I’m making good money. So why does everything still feel like a slog?

August 11, 2026 — 2:11pm

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I had a business which I successfully sold. I was pretty burnt out by the end of it. Now, I’m self-employed, I’ve kept my team small, I make good money. I could be making more, but also I’m doing okay – I have decent savings and investments. My problem is that it just never feels like it gets any easier?

Over the past five years, my wealth has been growing, but I still feel like I’m slogging away. I’m not afraid of hard work. I’m proud of my work ethic. But sometimes I just feel like it’s meant to get easier at some point. Or do I just keep grinding until I get there, and then retire?

Here’s the short answer – it won’t start to feel easier, until you let it.

We are often sold this idea that “ease” exists at a specific milestone in the future. It starts with small milestones – when I get a certain amount in savings, when I can stop living pay-to-pay, when I finally get out of debt – then, life will feel easier. But it doesn’t end there.

Then it becomes when I buy a house, when I pay off the mortgage, when my business/income hits $X milestone … then I’ll be able to relax and enjoy my life. But that’s not really how it works.

Sure, financial progress can alleviate specific........

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