The 4 Biggest Challenges Faced by Singaporeans Running a One-Man Show

The 4 Biggest Challenges Faced by Singaporeans Running a One-Man Show

If the thought of having to deal with inconsiderate colleagues or listen to office gossip makes you want to sharpen your parang, being a self-employed person or working from home might sound like a dream. But as the many tuition teachers, taxi drivers and freelancers know, being a one-man show has its drawbacks. Here are four of the biggest issues sole proprietors face.


1. Maintaining work-life balance

You might blame demanding bosses and incompetent colleagues for poor work-life balance, but wait till you start working on your own.

If you don’t consciously put clear boundaries in place, you could end up suffering from a complete blurring of the line between work and free time. There is a reason many taxi drivers end up pulling 15 hour shifts.

When you’re the one who calls the shots, it’s so easy to convince yourself that you’ll work for just one more hour, or let a 2 hour task stretch out over 4 hours since there’s no longer knock-off time at 6pm to look forward to.

It may sound counterintuitive, especially as many people decide to work for themselves so they are no longer slaves to a 9 to 6 schedule, but you need to set your own work schedule if you don’t want to end up becoming a slave to your work. Decide what’s a reasonable amount of work and what’s too much, and at what time you will stop working each day.


2. Knowing when to outsource tasks

When you’re a one-man show, you can end up doing every freaking thing for yourself, from all your admin and accounting work to vacuuming your home office. And all these extra tasks can take up so much time they become a second job in themselves.

It’s easy to refuse to outsource work to others if you’re a perfectionist and want everything to have your golden touch, or if you simply see delegation as a waste of money that eats into your income.

But it’s worthwhile always bearing in mind that delegating some tasks can make your life better and be worth the money. If you’re a freelance web designer who’s got enough assignments to pull in a healthy income each month, you might want to just pay someone a few hours a week to invoice your clients and chase them for money. That way you can free up time to do income-generating work.

Often, the thing that stops sole proprietors from delegating work is the mental barrier that comes from not wanting to waste money on hired help, since it eats into your earnings.

To get over that, you might want to get help for just an hour or two each week for a start, perhaps to handle invoicing or other administrative tasks. It won’t cost you much, and it will help you get over the mental hurdle of delegating tasks. Once you experience how good it feels to not be a slave to your inbox, don’t be surprised if you start outsourcing more tasks.


3. Marketing yourself

If you want to succeed on your own, you need to find a way to get business.  Every self proprietor faces this challenge in some form or other.

Private tutors may rely on tuition agents and, later, word of mouth to obtain students. Taxi drivers need to know the most efficient ways to get customers, whether by using apps or hanging around Clark Quay at 4am on a Friday night. Freelancers need to know how to get a steady flow of work in order to survive. Real estate and insurance agents try all sorts of tricks, from advertising their services on Facebook to pasting ads on the tables of a relative’s prawn noodle shop.

This will be your biggest challenge when you’re first starting out as a self-employed person and could well be the key to success. Prospecting may not be a hard skill like coding or baking cakes, but it’s best to invest in learning how to market yourself at the start. Take a SkillsFuture course on social media marketing or attend a seminar on sales in your field to give yourself a head start.


4. Ensuring you get enough social interaction and build a network

Working all by yourself may insulate you from annoying coworkers and horrible bosses, but it can also get mighty lonely and boring.

No matter how misanthropic you think you are, never underestimate human beings’ need for social interaction. Now that work no longer guarantees you a steady stream of people to interact with, you might have to start being more proactive about getting out of the house and speaking to people in the real world.

Let’s just say there’s a reason taxi drivers so often spew forth verbal diarrhoea to their hapless passengers—working all alone for hours on end can take its toll.

If you’re the passive sort when it comes to socialising and networking, always waiting for others to ask you out and only participating in activities if someone else invites you to tag along, life can get very boring and frustrating when you work on your own. You may no longer have the benefit of spontaneous lunches with friends in the CBD or impromptu after-work drinks.

But if you are enough of a self-starter to go it alone as a sole proprietor, there is no reason you shouldn’t be able to build a healthy network and social life. Just think of it as a work in progress that you have control over, instead of being passive. Reach out to new people and folks in your existing network, and actually get your arse off the sofa and organise stuff from time to time, and you’ll have a much healthier amount of social interaction after work.

What other challenges do people running one-man shows face? Tell us in the comments!