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5 lessons from my first year of freelance writing

Recently, I celebrated my 1-year anniversary of freelancing. My biggest struggle hasn’t been with the book-keeping or finding clients, but with the mindset that comes with the hustle.

What’s appropriate? What’s OK? What should I do here? At times, I can be neurotic and socially awkward, so I often ended up worrying myself into a corner. Well, after 12 months, I think I’ve got the hang of those worries.

If I could go back in time and mentor my year-ago self, just starting out on her freelance writing journey, this is what I would say:

1. Worry if you want, but don’t let it dictate your day.

The first year is where you work your arse off to lay foundations that will carry you into subsequent years. There’s a lot of work to do and frankly, worrying won’t get it done.

Now, this doesn’t mean “don’t worry at all”. And it certainly doesn’t mean “take it easy”. It means using your meta-cognition and mindfulness to catch yourself before you spiral into a worry loop. By all means, worry if you want, but do that while getting your work done. Don’t let it be the reason you sit sulking in the corner for hours.

Nothing staves off the rampant emotions and crippling anxiety like focus and flow. If you’re the kind of person who can switch off your emotions, use that talent to buy yourself some time. It may only be a short time, but if it’s time you can use productively, then hey, it’s good enough.

This cold, hard pragmatism — while probably not the reason you decided to start freelancing — will help until you grow accustomed to the lifestyle. Just put your head down and do your work.

Also, narrow down the stuff you think you need to worry about, eg:

  • Instead of trying to appeal to everyone in the world from the get-go, pick a handful of specific niches, industries or clients and see how they feel.
  • Don’t take a million years creating a giant website with all the things. That’s way too much work if you haven’t got cashflow yet. Start out with a simple one-pager telling potential clients exactly what they need to know before they can hire you (that yes, you’re a professional and yes, you can write).

2. Be your own client too.

Quiet days aren’t a sign you’re failing — but they bloody well feel that way when you’re not used to them. After going stir-crazy in the quiet for a few months, I realised what blessing it was to have days where I wasn’t swamped with client work.

Those were the days I got to be my own client; the days I had to fight tooth-and-nail for when I was employed full-time. Here are things you could be spending your quiet days on.

  • Develop your business. Pitch to new clients. Research your target market. Work on your website (if you still want all the things).
  • Study your craft. Learn to produce better quality stuff. Get more familiar with your niche.
  • Brush up on your soft skills, like communication, customer service and assertiveness.
  • Keep house — admin, bookkeeping, filing, organising, stock up the pantry and freezer for busy days.
  • Figure out what to do with your life. You have the time and space for it now that you’re not workin’ for the man.
  • Work on personal projects. They may lead you to things that grow your business, or help your life and career goals shift toward your passions.
  • Just rest. Breathe in. :)

3. Establish and respect your professional boundaries.

For work to be truly fulfilling, it either needs to align with your values or pay well enough to fill the giant hole in your soul. Let’s assume your first year will lean towards the value side of this spectrum.

In my first quarter, I got invited to pitch to an online betting client. It sounded like easy money, but I couldn’t shake the idea that if I won the work, I’d be supporting an industry that ruins so many lives and families. Sure, maybe reality differs from my perception, but I didn’t want to gamble on finding out. So I declined. I imagine a writer less exposed to the dark side of betting made a pretty penny with no need to feel guilty. Yet, I don’t feel I missed out.

Boundaries are subjective, different for everyone. And I think that’s OK. As a creative professional, you do your best work when you’re invested in the outcome. As a freelancer, you can pick the outcomes you can get behind. So do that.

Make a ‘definitely not’ list of clients and industries — it’ll save you having to umm and ahh and go through the decision-making rigamarole every time a job comes up. This frees up your mind to make smarter choices (and negotiate better) when your ‘definitely maybe’ and ‘definitely yes’ opportunities appear.

4. Drop bad clients asap.

What makes a bad client? If you polled all the creative professionals you know, you’ll probably notice similar answers emerge, and they’ll probably bear resemblance to what’s listed here:

Late paying/non-paying. Poor communication. Lack of respect for time. Lack of respect for sign-off. Unclear briefs. Undermine the work. Changing objectives mid-project. Contract dodging. IP theft. Unreasonable terms. Unprofessional behaviour. Inappropriate behaviour. Harassment.

In isolation, some of these traits may be taken in good faith. For example, you might have a late paying client who you still love working with because they’re great on all the other factors and their industry aligns with your values. Or maybe a client talks to you salaciously, but it’s OK because you have a long, friendly history of mutual trust and sometimes you make rude jokes at them too. Contracts and interpersonal relationships can be so colourful and varied that any of these ‘bad’ traits can still be ‘good’ if the circumstances permit.

But I’m talking about when those circumstances don’t permit. You’ll know it in your gut when you’re dealing with a bad client. On top of seeing the traits listed above, you also dread working for them. Your shoulders tense up when they send you an email. You cringe if it’s their name on the caller ID. They’re glib about you charging what you’re worth. You feel either way too high or way too low after any dealings with them.

Sound familiar? Drop them. It’s not that they’re objectively bad, just bad for you. It may be no one’s fault you guys are incompatible, but the blood, sweat and tears you’re sinking into their account still won’t be worth what you’re making back. And knowing what we’re like when we have to deal with jerks, you’ll still be paying for it long after you stop working for them.

There is, of course, the very real possibility you’re the jerk. But I’m assuming you’ll introspect the shit out of yourself before making any bold moves.

5. Network.

I hated networking. Until I read The Non-Sleazy Guide to Successful Networking in Facebook Groups and realised networking isn’t bad, I’d just never seen many good examples of it. I mean, the good examples were probably there, but maybe they were obscured by the many bad examples who milled around one-upping each other’s business cards.

Freelancing is a lonely life. Working by yourself for too long puts you far away from benchmarks and social support. And sometimes you may feel so overwhelmed that you don’t even know what to ask to pull yourself out of it. Here’s where networking — or at least building healthy individual professional relationships — can help.

You find mentors. People more experienced than you have walked where you’re walking, and may even tell you what you need to know before you figure out how to phrase the question. And they’re happy to help because they know what it’s like to be new and scared. Your relationships with these people reassure you that your next step won’t be through a hole in the ice. And they show you, by example, how to be a good mentor to someone else.

You build confidence by mentoring others. In helping someone less experienced, you’re forced to frame your knowledge in a logical, explainable way. If you’ve ever done this before, you’ll know what a huge confidence booster it can be, and how much closure it brings to old chapters in your freelancing story. Sometimes this confidence boost can be just what you need to lift your game in your own field. All while doing a kindness for someone else.

You make friends. In my view, competition is silly when you’re a solo freelancer. After all, you can only handle so much work at once before you go mad. If you can refer good work and clients to fellow professionals you trust, you’ve not only done something good for a peer, but for your potential client too. Maintaining good professional friendships is a win-win-win. Not to mention it’s nice to share those wins with someone who understands.

Pick your friends and networks wisely. Give and take equally. And most importantly, remember to have fun. That’s why you made this career move in the first place.

Sandy writes here and here. Please if you liked this post!

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