It has now been almost two years since I made one of the biggest decisions of my life — to step fully into the world of entrepreneurship. As I write this, I’m reflecting on the twists, surprises, disappointments, and small victories that brought me to where I am today.
If someone had told me in 2016 or even 2019 that I would one day be a full-time retail investor, trader, content creator, and global traveler building something called Streetwise Economics, I probably would have laughed. But life has a strange way of guiding us toward what we are meant to do, even when we are determined to follow a completely different plan.
From Zimbabwe to Vancouver: A Different Dream
My journey didn’t begin with entrepreneurship in mind.
I worked in Zimbabwe, gained meaningful experience, and eventually moved to Canada to pursue graduate studies. At University of British Columbia (UBC), I completed not one, but two master’s degrees — a period that shaped me intellectually and personally. At that time, my ambitions were straightforward: I wanted to work for major international institutions like the World Bank, IMF, or AfDB.
I applied. I tried. I pushed.
But life had other plans.
For a long time, I didn’t understand why doors weren’t opening in the places I thought I belonged. Today, looking back, I realize those closed doors were quietly redirecting me toward a path I didn’t yet have the courage to see.
Discovering a Different Passion
Somewhere along the journey, I discovered something unexpected:
I was deeply fascinated by wealth-building, financial markets, and the psychology of investing.
I found myself spending more time analyzing publicly listed companies than preparing for traditional job applications. I became consumed by how businesses grow, how markets behave, and how everyday people can build wealth through smart investing.
Nearly two years ago, I made a decision that surprised even me:
I chose to take the entrepreneurial route and make full-time investing, trading, and content creation my primary focus.
It wasn’t glamorous.
It wasn’t predictable.
And it certainly wasn’t easy.
The Hardest Year: Adjusting from Employee to Entrepreneur
The transition from being a manager — leading teams, following structure, reporting upwards — to becoming my own employer was one of the most difficult psychological shifts I’ve ever experienced.
In my first year of trading (2024–2025), I made almost every mistake a new trader makes:
- Trying to make money too fast;
- Overtrading;
- Buying into the illusion that intelligence alone beats markets;
- Underestimating risk;
- Overestimating my emotional discipline.
It was humbling. Painful at times.
And yet, it was one of the most important phases of growth.
Interestingly, my investing portfolio — the long-term one where I simply bought and held great businesses — performed far better than my overactive trading. That realization was almost funny. But it also taught me something essential:
Success in markets doesn’t come from speed — it comes from patience, discipline, and simplicity.
That lesson changed everything.
Becoming a Better Investor
As my trading mistakes piled up, I didn’t quit. Instead, I decided to improve:
- I studied more.
- I tested more data.
- I refined my risk management.
- I started using options more strategically — not recklessly — to hedge risk and create income.
- I focused only on companies I understand deeply.
The more disciplined I became, the more consistent my results improved.
Today, my trading account is beating the S&P 500, which remains my benchmark. That doesn’t mean I’m a genius. It just means I’m finally beginning to respect the market for what it is — a long-term game of patience, behaviour, and strategy.
Learning Every Day (Humility Required)
Markets will always humble you.
There’s a saying: “Everyone looks smart in a bull market.”
I don’t want to fall into that trap.
This letter is my attempt to document the journey as it unfolds — the wins, the mistakes, and the lessons — so that years from now, I can look back and see how far I’ve come, or what I still need to learn.
Building Streetwise Economics: The Unexpected Path
Alongside investing and trading, something else happened unexpectedly:
I started creating content.
At first, it was just an experiment — a way to share what I was learning, mostly for fun. I didn’t think it would go anywhere. But slowly, people started watching. Some resonated with my work. A few reached out for coaching.
I began interviewing people I admired. I built relationships. I learned to reach out boldly, to ask for conversations, to embrace rejection, and to be patient with others’ time.
Content creation became a “wild card” in my journey — not something I planned, but something that has brought me deep fulfilment.
Traveling the World: Seeing Life Through a Bigger Lens
Another unexpected gift of this entrepreneurial path has been travel.
By the time you read this letter, I should be in Europe for a business trip and a family vacation.
Travel has become one of my greatest teachers.
Observing economies, lifestyles, and different cultures has shaped my understanding of global investing and life in general. It has broadened my perspective and sharpened my curiosity.
I always learn something new when I travel — sometimes about money, sometimes about people, and often about myself.
The Quiet Wins
Entrepreneurship has taught me that sometimes it feels like you are working in silence, but people are watching. Opportunities arise quietly. Respect builds gradually.
I’m learning to trust the process.
To fall in love with the craft.
To keep showing up.
And the truth is: I am happier now than I have ever been.
Not because everything is easy — it isn’t.
But because I am finally doing something I’m passionate about.
Realizations After Two Years
Here are some of the lessons that stand out so far:
- Learning never stops.
- Markets reward discipline, not emotion.
- Humility is part of survival.
- Patience is underrated.
- Passion needs structure.
- People notice silent consistency.
- Confidence grows by doing, not thinking.
- Relationships matter — deeply.
- It’s okay to start over.
- Flexibility is a blessing.
Above all, I’ve learned that life is not linear.
If It Doesn’t Work? I’ll Always Be Okay
I am fully committed to this path, but I’m also realistic.
If it doesn’t work, I can always return to traditional employment. My education, experience, and skills won’t disappear.
But for now, I’m embracing this season with everything I have.
Because the truth is, I love the freedom, flexibility, learning, growth, travel, and challenge that come with building something of my own.
What’s Next
I have exciting projects coming up — some already in motion, some still in the planning stage.
You can follow everything at: www.streetwiseeconomics.com
This journey is far from over.
If anything, it feels like it’s just beginning.
Thank you for reading this letter.
I hope it inspires you to pursue something you’re passionate about — even if it scares you, even if others don’t understand, even if the path isn’t guaranteed.
One day at a time.
One lesson at a time.
One step forward.
See you in the next letter.
— Isaac Jonas
Founder : Streetwise Economics
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