Why can't I ask for help?

A little note before we begin…

If you’ve just found your way to my Substack, welcome! If you’re having a moment of déjà vu, no, you’re not seeing things.

The behind-the-scenes reality check

There’s one thing that’s annoyed me about launching this Substack: I don’t have a bank of content sitting here yet. So when I point people this way, I’m painfully aware they land on a page that’s giving… crickets (not the vibe I was going for tbh)

So I’ve decided to fix that the honest way. Over the next week or so I’m uploading some of my favourite editions of A Letter to My Readers. It’s my monthly series where I basically use this newsletter as free therapy and take you behind the scenes of the highs, the lows, the wins and the losses of working for myself.

If you’ve never read these, you’re about to see them pop up (enjoy!) If you’ve read them before, then no, you’re not going mad, they’re repeat editions. I just want to bulk this place out a little so it feels like the home it’s going to be.

Right, let’s get on with it. 🖤

My resistance to asking for help & why I need to get over myself.

You might remember that in the last edition of Letters to My Readers I casually mentioned that I was starting therapy. Or counselling. Or… something in between? (Honestly, I still don’t really know what the official label is, and that’s probably a question I should ask my therapist/ counsellor at some point?!)

Either way, I’ve been talking to someone every single week and pouring my heart out, which means one thing, these monthly letters are about to get deeper.

If you thought I was already exposing my inner thoughts before, buckle up, because now they’re all right there at the front of my mind, overflowing and ready to be shared.

So, welcome to February. How are we feeling? Have you already smashed all your goals for the year? No? Same.

January is always a heads down month for me. I usually have very few events, I’m coming off the back of a hectic end to the year, and the non content side of my business takes centre stage. You know the stuff, meetings, PowerPoint decks, onboarding strategies, migrating systems, migrating email platforms… all the unsexy but absolutely essential work that keeps getting pushed to the bottom of the list during Q4.

This happens every year, but this January has felt different.

It’s the first one I’ve experienced with my own social media marketing agency, and suddenly none of these backend tasks feel small anymore. This time last year, I had one full time employee and a handful of freelancers. Fast forward to now and I have three full time employees, a lot of freelancers, and I’m in the process of hiring two more full time team members (by the way, if you want to hear about those roles, make sure you’re following me on LinkedIn).

All of that to say, every decision feels bigger, significantly more expensive, and honestly, a lot scarier.

What should be comforting is the fact that I’m not doing this alone anymore. I’ve got an incredible team around me and some very experienced, very high level people supporting me too, which feels like a good moment to properly share something I’ve alluded to in vlogs but haven’t really spoken about in detail.

I’ve been working with the very talented Nicole Finnan, a commercial executive from the screen industry who’s produced shows like Becoming Jane and Peaky Blinders (my fellow Brits will understand how major that is).

We met at an event and have been working together for a few months now, and she’s not only brilliant in her own right, but she’s also connected me with an incredible network of people who specialise in areas of business I simply don’t know enough about.

And yet, despite having all of this support, I’ve caught myself time and time again not using it.

Why am I like this?

A few therapy sessions in, I’ve realised that I seem to have an issue with asking for help. Not because of pride, it’s not that I think asking for help makes me lesser than, it’s more that I’m so used to operating solo that it genuinely doesn’t cross my mind to ask if there’s a better or more efficient way of doing something.

You might remember I went on a workcation last year, which I credit as a huge turning point in my business. The reason it was so impactful was because I was surrounded by incredible female entrepreneurs in an environment where asking questions was the entire point. We were encouraged to ask, so I did. I asked loads. I left with pages of notes and insights that massively fast tracked my journey.

The funny part is that I still have access to all of those women. We still talk. And on top of that, I now have access to an even bigger network through the connections I’ve made since.

And yet, I’m still making the mistake of not leaning into it.

We talk a lot about how lonely entrepreneurship and content creation can be, but I’ve realised that surrounding yourself with people who get it isn’t enough if you’re not actually willing to lean into those relationships.

Even though these letters are basically me using you as a free therapist alongside the one I pay handsomely for, I can’t help but think that a lot of you reading this are making the same mistake.

Case in point, I have a membership called The Collective with hundreds of creators inside it, and we have a Discord where you can ask me and my team anything about content creation or entrepreneurship. And I know those questions exist because I see them in my comments every single day, and yet the resource designed for exactly that is right there, waiting to be used.

Lately, I’ve been wondering if there’s something else at play here, which I’m calling the curse of the value led creator.

I talk a lot about sharing value online, but after five years of doing that consistently, I’ve realised I struggle with interactions that don’t involve me giving something, advice, motivation, a resource, something useful.

That discomfort becomes even stronger in working relationships. Being given an opportunity or an introduction without knowing how to return the favour makes me deeply uncomfortable. It’s almost as if asking for help feels wrong unless I have something equally valuable to give back.

So how do I fix this? Honestly, I don’t know yet.

Maybe I just need to get over myself. Sometimes the solution really is that simple.

What I do know is that if I want to achieve what I’m trying to build with this agency, I don’t know enough to do it alone. I need the people around me, and I need to actually use the network I’ve spent years building.

So that’s my challenge for the next few months, to lean in more, to ask better questions, and to stop trying to do everything by myself. And I want you to feel challenged to do the same.

We all love AI, but sometimes lived experience is what gets you over your next hurdle, and that can only come from real people.

Let me know if this resonated with you, I have a feeling it might.

Thanks for reading, and I’ll be back to spill my heart out again soon.

Jade 🖤