It’s a Jungle Out There: 10 Survival Tips for New and Aspiring Freelancers

Recently, I was invited by my former professor Kathy Patterson to return to St. Lawrence College in Kingston, Ontario to participate in a panel discussion consisting of several handpicked alumni. Our ‘audience’ would be a group of students from the Advertising and Marketing Communications Management (AMC) program.

First of all, it’s an incredibly humbling experience to sit with a group of seasoned pros working with some of the top names in local agencies, media companies, etc. – and talk about my life and work as a freelancer. It wasn’t all that long ago that I was on the other side of the table, and I always jump at the opportunity to give back to the college community.

The night before the panel, I tried to come up with a list of at least five things I’ve learned in the three-ish years I’ve been doing this. I ended up with a list of ten.

The event was reminiscent of speed dating, where each alumnus would sit at tables, and groups of students would rotate to each spot for about an hour and a half. I had some great discussions with students, and several of them showed a keen interest in freelancing.

By the time the panel had wrapped-up I hadn’t had a chance to speak with each group, and in the interest of time, I had to cherry-pick from the list of “tips” I had feverishly scribbled into my notebook.

As promised – here are my top ten survival tips for new and aspiring freelancers.

1. Kiss Your Comfort Zone Goodbye.

The reason why I chose to freelance in the first place, is because I want my work to help my clients, colleagues and partners succeed, not my boss. When they succeed, I succeed along with them.

After much trial and error in the stifling world of cubicles, coffee room drama and brutish micro-managers, I quickly realized that I’m what you’d call an outdoor cat. Within six to eight months of that noise, I am scratching at the windows looking for a way to escape.

I’ll level with you.  Full disclosure: freelancing is “scary AF,”

Deciding to put the land of regular paycheques, benefits, and predictability in your rear-view is one of the biggest and scariest steps you’ll make in your career – should you decide to freelance full-time. However, many of my colleagues and fellow freelancers work a full-time gig and freelance as a side-hustle, which is a completely viable option.

I had to go all-in.

If I can’t dedicate 100% of my focus and energy to a project, or a story that I’m passionate about – I end up fragmented between balancing that 9-5 job and nurturing my true love: writing. 

Whatever your particular craft or specialization is, be it sales, graphic design, web development, consulting or whatever – deciding to go fully independent means that you must do away with the conventions of those comforts – which I promise, will both motivate and drive you like you never thought possible.

It means that you need to go out there and hunt down the opportunities, leverage a professional network and build a reputation from scratch. But, if you redirect all that FEAR and repurpose it as MOTIVATION  – you will get a good sample of what success tastes like.

At the end of the day, your unique recipe for success is one that you must discover, improvise and create for yourself. Everybody’s story is different – but the beauty of it is, you get to write your own.

2. Always put your pants on!

This is unequivocally the most important rule as far as productivity goes.

To the fresh, newbie freelancer, putting in a day’s work while rocking the PJ pants might seem like a good idea at first. When your morning commute is an easy five steps from your bed to your desk – it’s easy to get just a wee bit too cozy in your newfound freedom.

So whether it’s one leg at a time or some kind of fancy-schmancy jump-rope style leap – hop into your productivity pants every morning.

Treat each and every day as a work day. Put the phone in flight-mode and place it 100 feet away from you, go to a public library for some isolation, or hit up your favourite cafe and work out in the open – if that’s your thing. You have to be your own supervisor, boss, financial, sales and customer service departments all rolled into one superhuman being.

Time to get busy soldier.

3. Don’t be obtuse to pro-bono work (for the right client that is).

First of all, whoever decided to invent the word “FREElance,” needs a crisp slap upside the head. They should have called it “Pay-lance,” or “Money-lance,” but alas, this is not the case. You may encounter potential clients that are outright flabbergasted when they realize that you expect to get paid for your hard work.

For a student trying to score some work on the side, or a recent grad building their brand – this is a real and common encounter.

But. Putting in some pro-bono hours for the right client or partner can undoubtedly pay dividends into your long-term career development. For starters, it helps build Klout – and will help you establish some collateral eye-candy for your growing portfolio.

