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Personal Strategic Career Planning Activity For Academics

As academics, we’ve all been through the joy of department strategic planning days. We know the drill: show up, make a beeline for the coffee station, scoop a spoonful of instant into a paper cup, and hope that someone remembered to turn on the stainless steel urn. 

Then we brace ourselves for hours of post-it notes, flip charts, and brainstorming. The day is sold as an opportunity to share our thoughts, reflect on the past, and plan for the future. 

At the end of it all, the strategic planning day initiative gets a box tick, and we all move on with business as usual with little change to our individual careers.

But, take a poke around what’s going on in the world of AI advancement in relation to Higher Education at the moment, and it seems like business as usual will be anything but.

Below, I suggest a structure for a personal strategic planning day. One that focuses exclusively on you and your career so that if the Higher Education ship really is sinking, you’ll have a life raft to sail into a positive future. 

The approach I use for personal strategic career planning is based on attending a Stanford University Design Your Life for Educators workshop. (Which was absolutely amazing!)

So grab a coffee (instant or otherwise), settle in, and let’s delve into the world of personal strategic career planning.

What is personal strategic Career planning?

Personal strategic career planning is about exploring alternative pathways to a better future.

Putting time aside for a personal strategic planning session is gifting yourself time to reflect on past accomplishments, assess your current situation, and map out a path for your future. 

Designing a personal strategic planning Session 

Here’s a sample plan for structuring a personal strategic planning session. 

Recommended materials:

  • 4 x large sheets of paper (A3) to draw your career paths
  • A notebook or loose-leaf paper for making notes and journalling reflections
  • Pens and markers

By the end of the session, you’ll have used a technique called Odyssey Planning to create a vision for your future self.

What is Odyssey Planning?

Odyssey planning is a process for exploring multiple potential future paths for career and/or life development. The process involves identifying several options or scenarios, visualising yourself in each of them, and weighing the pros and cons of each path. 

The goal of the exercise is to create a flexible and adaptable future pathway that accounts for uncertainties and helps you make informed decisions about your career and life direction.

For a detailed explanation of Odyssey Planning (and career design generally), I recommend getting a copy of Designing Your New Work Life, by Bill Burnett and Dave Evans

If you don’t have time to read the book, below is a shortcut for getting started.

Start by Sketching 3 future paths

In this exercise, you’ll create three different paths your future could take.

Start by taking the three large sheets of paper, orient them in landscape view, and draw a line along the bottom of each page to represent a time horizon.

The Design Your Life method recommends dividing this line into a time horizon of 5 years. I generally work with a time horizon of 2-3 years (if you have any idea what I’ll be doing in 5 years I’d love to know!)

Then, take one of the sheets of paper and get ready to sketch your first life path: Path A.

Path A: The Likely Path

Path A is the career path that’s most likely to play out if you don’t take any direct action towards changing your current career. It’s your most probable future, assuming you continue on your current career trajectory.

Using markers, pens, and pencils (whatever is available), sketch out how life might play out – use the time horizon line to situate when activities/events/achievements etc. will likely occur.

Try to draw rather than write.

Sketches, images, doodles etc. can be used to represent the events (and characteristics of those events) that illustrate the career pathway. If you absolutely have to use words, try to stick to 1-3 word sentences (i.e. no academic essays on the page!). 

No one needs to see what you’re creating except you, which means no one is judging your drawing skills 🙂

You could spend days doing this. Please don’t.

Limit yourself to a maximum of  5-10 minutes. Set a timer, and start drawing.

When time’s up, sit back and look at what you created.

Does it spark joy?

Does it feel like something’s missing?

Set another timer for 5 minutes and reflect on your plan by journaling your thoughts. 

Afterwards, put Path A and your journaled reflections aside and move on to the next step: sketching Path B.

Path B: The Alternative Path

Path B is the path you’d pursue if Path A was no longer possible.

For example, if your current job disappeared (perhaps replaced by AI!), what would you want to do instead?

Take another large piece of paper (with the time horizon along the bottom), and sketch out a career/life path that you’d take if Path A wasn’t an option. 

The point of this plan is to explore an alternate future.

Again, spend 5-10 minutes maximum on the task.

Then take ~5 minutes to journal a reflection.

Once you’re finished, move to Path C.

Path C: The ‘lotto’ path

I call this plan the ‘winning the lotto’ path because it’s the path you’d take if you had every resource imaginable.

Money – you’ve got plenty!

Time – in abundance!

Obligations and constraints – what are those?

What would you do if you were completely untethered from life’s current responsibilities and had boundless resources?

Path C might reflect a dream job, starting your own business, or pursuing a passion project.

Spend no longer than 5-10 minutes sketching out the path. Then take 5 minutes to document your reflections.

Once finished, it’s time to work with Paths A, B, and C to sketch another possible future.

The Combined Plan

The Design Your Life method provides a detailed process for turning the three paths into an actionable plan to move your life and career forward. 

However, often short on time, I tend to just lay out the three plans on a table, and reflect on what I’ve drawn, while circling only the images/words/ideas that truly appeal.

Get a highlighter (or a pen in a colour you didn’t use earlier) and circle the things in your A, B, and C paths that appeal to you.

Once you’ve identified the characteristics of a career you want to take forward, use the last large sheet of paper to draw another path.

Again, draw a timeline along the bottom, and start to sketch out a new path that combines the desirable elements from Paths A, B, and C.

I find this exercise useful because it helps distil the noise in my head into a single visual.

This final plan, while unlikely to have solved all your existential career questions, can help you define an anchor narrative to guide you moving forward.

The combined plan can be a useful visual to stick on the wall, and refer to when needing to sense-check decisions, or evaluate whether to engage in opportunities. 

In essence, it can help guide your choices for how you spend your time.


Taking the time to engage in personal strategic planning can be a valuable investment in your career and future. 

Exploring alternative pathways through Odyssey Planning and creating a vision for your future self can help you to gain clarity about your future direction.

While departmental strategic planning days can often induce eye rolls, I generally find personal strategic career planning worth showing up for.

Personal strategic career planning provides an opportunity to craft a roadmap to help guide you through uncertain times, whether the higher education ship is sinking or not.

If you’ve enjoyed this blog post, consider signing up to my newsletter ‘T3’, where I share tips, tricks, and tools on AI + Technology for the higher education sector.

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