I Hate My Job but Don’t Know What to Do Next

For the record, I love my current job. But I’ve certainly hit bottom with some of my previous ones. Hence, the title.

So, if you dislike or hate your current role, or are looking to transit into another one, but not sure what that looks like, you’ve found a kindred spirit.

In this article, I will share how I arrived at the difficult decision of quitting my job without another. And the steps that I took to identify my subsequent interest.

Quarter-life crisis, much?

Since I was about 25, I have had a quarter-life crisis. I would begin a job full of optimism and energy. That would usually last a few good years.

Insidiously, my motivation would start to deflate, and I’d feel disengaged.

As fearful as I was, I just couldn’t shake off the deepening sense that I needed to do something about it.

In my entire work life, I’ve twice left my job without first securing another. I was 34 and 46 when the ‘big resignations’ happened.

In both instances, I had been doing well – first as an advertising copywriter, and subsequently, as a course manager/lecturer at a polytechnic.

The decisions to quit were difficult. Made after intense introspection and debate with self, and exasperated discussions with family.

What I learned from my first big resignation

A few years after my first big resignation, mentally, I was in a much better space. And I was thankful for that. But financially, there was a lot of work to be done.

I decided to take specific actions that would help me to gain a stronger financial footing over time:

  1. Kept my expenses low by having a simple lifestyle
  2. Saved and invested more than 50% of my income and almost 100% of my bonuses
  3. Worked towards paying my mortgage within 5 years
  4. Regularly topped up my CPF Special account and made voluntary housing refunds to try to attain the CPF Enhanced Retirement Sum of my cohort as soon as possible. This would help me to secure a higher CPF life pay-out from 65
  5. Topped up my CPF MediSave account every year to the prevailing Basic Healthcare Sum

Before my second big resignation

In 2021, the whole process of quitting took considerable effort and about a year in the making.

Essentially, I had wanted to explore all my options within the job and organisation before calling it quits.

To a large extent, the way I went about it was through a process of elimination. Here were the steps I took:

1. See the shrink. I hit the wall in trying to figure out why I had felt so disengaged and decided to seek out a psychologist. I believe that to have a fighting chance at finding a solution that works, it’s necessary to identify the real problem. Otherwise, I would be shooting in the dark.

Two hundred dollars later, I realised that the pace of change that I had endured during the last five years had been too fast, too furious. I had three portfolio changes and led three vastly different teams. That had tipped me over the edge into the burnout abyss.

2. Role change. I also spoke to my supervisor to see if a change in role was possible. Specifically, I was looking to step down from managing my team or join another team as a member.

When those were not available to me, I tried to explore an alternative role in another department within the organisation. There was a hiring freeze and that option fizzled out too.

3. Mission critical. Another key question I asked myself is how well I was aligned to the mission of the organisation. I found myself disagreeing with some of the ‘whats’ and ‘hows’ of my department, and I wasn’t in a position to effect the changes that I felt strongly about. Hence, I concluded that it was time to move on.

4. Count the cost. I needed time to figure out my interest. And given my age, I thought it’d be wise to factor in more time to land a job.

Mentally, I wanted to give myself two years to find my next role. Next, I had to calculate if I could afford two years without income.

As a single person and free of mortgage, I needed an ‘I quit’ fund equivalent to two years of all my foreseeable daily household expenses, including holiday expenses, taxes, insurance, private annuity premiums and giving to parents.

In short, the ‘I quit’ fund I set aside would enable me to be comfortably unemployed for two years without adversely affecting my long-term financial goals.

Purpose or paycheck?

This is a classic conundrum.

Ideally, the job that we look for achieves both goals to a large extent. For some, the paycheck is more important. This means we can tolerate more stress and annoyance at work as our focus is on the prize.

For others, finding purpose or meaning in what they do is the most important. It doesn’t matter how big the paycheck is. If they’re not doing something meaningful, they’d be happy to walk.

At my current life stage, I leaned more heavily towards purpose.

And finding my purpose took exactly 12 weeks.

Encounters with self

This happened after I had resigned from my job.

In trying to identify my ikigai, I chanced upon The Artist’s Way, a 12-week book course that is targeted at helping artists to recover their creative selves.

