How to make a career plan that actually feels achievable

Making a change in your life can be daunting and it can be difficult to trust your intuition if you feel you are taking a big risk. Setting out your ambitions and goals on paper can sometimes feel restrictive – and possibly even unrealistic.

But luck favours the prepared, and with the right plan you can gain the clarity, structure and confidence you need to take a step in the right direction.

You can imagine a career and a life that don’t exist; you can build that future you, and as a result your life will change.” ― Bill Burnett, creator of the Odyssey Plan

You may be planning to continue in your current role (business as usual), suddenly facing the unforeseen (such as redundancy) or coming to a crossroads (is a career change calling?). Creating an Odyssey plan is a process that can help you to more clearly visualise where you want to be and importantly, how you’re going to get there.

Bill Burnett, Stanford Professor and author of Designing Your Work Life, created the Odyssey Plan to help people envision what they want their future to look like. An Odyssey is as a ‘long and eventful or adventurous journey or experience’. 

Sometimes, the decision to make a change can be just that.

Review your current position

Before making any significant decisions about a professional or personal change, the most logical place to start is with the here and now.

Dysfunctional Belief: I should already know where I’m going. Reframe: You can’t know where you are going until you know where you are.” – Bill Burnett

Take an audit of your career by looking at your current situation. Ask yourself: 

  • What does your day to day look like? 
  • What are you working on? 
  • Do you feel a sense of passion or achievement where you are right now?

Once you feel comfortable with your current position, you may feel more ready to look to the future and begin your Plan.

Begin a process of ideation

The Odyssey Plan is not so much a rigid plan of action: moreover, it is a process of ideation that brings in all the underpinning values and belief systems from your work and life views, so it becomes a cohesive and multi-dimensional vision, rather than just a career trajectory. 

No plan completely survives first contact with reality, but being prepared allows us to remain flexible, engaged, and able to make thoughtful decisions on whatever life throws at us. 

Map each scenario

To build an Odyssey plan, you create three alternative realities on three sheets of paper. Each reality projects a five-year trajectory of both personal and professional milestones – at least one for each year. 

Planning is everything, but the plan is nothing” – Dwight D. Eisenhower

To create your plan, build each timeline as follows:

  • Plan #1 – What would the next five years look like if you stay on your current career path? 
  • Plan #2 – What would the next five years look like if Plan #1 disappeared? 
  • Plan #3 – What would the next five years look like if money and image were no object? 

For each plan, include the following:

  • A six-word title that captures the essence of the plan
  • Three questions to ask yourself – what would you like to learn from the five years? 
  • A dashboard that indicates how you rank the plan against four criteria:
    • Resources: Do you have what you need to execute the plan? 
    • How does it feel: Do you like the plan? 
    • Confidence: Are you confident about executing the plan? 
    • Coherence: Is the plan consistent with who you are?

Discover what you want your career plan to achieve

Once you have created three separate timelines, you can extend one of these into a 10-year plan. The 10-year plan can include elements from all three timelines but should still contain a dominant framework. 

As a life designer, you need to embrace two philosophies: 1. You choose better when you have lots of good ideas to choose from. 2. You never choose your first solution to any problem.” – Bill Burnett

Reflecting on three different plans with three different scenarios and outcomes will help you to find clarity in what you are looking to achieve. For example, whilst Plan #3 may seem unrealistic at face-value, the elements that feature may remind you of what is really important.  

The 10-year plan follows the same structure as the five-year plan in that it should encompass both professional and personal milestones. It should also include three questions, and a dashboard to indicate your ranking of the plan. 

It should also include a thank you note. Imagine yourself at the end of your 10-year plan and write a letter to the person who designed it. Write about your plan as if it has already been completed, thanking the designer who created the plan for specific things that happened in those 10 years:

  • What will you be most thankful for? 
  • How will you feel knowing that you’ve achieved what you set out to do 10 years prior? 

This reflection is a valuable exercise because when you look backwards from the future, you can draw out the things that are most important to you. 

Confidently say where you want to be in five years!

So, no matter how scary change can seem and how big the perceived risk, now you have the tool to review your goals to find what truly brings you meaning and purpose. By breaking down your goals into manageable steps, you will be well-equipped to build a plan that feels far less daunting, and far more achievable. 

The Odyssey plan will not only help you to visualise your future, but also provide you with the framework to get you there.

Enjoy the adventure!

Interested in finding out if a career in financial advice could meet all of your goals and ambitions? Why not read this article next? 

Download your free printable template Odyssey Plan here