One of the best ways you can retire early is by upskilling. Upskilling is the practice of acquiring new skills to remain competitive in your job.


One of the best things that ever happened to me was being able to retire early. Not having to wait until I was 67 before leaving work has been an unexpected joy. I'm so glad that we made good decisions leading into our 50's that paved the way for an early retirement, I know others are wanting to head in that direction but need a little boost to get there.

Today on the blog I have a great collaboration that gives some excellent suggestions that might help to give you that little push you need to get there sooner than you expected....


Well, one of the best ways you can do this is by upskilling. Essentially, upskilling is the practice of acquiring new skills to remain competitive and adapt to the changing demands of your job and industry. Enhancing one’s current skills and abilities, is a good tactic to adopt for those who want to advance both within their existing role and their future careers.

With a bit of luck, strategic job moves and some savvy investing, you can find yourself in a position to retire five, ten or even more years earlier than most other people do at 67. If this sounds like an appealing thought, you might be asking yourself how you can best upskill to achieve this. Well in this article, we’ll highlight seven of the most common options available.


If early retirement is something that interests you, then you should take the opportunity to map out how you would like your career to progress. For instance, this could involve identifying that you want to be in a management role in five years-time, a director role in 12-years and at board level in 20-years.

Once you have worked out your ideal career path you will be better able to establish what skills and experiences you will need to help you achieve your goals.


One thing you will need to do to advance your career towards early retirement is commit to continuous learning. Without it you will struggle to meet your goal. For instance if you were once a teacher you could consider extending your knowledge and passion with a Master of Education, which you could study for at an institution of higher education such as UTS Online.

You should also commit to improving other skills like your strategic thinking, written and oral communication, IT skills and negotiation abilities to make yourself recognised as a more rounded and valuable employee.


Another really good way to upskill is to get yourself a mentor. While you might need to pay to do this, establishing a mentorship can be an invaluable way to boost your personal development.

By tapping into the insights and advice given by your mentor you can significantly improve your leadership potential, enhance your skills and knowledge base, make new connections and gain different perspectives on business.

One of the best ways you can retire early is by upskilling. Upskilling is the practice of acquiring new skills to remain competitive in your job.

A good mentor will also boost your confidence and identify what areas you might need to work on to help you take the next step in your career. You can find a good mentor either through your current company, via industry associations and professional organisations or through platforms like LinkedIn.


Talking of industry associations and professional organisations, they are well worth joining if you want to advance your career towards early retirement.

Every industry has at least one and it's a place where you can learn insights from more established movers and shakers, and make connections with them. You can also gain access to the latest research and invites to specific events which might be of relevance to your planned career path.


Networking is a very important way to advance your career as it can open doors for you and lead to connections which you otherwise would not have made.

Try to attend as many relevant industry and business events as you can, as this will provide you with an excellent opportunity to meet other business professionals, share ideas, and could even be a stepping stone to more lucrative job offers.

One of the best ways you can retire early is by upskilling. Upskilling is the practice of acquiring new skills to remain competitive in your job.


If you are serious about early retirement, then you will need to be able to fund it. Therefore, it is a good idea to gain an appreciation of how you can best invest the money you make.

Through savvy investments you may be able to fund a lifestyle that sustains you from a retirement age of 50 or 60. Subsequently, you should take the opportunity to learn about what investment opportunities are available and set them up accordingly.


Perhaps the biggest way you can upskill is by developing a positive mindset. Ultimately, you won’t be able to achieve any successes in your career without the drive, determination and belief that you can do it.

There are several ways you can develop a positive mindset, including reading books, watching videos on YouTube, listening to podcasts and Ted Talks and taking specific courses. If you make the investment to upskill in this area, you can benefit exponentially over the course of your career.


I know I was thrown for a loop when early retirement presented itself to me, I'd have loved to have had a plan in place and to have been prepared for the transition. I'd never thought of my job as a "career" and how I could have used it to better position myself for the future, so these tips would have been really useful. If you're still in the workforce, I hope you find at least one of them helpful as you look towards leaving your job one day and joining me in this delightful retirement phase.

One of the best ways you can retire early is by upskilling. Upskilling is the practice of acquiring new skills to remain competitive in your job.


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Cresting the Hill - a blog for Midlife (Middle Aged / 50+) women who want to thrive


  1. Hi Leanne - This is a good list.
    Learning is a continuous process. I don't think that ever stops. It should never, actually. A part of that learning is upskilling.
    Also, it makes better sense to work to our full capacity during our younger days, when we are capable, rather than in later years when both our mind and body are beginning to wear off.

    1. Hi Pradeep - you're so right, upskilling early can make a huge difference. That being said, it's never too late to pick up new skills and diversify along the way. I changed professions in my 30's and then did smaller changes in my 40's and 50's. Each time for an increase in pay and a new workplace - it kept things interesting and certainly helped edge me towards being brave enough to retire early. No regrets at all!

  2. Oh dear. All I could think about while reading this was, "I am so glad I do not need to do this any more!" OK, maybe not the continual learning - that I still do. And a positive mindset, which I try and keep (note the try!). But I am glad I no longer need to worry about career progression, skill set updating, mentoring, and networking. A nice list though, for someone younger.

    1. Hi Pat - I feel the same way - but I also thought that nobody gets to retire early if they never take a step towards being proactive or improving their skills along the way (unless they win lotto or inherit a fortune). I liked that I don't have to this anymore, but so glad that I put in the effort when the opportunities arose. Retirement is just such a joy!

  3. Hi, Leanne - I echo Pat's words above. Thank you for another thought provoking post. Great tips here!

    1. Hi Donna - I can't believe how lovely it is to be retired, I thought it would be hard to fill the time etc, but it's such a lovely phase of life. If I can share anything that helps others get here too, then I'll be shouting it from the rooftops. We worked hard to get here, but it we're also so blessed to be able to look back and not have to repeat it all, or keep striving in the hope of getting to the end and not be living under a bridge :)

  4. Good ideas for sure. However, I am way past needing them but can attest to using the upskilling to become a teacher of English as a Second Language which gave me a part time teaching job from 2006-9 after my “first” but forced medical retirement in 2002. I too am a learner for life! Denyse

    1. Hi Denyse - I think becoming a Principal, and then upskilling for the remainder of your teaching career are perfect examples of making a career last the distance and help you get set up for retirement. Being proactive and making the most of opportunities to earn more and to set more aside for retirement are definitely keys to making the process smoother.

  5. I too am happy to have been able to retire early, Leanne. One thing that really helped me was paying attention to retirement benefits offered by potential employers and then taking full advantage of those benefits and opportunities for investing in my retirement accounts.

    1. Hi Christie - I realized towards the later part of my working life that superannuation and funding my own retirement was key to being able to leave work early. If you can't support yourself without govt assistance then you need to stay til the bitter end. I'm so grateful I put aside whatever funds I could, so (like you) I could make it happen!

  6. I took such an "early" retirement that i do not even call it retirement. I moved forward to a much fuller life and have never been sorry. Most important for me was mindset and to believe "I can do it"

    1. Hi Judith - I literally jumped into retirement early - not realising that was what I was choosing....and it's been the best thing EVER! I'm grateful though that I'd worked hard, saved hard, invested well, and could financially sustain being retired early - so much so that my husband has jumped onto the early retirement bandwagon with me!


Thanks so much for your comment - it's where the connection begins.