After moving to Toronto, I discovered how many people actually do it, no matter how scary it sounds, and how they almost always end up booking another one because of how much fun it is — how uplifting and freeing it feels to have full liberty to do whatever you want, however you want. Now, if that’s not your thing, that’s totally fine and understandable. But if it’s something you constantly think about, or you wonder what it would be like when you see other people doing it, or you get a little excited imagining what you’d do — it’s worth trying. Even though I’ve never been on one myself, I feel like it would be such a cool adventure, and I’m excited to experience it for the first time in 2 months.

What confused me the most was figuring out what I would actually do. After talking to friends who’ve done it multiple times, I noticed a trend: people tend to go for a specific activity the first time, or join a tour group, so the excitement of trying something by yourself is still there, but with some built-in certainty. For me, I’ve always wanted to try scuba diving, but I kept telling myself it was something I could do “later,” or once I’d saved up for other things — I realized I was delaying it for no reason. After 4 months of doing nothing and feeling frustrated because of my injury, I realized how fast time goes by and how important it is to do things while you’re healthy and have the energy for them. Money was another excuse — even after hitting some of my financial goals and landing a higher-paying job, I was still finding reasons to put it off. So I decided to just go for it.

Booking the activity turned out to be a great way to anchor an exciting adventure. Then came the research phase, which is really important for the logistics and insurance side of things. After digging in and talking to friends who’ve been on similar trips, plus my cousin who’s done a diving trip before, I figured out all the unglamorous items that don’t come up when you’re booking flights and daydreaming about the trip. The ones people most often miss are:

1. Travel AND health insurance through your credit card

2. Having local currency on you at all times

3. Sorting out roaming and an eSIM (some credit cards offer this)

4. Diving insurance, separately (in my case)

The next thing on my to-do list is building an approximate budget for while I’m there, and remembering not to overspend on souvenirs unless it’s something I truly want (can’t think of anything yet). I’d already accounted for flights, accommodation, and a rough sense of overall costs, but I think it’ll help to have a spending range in mind so I don’t have to overthink my budget day to day — just stay within the range and prioritize accordingly. Since I’m only taking a backpack, I’ll be pretty limited on the shopping front anyway, which just means more room to enjoy the actual vacationing part.

I’ll share my honest take on the solo trip once it’s done!

Shermeen

Years later, I’m currently feeling a similar low. Not in terms of being surrounded by toxicity, which from the little experience I’ve had in life is the worst kind of low, but something more health-related. Four months ago I fell on my head trying to do a pull-up and suffered a concussion. It destroyed me in a way nothing has in the last five years. It’s one of the few injuries where the physical hit itself - not just the pain or disruption of it - directly alters brain chemistry and function and can have a bigger mental impact than the physical pain.

My reaction to it (not great) is what has surprised me and has helped me realize where I currently stand - in the sense that I don’t really know how I want to spend my time. Doing something outside of my regular job felt great, but I realized I’m not exactly sure what the purpose is. The last four months haven’t been great, to say the least, but there have been lots of small and big realizations.

The good thing is I’ve been through a few difficult phases in life, and once you’ve seen something happen before, it’s easier to spot the signs and fix things. Journaling was one thing I stopped doing that helped a lot back then, and I think I want to keep that going here.

Today something I read caught my eye and stuck with me, which is what made me want to start this back up. I figured since my “newsletter” is essentially dead, I could just jot things down here instead, whenever I feel like it, since it helped before.

So here’s the paragraph from His Highness Prince Rahim Aga Khan that has been the focus of my reflection today:

“Think about who you are. Engage your intellect in your journey to self-awareness. Not to become self-centered, but if you do not know who you are, how can you become interested in who anyone else is? Get to know yourself, notice the lens through which you see the world, explore what matters to you, what makes you happy, what disturbs you, and what you are good at. Get to know yourself, because your world starts with you and emanates outwards in concentric circles widening to incorporate all of humankind. Know yourself so you may know others.

Your identity is shaped by your history and your beliefs, and by your self-awareness, by what you repeatedly do. You could take the easy road through life and just coast through it, you could avoid the discomfort of difficult things - this is not the best thing for you. Life has hard moments. Be well-equipped to navigate those hard moments when they present themselves. This means building resilience. Like a muscle - it gets built when you stretch yourself, when you challenge yourself, when you persevere, when you are voluntarily willing to work through the discomfort to get to the other side. It is okay to struggle because struggle is where growth happens. This is not the same as suffering. Suffering is of no benefit to you, but struggling is the cost of resilience. So embrace the challenges that you face”

This really struck a chord with me. I remember before, penning down my thoughts helped me take relevant actions and I got so much more than I had dreamt. One of my recent actions has been booking a really interesting vacation that I’ll talk about later.

