Coming up with the decision to switch careers, especially when you are older and established in your current one, takes a lot of guts. But it is not an impossibility, and neither is the success after a mid-career switch. Many others have done it before. But still, we are not going to deny that it is no piece of cake.

However, what we can tell you is that there are ways or techniques you can follow that can make your career reinvention more fruitful and increase your chances of success.

Think of it as an art; while there’s no one, clear-cut way to do it, there are some skills you can try to improve on as well as tips and techniques you can bear in mind as you make it in the field.

Handy Ideas to Help You Thrive in A New Job

Plan well.

As the saying goes, those who fail to plan are planning to fail. While this is not true in every case, planning beforehand can get you a long way. Better be sure than sorry, right?

So how exactly do you do your planning when it comes to mid-career reinvention? Go back to the basics. Grab a pen and paper (or your laptop, if you prefer), and write down all the facts.

Is money a big factor?

If not, then there is more room for you to take greater risks. If otherwise, then maybe you will have to take things slowly, step by step. When are you planning to retire?

If you have a decade and more ahead of you, then you can be more flexible on your reinvention and can make bigger changes. If you only have a few more years before retirement, consider opting for a smaller reinvention.

Do you have a lot of resources? What kind of resources do you have?

Based on your answers to questions like these, you should be able to create a timeline. This timeline should serve not only as your schedule but as a reminder of your goals. Set a deadline for each goal/task, and reward with little somethings whenever you cross a certain number off the list. Such habit boosts motivation and determination to face the other tasks ahead.

Get inspired.

Learn from the stories of other people – those you know and those you can read in magazines and books or the Internet. Many tend to underestimate the power of listening to others’ stories, while really, they are not only a good source of motivation and inspiration, but they can also serve as a guide as you plan and make decisions on your new career path.

So don’t be afraid to ask a friend or invite a colleague to a cafe to discuss these ideas.

Read: 9 Must-Read Women Biographies

Hone skills.

Identify the new skills necessary to survive and succeed in the new course you are about to take. Your approach to developing those skills would vary depending on your background knowledge and your current level of each skill. Consider the following options:

  • Take formal classes: While this is not always necessary, this is the best way to go if your new career path requires some certification. This is probably the most costly among these options, but if you get to a good school and have a good teacher, this will be beneficial.
  • Take online classes: This is an option if your schedule is more complicated to welcome a fixed schedule of formal classes and to have to go to the school physically. Some online classes are free; others require payment; you have to research if you want to find the free ones. Once you do find these, it would be better to enrol early so you can save yourself a spot.
  • Get a sideline job: Make sure you can develop the said skills in this job. This is a good option if you have some free time and would want to earn while you are learning.
  • Reading skills book: This is less costly and perhaps less time consuming than going to classes, but of course, this means you have to have the patience and determination to absorb and understand these, to actually finish through these books, and to practice the skills they are teaching you.

On the flip side, you should also be able to identify your current skills and to bring to mind the past lessons you’ve learned from your former career. Do this no matter how irrelevant you think your past career is to the new course you are taking.

If a previous model can apply her skills and the lessons she learned from her experiences in this career to her new business venture, so can you.


You can’t do it all by yourself, and that’s the truth you have to accept, especially if you are in the midst of a career reinvention. You will have to ask for help from others one way or another; so always take the opportunity to expand your network effectively and fill it with skilful people from various fields and expertise.

In order to succeed in a certain field, especially one that is new grounds to you, you have to find the right people. If you are planning to start a new venture, this is a necessity; you’ll need a lot of people working for and with you, and networks that can fill these positions or at the very least help you find qualified people who will.

Networking is not as difficult as you might think; in fact, it is a practice you can do on a daily basis!

Toughen up.

You are in a new field, and you probably think that there are much more qualified than you. But that does not be limited by such thinking. More than certifications and past experiences, persistence, enthusiasm, and dedication pay off.

Accept that there will be rejections and failures on your journey to reinvention, and that is okay. Instead of seeing them as mere setbacks, perceive them as stepping stones towards the realisation of your goals and learn from them instead. Ask yourself: what did I do wrong this time? How can I improve to increase my chances of succeeding?

More importantly, you have to stop doubting yourself and start believing in your capabilities. Stop thinking it’s impossible – everything is impossible if we keep on thinking it is. Just do it and see for yourself!

This is perhaps the most important step because you have to be able to be confident and project this confidence so that others – family, friends, colleagues, co-workers, and other networks so that they will be even more willing to help you get to the top. Surround yourself with people who will support you and at the same time, are willing to correct and guide you along the way.

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Founder @ The New Savvy
Anna Haotanto is the Advisor (former CEO) of The New Savvy. She is currently the COO of ABZD Capital and the CMO of Gourmet Food Holdings, an investment firm focusing on opportunities in the global F&B industry. She is part of the founding committee of the Singapore FinTech Association and heads the Women In FinTech and Partnership Committee. Anna is the President of the Singapore Management University Women Alumni. Anna invests and sits on the board of a few startups. Anna is also part of the Singapore Chinese Chamber of Commerce & Industry Career Women’s Group executive committee. Anna’s story is featured on Millionaire Minds on Channel NewsAsia. She hosts TV shows and events, namely for Channel NewsAsia’s “The Millennial Investor” and “Challenge Tomorrow”, a FinTech documentary. Anna was awarded “Her Times Youth Award” at the Rising50 Women Empowerment Gala, organised by the Indonesian Embassy of Singapore. The award was presented by His Excellency Ngurah Swajaya. She was also awarded Founder of the Year for ASEAN Rice Bowl Startup Awards. She was also awarded the Women Empowerment Award by the Asian Business & Social Forum. Anna has been awarded LinkedIn Power Profiles for founders (2018, 2017), Tatler Gen T, The Peak’s Trailblazers under 40 and a nominee for the Women of The Future award by Aviva


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