STACK Sessions

Well-known as a rapper, poet, artist, author and MC with a massive YouTube following, Kanwer Singh (aka Humble the Poet) is rich in wisdom and, luckily for us, happy to share it. His own experiences with debt, defining success and the true value of self-worth have given this artist we love a wealth of mindful and candid straight talk about money. Along the way we were inspired by his vulnerability, dedication to speaking his own truth and willingness to use his personal story to expose the hidden, personal shame at the centre of bad financial habits… and how to use it to become truly rich for the first time.

We knew that while chatting with Humble the Poet we’d be met with some serious wisdom, but we didn’t anticipate the number of mind-blowing ah-ha money moments that he was about to drop on us. As a professional wordsmith and former teacher, we shouldn’t have been surprised. With the straight talk of an MC and the clarity of a poet, Humble is so in tune with the core truths of what he wants to share that our first-time meeting was filled with deep realizations around just how personally our finances impact us and what we can do to make sure that the relationship is nourished and not ignored.

As authentic as he is artistic, Humble’s path led from passing the days as an elementary school teacher with a comfortable gig and predictable pay cheque to finding the courage to pursue his creative passions and become an artist and beloved YouTube star. (Being BFFs with Lilly Singh didn’t hurt, either.) On the way he learned about the complexities of career and finances the hard way and came out the other side finding a voice of incredible insight and eloquence. Now he’s discovered that the bravery he found to pursue his creative passions also crosses over to a willingness to speak openly about the shame associated with debt and the discomfort that, if left unspoken, can turn hard conversations around money into full-blown debt disasters.

Photo: Bella Francis

From humble beginnings

Humble’s career journey is undeniably unique but starts where many kids find their first financial lesson and adolescent income source: a paper route. The child of immigrant parents, his upbringing was a constant lesson in smart saving and even smarter spending. He watched as his father paid off the mortgage quickly and celebrated with one of the family’s rare splurges: a pizza party. Growing up in the Toronto area of Rexdale, Humble’s friends came from a wide variety of income brackets. Some friends had to work to help their parents cover the bills while others got to choose what car they were going to drive to school that day. His early worldview was formed early by seeing firsthand just how differently people experienced and understood their own relationships with money.

“You can always focus on people who have more than you, but you can also choose to appreciate where you’re at based on those people you know, too.”

Humble’s own relationship with money wasn’t always so wise. Like a lot of young people early in their careers, he spent cash as quickly as he made it. A natural storyteller, he was making a decent living as a full-time teacher, but, lacking a strong financial education, the way he budgeted didn’t allow for much long-term saving. When he made the life-changing decision to leave the security of his traditional job path and take the chance on his creative dreams, things weren’t easy. He had no idea how to make a living as an artist, and, thanks to some unclear contracts and bad management decisions, over time he landed himself $80,000 in debt. That’s when his real education began…

On changing habits to change yourself

Humble had an eye-opening moment when he hit financial rock bottom: he finally admitted to himself that ignoring the problem and hoping for a miracle wasn’t going to work. Instead, he would have to be realistic and face some of his greatest fears. Starting these honest conversations with himself and determining where he truly found value in his life brought him to a much happier, more truthful place. He took inspiration from his past and thought back to his father and how he paid off that mortgage so quickly, celebrating with just a pizza. He knew that he had to get real with himself before anything else.

Humble’s new mindset led to meaningful actions. He made a lifestyle switch and actively embraced minimalism, selling what he didn’t truly need and focusing all of his time and effort on work. After four years he was able to get back to zero and felt “richer” than he ever had before. Through his experience he learned invaluable lessons and immediately knew not to celebrate by spending like he had before. He patted himself on the back, maintained his current minimalist lifestyle, and was eventually able to turn what was once a black hole of debt into an upward spiral of savings. That financial security and increased confidence fed his creative momentum and led him into a new world of artistic opportunities that led him to the creative career he had always dreamed of.

Photo: Bella Francis

“Your immediate company matters. Find people who share your priorities.”

Changing your relationship with money starts as a journey for one but grows to include decisions on how you’ll need to interact with everyone in your life to maintain your newfound habits. Instead of heading back to the same old friends that preferred his (former) baller lifestyle, he chose friends who more closely shared his new values as his role models. His modest and financially savvy father, of course, but also some friends you might not suspect: artists and entrepreneurs on the Forbes’ list. People who, despite having the finances to spend millions, mindfully chose to live simply and valued their relationships with people over their ability to buy stuff. Humble has met billionaires whose approaches to life and money has taught him one of his most valuable lessons: that true wealth is not feeling the need to show off how much money you have.

“What you feel on the inside won’t get resolved by what’s going on on the outside”

As much as he could see it was a cliché, he also had to admit that the more he pursued what he loved and the less he cared about an ego-driven need to make money (sound the cliché alarm…) he began to make more money. By saving, spending within his means and knowing that placing value in what you spend your money on isn’t a true representation of your worth, he found that financial security followed. He created his own definition of success and that’s what he achieved – personally, spiritually and, eventually, financially.

The direct connection between financial and mental health

Humble knows firsthand the impact money has on self-esteem. When your finances are out of control and you start to tie this to your own experience of self-worth it’s a slippery slope to begin questioning what you deserve from your life overall. For Humble, this manifested in wondering if he deserved to have fun or be with his friends. Did he even deserve to be pursuing his own art? In the middle of his most challenging days he was solely fixated on his debt and nothing else, forgetting the importance of self care and physical health. He lost 20 pounds and one day was just “a beard and his two front teeth” – proof that stress can eat away at you both mentally and physically.

“When you’re not feeling good there are so many options to address that – go to the bar, a movie, shopping, buy something, medicate the way we feel, but it’s all short-term.The best thing I do is just go for a bike ride. Focus on staying mindful.”

When he began to focus on protecting his inner-peace he found this naturally led him to spend less. Small steps toward saving money made him feel better about his choices and more confident in his own ability to control his life. As his self-awareness grew and his situation improved he was able to pull himself out of debt but admitted that, even years later, he still felt shame. Only now is he able to to talk about it openly, but with an excellent motivation: the hope that his story can empower others.

Humble is highly aware of the power he gained by asking for help, reaching out, and being vulnerable. Nothing can be gained from keeping quiet and avoiding hard personal conversations. In fact, doing so can set you back even further. The moment you open up you’re able to live life on your own terms, which is exactly what Humble is doing now – both grateful for how far he has come and defining success on his own terms as he continues to grow.

“Live the life you want. Live a simple life, maybe a life of routine. The only way to be successful is to know yourself, figure out what gets your juices going, and pursue your enthusiasms. You have to know yourself and practice a life of gratitude and appreciation”

Header image created by Max Rosenstein for STACK Sessions. All other photography created by Bella Francis. Video courtesy of Kanwer Singh.

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