We say it all the time: career change is the new normal. Many of us reach a point in our careers when things no longer make sense - or at least come into question. What is the value and meaning of work? Why do I wake up each morning? Is all this soul- and time- sucking effort really worth it?

We all need to eat, pay the bills, and afford our personal lifestyles, but this shouldn’t be at the expense of your personal wellbeing, professional growth, or sense of balance and abundance in life and work. Fulfilling work and financial reward are not mutually exclusive. Yet, the number on reason so many aspiring career changers fail to start is because they fear losing job security or financial stability.

In this article, I want to share three pivotal moments in my career where I was able to make a bold move by transforming m money mindset, having a financial plan, and making small adjustments to my spending habits without going broke.

Bold Career Move #1 : Making Ends Meet Out Of College and Into My Career

Working through college was never an option for me. Thankfully, as an American, I was eligible for financial aid which meant working part-time student jobs to help fund my tuition. So from a pretty early age, I came to appreciate the importance of managing personal finances and spending habits.

Right out of college, I was in more than 80K of student loan debt. As I explored my career options, I was also working 3 part-time jobs to afford my rent and living expenses. My big break finally came when I landed an Office Manager position at Harvard’s Global Health Research Institute which came which came with some great perks: medical and dental insurance, a ‘matched’ retirement savings (401K) plan, and an optional housing loan which allowed me to move out of my shared apartment and into my own little 1-bedroom flat.

It was during this three year period that I developed a practice of tracking my debt and bill payments and creating a monthly budget to keep my spending in check. Saturday mornings became my ‘life admin’ day for ensuring auto payments were made from my bank account, any outstanding bills were settled, and setting a monthly or weekly budget for myself to keep my spending in check.

Nearly three years later, I’d managed to pay off my housing loan, a healthy portion of my student debt, and even accumulate a personal savings fund. With this, I was free to dream bigger and set the next career milestone for myself: a big bold move to NYC.

With my personal savings and returned rent deposit, I knew I could cover my daily living expenses and monthly bill payments for two months which meant I’d have to land my next job in that time. I was also fortunate to have a friend agree to help me with the move out of my Boston flat and into another friend’s Soho apartment where I was fortunately able to crash rent-free for the first few months of getting setup and settled into New York.

Having friends who can support your career transition is always a huge plus, but the key to making my first bold career move possible despite my financial debt obligations, was to have a personal management system for staying on top of my finances and spending. The goal isn’t to complicate or restrict you, but to help you sustain your financial standing so that money worries don’t restrict you from dreaming big and being bold.

Download this FREE Financial Management Guidebook and Workbook to help you get on top of your personal finances. 


Bold Career Move #2 : Financing Career Change and Relocation

My New York life chapter was one of discovering my professional talents and interests, and exploring different career possibilities. From product design, development and China sourcing with a fast-growing startup, to freelance consulting for fashion designers, print media, and a renowned portrait photographer, working in New York taught me how to leverage on my natural strengths and transferable skills to position myself for just about any career opportunity that piqued my interest or presented a new professional challenge.

Financially speaking, keeping up with the ‘work hard, play harder’ lifestyle of New York wasn’t easy - particularly at the ‘wild’ years of my mid-20’s. Sustaining a personal savings was near impossible during this period, but cutting my business teeth, building my client portfolio, and developing true grit of this four year period proved to be invaluable well beyond my years in New York.

So after four hard years of grinding in the city that never sleeps, once again I found myself longing for the next big challenge and bold career step. The big ‘nudge’ I needed to take that first step came with the fall of Wall Street in 2008. As the weight of financial crisis could be felt more and more, Asian economies were on the rise and booming with opportunity.

My partner (now my husband) and I decided it was time to ‘return’ to Asia - where we’d both grown up and gone to school - to see what we could make of ourselves. We knew ‘Project: Asia’ would be a big financial commitment as it would also mean reinventing our careers and carving new professional paths. It would take time, resources, and a financial runway of at least 6 months. We figured that together, we could save enough runway to travel in the region while exploring career options and re-adjust to living in a cultural context we’d been away from for so long, we could make the transition with ease and enjoy the journey!

We set ourselves a 6-month timeframe to get our financial house in order and make it all happen.

Here’s what we did:

1. Savings - We agreed to contribute our earnings toward a 10K (Singapore dollar) savings target to cover our flights, moving expenses, and 6-month basic living expenses (ex-rent since we set our ‘base’ at my husband’s family home in Singapore).

2. Debt - I researched how to consolidate and refinance my credit card debts and defer my outstanding student loan payments for one year.

