Why 'winging it' is costing your small business more than you think...
Nov 15, 2025
If you've ever said 'I'll sort that later', your in good company!
Most self-employed people and small business owners I meet didn't start their business because they love cashflow forecasts, onboarding processes, or compliance checklist. You started because you're good at what you do, whether that's plumbing, photography, copywriting, coaching, trades, treatments, you name it...
The problem is, 'winging it' behind the scenes quietly eats away at your time, money, and sanity. And it often does it so slowly, you don't notice...until something goes wrong.
The hidden costs of not having simple systems
When I talk about 'systems', I don't mean expensive software, or a 200 page operations manual. I mean the basics...
- how you bring new clients in
- how you deliver your service consistently
- how you get paid
- how you keep on top of your legal and financial responsibilities
When those things live only in your head, a few things tend to happen...
- money slips through the cracks. Invoices not sent, late payments are not chased, quotes are forgotten about.
- work takes longer than it should because you're reinventing the wheel every time.
- clients get mixed experiences. One gets gold standard communication, another gets radio silence!
- compliance becomes a last minute panic. Tax returns, contracts, policies, all done under pressure.
Individually, these might feel like 'little niggles'. Together, they are the difference between a business that feels calm and one that keeps you up at night.
Being good at your trade vs running a business
Here's the bit nobody really tells you...being brilliant at your trade is NOT the same as being good at running a business. There I said it!
You can be the best electrician, beauty therapist, consultant, or designer in the world and still undercharge, overwork, miss deadlines, lose track of who owes you what.
That doesn't make you a bad business owner. It just means you were never taught the business side properly. Most people aren't.
What I see over and over again, is capable, hardworking people feeling like they're 'failing' because their back-end is messy. In reality, they just need some simple structure and a bit of support.
Small changes, big impact
In my work with small businesses (and my day job in a busy law firm), I've seen how one small change can make a huge difference.
Things like
- a standard way to bring on a new client, so you're not chasing forms, ID or information for weeks
- a weekly 'money hour', where you send invoices, check payments, and follow up on anything outstanding
- a simple checklist for each service, so you don't miss steps, even on your busiest days
These aren't glamourous. You can't really show them off on Instagram! But they are the things that free up your headspace so you can actually enjoy your work (and your evenings!).
Why 'I'll sort it later' is so expensive.
'I'll sort it later' usually means...
- you spend more time fixing problems than preventing them
- you miss opportunities because you're too busy firefighting
- you feel guilty when you're not working, because there's always something you've forgotten
And that has a cost...emotionally, financially, and sometimes legally.
The good news is that you don't need to turn into corporate robot to fix it. You just need a few clear, repeatable ways of doing things that work for you and your business.
How Cari on Regardless fits in
Cari on Regardless exists for exactly this reason. I'm building a subscription based space for self-employed people and small business owners who are brilliant at what they do, but tired of winging it behind the scenes. Think...
- practical templates you can actually use
- straight talking workshops
- training videos that explain the 'boring but important' stuff in normal language
No jargon. No judgement. Just the support you should have had when you started.
If any of this feels uncomfortably familiar, you are not alone and you are not broken. You're just ready for your business to grow up a bit behind the scenes.
For now, you're early. I'm still building everything out and piloting it with real businesses. But if you're reading this and thinking 'Yes that's me', you're exactly who I'm creating Cari on Regardless for.