Picture this: You're standing in a hotel room in Thailand at 2am, holding your phone like a decibel meter (because apparently that's what jet lag does to your decision-making), discovering your air conditioner is as loud as a busy restaurant. The pillow feels like it was stuffed with concrete, there are actual holes in the walls, and you're pretty sure the paint is peeling in real-time.

So naturally, you do what any reasonable person would do: panic-book a $1500 upgrade to the Hyatt for the rest of your trip.

This was me a few months ago on a business retreat. I'd tried to save money by staying a "short walk" from the venue (turned out to be a mountain climb via disco tuk-tuk... I'm not making this up). After one night of zero sleep and maximum frustration, I was ready to throw money at the problem faster than you can say "the write-off people will pay it."

But here's where it gets interesting.

The next day, after my nervous system finally calmed down and I'd made some new friends, I found myself sheepishly explaining my room situation to a group walking back from the Hyatt. One of them, Kristy, asked me the simplest question that hit like a lightning bolt:

"Have you asked for what you want?"

I stopped mid-sentence.

Had I asked the front desk about moving rooms?
Had I mentioned the noise, the holes, the general state of despair?
Had I even tried to negotiate or find a solution before opening my wallet?

Nope. Not once.

I'd skipped straight from problem to panic to payment... bypassing the most obvious step of actually asking for help.

So I walked back to the front desk, explained the situation, and guess what? They moved me to a perfectly decent room immediately. They understood. They wanted to help. I just had to ask.

Now, you might be wondering why I'm telling you about my accommodation disasters in Southeast Asia.

Because I see freelancers making this exact same mistake every single day... just in different scenarios:

The client asks for "just a small revision" (that's actually a complete redesign), and instead of setting a boundary, you work weekends to deliver it "for free" to keep them happy.

The project scope starts creeping beyond what you quoted, but instead of addressing it, you absorb the extra work and stress, hoping they'll notice your dedication.

A client pays late repeatedly, but instead of having an honest conversation about payment terms, you just build buffer time into your cash flow and stress about it privately.

You're undercharging and you know it, but instead of raising your rates, you just take on more clients and work longer hours to hit your income goals.

In every case, you're doing what I did in that Thai hotel room: throwing time, energy, or money at a problem instead of simply asking for what you want.

The truth is, most clients (like most hotel front desk staff) actually want to find solutions that work for everyone. But they can't read your mind. They don't know you're struggling with scope creep if you don't mention it. They don't realise their revision requests are actually new projects if you don't explain the difference.

Here's what I learnt on that mountain in Thailand:

The most expensive question is the one you never ask.

Whether it's about rates, boundaries, timelines, or basic working conditions... the cost of not speaking up is almost always higher than the temporary discomfort of having the conversation.

Your clients aren't mind readers. And neither are you. Instead of assuming what they will or won't accept, try actually finding out.

Sometimes the solution is simpler than you think. Sometimes all you need to do is ask.

What question have you been avoiding asking in your business? What conversation are you putting off because you're afraid of the answer?

Hit reply and let me know. I promise it's probably not as scary as spending a night with a concrete pillow and a jet engine for an air conditioner.

Cheers from someone who finally learnt to ask,