. As a result, we may change our career goals, which may require new skills and knowledge. It’s natural for this to happen. Don’t get flustered. As your career evolves, you can adapt and make changes, pivoting as necessary. Regardless of how you pivot, or what changes take place, making that important decision at the start, or when you pivot, will help you to properly plan for your goals.

Milestone and Goal Setting

Once you have decided on what you want to do and what your career will entail, you can begin the most crucial step: planning. Create milestones for your larger goals. A milestone is a sizable achievement that indicates significant progress toward a goal. Your milestones could be the roles that you must rank up through to get to your dream job, the jobs that will provide you with the experience to become the entrepreneur you want to be or even the certifications that will make you an expert in your field of choice. Once you have decided on your milestones, do some additional research on each. Find out what the best way is for you to target each milestone. Think about the activities you need to complete or the sacrifices that are necessary to achieve each one. Afterward, convert each of these activities into SMART Goals. With each milestone and sub-goal defined, it’s time to visualize your roadmap. Whether you create a digital board or fancy wall poster, it is important to visualize your milestones. Putting your roadmap on your wall or reminding yourself to look at it daily, weekly or even monthly, will remind you of what you are working towards and help you to keep track of your progress.  With your visualization complete, you can finally start executing your plan and working towards your first milestone, just like that.

In summary, you can make better decisions about your career if you spend time getting to know yourself and exploring the wider range of options. But it is also imperative to create and work towards small incremental goals. Your career roadmap will change as your circumstances change, but if you follow these steps, you will be able to avoid some of the clutches that keep so many people shackled in unfulfilling jobs or stuck at the same level for decades. Get your drawing board out and start to curate your career roadmap today!