What Does “I Was Running Through The Six With My Woes” Mean?

If you’ve heard the line “I was running through the Six with my woes,” you probably recognize it from Drake’s hit song Know Yourself. It’s one of those lyrics that sticks. People quote it on social media, in captions, and in memes. But what does it actually mean?

The phrase sounds cool, but it can be confusing if you don’t know the slang. “The Six” and “woes” both carry local and emotional meaning tied to Drake’s hometown of Toronto. The lyric blends pride, struggle, and loyalty all in one short line.

Let’s break down what the phrase means, where it came from, and how to use it the right way.

What Does “I Was Running Through The Six With My Woes” Mean?

The phrase comes straight from Drake’s song Know Yourself, released in 2015. When he says, “I was running through the Six with my woes,” he’s talking about moving through his city — Toronto — with his close friends and dealing with life’s ups and downs.

“The Six” is a nickname for Toronto. It refers to the city’s two main area codes, 416 and 647. Drake helped popularize that nickname, and now it’s used worldwide.

“Woes” stands for “working on excellence.” It’s also slang for friends, crew, or people you came up with.

So when Drake says he was “running through the Six with [his] woes,” he means he was out in Toronto with his closest friends — sharing experiences, chasing success, and facing struggles together.

In short:
It’s about loyalty, hometown pride, and sticking with your people through everything.

Example:

“Weekend vibes! Running through the Six with my woes.”

Here, it’s used playfully to describe hanging out with friends or celebrating a fun moment.

The Origin and History of the Phrase

The phrase first appeared in Drake’s 2015 single “Know Yourself” from his mixtape If You’re Reading This It’s Too Late. The line became instantly famous and turned into one of the most quoted lyrics in modern hip-hop.

Before this song, “The Six” wasn’t widely known outside of Canada. Drake took that local nickname and turned it into a symbol of pride for Toronto. Since then, many artists, athletes, and fans have used “The Six” to refer to the city.

The word “woes” has deeper roots in Drake’s circle. It came from his friend Baka Not Nice, a fellow Toronto artist and member of Drake’s crew, OVO (October’s Very Own). Baka once described “woes” as short for “Working On Excellence.” The phrase captured their shared drive for success and improvement.

Drake’s lyric combined both elements — local slang and emotional meaning — into one iconic line. It showed how personal connection and city pride could mix perfectly in music.

Soon, fans began using the phrase everywhere:

• On social media captions
• In memes
• On T-shirts and merch
• Even as motivational quotes

For many people, the line became about more than friendship. It represented loyalty, grind, and identity.

Even people outside Toronto adopted it, often using it to describe being with their “crew” or expressing hometown love.

When & Where to Use “I Was Running Through The Six With My Woes”

You can use this phrase in many casual situations. It’s not something people say in formal writing, but it works well in everyday talk, social media, or fun captions.

Here’s how you can use it naturally:

1. Hanging out with friends:

“Running through the Six with my woes tonight!”
Meaning: Spending time with your close friends, enjoying the moment.

2. Expressing pride in your city or roots:

“Still in my hometown, still grinding. Running through the Six with my woes.”
Meaning: You’re staying loyal to where you came from.

3. Celebrating success:

“Finally made it! Running through the Six with my woes.”
Meaning: You’re proud of your team and the journey.

4. Social media posts:
It works great as a caption with pictures of friends, parties, or travel. It shows confidence and connection.

When not to use it:
Avoid using it in professional or serious conversations. It’s casual slang that fits music, culture, or social settings better.

Tone matters.
If you use it jokingly or playfully, it sounds light and fun. If you use it seriously, it carries emotion and loyalty.

Discover More: What Does “Tread Lightly” Mean? Definition, Origin & Alternatives

Alternatives to “I Was Running Through The Six With My Woes”

Sometimes, you want the same vibe but with different words. Here are a few alternative phrases that capture the spirit of loyalty, friendship, and pride.

1. “Out with the crew”

Meaning: Spending time with your closest friends.
Explanation: This phrase has a relaxed, casual tone. It focuses on friendship and shared fun.
Example: “Out with the crew tonight — good times only.”
Best Use: Social media captions or casual conversation.

2. “Day ones”

Meaning: Your oldest, most loyal friends.
Explanation: “Day ones” refers to the people who’ve been with you since the beginning. It’s common in hip-hop culture and casual talk.
Example: “Still rolling with my day ones after all these years.”
Best Use: When you want to show loyalty or appreciation for close friends.

3. “Hometown pride”

Meaning: Pride in where you come from.
Explanation: This phrase focuses on roots and identity rather than friendship.
Example: “Always got that hometown pride wherever I go.”
Best Use: Blogs, posts, or bios that celebrate where you’re from.

4. “Squad goals”

Meaning: A phrase that highlights friendship and shared ambition.
Explanation: Popularized by social media, “squad goals” often means admiration for a group that looks happy or successful.
Example: “Running errands with my best friends — total squad goals.”
Best Use: Social captions, lighthearted moments, or fun group photos.

5. “Ride or die”

Meaning: Someone who’s always loyal, no matter what.
Explanation: The phrase describes deep trust and long-lasting friendship.
Example: “We’ve been through everything together — my ride or die.”
Best Use: Talking about someone who’s stuck with you through tough times.

6. “Grinding with my team”

Meaning: Working hard with your group to reach goals.
Explanation: This one keeps the loyalty theme but adds effort and ambition.
Example: “Late nights, early mornings — grinding with my team.”
Best Use: Motivational posts or captions about work and dedication.

Simple and Polite Responses to “I Was Running Through The Six With My Woes”

If someone says this phrase to you, your response depends on context. It can be a fun way to connect or a playful nod to Drake’s song.

Here are a few ways to respond:

Playful replies:

• “Same here — always with my woes!”
• “Toronto vibes only!”
• “You know the feeling!”

Friendly and polite responses:

• “That’s a good one.”
• “I like that line.”
• “Classic Drake!”

Humorous replies:

• “Still running, but not in the Six!”
• “More like walking through the suburbs with my woes.”
• “I left my woes at home today.”

These responses keep the mood light and friendly. You’re acknowledging the phrase without overexplaining it.

If someone says it seriously — for example, to express pride or emotion — you can match their tone:

“That’s real. Always good to have your people with you.”

This shows understanding and respect for the meaning behind it.

Conclusion

“I was running through the Six with my woes” isn’t just a lyric — it’s a cultural phrase that blends music, friendship, and identity. When Drake wrote it, he wasn’t just talking about Toronto. He was talking about sticking with your friends, staying loyal, and remembering where you came from.

Over time, the phrase became bigger than the song. It turned into a symbol of unity and ambition. Whether you’re from Toronto or anywhere else, the message still hits: life’s better when you move forward with people who’ve been there from the start.

So the next time someone says they’re “running through the Six with their woes,” you’ll know it’s more than just words. It’s a statement of pride, loyalty, and belonging — and maybe a reminder to keep your friends close while chasing your dreams.