The Failure Perspective

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Welcome to the third week of January, my goodness time flies. Yesterday was technically quit day, the day of the new year where everyone quits their NY resolutions/goals... did you?

Yesterday we saw the inauguration of a new president with new policies, a celebration of one of the faces of human and civil rights leadership, Martin Luther King, & a ban reversal of the biggest social media platform. A lot to unpack here however for another time.

As rising leaders and global execs, there are really two areas that are taboo to speak about. Failure and Sex. For today, we'll be focusing on the former, but in the coming weeks, we will absolutely pattern disrupt and talk about the latter.

Today we’re talking about:

1. Failing Harder

2. Global affairs / Industry updates

3. Budgeting for your wellness

4. Upcoming events you can’t miss

⌛️ Estimated reading time: 3 minutes 56 seconds

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A (Polaris) Perspective on Failure

In my immigrant household, failure was frowned upon - a mark of a job incomplete, an error, an “excuse”.

As a result, I grew up fearing failure. I was scared of it and often times realised that I was trying to do something not neccesarily to win, or enjoy, or learn it, but just to avoid failure.. It wasn't until many years later, well after my parents went bankrupt and then recovered, did I truly learn to embrace failure as a gift & experience worth living for.

1. Failure isn't forever

During the Holidays, I was visiting my parents in Ajax, a quiet suburb of Toronto. As I was standing outside on the driveway, admiring the cars on the drive and the external aesthetic of the sleek bungalow, I had a flash back to the day I found out we had gone "bankrupt".

I was 12 years old, about to enter highschool, and suddenly, had to understand that "credit" was now taken away from our family. It's a long story that involves my extended family, bakeries, and the challenges of mixing family and business. I remember going into the grocery store and watching my mom at the sales counter, whip out the coupons that she had meticulously set aside along side her 20$ bill and 2$ in change.

In a personal bankruptcy world, if you have $22 and coupons, you only have 22$ and coupons… no ifs ands or buts.

It was an arduous journey for them to build back their credit. They had to make moves, fight hard, and leverage their skillsets to create their own opportunities. 

Eventually, step by step they crawled out if and re-built their foundation. I often reflect that this is the best thing that ever happened to me personally as it taught me how quickly things can be taken away from you, and also taught me the value of money.

Translation: Often when we fail as leaders, we feel vulnerable, naked & we feel like it’s the worst thing on the planet and we will never recover.

But if you have the right resilience, you have a keen eye for the learning lessons absorbed, and a good support system around you, that mega "failure" turns from a hiccup into a blessing for whatever your future holds. Failure isn't meant for dwelling.

2. Actively Seek Turbulence

As I was day dreaming about the Sky-Dweller Rolex, (75K investment is all it takes if you feel like buying me one) a website visual of the airy clouds through the airplane window made my mind turn from passenger to pilot. Much like those clouds can quickly change and give way to insane turbulence, life changes similarly on a dime.

I never understood this. I think back to a horrendous interview as a BDR trying to get to the coveted AE spot at Salesforce.

The only thing preventing me from getting the job was to basically not pee my pants in the room... safe to say I did worse than that and I absolutely bombed the interview. For a week I couldn't talk, breathe, or even look at my friends-in my mind, I HAD FAILED HUGE. I thought my whole career was wiped away in an instant.

Little did I know that the experience would provide with a chip on my shoulder, a yearning to put in the work an analyze where I went wrong, and an armour to help me get through the emotional rollercoaster of selling in a high pressure environment.

Luckily I got another chance, nailed the interview & that same year, I was the youngest person in the company to make Presidents Club.

Translation: You always hope the path will be linear and to avoid the turbulence, but the truth is, more turbulence gives you more insulation. I've grown to enjoy the journey that failure takes you on, my only wish is that I would have experienced turbulence early on so I'd be more comfortable navigating uncomfortable situations in the future.

As a global leader in an ever changing world, your job becomes figuring out how to navigate the everyday turbulence that comes your way, so that you can be the best for your people. Your job needs to be to seek that Turbulence instead of shying away from it.

What’s the turbulence you are currently avoiding in your personal or professional life? What will you do today to seek it out?

3. Investing in a Fail Harder Environment for your Team

As a young soccer player on an elite team, we were used to pressure. Scouts would come watch us, videos would be taken of us, guys would get approached after games as we were nearing our college commits.

