Do you love chasing invoices and making sure every single penny you invoice is collected on time? Do you see invoicing as a valuable business activity or as something else?
Written by:
Justin Walton
Date:
January 17, 2025
Ask any small business owner what they love most about their work, and you’ll hear about their passion for their craft, their customers, or the freedom of being their own boss. What you probably won’t hear is:
"I love chasing invoices and making sure every penny owed to me is collected on time."
For some, sending invoices and following up on payments feels like a necessary evil; an admin task that takes time away from more meaningful work.
For others, it’s something they actively avoid, whether from discomfort, fear of seeming “too pushy,” or simply because money isn’t their main driver.
But not everyone struggles with this. Some business owners are highly disciplined about invoicing and cash collection. They set clear payment terms, follow up rigorously, and maintain a steady cash flow. So, does that mean they have nothing to gain from examining their money mindset?
Not necessarily.
If you regularly delay sending invoices, fail to follow up on overdue payments, or undercharge for your work, it’s worth asking:
The risk of this mindset is clear: inconsistent cash flow can create financial stress, limit your growth, and even affect your confidence in running your business.
If this is you, then consider how you can shift your perspective and build a system that supports you, without forcing you to become someone you’re not.
For those who have strong financial habits, there’s still an opportunity to take things further:
Sometimes, a highly disciplined approach to money can create blind spots of its own. Like being overly cautious with investment, missing opportunities for strategic growth, or becoming so focused on numbers that other priorities, like wellbeing or work-life balance, get overlooked.
If this is you, remember that there's always room to optimise what is already working.
Whether you struggle with billing or have mastered your cashflow, your relationship with money shapes your business in ways you might not even realise. The real question isn’t just whether you’re getting paid—it’s whether your financial habits are truly supporting the business and life you want to create.
Curious about what that could look like for you? Let’s start the conversation.
Justin Walton is an Executive and Financial Coach, and Consultant working in Essex and London. He writes regularly on financial well-being and brings his lived experience and professional expertise together to benefit clients and partners.
Don’t hold onto what is holding you back.
I offer a range of executive and financial coaching and consultancy solutions for business leaders and their teams and can tailor my services to help you meet your goals.