This is my current view btw - Canadian summer is the best 🌞

Shermeen

One thing I think most people relate to is wanting to do more in life — and somehow ending up doing less.

Do you ever feel that foggy mental pressure, jumping from one thing to another until you end up cooking or cleaning just to feel productive?

A small percentage of people don’t seem to struggle with this. They’re the ones we see creating, building, achieving — the “disciplined few” who make it look effortless. I’ve been studying them lately, and they all share one thing in common:

Clarity.

Clarity in a specific task.

Whether it’s short-term or long-term doesn’t matter. What matters is having something defined enough to direct your energy toward.

🔧 1. What’s Working for Me

I’ve realized that clarity isn’t a switch you turn on — it’s a skill you build. It takes time and iteration, but every step makes life a little less noisy.

When I started YouTube about a year ago, I didn’t have clarity. It was something I wanted to explore beyond work — though I also had to push through social media anxiety (my Instagram is as empty as my gallery is full).

Then I made an Excel video that unexpectedly got me monetized. It was exciting, and I was proud of that milestone — but I still wasn’t sure where to go from there.

Part of my confusion came from having too many directions that made sense on paper. I’ve always been analytical — I studied finance and stats, grew up around structure — but clarity isn’t about knowing how to plan. It’s about knowing what to focus that plan on.

That’s when it hit me: progress doesn’t come from doing everything — it comes from deciding.

Having an idea of what you want in life, breaking it down into small, achievable goals, and staying consistent — that’s what compounds. That’s how I found a good job in a tough market and monetized my channel without a niche.

Maybe now that I’ve worked through those early hurdles, this is what I need to do next — decide.

🎧 2. What I’m Listening to / Reading

Lately, I’ve been watching interviews and breakdowns of creators and entrepreneurs who’ve built something from scratch. What they all emphasize isn’t luck — it’s clarity. The clearer your focus, the faster things move.

I’ve also been experimenting with my own system for breaking goals into small, optimized steps — inspired by how investors think about compounding growth. I’ll share more about this in an upcoming video.

🏙️ 3. Life in the City

Toronto is actually a great place to meet people — if you’re the one who initiates.

People are craving genuine, in-person conversations again. Most of the time, if you reach out, they’ll say yes simply because no one else tried.

I’ve been reconnecting with old friends and meeting new ones lately. You never know which conversation might spark an idea or give you the clarity you’ve been missing.

Sometimes it takes a few follow-ups before plans actually happen — and that’s okay. Be the one who reaches out. Don’t let pride get in the way.

💭 4. Thought

One thing I’ve learned watching successful people — whether YouTubers, execs, or founders — is that clarity doesn’t come before action. It comes through action.

When I look back at the times I’ve felt stuck, it’s never because I didn’t have potential. It’s because I didn’t have direction. I was spreading energy everywhere and wondering why nothing was moving.

Clarity is like building a muscle — it grows the more you use it.

If you can break down what you want into smaller time periods — a week, a month, a quarter — it takes the pressure off. And over time, those clear, consistent steps compound into something real.

Just like investing, small, focused actions multiply. Every bit of progress — every video, project, and intentional decision — adds up in ways you can’t see yet.

Clarity gives those small actions direction, and direction gives them power.

It’s the same principle as investing — not in money this time, but in focus.

👉 I shared a video breaking down my approach to goal-setting and clarity — the mindset behind how I’ve seen creators and entrepreneurs stay consistent. You can watch it here.

I’d love to hear — what’s one area of your life you’re craving more clarity in right now?

Shermeen

Lately, I’ve been thinking about the difference between making quick money and building something that lasts. If I were to win the lottery today, would I even know how to use it to actually improve my life? And why is it that nearly one-third of lottery winners end up broke?

Having money and knowing how to use it are two completely different things. Entrepreneurs who’ve been through the ups and downs—making money, losing it, and then making it again - often build generational wealth. But those who come into quick money without financial knowledge or a clear sense of needs vs. wants tend to lose it just as quickly.

🔧 1. What’s Working for Me

Reframing money as a tool instead of a solution. Asking myself: Why do I want this? What would I actually do with it? The more I clarify the role money plays in my life, the easier it becomes to spend (and save) in a way that aligns with what I value.

🎧 2. What I’m Listening to / Reading

Two books that shaped my thinking on this: Rich Dad Poor Dad and The Psychology of Money. Both explore how mindset and behavior around money matter far more than the numbers themselves.

