Being an entrepreneur is brilliant, right? You’re your own boss, you set your own schedule, and you get to work on something you’re passionate about. But let’s be real—there are always those tasks that feel like a slog. You know the ones: bookkeeping, sales prospecting, filing taxes… basically, the stuff that doesn’t excite you but is absolutely essential if you want to stay in business.
So, how do you tackle these terrible tasks without them completely draining your energy or getting endlessly pushed to the bottom of your to-do list? Andrew and Jon recently sat down to discuss exactly this, and their insights are gold. Here’s a breakdown of their best strategies:
The Power of Habit: Just Get Started
Andrew kicked things off by admitting that he used to dread sales prospecting. The idea of cold emails and follow-ups gave him that same sinking feeling we all get when we realise we haven’t done our taxes yet. But, over time, something shifted.
He forced himself to build a habit around it. Every day, before allowing himself to do something he enjoyed, he’d knock out a set number of sales emails. At first, it was a struggle. But after a while, it became just another part of the day.
Jon agreed, explaining that the thought of doing a task is often worse than actually doing it. It’s like going to the gym—dragging yourself there is the hard part, but once you start, it’s not so bad.
So, if there’s a task you hate, make it a routine. Set a specific time for it and stick to it. Whether it’s first thing in the morning or after your second coffee, make it a non-negotiable part of your schedule. Eventually, it’ll become second nature.
Systemise the Boring Stuff
Jon brought up a great phrase: ABS – Anything But Sales. It’s what happens when you suddenly find yourself updating your website, tweaking your LinkedIn bio, or redesigning your business cards instead of actually doing the thing that drives revenue.
We’ve all been guilty of it.
The solution? Systemise the process. If something feels overwhelming, break it down into a step-by-step system so it’s easier to tackle. For example:
- If you hate sales outreach, create a repeatable process with templates and a fixed time in your calendar to send emails.
- If finances stress you out, set up automated systems to track expenses and invoices, so it doesn’t pile up at the end of the quarter.
- If you struggle with admin, batch similar tasks together (more on this below).
Once you remove the mental load of figuring out how to do something every time, it stops feeling so painful.
Chunking: Tackle Tasks in Batches
Another brilliant approach Jon shared is chunking. Instead of spreading unpleasant tasks throughout the week, he bundles them together and smashes through them in one focused session.
For example, when managing rental properties, he realised that instead of making multiple trips for viewings, tenant check-ins, and maintenance, he could group all the tasks together and handle them in one go.
The same principle applies to business:
- Sales outreach? Block out an hour, write all your prospecting emails in one go, and be done with it.
- Bookkeeping? Set aside a fixed time once a week rather than scrambling every time a tax deadline approaches.
- Content creation? Record multiple videos or write several blog posts in a single session instead of doing it piecemeal.
By grouping similar tasks together, you minimise context-switching, get into a flow state, and finish them faster.
Remove Excuses: Make the Task Easier to Start
One of Jon’s cleverest tricks? Removing excuses before they even pop up.
For example, he follows a regular exercise routine. To make sure he doesn’t talk himself out of it, he lays out his workout clothes the night before, so the first thing he sees in the morning is a clear signal: no excuses, time to train.
This same principle works for business. If you struggle to make sales calls, write out a call list the night before. If you hate doing finances, keep your receipts and invoices organised in one place so it’s easy to tackle.
The less friction there is to starting, the more likely you are to get it done.
Face the Fear: It’s Never as Bad as You Think
Andrew’s final realisation? A lot of the dread around terrible tasks is mental.
A year ago, he’d break out in a cold sweat when faced with a sales prospecting list. He’d put it off, procrastinate, and avoid it until his boss started chasing him. Now? He knocks out prospecting emails with ease, because he’s conquered the fear and made it part of his routine.
The takeaway? The more you avoid something, the scarier it feels. But the moment you actually sit down and do it, you realise it’s not that bad. And over time, it becomes just another part of your workflow.
Final Thoughts: Eat the Frog
Jon summed it up perfectly with the phrase: “Eat the frog.” In other words, tackle the worst task first, and the rest of your day will feel easier.
Terrible tasks aren’t going anywhere, but they don’t have to rule your life. By building habits, systemising tasks, batching work, removing excuses, and facing your fears, you’ll get through them faster and with far less stress.
And hey, once you’ve smashed through those boring-but-essential jobs, you can reward yourself with the stuff you actually enjoy—without the guilt. So, what’s the one task you’ve been avoiding? Time to tackle it head-on!
(If watching or listening is more your thing, this article is a summary of the discussion available on YouTube below)
