Spark’s NotesNovember 6, 2026By Anthony Spark

What Is That Conversation Costing You Not to Have?

Sometimes avoiding an uncomfortable conversation costs more than having it. Are you waiting for the right time, or just avoiding the discomfort?

People can spend a remarkable amount of time preparing for a conversation they already know they need to have.

They think about what to say, whether the timing is right, how the other person might react. A week goes by, then another, and nothing has really changed except the amount of time they've spent thinking about it.

I was thinking about this with compensation. Suppose you're doing well at work and believe you've earned a better arrangement.

You know you should ask, but somebody else just got a raise, or you don't want to come across as ungrateful, or you figure your boss will notice eventually. Those aren't crazy concerns. Relationships matter, and timing does matter.

Still, I think it's worth asking

what waiting actually costs you.

If the difference between having the conversation this week and having it next month is a few thousand dollars, that's part of the decision. Maybe you look at the number and decide you'd rather wait. Fine.

At least you've made that choice with your eyes open instead of letting discomfort make it for you.

The other thing people do is imagine that a no would mean something terrible about them. If your boss says the company can't do it right now, you might hear,

'I'm not worth it.'

You don't actually know that.

The company could be bringing in plenty of revenue and have very little profit. There might be other commitments or expenses you're not aware of.

You can be valuable to somebody and still not get the answer you want on the day you ask.

I like approaching these conversations with some curiosity. You can say you're interested in a different compensation arrangement and ask what you'd need to accomplish to get there.

Maybe you're already there. Maybe there's a number or a timeline you didn't know about. Maybe you find out the business doesn't have a clear process at all, which is useful information for both of you.

That last part happens more often than people think. Small businesses grow, people make different arrangements at different times, and eventually nobody is quite sure what the rules are.

The person asking feels awkward, and the person running the business has to figure out how to be fair while keeping the numbers working.

You can't solve all of that by staying quiet. You also don't need to make the other person the villain to advocate for yourself.

I wouldn't tell somebody to have every difficult conversation immediately. There are times when waiting makes sense.

I would want them to know

why they're waiting, what it may cost, and what they're expecting to change

before they finally speak up.

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