If you spend time around musicians, may not hear the phrase exactly.
“When I make it…”
But if you were given access to their personal narratives for even a little while, I’m fairly certain you would encounter the dialogues around “I’ll know I’ve made it when…”
It may be half joking. Half serious. Fully hopeful.
I’ve spent more than twenty years on the indie side of the music business – touring in a van across frozen highways in February, running a small label, booking tours, managing artists, promoting shows in rooms that were either beautifully electric or painfully empty.
And I can tell you this with complete certainty:
No version of “making it” is the same. We generally don’t know what it means.
We just know we want it.
The Promise We’re Sold
From the outside, “making it” looks obvious.
- a JUNO.
- a tour bus.
- a gold record.
- a blue checkmark.
- a sold-out theatre.
But the music industry has always sold a simplified version of success because simple stories are easier to market.
- you get discovered.
- you blow up.
- you tour the world.
- you’re financially set.
That story works in headlines. It rarely works in real life.
What I’ve seen instead – and what we explore constantly on Almost Famous Enough – is something far more layered.
There Are Levels to This
There are artists who:
- Had a radio hit but couldn’t replicate it.
- Tour steadily and make a modest, sustainable living.
- Built loyal niche audiences without ever charting.
- Signed deals that looked impressive but weren’t financially stable.
- Became “known” but never secure.
And here’s the part that surprises people:
Many of them technically “made it.”
They reached the goal they once dreamed about.
And yet… the story didn’t end there.
Because the industry doesn’t hand you a permanent badge that says You’ve arrived.
Success in music is almost always temporary, cyclical, or evolving.
You don’t make it once.
You make it in seasons.
The Canadian Reality
In Canada, especially Western Canada, the idea of “making it” carries even more weight.
We grow up geographically removed from the major industry hubs. Touring here is expensive. Markets are spread out. Winters are long. Grants matter. Community matters.
For many Canadian artists, “making it” quietly means:
- Getting FACTOR funding.
- Securing national radio play.
- Playing a festival slot at 6:00 PM instead of noon.
- Selling 300 tickets consistently.
That might not look glamorous on Instagram, but inside the ecosystem, those are real milestones.
And yet even there – once you reach one milestone, another one appears.
The horizon keeps moving.
The Middle Space
There’s a category of artist I find endlessly fascinating.
- they are recognizable.
- they’ve toured nationally.
- they’ve had press.
- they’ve opened for major acts.
They’ve built something real, but they are not household names.
This middle space is psychologically complicated. You’re visible enough to feel pressure, but not visible enough to feel secure.
You’ve achieved something, but not the thing you once imagined.
And here’s the quiet truth:
This is where most careers actually live.
Not at the top.
Not at the bottom.
But in the middle.
What “Making It” Actually Feels Like
On the podcast, I’ve noticed something consistent when guests talk about their breakthrough moment.
It rarely feels cinematic.
It feels fragile.
- A tour that could collapse if ticket sales dip.
- A label deal that comes with compromises.
- Momentum that needs constant maintenance.
There’s pride, yes. Gratitude, often. But also anxiety. Because “making it” doesn’t eliminate uncertainty.
It just changes its shape.
The stakes get higher.
The visibility increases.
The expectations multiply.
You trade one set of problems for another.
The Long Game Nobody Talks About
What fascinates me now is longevity.
Not flash.
Not virality.
Not the moment.
Longevity.
The artists who are still creating.
Still touring.
Still evolving.
Still connected to why they started.
Many of them didn’t “blow up.” They built something steadier.
A career that supports a family.
A catalogue that keeps working.
A reputation that opens doors.
And sometimes, from the outside, that doesn’t look like making it.
But from the inside?
It often feels far more sustainable.
The Generational Conversation
Hosting this show alongside my daughter adds another layer to this conversation.
At 20, the industry looks wide open. Digital platforms remove gatekeepers. You can build an audience from your bedroom.
That’s exciting. And it’s real.
But the core tension hasn’t changed.
You still need resilience.
You still need relationships.
You still need to survive the emotional swings.
If anything, the comparison culture has intensified the illusion of “making it.”
Because now success is quantified in public.
Streams.
Followers.
Views.
But numbers don’t tell you:
Who is financially stable.
Who is fulfilled.
Who is exhausted.
Who is quietly building something meaningful.
So What Is “Making It”?
After two decades on the indie side – and countless conversations with artists who have chased the dream from every angle – I’ve come to a different definition.
Making it is not fame. Being known is incomplete.
Making it is not virality. Nobody trusts it.
Making it is not a single moment.
Making it is:
Doing meaningful work.
Building real relationships.
Creating something you’re proud of.
Surviving the inevitable disappointments.
Simply surviving – and being able to continue.
If you can continue – creatively, emotionally, financially – you’re doing better than most.
The Sweet Spot
There’s something strangely beautiful about being comfortably in the middle.
You get:
- The connection.
- The stories.
- The community.
- The art.
- The growth.
Without always losing yourself inside the machine.
Not everyone who “makes it” keeps their joy.
Not everyone who goes viral keeps their identity.
Not everyone who becomes famous keeps their freedom.
But many artists in that middle space?
They build lives.
And sometimes, when I look back at my own years in vans and venues and small offices trying to piece things together, I realize:
We might have been closer to “making it” than we thought.
Just not in the way we imagined.