One of the key things I did in the programme was The Morning Pages. Every day, for 12 weeks, I wrote three pages in longhand of whatever came to mind. Capturing this “stream-of-consciousness” gave me a deeper awareness and connection to myself, and helped to unearth my subconscious fears, hopes and emotional blockages.

The other thing I did and really liked was to go on Artist dates. These were blocks of two or three hours every week, set aside for me to nurture my inner artist. The nourishment came in the form of doing things I like or trying my hand at something new, all by myself.

During these sacred hours, I’d explored different sections of the rail corridor; sat on East Coast beach; took part in We Are Hear, a social listening project where I shared with and also listened to strangers in a safe space; started gardening; and tried pencil sketching.

At the end of 12 weeks, I learned that:

  1. I’d spent an alarming amount of time weeding my mum’s garden
  2. Accepting who I am, even when I cannot fully understand myself, is vital
  3. My purpose is found in helping others
  4. I shouldn’t have to wait until I had enough money to do something I really love or to explore options

Do, don’t think

The learnings from The Artist’s Way gave me the impetus to explore. I took a 6-month urban farming course and an 8-week basic sketching course.

I chose these courses because they sounded interesting and I wanted to give myself a chance to try something different. Even if they weren’t immediately practical or necessarily useful for finding a job.

The whole point was to expand my mind and discover new interests.

My biggest takeaways from both courses were:

  1. Be willing to try and be receptive to all experiences – the good (being a student), the bad (anything mechanical) and the ugly (when pencil meets paper, urgh!)
  2. Give everything time because first impressions can be misleading

Piecing the puzzle

At the same time, I was trying to narrow down what “helping others” might look like.

I went back to examine the skills and qualities that featured most frequently when I was doing the tasks/projects that I enjoyed. In my next role, I’d want these skills and qualities to dominate as they empower and energise me. I also made a list of my interests.

My top three in each category were:


  1. Planning and organising
  2. Synthesising information
  3. Communicating clearly


  1. Team player
  2. Dependable
  3. Decisive


  1. Personal finance/investing
  2. Pilates
  3. Gardening/Farming (yes, a new interest made it to my top three)

This might work

As I had no prior working experience among my list of interests, I was prepared to apply for an entry level role.

I’d be willing to pursue a job with a lower salary if it checks the box in terms of purpose.

Next, I tried to determine the smallest paycheck that I could afford to live off.

I listed my current savings/investments, noted my current expenses and forecasted future expenses, decided on an arbitrary but realistic retirement age, and tried to work out the size of the nestegg I needed when I retired.

By estimating the shortfall in my pot and considering my foreseeable expenses, I was able to come up with a number for my next paycheck.

The calculation for this portion is complicated, to say the least. If I were to share it here, I’m pretty sure I’d lose most of you. So I’m going to detail it in my next article.

With the baseline salary acting as a filter, I trawled through various job listings that aligned with my interests and narrowed down to those in personal finance.

I felt discouraged as I had no experience in finance and was pretty sure the chances of landing a job in the field was close to zero.

Silently, I prayed that if this were the right path for me, a door would open.

It did.

My sister saw a blog post on Investment Moats, a personal blog authored by Kyith Ng, who is the Senior Solutions Specialist at Providend. The post mentioned the hiring of Associate Advisers by the firm.

Kyith wrote that the Associates hired by the firm had come from very diverse backgrounds and not everyone had financial experience. After much deliberation, I applied for the role.

And we’re a match.

What’s your move?

Roman philosopher Seneca said: “It is not because things are difficult that we do not dare; it is because we do not dare that they are difficult”.

Should you find yourself at a similar crossroads, I’d like to encourage you to take the step to do some soul searching. Understand your personality, preferences and interests, and gain clarity on your finances.

And when you’re ready, leap.

This is an original article written by Annette Lee, Associate Adviser at Providend, Singapore’s First Fee-Only Wealth Advisory Firm.

For more related resources, check out:
1. Why I Quit Architecture School
2. The Reason Why I Left the Insurance Agency
3. Money Advice for My Younger Self

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