The first phrase means Do your Best. The second means Be Contended and you will be Happy.
We cannot be too easily contended. Otherwise there will be no improvement and progress. Technology will not improve. Singapore will not progress. So, do your best first before you can be contended.
Wealth is not the key to happiness. However, I believe money is an important key.
Decades ago people would be happy if they had a job, a roof over their head and food on the table. Society has changed. Now, people have many wants and more worries.
I think the key is for everyone of us to have its own strategy for happiness. We may re-look at our priorities in life, plan realistic goals and should be prepared for hardship and to accept disappointments and failures.