drake when to say when

Drake – When to Say When | Lyrics Meaning & Song Review

Drake surprised the fans with a double release titled “When to Say When” and “Chicago Freestyle” as the March 2020 began. Both tracks are played back-to-back, complete with a music video. In this article, we will take a look at the “When to Say When” part of the release.

On February 8, 2020, Drake was seen shooting a music video in Brooklyn, which suggested that new music was on the way.

On “When to Say When,” Drake is heard reflecting on his journey in music so far. More than anything he is heard telling us how blesses he is to have it all–the money, the fame, fans, and God on his side. He also says that he has a lot to give to the world now–possibly in terms of advice, money and positive thoughts.

Watch “When to Say When” & “Chicago Freestyle” Music Video by Drake

Lyrics Review and Song Meaning of “When to Say When”


Drake discusses an event in his life. Somebody contacted him and asked for his advice. It is a strange feeling for him. He was a “nobody” some time back, and now a ‘somebody’ looks up to him. Drake is glad about this turn of events because he “got all these blessings, just to give it to others anyway.”


At the start of the verse, Drake tries to establish why he holds bragging rights in the music scene. He is 33-years-old at the time of this song release. Along with that, he says that he has $33 million saved up for a rainy day, meaning an “emergency.” So this does not take into account his daily expenses. CelebrityNetWorth.com estimates that the Canadian rapper at $170 million in 2020. So Drake’s $33 million emergency fund could be far from bogus.

In 2017, Drake was recorded to have stayed on Billboard Hot 100 chart for 431 weeks. Drake wants 500 weeks! He also suggests that $500 million net worth might be his retirement target.

Drake also tags Michael Jackson in these lyrics to compare himself to one of the biggest stars in the music game. But how is Drake better? Because his palace is actually safe for children.

Humbly enough, Drake also credits his success to Lil Wayne and his manager Tez for recognizing him and giving him a chance. So he wants to do justice for them and the music game no matter what.

In the next few lyrics, Drake does not forget to shout out to his mother, Sandra Graham. Without her, none of this would be possible.

Drake also talks about some of the “one-hit wonders” in the music game. He had to grind from day one to reach the status he is in today. So he challenges these one-hit wonders to make another hit, consciously. And he wonders why anyone who has already won the game needs a manager who hasn’t been there to help them get up.

Towards the end of the verse, Drake shares some advice for succeeding in life. He tells us never to be insecure about yourself. Earlier in the verse, Drake reminded that no matter what happens, he stays confident about himself 24*7. So to win the game of life, you need to trust yourself. And learn when to say when, says Drake!

So what do you think about “When to Say When” by Drake? What do you think these lyrics mean? Drop a comment below.

Check out the complete lyrics and further song meaning breakdown on Genius.

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