🌆 3. Life in the City

I’ve been noticing how people around me spend. Some prioritize experiences and self-development, others stretch for status symbols like cars and brands. It’s fascinating to see how different money philosophies play out in day-to-day city life.

💭 4. Thought

If you talk to someone who’s built wealth from the ground up, they’ll tell you it’s a long game. Yet so many of us look for shortcuts - wanting results without the patience it takes to get there.

The irony? Most people who fantasize about winning the lottery don’t even buy a ticket. Not that I recommend it (statistically, you’re more likely to be struck by lightning). But it highlights something: we want outcomes without action.

That mindset often leaves us dissatisfied, when instead we could ask: What’s really holding me back?

What I’ve noticed is that entrepreneurs - those who do build lasting wealth - spend differently. They invest in self-development, education, and experiences that genuinely bring them joy. Compare that to lottery winners or those who inherit money without learning its value - spending big but often ending up empty.

Seeing money as scarce creates fear. Seeing it as a tool creates freedom.

👉 If you’re just starting out with personal finance, I made a video breaking down the basics - from mindset to first steps. You can watch it here.

I’d love to hear your perspective: what does money mean to you, and how satisfied are you with your relationship with it?

And as we build this community, I’d love to know what topics interest you most. What’s one thing you’re currently struggling with that, if solved, could have the biggest impact on your life?

Shermeen

This weekend has been a little frustrating, and I’m finding it quite difficult to be polished and follow the specific format I’ve set up for this newsletter.

The main reason for my frustration is unknown - which is usually the case when multiple things add up - but I’m noticing a pattern to it and figured that could actually make it more relatable. This might end up saved in my drafts forever… unless I’m impulsive enough to press send at the end lol.

Several things, mainly around confusion about what I want to do with my life and how I’m taking care of my health, are contributing to this frustration. But I also find myself procrastinating as a result. I made pasta, cleaned the house, went out for three walks, and fast-forwarded through a movie (Coach Carter) on Netflix, then finished four episodes of Schitt’s Creek. What I wanted to do instead was figure out if I want to pursue an MBA, finish two scripts for my YouTube channel, write up a job description for hiring a video editor, and make a better thumbnail than the one I posted.

The difference from last year, though, is that I still got up early, finished editing the video, and typed up a newsletter - because I promised I’d write it biweekly and the thought of not dedicating time to my own project feels unacceptable in my head. Last year I would’ve delayed it and ended up in bed all day. Which makes me think: we can control our behaviour. For some people, it’s easy. For others, not so much - but clearly it’s possible for everyone. The thumbnail quality of both the video I posted today and this post is below par, I think, but at least I got it done, right? Fixing it can be a problem for another day. Procrastination is the killer of joy, but it can be overcome - and that realization has been like a breath of fresh air.

This post is just a way to let out my feelings while I still feel them strongly. And instead of doing that in my journal, I figured typing it out would be faster.

So, if I end up posting this (and regretting it later), let me know if you relate - and if you have any methods that help you reset on days that just don’t go as planned.

Shermeen

P.S. The one benefit of this frustration is that the newsletter only took 10 minutes to type because I just let everything out. Pretty effective, right?

I came across this quote and it helped bring about a major shift in how I’m planning and strategizing my first goal of reaching $5K a month:

"You can do anything, but you can't do everything."

Managing my time has been one of the hardest things I’ve tried to figure out, and the irony is, trying to get it just right has probably wasted more time than anything else. I’ve spent hours watching videos on time management, trying different techniques, but the pressure to be productive has been tough. And when you’re feeling like time is slipping through your fingers, the guilt and regret that come with it make it even worse.

🔧 1. What’s Working for Me

Regret over wasted time hits hard. I’ve realized that chasing the “perfect” system often just adds pressure. What’s been helping instead is letting go of the idea that there’s one right way to manage time — and just focusing on a few simple steps that actually work for me.

🏙️ 2. Life in the City

I went to watch the tennis ATP Tour over the weekend, and the hot weather almost killed me. Canadian weather is always at the extremes — too hot in the summer and freezing cold in the winter 🥵❄️

💭 3. Thought

If you’re constantly searching for a magic method to finally get things done, you’re not really focused on the work itself. What you’re craving is that feeling of being productive. But the reality is, there’s no perfect system. It’s about figuring out how to get things done in a way that doesn’t leave you feeling overwhelmed or trapped.

