A guide to selling without the cringe

Illustration by
Words by

I spent the first five years of my freelance career in, ‘I’ll take anything that comes my way’ hustle mode. My schedule, bursting with work, I’d landed on the freelancer sweet spot – a steady flow of clients, without having to sell myself. Phew! Because really, my body (and soul) cringed at the thought of selling.

I know what you’re thinking… why would you need to do any selling when you’re busy already? Well, therein lies the conundrum. I was busy doing work that I didn’t seek out, which inadvertently shaped my business. And if I’m being honest, probably only a quarter of that work were projects I would have wanted to do enough that I would have actively chased them.

My version of freelance ‘success’ morphed from just matching my full-time salary, into one that strokes my income goals, lets me live out my dream lifestyle, and fill my days with the work I’m passionate about. Because I’m constantly changing, my interests do too. Selling isn’t something to avoid but rather, a compass that points my business in the most fulfilling, aligned direction.

It’s my business, after all. In switching from inbound to outbound thinking, here’s what I’ve discovered.

Ask yourself: ‘What type of work do I really want to do?’

How often do you reflect on your business and dissect the projects and clients you love, and those you don’t? As freelancers, we’re so busy wearing so many hats, that interrogating what’s making us satisfied (and what isn’t) just doesn’t get prioritised. Well, this is your permission slip to spend a few hours dreaming up your ideal freelance business. From that empowered stance, you’ll be able to clearly see what’s missing in your roster of work.

Give ‘selling’ a new meaning

If you’re a creative, an introvert or, dare I say, a member of the large portion population who doesn’t like selling, reform your relationship with words. Change your language and never use that word again, if it helps. To soften the process, you could call it ‘relationship building’, ‘pitching’ or even ‘dream client chasing.’ Have fun with it. You might just find these are the sessions you look forward to the most (I certainly do).

Block out the time

Raise your hand if, even with a goal and the best of intentions, you went back to your old ways. You said yes to that client, even when your gut was telling you ‘no, it’s pitching day.’ That people pleasing, feast or famine conditioning creeps back in if you don’t tame it. Minimise any emotions getting in the way and refer to the holiness that is your schedule. Today’s my pitching day! So no, lovely client, I’ll have to that to you tomorrow.

Work out how much time you’re comfortable carving out of your schedule for outbound ideal-client-seeking, then honour that time like it’s your firstborn child’s. A good place to start is one day a week.

Just do it! 

Borrowing from Nike, you just have to. Start! It’ll feel awkward and may even seem a waste of time but it’s important to persist. If you have a coach or mentor you can lean on to keep you accountable and share wins, this helps. Each time you get a new dream project or client on board, send a celebratory GIF to your coach.

Now you’re in dream client, ‘look at this work I just did’ territory, you’re more likely to share it with your network. This positively reinforces your new selling skill, which inspires you to do it more.

Create processes and refine. Always refine.

Keep track of the people and companies you reach out to. A simple spreadsheet will suffice, as well as the Notes app on your phone to capture any spontaneous ideas. You’ll likely be speaking to more people than ever before, so record any important information to help make your life easier (especially when you do your follow-up emails).

Speaking of follow ups, there’s something I want you to write down and keep close to you: Rejection is part of selling my services. It’s not personal. Repeat that three times.

When you switch to an outbound selling approach, you’re opening yourself up to all kinds of responses and situations you can’t control. People will say yes, no, maybe, not right now, and thanks but no thanks. This is just how selling goes. And it makes the “yes!” replies all the more exciting.

The good news is, the more you do it the better (and more creative) you’ll get with your approach.

Let that first ‘high’ carry the momentum

Just. You. Wait. That first “yes, we’d love to work with you” from Ms Dream Client will dissolve any last icky associations you have with selling. When you experience the thrill of dreaming up, seeking out and securing work that really matters, you’ll learn anything is possible. And you don’t have to rely on your website or your network for work to come to you. It’s here, with a dash of adrenalin, that selling (self-promoting, engaging or whatever you want to call it), gets really fun.

Your schedule will start to fill up with those dream clients. Your days feel more meaningful and you rarely fight against that little ‘I don’t want to do this’ voice. And it shows in the quality of your work, that this is, unquestionably, your beat.

You didn’t become a freelancer to take instruction from 5-10 micro bosses, did you? You freelance because you’re bold. You don’t subscribe to the narrative that work is a drag. It’s joyous, fulfilling, and ever evolving like you are. Your freelance business is a reflection of your interests, passions, and curiosities. That’s exactly why people say yes to you… because there’s no one better to do that work.

You deserve this and truthfully, so do your dream clients. And it all starts with selling.

You may also enjoy

How to onboard new clients as a freelancer

If you’re signing new clients, that’s fantastic. But the first and second steps of the relationship are vital to keeping things positive. Having a consistent onboarding system can get your started in the right place.

How to Switch Off

When you’re a freelancer, that means you can literally aspend all of your time working. How do you avoid that?