10 Ways To Survive As A Freelancer Or Independent Contractor

Jun 20, 2018 9 Min Read

Over the span of around three years, I’ve worked with over 30 clients big and small, in Malaysia, the US, Philippines, and Australia. I’ve been fortunate that some of my earliest clients started off as three-month projects evolving into year-long collaborations (yay for stable income!). One even turned into a summer internship at the center of New York City!

Many people have asked me how I managed to do this while pursuing a demanding MBA which involved 40 hours per week of face time with professors and classmates (not even counting homework hours!). And I know people who have tried freelancing only to return to employment after deciding that it wasn’t for them.

Now that I’ve ventured back into the stability of a 9-to-5 job, I thought it would be a good time to reflect and share some of the things I learnt along the journey.

But first, a preface 

I don’t believe in any of these absolutes: freelancing is better, working a 9-to-5 is better, people who work an office job are risk-averse, freelancing will give you more time and freedom (you may have more flexible time, but you may be working just as many hours if not more than a corporate job!), and freelancers are commitment-averse people who cannot be tied down to one thing.

None of the above is true. There are freelance one-wo(man) agencies out there who are as professional as any other large-scale agency. And there are office warriors out there who are ‘intrapreneurs’, starting every Monday with as much purpose as someone who is his or her own boss.

Freelancing, like any other career choice, is not just a choice about the work you will do or the kind of money you can make – it is very much also a lifestyle choice. There are trade-offs I’ve made in exchange for the flexibility freelancing gave me while I focused the bulk of my time on achieving my Master’s dream.

As a freelancer, I’ve met people who are skeptical about remote work (“Can it really be productive and can you truly build connections with someone you’ve never met in person?”) and others who are envious (“It must be so nice working out of a cafe every day!”).

The point of this article is not to glamorize or criticize life as a freelancer – it is simply to share my experiences. Hopefully, as you read this you’ll come away with a useful nugget or two!

Understand that what the client is asking for is not always what they really want. 

I’ve had many quotation requests start out with asking me to write blog posts or social media posts. As I began to ask more questions and dig deeper, I found out they needed help with PR, with brand direction, or even with their entire marketing strategy. I was able to tell them, “Hey maybe you don’t really need to be churning out one new blog post a week but here are some quick ways you can have a more active online presence”.

You are the expert, so don’t just act do what you’re asked to do. Ask more questions. Understand their business goals. Explain the difference between long-term investments (SEO, branding) and short-term gains (ad campaigns, store traffic, conversions), and help them align your work with their business.

Seek to understand before being understood. 

Although you may be the expert when it comes to your field of work, always maintain respect for the client. (If you cannot respect a potential client, then politely turn down the opportunity and say “I don’t think this is a fit”, or if you want to be a bit more subtle, say “I don’t think I have the bandwidth to give this project the commitment it deserves”.)

As a creative person, I have been guilty of assuming everyone has the same marketing background and experience (“How can this person be running a company and not even know how to set up a Facebook page?”). But when I began to ask questions unrelated to the work I was doing, but about their business goals and their biggest challenges, I began to learn more about how I could really add value than just prescriptively telling them what I should do.

Build a collaborative relationship – trust is everything. 

This is all about mindset. Don’t think “I’m just a freelancer, I can’t tell my client that his or her strategy may not be working. I just need to do what the client tells me.” A good client will value your feedback. There are times clients will pay you late, or get back to you with feedback late. You could get angry and think, “Well, all clients are like that – typical.” Or, you could be understanding and patient, and also expect them to do the same for you in return.

There are times I’ve asked for deadline extensions, and the clients were completely cool with it when I explained to them I was rushing MBA deadlines. They know they’ve also been late in getting back to me with approvals as well. Some freelancers may prefer to keep their distance from clients, but my ideal working relationship is one where my client trusts me enough to say they’re running late to a call because they need to pick up their kids and where I trust them enough to ask for an extra day to work on something because I have an exam tomorrow morning.

Factor in time and money for prospecting.

As a creative person, I didn’t like to think about sales. And I never really consciously or intentionally set up “sales meetings” or “exploratory chats”. But I found myself doing it quite intuitively by having the mindset I described in point one of wanting to share and educate people about the work I do. Often, referrals would come in the form of “Hey, I have a friend who was looking for some help with his social media – maybe you could have a coffee with him and see how you can help.”

