Getting comfortable with bothering people

A life lesson I'm learning literally everyday

Hi, if you’re new here, I’m Ellen, and I’m in the early days on my freelance journey.

I left my full-time job in March for greener, more flexible pastures, and a violent urge to be able to go to hot yoga at 11am on a Monday morning if I so desire.

For the most part, it’s going well. And in hindsight, I shouldn’t be surprised by that. I was well prepared beforehand, I’m not afraid of hard work, I’m alright at my job, blah, blah, blah.

But, before I officially made the leap, there was a tiny little gremlin inside me that would wait until I couldn’t sleep at 3am and whisper, “you have everything to make this a success, apart from the most important thing — the networking skills” in my ear.

Because I hate the thought of bothering people. In any capacity. And that’s not a noble, nice thing, before you get any ideas. It’s less about not wanting to put people out, and more about wanting to make sure people aren’t annoyed at me.

That, and a pathological urge to be perceived as polite and self-sufficient.

If anything, it’s quite selfish. But anyway, the point is, I’m a neurotic little introvert masquerading as an outgoing, confident people person.

So, when every piece freelancing advice told me to “use my network”, “reach out to people you’ve worked with across your career”, and “don’t be afraid to ask for quotes, testimonials, referrals”, I thought “this isn’t going to work.”

And it’s not like the network doesn’t exist. I’ve been in the marketing industry for around 9 years, if we’re including university and internships. I’ve worked with a lot of handy-to-know people across agency and in-house, I liked them, and I’d say most of them liked me?? But sliding into the inbox of someone you haven’t spoken to for a while and asking them to listen to your elevator pitch felt at best cheeky, and at worst soul destroying.

I really, really, wanted freelancing to work, though.

There was no way around it. I was doing it. So, I’d just have to… get good at it. Or at least get okay at it.

I started small. I planned to message an old agency colleague I knew was freelancing full-time. He’d recently written a LinkedIn article about his own freelancing journey — and the importance of leaning on your network.

I thought about my draft for a ridiculous amount of time before I sent it. How would I approach it? Was it cheeky? Would he think I was a bit of a dick for only messaging him when I wanted something? I didn’t want it to sound like I thought I was entitled to his advice.

Then, something wonderful happened. I actually got so sick of own thoughts, I had an epiphany. And that epiphany was, “ohhhhmygod get over yourself”.

I settled on just… saying it like it is. I typed out a message in less than a minute.

Hey, hope you’re doing well! I know you’re freelancing full time now, and I’m about to take the plunge myself. You have absolutely no idea how helpful your article has been! Any chance you’d be up for a chat? I’d owe you a drink! Thanks :) x

We had a zoom call arranged within the hour. And it was unbelievably helpful.

It was also actually just really nice to catch up.

I left that call with some great advice, a few more contacts, and a promise to stay in touch/pass work to each other whenever we can. In other words, it was so much simpler than I had made it out to be.

So simple, in fact, I started thinking about how much time I’d wasted over the years worrying about what people — who genuinely won’t think about me AT ALL — might think of me.

I told myself, no more.

You’re a grown up, and you’re setting up your own business. You’re not going to fail because you’re too scared to message people you know telling them you’re setting up your own business??? That’s an unhinged and embarrassing reason to fail.

That first call had really helped with all this, though. It made me realise it didn’t have to be promotional, or salesy, or beggy. It would be nice to catch up with these people, regardless of what came from it, and I think… I think that just might be the secret to good networking.

I made a list of people I had worked with or connected with over the years.

The ones I’m still close to/in touch with regularly each got a WhatsApp that basically read “I’m going freelance by the way, you have to promise to help me please, hahaha”.

People I always got on with, but hadn’t spoken to super recently got a version of my initial draft, “Hiii! I hope you’re doing good! Very out of the blue message but I have news (and I’m basically using it as an excuse to catch up with all my old friends). I’m going freelance, so obviously if you know anyone in need of content writing, I’d looove it if you’d consider me! Aside from that though, fancy a catch up soon?”

People I knew mainly in a professional capacity got a much more polished version politely asking if they’d consider giving me a quote or testimonial but assuring them there was no pressure.

I never want to be the person that’s just firing off promotional messages to people they barely know, but I’m fairly confident I won’t be.

It became less about asking for favours and more about genuinely wanting to catch up, chat about the industry, and use that catch up to network appropriately, if it was relevant.

Since my epiphany, I’ve had coffee with a former boss, arranged lunch and drinks with a colleague from an old internship, set up a group chat with some girls I started out agency-side with, chatted on zoom with another old boss, caught up with countless work friends I haven’t spoken to for a while, received some amazing advice, accepted an invitation to a networking event for freelancers in my town, and joined two different online communities based on various recommendations.

Some of these conversations paid off in actual clients, or leads, or advice, or testimonials… and some just proved really nice and fun to do. But they were all absolutely worth doing — rather, they all made me feel a little bit warm inside.

If you’re a freelancer, obviously, this is the way forward. But beyond that, it’s actually been really helpful personally, too. In the past, I wrote about feeling lonely, or more specifically feeling like everyone else is busier than I am. But since I’ve taken on this approach, I feel like one of those busy people. Or at least, I feel more like them.

So, I’m telling you, if you are the person lying awake at 3am listening to the gremlin that tells you you’re bothering people, tell it to shut up.

You’re not bothering them. You’re interacting with them. You can send the message. People won’t reach out to you if you don’t reach out to them. And… You’ll probably be super glad you did in the end.

---

A small heads up

As of next week, I’ll be launching a brand new paid series, Freelancer Diaries. If you’re a free subscriber and you want to stay a free subscriber, great! Nothing is going to change for you, I’ll still be putting out all my usual content — AI ramblings, life lessons, rants about Hinge, etc etc.

But, if you’re new to a freelancing journey (like me), looking for practical freelancing lessons from someone who is literally going through it (and learning the highs and lows firsthand), or just curious about making your full-time living as a writer, I’d love love love if you’d consider becoming a paid subscriber. I hope it’s helpful, but more than that I hope it’s a relatable, no-nonsense, no jargon, real life look at freelancing.

Posts will be coming out weekly, and the first few are already lined up:

• Freelancer Diaries: How I found my first three clients

• Freelancer Diaries: How I set my rates

• Freelancer Diaries: How I stay sane WFH in a team of one

---

About The Content Girl

Opinions, insights, and the occasional marketing musing from a professional Content Writer giving writing in her own voice a go. You can expect:

• Commentary on pop-culture/regular culture and the like

• Insights/tips/information around professional Content Writing/Marketing and freelancing

• Personal essays (I’ll try to make these not insufferable, I swear)

• Book reviews, recommendations, and roundups

• The odd piece of flash fiction