The Dark Side of Doing What You Love

Why chasing your dream doesn’t always feel like a dream

Author

Sammie L
July 05, 2025

What if doing what you love doesn’t make you happy?

But how can it not be?

A recent speech by Jensen Huang, CEO of NVIDIA, got me thinking.

There’s a phrase that says ‘you should choose your career based on your passion.’ And usually people connect passion with happiness but there’s something missing. when you want to build something great, it’s not easy to do. And when you’re doing something that’s not easy to do, you’re not always enjoying it. 

I don’t love every day of my job… And every day I’m not happy… But I love the company every single second. I think what people misunderstand is [they think] the best jobs are the ones that bring you happiness all the time.

You have to struggle. You have to do those hard things and work through it in order to really appreciate what you’ve done. There’s no such thing that is great that was easy to do.

It reminded me of why I started in the first place…

I’ve said it over and over:
“I love making videos.”
And I really do. It’s the dream I’ve chased for years. But chasing your dream doesn’t mean it always feels good.

Febuary 2019, SFU Campus

I was walking around campus before class and noticed a sign for Media Minds, a film-based after-school program. It said, “No experience needed.”
I had just taken a film analysis course — one of the only classes I genuinely liked — so I thought, why not?

I didn’t know it yet, but that tiny decision changed everything.

To help lead the workshops, I had to learn how to film and edit.
That’s when I discovered my passion.

Growing up, I wasn’t the kid who stood out. I definitely didn’t have straight As or win any awards. I didn’t have any special talents. I just felt like a very ordinary kid.

But the first time I opened Premiere Pro I was immediately hooked.

I remember dragging clips onto the timeline, layering music under a shot, trimming one second off and I felt immense joy.

For the next few years, I’d sit at my computer for hours, obsessing over 2-second cuts. (ADHD peeps, you know how rare that kind of focus is.)

And when I’d finally export a video? I felt accomplished.
That sense of pride — the one I never found in school — I found in storytelling.

May 2025, Bali, Indonesia

Three months after leaving Canada to chase this dream.

I was sitting by the pool at a gorgeous Airbnb, birds chirping, a breeze on my face.
On paper, everything was perfect.

But inside, I felt… numb.

In my journal, I wrote:

I want to suffer. I want to go through hard things.
Because you don’t get to feel your highest high without your lowest low.

Lately, I’ve been filled with self-doubt.
Initially I thought building a following would quiet the fear.

But honestly, it’s gotten louder.

I’ve been procrastinating on this new video series for weeks.
Why? Because I’m afraid of mediocrity.
The more I scroll and see everyone else’s work, the more I feel like an imposter.

And I’ve been asking myself:

Why don’t I feel happy doing the thing I always said I wanted?

And I think I’m beginning to understand.

Pursuing your passion doesn’t mean you’ll be happy all the time.

It means the lows hit harder because this matters to you.
You’ve tied your identity to this thing.
So when it flops, it feels like you’re the one who failed.
I’ve been afraid of putting things out there…
What if it’s not good enough? What if I’m not good enough?

But today, I’m finally going to film.
No more overthinking in my head.

Just me sharing lessons I’ve learned since leaving Canada.
The raw, the uncertain, the real.

By the way, this isn’t July’s official newsletter (that’ll hit your inbox in early August).
Just something I needed to get off my chest.
Thanks for being here :)

With love,

Sammie