You’ll need to use your instincts and follow your gut when it comes to deciding between who deserves your skills for free – and who’s out to take advantage of some free labour.

Not for profits or charitable organizations, to me can be classified as prospective clients that are worth contributing content to on a pro-bono basis. There are also small Mom & Pop businesses like restaurants and shops that need help with social media, design or blogging. They might not always have the cash, but might consider a trade of services that could help you reduce some of your costs.

Now.  If someone who is organizing, say, a trade-show type event with a list of 20+ confirmed vendors that are each paying over a grand for a table or booth – insists that you should spend the summer managing their social media accounts for FREE to establish experience…. your spidey sense should be tingling.

Your time has value. Don’t let anyone convince you otherwise. Sometimes, that value isn’t necessarily going to be of a monetary nature.

4. Get yourself an accountant.

If you are spreadsheet savvy and have a knack for numbers, you can likely skip this tip.

Not everybody is number savvy though. For example, you want to be sure that you are collecting and paying the correct taxes according to your income level. What expenses count as a taxable write-off and what counts as a personal purchase?

If you’re asking these or other similar questions – I would highly recommend getting a professional accountant.

You don’t want to wake up one day to learn you’re going to be audited. But it’s something that could very well happen. If you do, having a professional handling your taxation and other related functions will ensure you are up-to-date and not making expensive mistakes with your income taxes.

Of course, you could always enroll in a part-time accounting course and tackle this operation yourself. It’s really a matter of personal preference and how comfortable you are with managing this important aspect of freelancing and self-employment.

5. Don’t get too attached to your work. Don’t let things get personal.

Technically, this is two tips for the price of one, but it comes from personal experience.

Some projects or contracts might last anywhere from six months to two years. During that time you’ll be lucky enough to revel in the joys of having a regular revenue stream, and once again taste all those cozy comforts we talked about in Tip #1.

You might lose sight of why you got into freelancing – and start thinking “ooh, maybe they’ll want to offer me a full-time job and keep me!”

But, these jobs are typically temporary at-best. Soon enough you might find yourself training your replacement and handing over precious responsibilities, tools and metrics that were once yours to manage and safeguard.

This process of transition is very delicate and how you conduct yourself on the way out is going to determine whether the client leaves the door open, or barricades it once you’re out.

Learning to simply wrap-up a project, let go of the things you can no longer control – and moving on is one of the most crucial lessons when it comes to establishing and building-out your reputation.

6. Failure is the best teacher. Take pride in your work – but let go of hubris.

Directly linked to the previous tip – this is not a new concept. You’re not perfect. Nobody is. Everybody can and will make mistakes from time to time. You might make a bad call, or let your emotions dictate your actions.

How you take ownership of these inevitable mistakes – and apply the lessons learned from them is how you will continue to evolve as a professional.

You must take pride in everything you do, but know when to admit you’ve screwed up*.

Additionally, you will have to endure sometimes harsh feedback and criticisms about your work that at the moment might seem utterly bizarre. You might find yourself thinking – “this logo or blog post is perfect, what the hell is this person talking about!?”

Here’s the ticker.  It’s not all about you.

It’s about working with the client to deliver what they want – while also providing their audience with relevant content that they will engage and identify with.

There are times in these instances where you will have to push back and defend your work – but at all times you must be approaching the client-vendor relationship as a collaboration or team effort. Sometimes the client will regard you as an employee rather than the all-knowing  Jedi Knight of knowledge and wisdom that you think you are. Regardless, you must always be open to criticism and do your best to roll with the punches, while knowing when to pick your battles.

Pride is a good virtue. You should be proud of what you create.

Hubris is the poisonous level of conceit and toxic arrogance that makes one blind to their natural flaws. It is the state of mind that makes you need to compare yourself to others while silently belittling them and making them inferior in your perception. It’s the epicentre of many of the classic Greek Tragedies – and will only lead you to absolute ruin.

Eat your humble pie, and always look for ways to improve.

