The Shame of Asking for Help and the Hidden Cost of a Chaotic Business Backend

June 15, 20267 min read

A chaotic backend can lead to founder burnout and a business that depends entirely on you. Here's why asking for help changes everything.

Why Entrepreneurs Resist Hiring Systems Support

Recently in our business mastermind my coach posed a question about what were the biggest reasons people resisted hiring someone to help them with their systems.

There was the standard... I didn’t think I needed it, I didn’t understand the value, I didn’t have the money, it didn’t seem like a priority... all essentially saying... I couldn’t justify investing in it.

But once she dug a little deeper there was another common thread.

“I was too embarrassed for anyone to see the way I was running things.”

So many business owners pride themselves in being really good at what they do, and rightfully so.

They’re highly qualified, highly skilled, have sooo much value to offer. They’re great at performing the role of successful business owner.

They have the branding, the aesthetics nailed, the content going out, offers that are mostly working.

So when it comes to looking at the chaos in their backend, it challenges that. And to have someone come and look at the mess behind the scenes is confronting.

The Cost of a Chaotic Business Backend

I’ve seen a lot in my time doing this work:

  • email lists handed to me on sheets of paper

  • google drives with no order

  • courses and programs living across multiple different platforms

  • everything being done manually when all it would take is a click of a button to automate the whole process

  • pages going out without being linked to the right places

  • broken links all over the place

  • communications being missed, frustrated emails or messages from clients that went unanswered for months

And the result of a chaotic backend is usually:

  • dissatisfied clients

  • low retention and repeat clients so the business is constantly depending on finding ways to bring new people in

  • poor delivery because everything is dependent on the founder to show up

  • a burnt out business owner

  • everything stops when the business owner is sick, something unexpected happens

  • holidays become impossible

  • life gets missed... relationships strain, personal satisfaction fades

When Your Business Starts to Feel Like a Cage

The business that was once the source of great liberation starts to feel like chains.

But this is the whole reason why people hire me. Because I handle the systems things that don’t come naturally to them.

And that’s nothing to be ashamed of. I’ve seen enough backends to know the shame is always worse than the mess.

We all have strengths and we all have weaknesses. It’s the same reason I’ve hired a business coach, particularly one who has a background in money, trading, and finance, plus psychology.

Because I recognise this is a blindspot for me and I’m tired of looping in my own patterns.

It took me months of looping to finally commit though.

I spoke to my coach in July last year. She said I needed to get clear on what business I actually wanted help with (I was deciding whether I still wanted to do done for you services or lean into something more creative). I took that to mean she didn’t want to work with me.

Instead of just leaning in and asking more questions... I spiralled for 9 more months. I was ashamed that I couldn’t just “get it together”.

I wanted to figure it out on my own. Make sure I had the perfect business model for her.

I wanted to become the person she would want to work with, when she had already said she was holding a spot for me and wanted to work with me.

It’s like the person who cleans their house before their cleaner comes over. We know we’re hiring that person for a specific thing, but then we’re too embarrassed to let them actually see our mess.

I waaayyy overcomplicated and spiralled over one little comment for monthssss.

And then went into complete avoidance. Hiring other mentors. Convincing myself I just needed to live more. Create more. Have more fun. Be present in life.

Everything except show up for my business in the way I knew I needed to.

Why Shame Keeps Founders Stuck

I was too embarrassed to just admit that after all that time I still couldn’t figure out what I really wanted to do.

The thing I really needed support with was clarity on how to present my offers. Because I LOVE the work. There’s never been a question about that. I am a nerdy, witchy, tech girl through and through.

What I felt frustrated by was that I seemed to keep attracting clients that didnt want to pay me. I didn’t know how to stop undercharging and overgiving. I didn’t know how to shift my message to attract people who would actually value me.

But instead of just saying that.. I went off and tried to do it on my own. I tried to create the success before hiring the coach, even though I knew the coach would support me to create the results I was after.

I let it get so much worse, before I finally said, heyyyy I’m tired of trying to do this alone, and asked for help.

In a few months of working together, sooo much has shifted.

I have clear offers. Clients who see the value in what I offer and don’t blink twice at the rates. Friends who said they would actually pay me more .

I’m holding myself differently, not making myself available for everything like I used to, so people are responding to that energy.

Things that would’ve made me spiral a few months ago, no longer are, because I have someone reflecting stats and data back to me. Not falling for my emotional chaos.

Reflecting on this journey, I can see how much time I wasted trying to figure things out alone. Telling myself I should know this stuff.

I was too embarrassed to ask for help because I’ve been in this world long enough, I felt like I should be able to just know what to do.

When all along, it was the attachment to needing to figure it out all by myself that was keeping me blocked.

People get way too attached to needing to look like they’ve got it all together.. They refuse to admit that what they’re doing is keeping them stuck.

Meanwhile, this avoidance of their backend is exactly what’s creating a business that cannot function without them.

Creating a Business That Supports You Back

If you go to bed at night with a mind racing about all the things you have to do the following day.

If you’re constantly trying to remember if you messaged all the people back, if you sent all the links, if the money has been collected yet...

If you cannot take a few days off without everything coming to a halt.. have you actually created a business or a cage?

If you feel guilty because your family, friends, partner, or other important relationships are telling you you’re always working, and then you can’t seem to switch your mind off when you’re “off”, what message is that sending?

If money coming in is totally dependent on you being “on” and “feeling it”... then are you actually running a business?

At some point you have to take a look at what’s going on and ask if what you’re creating is sustainable?

Could you keep operating this way for years to come? Or would it all fall apart and get way too much to hold at some point?

If you’ve been recoiling in embarrassment even just reading this, feeling tightness because you’re so called out... then maybe it’s time to admit you’re ready to let someone else take a look at that part of your business.

We don’t shame ourselves for hiring an accountant because we’re not accountants.

We don’t judge ourselves for hiring a designer because we’re not designers.

We don’t think we’re failures because we need a plumber, a lawyer, or a mechanic.

So why are we so hard on ourselves when it comes to asking for support in our businesses?

Why do we expect ourselves to be the strategist, marketer, salesperson, tech expert, systems manager, bookkeeper, and customer service team all rolled into one?

Just like all those other areas of life are alleviated with support, a chaotic business backend is fixable too.

I’ve seen enough of them to know the embarrassment about it is almost always worse than the actual mess.

You don’t need to get everything together before asking for help. That’s the whole reason my services exist.

The business you’re trying so hard to hold together on your own might just be one diagnostic away from becoming something that actually supports you back.

Jade Scarfone

Jade Scarfone

Jade Scarfone is a tech witch and digital creatrix here to help visionary leaders turn messy businesses into profitable ecosystems.

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