derisk first, then follow your heart
Following your heart isn't great advice. Neither is following your highest excitement. Not for all of us.
You can follow your heart—but only if you’ve figured out how to land safely. Otherwise, the fall can break more than just your dream.
There’s a fat asterisk next to all those romanticized “follow your heart” narratives. Some of us are born with the circumstances to follow our passions unhindered. Many of the most accomplished artists and the richest entrepreneurs grew up with a net underneath them. When your downside is capped to failure -- not financial and personal ruin -- it is the best circumstance in which to pursue your dreams.
Yes, it's a class issue. Also, it's not a reason to stop dreaming. We'll get to that -- but first let's talk about following passion.
If you follow your passion blindly, you might run into a street pole (side note: I've done this in real life and had to go to the hospital for it). You have to know what you're getting into. If you don't have ways to protect yourself, following your passion can actually lead you to places you don't want to be.
Let me illustrate what I mean.
Years ago I spoke to a college professor who followed his passion in music. He taught sound design at a prestigious university. I was full of curiosity and asked him about his career -- hoping to hear a story of triumph. It was the opposite -- deflating. He was underpaid, not really doing work he enjoyed, and frustrated with the limited prospects. Following his passion wasn't all it was cracked up to be.
It wasn’t the fairy-tale ending he'd hoped for. But that’s only part of the story.
Now, let's touch back on the issue of circumstance. You grow up poor -- or just not rich. Finances are something you need to pay attention to in order to survive (and survival isn't owning a luxury apartment in New York or SF). If you fail when you follow your passion, your circumstances will materially limit your quality of life.
So how do we make this work? Not by giving up—but by adapting.
Adjusting your dream to meet your circumstances is a very mature and respectable path. Your adjustment may be changing the nature of the dream. It may be postponing it. That's up to you.
But step one, get on the playing field to go for your dream. Derisk yourself.
Rome wasn't built overnight, and neither is your legacy as an artist. Skill takes time. So does success. If you're born into privilege, that time is often given. If not, you have to carve it out.
Find your way to have money, a happy place to live, and time to pursue your craft. Be your own trust fund parent -- even if your funds and your time are limited. One part of you is the patron, and the other part is the artist.
Moonlighting is a respectable hustle, but it often drains the exact energy your art needs most. If you can carve out even six months where your art gets your best hours—not your leftover ones—you’ll build momentum faster.
Follow that highest excitement, but do so in a way that you would for your own child. Make sure you are guiding that little one and creating a good life for them.
Following your heart is beautiful—but building a home for it is crucial. It's one of the most compassionate and responsible things you can do for your inner artist.