7. Don’t. Give. Up.

When I sat down to write this blog, I debated making this the number one survival tip. This one is heavy.

A friend of mine who does some freelance graphic design described freelance life as “hills and valleys.”  When you’re working on a killer project and slaying deadlines while raking in the cash – you’re climbing and cresting that proverbial hill. But there will be times of decline -and stretches where it seems every client either doesn’t want to pay – or wants to spend next to nothing.

Again – freelancing can be very scary and stressful.  For example, I have had significant gains in writing stories for the travel & tourism sector, but it’s a very seasonal niche to work with. During the winter months, I need to go into survival mode and start hunting down opportunities while preparing the next round of pitches for the spring.

You might have to take a part-time job.  You might have to live off Kraft Dinner or Mister Noodles and delete the word takeout from your vocabulary while adopting a more frugal way of life.

Truth is, your full-time job is trying to find the next job.  It’s a real grind. But if you keep digging, scarf those mister noodles and refuse to give up – while believing in yourself – you will find that light at the end of the tunnel.

It sounds kind of “Tony Robbins-ish,” but it’s true. Determination, persistence and hard work are your most effective tools.

8. Don’t overload yourself.

This is a good segue from the previous point. Because you’ll only get paid once the work is complete – your first instinct will be to try and take on as much work and as many clients as humanly possible.

Understandably, you want to make that cheddar – but don’t turn yourself into a cheese-string in the process.

It’s hard to figure out what your true work-capacity is until you discover it the hard way. But I can’t stress this enough – you shouldn’t ping-pong yourself between too many projects or clients. If you hit overload and burn out, you risk collapsing the foundations of what you’re trying to build in the first place.

It’s also hard to establish a work-life balance when you work from home. Remember, you have to take care of #1 because you are master and commander your proverbial ship. Don’t overestimate yourself.

  • Don’t over-promise and under-deliver.
  • Know where to draw boundaries.
  • Make time for yourself.
  • Measure your success by how happy you truly are.

Wow – I just crammed a few bonus tips into that one, I think.

9. Networking, networking, networking!

In #1, I touched on leveraging a network.  This is huge.  And let’s start by understanding that “networking” and sending random LinkedIn requests are not the same thing.  You need to roll up your sleeves, get out there and hit the pavement. Attend mixers, book information interviews with professionals, and even other freelancers.

Your fellow graduates or even freelancers working in other trades can be valuable assets for assembling a team and taking on larger projects after which you get to share the spoils.

But engaging with and establishing a network of colleagues, friends and even former employers is paramount when it comes to discovering leads and opportunities for the budding freelancer.

10. The learning never EVER ends.

When I received my second diploma from St. Lawrence College (this time in Interactive Marketing Communications), I was admittedly a bit cocky. I was an expert in my field! I knew absolutely everything about the universe, and it was time to get out there and start kicking-ass.

But, rather quickly I realized that my diploma was not, in fact, a magic ticket or an all-powerful entitlement to fortune and glory. My studies had prepared me to enter this workforce, but when weighed against the knowledge contained within the entire industry of marketing communications – social media – and digital content – I didn’t know a damn thing. 

It changes every time Facebook gets bored and updates the algorithm.

It changes whenever a new social media channel launches and becomes the latest big deal.

It changes alongside the light-speed flow of technological and social advancement.

Once you get that diploma, it’s not a ticket, but a key to the biggest classroom known to our species.

Your career.

Mind = Blown.

To Kathy Patterson and the #AMCSLC and #IMCSLC students – thanks for not only reading this blog – but inspiring me to take a literary journey through my career so far. I hope that it in some way, I’ve shared some valuable points, observations or even rules to help steer you toward a more informed career decision. Regardless of whether you decide to go lone-wolf or establish a positive working relationship with an employer I hope that this helps you in your quest to get that dream job.

Three years of freelancing is but a whisper in time. In the eyes of the grizzled veteran freelancers, I’m still a baby. But at this point in my career, I know that it’s where I want to be and how I want to roll.

And yet, I still have so much to learn.

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