These chats would consist of half an hour to an hour of just learning about their business and learning what makes them tick as a founder. These chats have costs associated – costs for expensive Starbucks coffee, costs for travel and parking, and so on. Factor that in!

Have a list of questions prepared when you meet a potential client, and be curious. 

During my early coffee chats, I used to bring along a printed out questionnaire with questions about what were their business goals, whom they see as their biggest competitors, which brand’s voice do they most admire, and what were some style references they’d like for me to emulate. Over time, these questions became more natural to ask so while I didn’t carry them around, I would go over them in my head before every meeting.

Meanwhile, I have been on the other end of the table trying to hire a freelancer, and many have just sat there waiting for me to tell them about the job, without having a single question to ask me about why I want the work done that way. That doesn’t look good! Always ask questions – not just to show you are interested, but because you are actually curious!

Image | pixabay

READ: The 9-to-5 Job Is Dying And Here’s Why


Don’t be afraid to talk about payment terms, and be firm. 

When I first started out, I was very “green”, and so desperate to close every potential client that I did not press them enough for details about whether they would be able to pay me on time, what time of the month they usually paid clients, and making a confirmation payment mandatory before work started on the first project. Have black-and-white payment terms, but don’t just expect to read it in the fine print of a quotation – bring it up again in conversation (not in the first meeting but when you get close to talking details).

Chasing people down for money is one of the most stressful and time-sucking things you can do as a freelancer, and the best way to not do that is to learn to spot a bad paymaster. There isn’t a checklist of telltale signs, but if a person takes forever to even respond to one email (without any apology whatsoever), or if the person seems that they aren’t on top of their accounts (for instance, if they haven’t even seen your Invoice Templates or realised that you’ve sent it in).

There are times people forget, but usually, people are apologetic about it. Someone who couldn’t care less about whether you get paid does not respect your services as a freelancer, and as a result, over time you will not be able to add much value to them.

At the same time, be flexible. 

A new relationship with a client is a bit like dating. At first, it’s important to first establish the boundaries – hence my point about payment terms above. Over time, the trust builds and things don’t need to be so rigid.

If someone already has a good track record of generally paying you on time, and they need to suddenly switch gears and ask you to put that project on hold and start a new project and change the way they are being billed, be flexible about it! It may cost you a small amount in the short term but in the long run, future revenue from a happy client will far outweigh the inconvenience.

Don’t neglect your health. 

If you keep track of your steps (a MiBand is a cheap way to keep track if you don’t have a Fitbit, and new Samsung and iPhone models count your steps too) – you might realize that if you are not intentional, you can end up walking a pathetic 1,000 steps or less a day. (Ask someone who has worked remotely or as a freelancer and they will tell you this is true.) Don’t let this happen for more than a few days in a row – your work will suffer and you will exhaust yourself!  

Schedule in regular runs or hit the gym. Eat your meals on time or schedule meetings around meals – this not only is important for your health, it’s also a nice way to feel less isolated and maintain a social circle by scheduling meals with other freelancers, flexi-workers, or your clients.

Learn from disasters. 

A client disappears without paying you despite all your best efforts to contact them on every possible method available. A person you’ve worked with leaves the company and your monthly retainer is canceled. Your laptop crashes with all your work saved on it. These are not “ifs” if you are a freelancer – they are most probably “when”. So you learn from them.

You learn how to pick your clients instead of jumping at any interested party. You learn to structure your projects better so there’s long-term continuity even if company structures change. You learn to backup all your work on the cloud. And so on.

Be proactive about staying inspired.

Being a freelancer will be downright boring and mind-numbing at days. Like most other jobs, there are many days when the work feels repetitive and mundane. You might feel stuck and like you have no new ideas. I would not have survived without subscribing to newsletters like those from Jeff Goins, Henneke Duistermaat, Copyblogger, Neil Patel, and other practitioners in the field. Being a freelancer requires a truckload of motivation and inspiration – you need to be reaching for outside sources. It will not only keep you inspired to know what others are doing – it will keep you relevant.

This article first appeared on LinkedIn.

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Crystal is passionate about all things marketing, storytelling, and communications. She has over 10 years of experience in inbound/outbound marketing, paid/earned media, and offline/online activation, specialising in marketing team/ops management, social media marketing, and copywriting.

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