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How To Be Successful When You Are Your Own Boss

By
Shashwith
March 12, 2020

“A goal without a plan is just a wish.” – Antoine De Saint Exupery

Imagine this: You’ve had a long frustrating day, and by the end of it, you find yourself fantasizing of being self-employed, working in exotic locations, sipping cocktails by the beach and just loving the fact that the internet allows you to work wherever you want.

Now, sorry to poke that bubble, but not everyone is cut to have a boss-free lifestyle. Being self-employed is a long, bumpy road and unless you’re ready with the grease paint and have what it takes, you’ll often question your journey. Yes, you don’t have a 9-6 job, but sometimes it can be longer and you’ll constantly need to work hard on marketing yourself well. Your personality will play a big role and you will need to be prepared to be a “Jack of all trades, master of some.”

There is a constant need to find the right balance between work and play, creative freedom and bills to pay. At our recent Singapore Creators Meetup, we traversed the path taken by most freelancers/business owners.

We were joined by Elizabethheartz, a Harajuku Fashion Influencer who has also been a cosplay judge for competitions across SEA; Greg Somerville, a Broadcast journalist turned business owner who owns Somerville Media and does lots of high-profile shoots (including interviewing the cast of Singapore’s favorite, Crazy Rich Asians); and, finally, some fresh blood, Huizhen Tay, who is an Effie award-winning freelance writer new to the freelance game.

Why Zig when others Zag?

  • Legality: For Somerville, It was the only way. With Singapore being a prime location for the headquarters to many of Asia’s largest companies, it positions itself as the place with the right opportunity and for foreigners looking to work independently and legally, the best bet is to start on your own.
  • Opportunity: Coming from an agency background, Tay had often felt the need to do more exciting projects. This didn’t mean those projects didn’t exist—it was just a matter of them landing on her desk. She then decided to take up freelancing in order to take on projects that she liked and could own completely. No ego massages needed.
  • Flexibility: Elizabeth found herself having to juggle a cosplay store, dressing up the part, and also being a parent. She had gained popularity cosplaying at her store and decided to take it up full time, tapping into the interwebs for creative freedom. This meant being able to spend more time with family, and that is precious.

The Good: Being a Bawse*

*A Bawse is a human being who exudes confidence, turns heads, reaches goals, finds inner strength, gets hurt efficiently and smiles genuinely – because they’ve fought through it all and made it out the other side. This word was created by Lilly Singh.

General bad-assery aside, some of the best things about being in the business of YOU is that you don’t have specific hours to clock in and no management to report to. You have complete autonomy over the projects you choose to accept, and you can work anywhere you want, which means you can sometimes skip the long commute to work.

You could take breaks whenever you want to (fancy a siesta?) and control your work relationships by deciding how much you want to communicate. Somerville however warns, “Never underestimate the power of word-of-mouth. You might decide to walk out of the bridge but make sure you don’t completely burn them,” stressing the need to balance people relations. This career decision often lets you experiment with your craft and can give you some of life’s greatest lessons along with the chance to earn more.

The Bad: Tiptoeing on the line

In a regular job, you often have a boss or a mentor to turn to for advice and that’s something you might miss out on. Tay shares that she usually tries to catch up with peers or seniors in the industry to take their advice.

Not having a regular 9-6 job can go either of two ways: You can work less, or sometimes work way more. It’s all about the right time management and making sure you keep a tab on ongoing projects. For example, when you work on projects that require extensive research before your final output, make sure to keep a tab on how long that takes so you don’t end up working long hours without being able to charge the client accordingly. There are also other risks, like insurance and medical costs that are usually covered when you are in a regular job.

Also read: Are You Ready For A Freelance Life

The Ugly: Hot Mess Alert

When you are self-employed, you can ricochet between certainties and doubts. There will be times when you won’t have enough jobs in hand and as humans, you could question your capabilities. This really brings the issue of mental health to the forefront. You can be an oyster in your shell but don’t let the water drain you or damage the pearl.

Heartz says the best answer sometimes is a digital detox. She shares, “Dwell in life’s simple pleasures. Remove yourself from a stressful environment and try to relax. Try a solo trip, you’ll feel rejuvenated as you choose when to wake up, explore and rest.” It isn’t easy but you have to find the light and conquer from within. Despite their successful freelance careers, the panelists were an open book, and did not hesitate to open up to the creators who attended the event. Somerville said, “Sometimes you feel like you’re in a hole but instead of digging down further, dig upwards and pull yourself out of the darkness.” When you work alone, you don’t necessarily have a team supporting you, so be cognizant of the effect of isolation and seek avenues to alleviate that.

Also read: 4 Practical Tips On Setting Up Your Home Office

How To Market Yourself Better

When you are self-employed, you have to be a go-getter, which means you can’t always wait for jobs to land at your door. To pique the interest of potential clients, you have to create a great shop-front first. What am I getting at? Yes, you thought right! Tapping into the gig economy. Try and find avenues where you can share your profile online and you better do a fabulous job with it.

GetCraft is the largest creative vendor marketplace in SEA and is a great place to gain inroads to some of the world’s largest companies and agencies. There are also Facebook groups you can join as well as keep your website and social pages fresh with always-on content (subject to your profession). That’s the online part of it.

Offline, bank on making connections with people. Tay shares she’s got some great gigs through word-of-mouth. Connect with peers in the industry, attend events and seminars, get in the groove and be part of the conversation. Our panelists were great examples of this. All, self-confessed introverts were right there, de-mystifying this shiny world. Finally, Heartz said, “Just be nice. You never know what will come out of it”.

Behold the goal-digging anarchist

When asked about what the three most important qualities every aspiring freelancer must have, the panelists agreed on the following:

  1. Patience: Rome wasn’t built in a day. Don’t just focus on the goal, learn to enjoy the journey too.
  2. Resilience: There is no shortcut to success. You’ve got to be tenacious. Will needs to overpower skill sometimes.
  3. Craft: Continuously try to hone your craft. You need to have good lemons if you’re selling lemonade.

That’s it, folks! I hope this article inspired you to think in different ways and remember:


Shashwith Uthappa is a passionate storyteller and has worked on consumer-facing and B2B brands in the FMCG, hospitality, beauty and wellness, and financial services industries. She has led international projects end-to-end, led marketing strategies, and augmented brand growth.

Shashwith has led the global award-winning home for ideas, debate and analysis, Ogilvy.com, where her expertise in editorial and content planning has helped create multi-form thumb-stopping content for numerous brands. She loves working with creators and shares the GetCraft vision to inspire, educate and empower them. Based in Singapore, Shashwith is GetCraft’s Senior Network & Marketing Manager.

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How To Be Successful When You Are Your Own Boss

By
Shashwith
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March 12, 2020

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How To Be Successful When You Are Your Own Boss

By
Shashwith
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March 12, 2020

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