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How to finish your career on a high


Many of my clients are in the “middle years” of their careers.  I’ve noticed a phenomenon among people who are about half to two-thirds of the way through their career.  These people want to plan out how they will finish the last 15 – 20 years of their career, ensuring that they (i) enjoy themselves, (ii) deliver value and (iii) finish their career feeling personally fulfilled.

As I work with them through the D.R.E.A.M. process, there is a pattern that emerges that I thought might be helpful to share.  If you’re looking ahead to your final decade or two, have you thought about what shape that ending will take? 

Here are the key things to think about.

Self Discovery

This is where I always start with clients and it is an ESSENTIAL step if you want to finish your career in the best possible way. 

You need to know your energising strengths and how you are going to use them every day.  Equally, you need to know what drains your energy and ensure you avoid those activities where possible.  You need to articulate your personal values and make sure that any career options you choose will enable you to live out those values.  You need to know your purpose – what contribution you want to make and what impact you want to have in the remaining years of your career.

One Big Role

Many people at this stage of their career feel that they have one or two “Big Roles” left in them.  This Big Role is an opportunity to take everything you’ve learned in the preceding decades to really make an impact. 

It is important that this Big Role is not just any role.  It needs to align to your purpose (see Self Discovery).  This often means that you may take your skills and experience into another sector; perhaps an industry that is more in line with your values or where you think you can make that impact.


When it comes to the last 5 – 10 years of a career (after the Big Role), oftentimes people want to create some kind of portfolio that will help them tick all the boxes of enjoyment, impact and fulfilment.  This is where you need to look at career possibilities that may sit alongside each other simultaneously. 

Maybe you have the skills and experience to take on one or two NED roles.  Perhaps you want to “give back” by doing pro bono work or becoming a mentor.  Perhaps you want to attract some freelance or consulting opportunities.  And, maybe it’s now time to start your own business – what is that idea you’ve always had but never had time to do before?

Start With The End In Mind

Stephen Covey said it best: “Start with the End in Mind”.  Now, I don’t suggest you imagine yourself at your own funeral, as Covey does.  However, I do get suggest you do a similar exercise where you imagine yourself attending your own retirement or “end of career” party.  Imagine who would be speaking and what would they be saying?  What would you be feeling?  What would be your legacy?

What path can you create that would make that party a reality?

What 3 Words

No, I’m not selling you a navigation app.  If you could choose three words that would sum up how you want to end your career, what would they be?  Now get these words somewhere visible – post-it notes on your computer monitor, pinned on the wall, laminated card in your wallet, wallpaper on your phone…  Keep looking at them, particularly when you’re making career decisions, to make sure you’re aligning your actions with your intentions.

Get Planning

Now you know a bit more about what you want the end of your career to look like, it’s time to make a plan to get there.  Fix on some goals, map out a timeline, create a plan and … get into action!

If you want to talk about how to end your career on a high, I’m here to chat.  Book a free 45 minute Discovery Call.

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