3. Spending - We restricted eating out / ordering in to once a week (max) which meant budgeting, planning and cooking meals at home every week.

4. Extra Cash - To help reach our savings target, we decided to sell everything in our apartment and any personal belongings we were ready to part with. We catalogued everything in a PDF flyer that we emailed out to friends, family, and co workers, and advertised our moving sale over a full ‘open house’ week. We sold everything down to our fancy little spatula and raked in a solid 4K towards our Project: Asia fund.  

The final piece of the puzzle was to see how we could continue to earn money while traveling and making the transition to Asia. Thanks to our freelancing experience and client network, we were both able to secure short-term projects that would allow us to work remotely and continue earning a nominal income.

Exactly 6 months from the date of conceptualising Project: Asia, we were ready and financially secure to embark on our journey from New York to Singapore and beyond!

If you’re thinking about a bold career move that could involve a relocation, download this FREE Financial Management Guidebook and Workbook to help you work out how much financial runway you’d need, where you can shave your current expenses, and decide whether starting a side-hustle would help you to make the transition with more ease.


Bold Career Move #3 : Investing In Yourself To Become An Entrepreneur


Making a career change will always involve compromise and trade-offs. Especially if you’re looking to make a major shift in professional direction. This was something I learned throughout my Asia career chapter - from the decision to work for a global MNC during at the start of my career chapter in Singapore, to ‘dropping out’ of corporate (and never looking back) two years later.


Going into the corporate world felt like a great sacrifice, on the one hand. I had less autonomy, flexible work hours, a steep learning curve (I was new to corporate PR), and had to ‘dress up’ for work. It also took time to adapt to the workplace culture, personalities and leadership styles (which were always changing). On the other hand, I had clear reasons for making that choice based on my priorities at the time: to gain corporate experience, work for (what I thought was) my ‘dream’ company, and develop a new transferable skillset. Plus, for the first time since the beginning of my career journey, I had job security, a clear growth trajectory, and a pretty decent salary.


In the end, suffice to say all didn’t turn out quite as expected. Less than 2 years later, the things I’d consciously sacrificed in order to have my corporate stint, no longer seemed worth the trade-offs. But in the final months of my corporate job, I was feeling anxious about my decision to leave. I’d become used to a certain lifestyle, buying nice things that I didn’t need, and finally living with my husband in our own home! But I was burnt out, was barely at home, and felt depleted of motivation or purpose. I had no idea what I would do next, but I knew I’d need some time off to recharge, recalibrate and figure out my next steps. And here was the career crossroads that forced me to shift my money mindset.


At this pivotal moment I had a choice:

Either, stick out my soul-sucking job in order to continue enjoying certain comforts and ‘nice to haves’ at the price of my health, relationship and happiness, or making adjustments to my lifestyle and habits to re-prioritise my life and wellbeing needs.


Choosing the latter, the next 8 months of this career transition saw me:

  • Participate in an immersive retreat in Bali to reconnect with myself, my values, and an intimate cohort of like-minds

  • Join a co-working space and community of social entrepreneurs that brought more collaborative projects, work opportunities and connections

  • Register my first sole proprietorship providing business advisory and strategic support to purpose-driven businesses and enterprises

  • Become a Design Thinking facilitator for first and secondary school students in Singapore

  • Work in collaboration with inspired tinkerers, makers and entrepreneurs driven by a mission and vision to shape the future

  • Launch a ground-up initiative aimed at bringing Singapore’s diverse communities together over food, brews and live performances

  • Establish Singapore chapters of global movements such as The Worldwide Feast, Jane’s Walk and Mashable’s Social Good Summit

  • Register my first sole proprietorship providing business advisory and strategic support to purpose-driven businesses and enterprises

  • Culminate all of the above to setup The Change School in partnership with one of my best buds from high school!

There’s no way I could have known what the future had in store for me at the time that I’d decided to leave my corporate job. I had a healthy savings, but I didn’t have a plan. But once again, there were sacrifices to be made and trade-offs to be had. No two-ways about it.

So if you’re thinking about making a bold career move, it’s not so much the what as the why that’s most important. Depending on your priorities, be prepared to give up something old, in order to gain something new. Whether it’s your job title, status, salary or perks, you need to get really clear about the exchange you’re willing to make: What sacrifices or trade-offs am I willing to make in order to (gain / explore / create…X)?

You can easily qualify your answer by reflecting on your current Life+Work priorities and evaluating how they measure up to different career options.

You can also quantify your answer by creating a simple Financial Plan to help manage and finance your career change or transition.

Download your free copy of our Financial Management Guidebook and Workbook.

Remember to save a copy and adapt it to your needs!