Jumping off the career ladder to be an entrepreneur is the best decision I’ve made

In December 2020, I attended a management meeting on Zoom. At the time, I was the principal counsellor and head of the counselling department at a local non-profit organisation.

I had entered the social service sector in 2009 hoping to work directly with clients and make a difference in their lives. But as I climbed the career ladder, I found myself doing less of that and more administrative and management work.

The meeting dragged on joylessly as we discussed strategic plans for the coming year. When it finally ended, I slouched on the floor, exhausted and emotionally spent.

For the first time, I asked myself a question I’d been avoiding: Do I really want to spend the rest of my working life like this?

A forgotten dream

Sitting there with my face buried in my knees, I realised I had forgotten a dream I once held dear.

Fresh out of university and navigating corporate life as a corporate communications executive in the late 1990s, I had a series of relationships that left me broken and depressed. Counselling helped me find myself again.

My therapist worked with me patiently in a cosy office tucked away in the Cairnhill area. The sessions were held in the evenings after work, in a space that felt safe and warm.

It was there that a dream formed – to build a similar space where individuals and couples could restore hope and rebuild connection.

The dream stayed at the back of my mind even as I got sucked back into the flow of high-pressure work as a full-time employee. I obtained formal qualifications in counselling, and officially joined the social service sector.

Life went on, I got married and had a little girl.

But I had never acted on my dream to have my own practice. It was too scary, stepping out of my comfort zone of full-time employment and a regular salary.

That day, however, was the last straw.

I resigned shortly after, and in March 2021, I set up my own practice, The Relationship Room. I chose to specialise in relationships and marital counselling, knowing first-hand from my own experience the importance of building healthy relationships.

It was the start of my entrepreneurial journey, one that was filled with uncertainties, self-doubt, fear – but also joy.

Joy amid the struggles

At first it was just me, in a counselling room that I rented by the hour. It was bare and sparsely furnished – a far cry from the cosy office my therapist had.

But even then, I could tell my clients felt safe there. We experienced meaningful breakthroughs in their relationships, and word of mouth slowly spread.

I realised that healing does not depend on beautiful spaces. What mattered more to clients was being heard, seen and supported.

That reassured me, even through the nagging thoughts of self-doubt and failure.

The financial anxiety was also real. In the first month after I started my business, I avoided shopping malls and cafes because I did not want to be tempted to spend money. The old me would not have thought twice about splurging on pick-me-ups.

But I focused on the impact my direct work had on my clients, and realised this was a sacrifice I was happy to make. I learnt to welcome the challenge that the fear and uncertainty brought, and trust in my careful planning, savings and community support.

For the first time in my life, I learnt to truly appreciate prudence.

A whole new ball game

As my practice grew over the years, so did the criticism. Some feedback – such as suggestions on how I could improve my counselling skills – was helpful. Others, such as claiming that I “appeared credible because of an excellent marketing campaign”, stung deeply. I had to learn not to take every comment personally.

Organisational psychologist Adam Grant once said: “The most successful people are the ones who can take criticism and turn it into improvement.” That idea of choosing growth over defensiveness stayed with me.

Along the way, I’ve developed a thicker skin and learnt to tell the difference between helpful feedback and unhelpful noise. This is personal growth I don’t think I would’ve experienced had I stayed in corporate life.

I’ve come to deeply appreciate this.

In 2023, I wondered if I should scale up the practice further and expand to a second location. At the time, it was just me and my husband, who had joined me to oversee the business operations.

Besides having to pay the rent for a second location, I would also have to hire more counsellors. It would be a whole new ball game and I worried constantly about whether I was making the right decision.

But a friend and fellow entrepreneur gave me some simple, liberating advice: There is no right or wrong path. Whether I chose to remain at our current strength or build a larger practice, these are simply different career tracks.

What mattered most was that I truly believed in what I was doing, because I would be motivated to stick with it despite the challenges.

That conversation validated my feelings. It helped me realise I was not alone.

In February 2024, I rented a second counselling room downtown. The uncertainty was terrifying. Yet, in deciding to move forward, I felt a sense of peace. Because even if I failed, at least I had tried.

Fulfilling my calling

Today, The Relationship Room has grown from a single-room, owner-operated practice to a main office and branch in Raffles Place, and a team of four, including two other counsellors and my husband. This month, we celebrated our fifth anniversary.

Looking back on the discoveries I’ve made, the growth I’ve seen in myself in stepping out of my comfort zone and learning to sit with discomfort and uncertainty, I’ve realised that I’ve grown into my true calling.

Entrepreneurship has not made my life easier. In some ways, it can be more challenging. I am constantly on my toes, responding to the trends and evolving needs in the mental health and social service space. Besides the core counselling work, I also have to run a business and keep up to date with social media trends and marketing.

But every morning, I wake up excited, knowing I’m living the dream I dreamed of two decades ago. And for that, I am grateful.