So here are the three simple rules I’m following to help me focus, make better use of my time, and stop feeling like the clock is always running out:

Create a Priority List by Quarter

We all want to make the most of the year ahead, but the problem with planning for a whole year is that it’s a long time. If you’re in a phase of your life where you’re trying new things or shifting focus, it can be hard to stick with one plan for 12 months straight. Breaking it down into quarterly goals—focusing on just three key things every few months—helps you stay on track without feeling stuck.

Don’t Keep Your Goals Vague

Ever looked at a restaurant menu with a hundred different options? It’s overwhelming. Sometimes there’s so much to choose from that you end up wanting nothing at all. The same thing happens with vague goals. Saying you want to “be healthy” or “be productive” doesn’t really mean much to your brain.

Use a Calendar

1I used to think scheduling every minute of my day was the key to success. But honestly, that just made me feel trapped—and the second I fell behind, my whole day would fall apart. Now, simply adding items to a calendar makes it so much easier to navigate the days and weeks. It actually gives me a sense of freedom.

Time is something you never get back, and figuring out how to manage it in a way that works for you is the real challenge. You don’t need a perfect system, just something simple and flexible. The more you let go of unrealistic expectations and focus on what truly matters, the better you’ll feel about how you’re using your time—and, honestly, the less stressful it’ll be.

Shermeen

I’ve been thinking back to when I was debating whether to start a YouTube channel — and how wildly out of character that felt. I barely posted on Instagram, deleting more than I ever shared. Making videos? Putting myself out there online? That just wasn’t me. Until, one day, it was.

After quitting my job, I needed a shift. I was anxious, unsure of what was next, and desperate to think differently. So I started doing something I hadn’t done in years — learning for the sake of curiosity. Podcasts, books, YouTubers, creators, events… anything that got me thinking beyond the job titles I was used to. And somewhere in that spiral of exploration, the idea of starting a channel didn’t feel as absurd as it once had.

🔧 1. What’s Working for Me
Studying people who think differently — not just founders, but anyone living intentionally. That energy is contagious. My dad is one of them.

🎧 2. What I’m Listening to / Reading
How I Built This by Guy Raz — the Instagram episode was a good one.

🏙️ 3. Life in the City
Parking in Toronto has been a nightmare these past two days while I rented a car for work. Honestly, giving up my car when I moved here was a solid decision.

💭 4. Thought

Starting something new always comes with fear — fear of wasting time, of failing, of looking stupid. But what’s scarier is staying stuck. The longer I stay in curiosity mode, the more I see how powerful it is to experiment. I don’t always have to know where something is going as long as the steps feel intentional and I know why I’m doing it.

For the first time, that uncertainty doesn’t feel like a problem. But it’s a new feeling — just last year, the fear of posting online and not having it all figured out felt like a huge problem.If you’re also on a path of trying something new, I’d love to hear what you’re working on. What’s pulling your curiosity right now?

Shermeen

I’ve been thinking about all the job interviews I’ve done over the years — from co-op roles and part-time gigs to post-grad full-time jobs — and how much trial and error went into getting better at them. Behavioural interviews in particular have always felt like the make-or-break moment. Even if you’re qualified, it’s this part where you either click... or don’t. I’ve made my fair share of mistakes but also picked up a few things that work — so I figured I’d share what’s helped me the most.

🔧 1. What’s Working for Me
Treating interviews like two-way conversations. When I go in with the mindset that I’m also interviewing the company — not just being evaluated — it changes everything. I’m more present, less rehearsed, and way more myself.

🎧 2. What I’m Listening to / Reading
The Almanack is ready for pick up at the library!

🌆 3. Life in the City
To manage my finances better while also enjoying my time, I’ve stopped my daily Tim Hortons coffee routine. Instead, I go to a nice café to meet up with friends or work every weekend. Adds up to the same amount (or less) for better coffee and more hangout time with people. Win win

💭 4. Thought
Behavioural interviews are really about how you think — not just what you’ve done. When employers ask about past situations, they’re not looking for a perfect answer; they’re looking to see how you react, adapt, and work with people. That’s what makes this type of interview both terrifying and empowering.

What helped me most:

• Confidence: not the loud kind, but the grounded kind that comes from knowing yourself. Interviews used to make me shrink. Now I treat them like real conversations.

• Prep based on the job description: I jot down stories that match the key traits the role asks for. Working independently? Think of a time you did that. Conflict with a teammate? Have one ready.

• Curiosity: A candidate who asks thoughtful questions stands out. It shows you care about the work, not just the offer.

• Clarity: I’ve rushed through so many answers in the past without even understanding the question. Now, if I’m not sure, I ask. And the interview goes way better because of it.