One day, I missed a massive penalty in a global showcase tournament in Michigan during the Semi Finals. I was so pissed I snapped my shoes in half after the match. Luckily we went on to win that game and get into the finals.

As we got deeper into the finals, the game was tied and pressure was becoming more intense. All of a sudden one of our players got fouled in the box-penalty awarded. I put my head down, not even bothering to look at the bench.

Surprisingly, my name was called. When I ran over to my coach in protest, him, alongside our vice captain pulled me to the side and said

That moment stuck with me forever. Here I was, fresh off a missed penalty and I'm given the green light to go take another one in an even bigger game by my coach and a key player leader. 

I scored, we won, and I ended up getting a juicy offer (which I didn't take because it wasn’t a full scholarship... see point number 1).

Translation: If I hadn't been in a team environment that enabled me to feel comfortable with failure as an outcome, I wouldn't have stepped up to take the shot.

As a leader, your team is going to make mistakes all the time, of course they are.

How do you curate and build an environment that makes them feel comfortable within failure is they key to getting the most out of them?

One exercise that I absolutely love is courtesy of my former professor, Eric Janssen, who runs "rejection bingo", a game where students have a bingo card of challenges that must be overcome. Big chance they will not be overcome, and failure will be the result, but it creates an environment that promotes failure vs reprimanding it.

How have you created an environment that fosters "fail harder" thinking? What has it yield?

When you actively seek to understand failure and all of its' gifts, you remove the fear. When the fear is removed, you are free to dream big and shoot for the moon. Worst case? You land amongst the stars.

This begs the question.

• Is Failing actually a Failure?

• Is it it some hidden present? 

Without Failure, Steve Jobs would not have created the Iphone, Opera wouldn't be the global philanthropist, and Elon Musk wouldn't have invented Space X. Failure is a stepping stone.

Some Soccer Pics for y’all:

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📆 EVENTS

Showcasing the best events across Fashion, Tech, Sales & Cannabis

1) 🗽 House of Bartholomew is hosting a private viewing of their Fall Winter 2025 collection. Bart and I met at Art Basel at his rooftop party at the SLS Brickell and is truly a one of a kind designer. Don’t miss this event.

📍 296 9th Avenue NY, NY February 8th @6pm

🎟️  Purchase tickets here

2) My former Regional Vice President, current sales leadership mentor & world’s best sales Trainer, David Premier of Cerebral Selling will be hosting a wonderful event for leaders in NYC alongside Vidyard. David is the reason I got my second interview for AE after I bombed it the first time:)

🗽 Vidyard is hosting a sales conference about the future of sales, their new product vision and more!

📍 NeueHouse Madison Square. February 6th @12PM EST

🎟️ Full Details Here

Got an event that's a must-attend? Share it with our executive focused audience! We're always on the lookout for exciting happenings in Cannabis and business to feature in our future events section. Whether it's a conference, workshop, or community gathering, let us help you spread the word. Reply to this email or send an email to ([email protected]) to be spotlighted in front of our engaged readers. Don’t miss the opportunity to get your event on everyone's calendar!

🧘 Longevity

Lebron James spends ~2 Million Dollars on his body each year. You might think, only athletes need to spend money or budget money towards their body and health. In reality, we all do, and we should all do it intentionally.

How much are you allocating each year to making sure the 1 body you have is going to thrive and make yourself feel good? (Better not be south of 2 million, we have high standards at Polaris)

Take an internal check, and make sure at the start of the month/quarter/year, you’re intentionally putting hard earned dollars aside for running shoes, a soccer league :), that gym membership you’ve been putting off getting, healthy food, etc.

What about as a leader? Are you encouraging/enabling your people to be the best they can be?

Stay tuned for next weeks longevity edition where we will feature my new favorite place to visit Trove Wellbeing.

Have you enjoyed this newsletter? Is it providing value? Do you know somebody that would find it useful? Send them this newsletter and if you refer 5 people your next coffee run will be on me. (5 referrals = $30 Starbucks, 1 Referral = 4$)

As the world becomes more complex, it becomes more and more challenging to stay grounded, focused and aligned. Stay ahead by fostering unity, innovation, and trust across your teams and yourself. Don’t miss out on upcoming events and insights that will help shape your success in the months to come.

- SKV