Photo: 123rf

For many of us, it’s a dream to break out of full-time employment and be our own boss.

The autonomy that comes with following that dream is a huge draw, so it’s no surprise that more Singaporeans are ditching conventional employment and choosing to be their own boss, either by setting up their own businesses or freelancing. 

But while perks of being your own boss include flexibility, freedom, and greater financial control, there is still hard work to be done in order to make it.

Particularly for entrepreneurs, financial investments can be an initial stressor.

And as the business and team grows, new challenges emerge along the way.

“Being a boss at a corporate job versus your own business is drastically different. First reason being – you face the immediate pressure of sustaining the business’s profit and loss; if the business ever bleeds, it bleeds out of your own pocket,” says Cassandra Riene Tan, founder of several ventures, including tech startup Bitsy and, most recently, casual dining restaurant Botany. 

“So the stress of managing a team is a whole new level of intensity when you are in your own venture as compared to being in an existing company.”

Here, Cassandra shares the things she wished she knew as a first-time boss.

1. You are bound to make mistakes and it’s okay

Photo: 123rf

“You could read up as much as possible on management and leadership or seek advice from mentors, and you would still make mistakes along the way.

Every circumstance is different as there are many factors at play – including the nature of your team, team dynamics, your management style, and the industry. The key is to learn from your mistakes and move on.”

Cassandra admits that she used to dwell on things whenever something went wrong or didn’t go according to plan, but, over the years, she has learnt to have faith that everything will eventually fall into place as she finds solutions in the meantime.

2. Don’t take things too personally

Photo: 123rf

“Perhaps you hired someone who didn’t work out, or your customers or clients aren’t appreciative of your services, or investors don’t understand your business. Don’t be too disheartened,” Cassandra advises. 

“During the first year of being an entrepreneur, I found myself on a constant emotional rollercoaster. I found myself vexing over every employee who didn’t work out – did I make the wrong hiring choice or is there something wrong with my leadership?

“Later, I met other female entrepreneurs and realised that it is pretty common to feel this way. You just have to accept it, learn from it, and move on. You can’t dwell on it too long, or you risk getting sucked into the vortex of negativity and paranoia.”

3. Hire slow, fire fast

Photo: 123rf

“Hiring the right team is very much like dating: you should never settle for just ‘good enough’, but focus on finding the right fit. Not perfect, but right,” says Cassandra. 

She shares that the first mistake she made as a newbie boss was that she hired too quickly and was slow to let employees go. 

“When I started out, I went through the same interview process as I would if I were in a corporate job hiring a team. It didn’t dawn on me until much later that we needed a very different type of candidate who could stick it through and help to grow a new business. My first venture was growing rapidly and I was anxious to make sure I had enough manpower.

“Now during interviews, I test their aptitude for uncertainty, resourcefulness and, most importantly, their resilience and grit. New business ventures need employees who possess the entrepreneurial mindset and ability to solve problems quickly. The cultural fit and chemistry between team members are also important as the team begins small. 

“And in any case if the hiring doesn’t work out, don’t try to force it. The mistake first-time bosses tend to make is getting overly attached to our first hires and we think we can mould them to fit what we need. Back to dating principles, you cannot try to change a person unless the person wants to. So it is better to just part ways as soon as you realise both parties are not a good fit, rather than to drag it on. Turnovers are very costly as you need to invest a substantial amount of time and resources into training,” shares Cassandra. 

4. Form a support group and make new friends

Photo: 123rf

Being an entrepreneur is tough, and being a female entrepreneur is even tougher, according to Cassandra. 

“There’s still a lot of prejudice and societal mindsets we need to overcome and change. Especially if one is also a mother while being an entrepreneur. 

“The reality is that you would probably grow apart from some friends over time, especially if they are in a 9-to-6 job, because first of all, your problems at work are very different and so are your solutions to problems.

“Secondly, your perspectives would have changed from being an employee to being a boss, so your friends in conventional employment would not share the same views as you. You will probably go through a stage where you feel pretty much disconnected from old acquaintances.

“It is a lonely transition into entrepreneurship, but you can ease that by making new friends through networking events that are relevant to your business, or friends of friends you do business with.

“It has been five years since I became an entrepreneur and my best friends now are all entrepreneurs whom I met under different circumstances. These entrepreneurs became my support group, my mentors, and peers. We relate to each other and grow our businesses together,” says Cassandra.

5. Remember to love yourself

Photo: 123rf

It is better to invest some time for self-care in between than to suffer an eventual burnout. 

“The journey as an entrepreneur is a marathon, not a sprint. In the midst of pursuing goals, we have to remember that our mental wellbeing and health are top priorities. When starting out with a business, burnout and depression are more common than one would think.

“Find time to take a breather at any point when you are feeling overwhelmed. I started going to bed earlier (before 11pm) and waking up early (5.30am) so that I have some quiet time in the mornings to meditate and go for a walk to clear my mind. This helps a lot during stressful periods,” advices Cassandra.