On September 10, most of Australia will be asking each other “R U OK?” Workplaces will run morning teas. There’ll be yellow everywhere. It’s a genuinely good day, and I’m glad it exists – it’s done a lot for getting these conversations out into the open where they belong, after years of them staying firmly behind closed doors.

But here’s the question I actually want to ask you, business owner to business owner… when’s the last time you asked yourself that?

We’re brilliant at checking in on everyone else. Staff, clients, family, that one supplier who always sounds a bit frazzled on the phone. But most business owners I talk to haven’t had an honest conversation with themselves in months. We’re too busy holding everything together to notice we might not be, ourselves. We’re the ones people come to when something’s gone wrong, which means we’ve quietly trained everyone around us, including ourselves to believe we don’t need checking on.

Running a business is one of the loneliest jobs going, if I’m honest. You’re the one everyone brings their problems to. There’s rarely anyone bringing you theirs, asking how you’re actually tracking underneath it all. Even the people who love you tend to ask “how’s the business going?” rather than “how are you going?” and those are very different questions with very different answers.

The performance of “fine”

There’s a particular skill business owners develop without meaning to, the ability to say “yeah, good, flat out” in a completely convincing tone while privately feeling anything but. It becomes automatic. Someone asks how you’re going at the school pickup, at the football, at a client meeting, and out it comes before you’ve even thought about it. Over time, that automatic answer starts to replace the honest one, even in your own head. You stop checking because you’ve gotten so good at performing that you don’t seem to need it.

So today, let’s flip it. Three questions, and actual permission to answer them properly, without the reflexive “yeah, good, flat out” that we all give without thinking.

Am I okay, or am I just coping?

There’s a real difference. Coping looks like getting through the week in one piece, ticking things off, keeping the wheels on. Okay looks like genuinely enjoying the thing you built, feeling proud of it, curious about where it’s going, energised rather than depleted by it. If you’ve been in coping mode for a while now, that’s worth noticing, not brushing off with “it’s just a busy season,” because busy seasons have a habit of becoming permanent if nobody names them.

There’s no shame in “coping” as an honest answer. It’s often the truest thing a business owner has said about themselves in months, once they finally stop and let themselves say it. The shame only comes from pretending otherwise for too long.

What am I carrying that I haven’t said out loud?

For a lot of business owners, it’s the money. The gap between what the business brings in and what it feels like it should be bringing in by now, given how hard you’re working. That gap is heavy to carry on your own, and you really don’t have to. I’ve had conversations with business owners who’ve been sitting on that particular worry for years, silently, because it felt embarrassing to say out loud, like admitting it meant admitting they’d failed at something. It’s not embarrassing. It’s incredibly common, and it’s fixable once it’s actually spoken about, usually far more fixable than the years of silent worry suggested.

Sometimes what people are carrying isn’t even the money itself, it’s the fear of what the money says about them. That’s a heavier load than the actual numbers ever are.

Who’s actually in my corner?

Not staff. Not clients. I mean the people who ask how you’re going, not just how the business is going. If that list is short, that’s your sign; a mentor, a community, or even just a standing coffee with someone who genuinely gets what this life is like. Business ownership can be surprisingly isolating even when you’re surrounded by people all day, because being surrounded by people isn’t the same as being known by them.

The physical signs worth noticing

Sometimes the “am I okay” question is easier to answer by looking at the body rather than the mind. Are you sleeping properly, or lying awake running through tomorrow’s problems? Are you short-tempered with people who don’t deserve it? Have you stopped doing the small things that used to recharge you – the walk, the round of golf, the Sunday paper, because there’s “no time”? These aren’t small details. They’re often the clearest signal available that the tank’s getting low, well before the mind is ready to admit it in so many words.

It’s okay to not have the answer yet

If you sat with those three questions and didn’t love your answers, that’s not a failure, that’s information. The whole point of asking is so you can actually do something with what you find, rather than carrying it around unexamined for another six months. Awareness on its own doesn’t fix anything, but it’s the step that has to come first, and it’s the step most business owners skip entirely because it’s uncomfortable.

You can’t run a healthy business from an empty tank. Checking in on yourself isn’t soft, whatever the old-school hustle crowd would have you believe, it’s strategy, plain and simple. A business owner who’s running on empty makes worse decisions, snaps more easily, and enjoys less of what they’ve built. None of that helps the business either – it’s not a trade-off between looking after yourself and looking after the business. They’re the same job.

And if part of what’s weighing on you is the money side of things, that’s exactly what The Edge exists for. A place where you’re not carrying it solo, surrounded by other business owners asking each other the real questions instead of the polite ones.

Join The Edge: https://financialmanagement101.com.au/work-with-karen/the-edge/

And if today’s the day you actually need to talk to someone, Lifeline is on 13 11 14, any hour, no appointment needed.

What to do once you’ve asked yourself

Asking the question is the easy part, once you’ve actually made yourself do it. The harder part is what comes next, because most business owners are excellent at identifying a problem and then filing it away under “deal with that eventually.” So if any of the three questions above landed a bit close to home, don’t let it end there.

Pick one small thing. Not a complete overhaul of your life, not a dramatic announcement to everyone that you’re “making changes.” One small thing; a call to a friend you’ve been meaning to make, an actual look at the money situation you’ve been avoiding, a boundary around one evening a week that’s just yours. Small, specific, doable this week, not “someday.”

Business owners checking in on business owners

There’s a particular kind of relief that comes from talking to someone else who genuinely understands what this life involves – the highs that nobody else quite gets excited about the way you do, and the lows that nobody else quite understands the weight of either. Friends and family love you, but unless they’ve run a business themselves, there’s a layer of it they simply can’t relate to, however much they try.

That’s part of why community matters so much here. Not a support group in the clinical sense, just other people in the same boat, who ask “how are you really going” and actually mean it, who’ve had the sleepless nights over cash flow and the quiet pride over a client win, and who get it without you having to explain the whole backstory first.

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