How to Work ON Your Business When You're Drowning in the Day-to-Day

If you're a small business owner, you've probably heard the advice "work ON your business, not just IN it" about a thousand times.

And if you're anything like the founders I work with, you've probably thought: "Great. Love that. But when exactly am I supposed to do that between serving customers, managing staff, dealing with suppliers, and everything else?"

Here's what no one tells you: Pret didn't become Pret by Sinclair Beecham standing behind the till every day. Gail's didn't expand to 100+ bakeries because the founders were icing cakes at 6am. At some point, they had to step back and work ON the business - the strategy, the systems, the structure that would let it grow without them.

But you're not Pret. You don't have their team or their budget (yet). So how do you actually make this happen when you're still very much the person serving customers, managing staff, and dealing with suppliers?

What Does "Working ON Your Business" Actually Mean?

Working ON your business means stepping back from the daily operations to focus on strategy, structure, and growth.

I've worked with businesses in retail and hospitality for over 20 years - from shop floor to senior leadership at places like Westfield and Transport for London. The difference between businesses that plateau and businesses that scale? It's not talent. It's not hours worked. It's whether the founder creates protected time to think strategically.

For retail, hospitality and lifestyle businesses, working ON your business might look like:

• Serving customers vs. improving your customer experience

• Running today's service vs. planning next quarter's strategy

• Dealing with staff issues vs. building a team structure that actually works

• Posting on social media vs. developing a brand strategy

• Firefighting problems vs. building systems that prevent them

Working IN your business keeps it running. Working ON your business makes it grow.

• Reviewing your customer journey and identifying friction points

• Planning your brand refresh or visual identity

• Mapping out your service offering for the next 6 months

• Building financial systems that give you actual visibility on what's profitable

• Developing your team structure as you scale

• Getting clear on positioning - who you're for and what you're known for

• Planning marketing strategy instead of just reacting to what needs posting today

The work that happens ON your business is the work that creates sustainable growth. The work IN your business is what keeps the lights on today.

Most business owners spend 95% of their time on the latter and wonder why they're not growing.

Why Most Business Owners Never Do This

Let's be honest about why this doesn't happen.

1. You don't have time

When you're in the thick of running a business - especially in retail or hospitality where you're customer-facing and service-driven - strategic thinking feels like a luxury you can't afford.

2. You don't know where to start

Even when you do get a spare hour, you're so deep in the weeds that stepping back to see the bigger picture feels impossible. Where do you even begin?

3. You're doing it alone

Most independent business owners don't have a board, a business partner, or anyone to bounce ideas off. You're making every decision in your own head, which is exhausting and isolating.

4. You feel guilty

Taking time away from the business to work ON it can feel indulgent - like you're not "really working." Especially in industries where showing up and being present is part of the job.

I see this constantly in my work with businesses owners. The café owner who knows they need to review their pricing structure but never does. The boutique founder who's been meaning to map out their customer journey for six months. The restaurant owner who keeps saying they'll plan next season's menu properly 'when things calm down.'

Things never calm down. You have to make them calm down.

The businesses that grow are the ones that make working ON the business non-negotiable.

They don't wait until they have time. They create it.

What Happens When You Only Work IN Your Business (Never ON It)

When you're constantly working IN your business without stepping back, here's what happens:

You stay reactive instead of proactive Every day becomes about putting out fires rather than preventing them. You're always one step behind instead of planning ahead.

You repeat the same problems That staffing issue? The cash flow crunch? The seasonal slump? They keep happening because you're dealing with symptoms, not root causes.

You hit a growth ceiling Your business can only grow as far as your current structure allows. Without intentionally building for scale, you stay stuck at the same level year after year.

You burn out Working harder doesn't create growth - it creates exhaustion. The businesses that scale sustainably are the ones where the founder isn't drowning in operations.

Your best ideas never happen All those things you think about at 11pm - the rebrand, the new offering, the better systems - they stay as ideas because you never have space to actually work on them.

What Changes When You Actually Make Time for Strategy

The businesses I work with that consistently make time to work ON their operations see:

Clarity on what actually matters Instead of ten vague priorities, you know the ONE thing that'll make the biggest difference. You stop spreading yourself thin.

Better decisions, faster When you've thought strategically about where you're going, day-to-day decisions become easier. You have a framework to work from.

Sustainable growth You're building structure that supports scale, not just working harder. Your business can grow without you burning out.

Confidence in your direction You're not second-guessing every decision or wondering if you're doing the right thing. You've done the work to get clear.

Actual progress on what matters The big stuff that's been sitting on your list for months? It actually gets done because you've created the space for it.

Right. So you get why this matters. You know you need to do it. The question is: where do you actually start?

Most business owners stare at a blank page for an hour and end up more confused than when they started. That's because they're trying to boil the ocean - think about everything at once.

I've got a framework that cuts through that. Three questions that force clarity on what's working, what matters most, and what's genuinely in your way. It takes about 2 hours to work through properly. But here's what you get: actual clarity on your next move. Not a vague sense you should "do marketing better" or "focus on growth." Specific, actionable clarity on the ONE thing that'll make the biggest difference.

Before you click through to the framework, do yourself a favour: block 2 hours in your calendar right now. Don't just read it and think "I'll do this later." You won't. Schedule it like a client meeting. Because you're the client.

Read the framework: The 3 Questions That'll Transform Your Business →

And if you're thinking "I don't have 2 hours" - that's exactly why you need to do this.