• Communication: You can be brilliant, but if you can’t explain your thinking or connect with people, it’ll hold you back. Practicing how you talk about your experiences is underrated.

If you’re in the middle of a job hunt or gearing up for interviews, I hope this helped! I’ve also shared a few of these tips — plus examples of real questions I’ve gotten — on my YouTube channel if you want to check it out. And if you’ve got a trick that’s worked well for you — hit reply, I’d love to hear it.

I’ve decided on a timeline for these newsletters: biweekly Mondays. Starting to set up a routine and I’m pretty excited about it. So cheers to the end of Q2, and see you two Mondays from now!

Shermeen

If I had a dollar for every time I “started again,” I’d have… enough to buy a matcha and a muffin. I’ve noticed the things we care the most about are the ones that take the biggest hit. I started a newsletter but only wrote a few posts and before I knew it a year was over and it was time to decide if I wanted to continue with my subscription or move to a new platform and start a new routine. I didn’t stop because I didn’t care — but because I cared too much. I also wanted to prioritize my job search but if I’m honest, I definitely had enough time to start something which had I continued would've had enough momentum by now.

Perfectionism and procrastination have been my two most persistent roadblocks. And I’m realizing more and more how connected they are.

🔧 1. What’s Working for Me
Getting specific. Not just “work on newsletter,” but “write about procrastination and perfectionism from 12–1 PM on Sunday.” It’s wild how much easier it is to follow through when the task and time are clear. Vague = delay. Specific = progress.

You might not get to it then too - but you’ll definitely be more aware about the barriers that stop you if you’re specific.

🎧 2. What I’m Listening to / Reading
Nothing at the moment. Taking a short content consumption break but the next item on my list to read is The Almanack. I currently have it on hold at the library but next in line to pick it up!

🌆 3. Life in the City
I tried Venezuelan food last week and it was DELICIOUS. 100% going back.

💭 4. Thought
The pressure to have it all figured out — your niche, your voice, your perfect content plan — is paralyzing. It becomes a barrier to even getting started.

For instance, I like learning and teaching different tools that help with work and personal productivity — but that’s not the only thing I enjoy. So if I gain momentum, how do I balance talking about different topics without worrying that a chunk of the audience might drop off?

Does that matter? Yes — because I want to offer value. But what would I enjoy? That’s the question I keep coming back to. The overall goal — building connection and figuring out my path — hasn’t changed. My “why” is solid in my head. So the rest becomes a matter of trial, error, and conversation. Especially if what I want is a real community.

What’s helped me lately is removing the need for it to be perfect. I decided to just start with what I know — and see what works. Some of my videos surprisingly did. So now, it’s about finding the balance between continuing that and trying out the other ideas in my head: topics I’ve been pondering, bits of my new life in Toronto, things like that.

If you’re navigating a similar loop, I’d love to hear how you’re working through it. And if you’re curious about how I’m building my YouTube channel (slowly and imperfectly), you can check it out here.

Shermeen

I’ve heard that writing regularly builds connection — and doing that online, with the chance to reach thousands, is kind of wild. I’ve tried starting before (procrastination always won), but if something keeps calling you back, it’s worth starting again. That’s what my YouTube channel taught me.

This newsletter will evolve as I find my voice, niche, and direction. You’ll be part of that journey — maybe even help shape it — as I explore how to bring value while building something from scratch. We’ve all seen people figuring things out online… well, here I am now joining that club 😂

🔧 1. What’s Working for Me

Letting go of perfection. The quote “Perfect is the enemy of good” has genuinely shifted how I approach things — especially creative work.

🎧 2. What I’m Listening to / Reading

The Dip by Seth Godin

🏙️ 3. Life in the City

I went to a founders networking event in Toronto yesterday which wasn’t well planned. Left early and got dinner with a friend instead — no regrets.

💭 4. Thought

I’ve had the urge to start something like this for a long time — but like most things, I kept waiting for the perfect moment, the perfect idea, the perfect version of myself. Looking back, I’ve lost count of how many times I’ve said, “I’ve been thinking about it, but I haven’t started.” It’s funny how often we hold back because we’re scared it won’t be perfect — even though the real regret usually comes from not starting at all.

Somewhere along the way, I heard the phrase “perfect is the enemy of good,” and it stuck. It made me realize how often I’ve sat on ideas — not because they weren’t worth doing, but because I didn’t feel ready or didn’t know exactly how to do them. But maybe being ready isn’t the point. Maybe starting — even imperfectly — is. I’ll see how it works out. That’s the mindset I’m bringing with me here.

Shermeen