A friend recently emailed me with a question: His little cousin was being pressured to go to medical school, but the cousin wanted to be a musician — did I have any advice for him? I get questions like this not infrequently, probably because I started off in the same position but wound up in a much different place: I headed off to undergrad intended for medical school (via computer engineering); years later, when I should have been in my second year of residency, I was in a rock band with a hit song on the radio. But then, after that, when I would’ve had a stable practice and career, I was back at school getting a second degree. The consequences are still playing out in my life.
I’ve reprinted the correspondence below, with identifying details taken out. If you want, substitute law school / engineering career / business degree / etc. for medical school, and writer / painter / entrepreneur / playwright / potter for musician. Children of immigrants, or any of you being pushed hard to choose “stable” careers early, this is for you.
Advice on giving advice?
Hey Jeff,
I was wondering if I could ask you advice on something.
My little cousin wants to be a musician, his mom wants him to be a doctor and is pushing him pretty hard for med school.
We grew up together, I’m wondering whether I should encourage and help him down the music track professionally, or down the medical track with music as a creative outlet.
Any advice on what I might say (or should avoid saying)?
Not really sure…
Hope all is well,
—
RE: Advice on giving advice?
Hey —,
Sorry for the delay in getting back to you on this. This is obviously is a bit of a tricky situation; what follows is just from my own experience, and not knowing anything about him or the specifics of the situation.
Being a musician professionally is a hard road — nowadays even harder than it used to be. I would guess your cousin is in college? There is a path for doing what he’s doing, but usually it’s for those writing their own music, and then you just have to keep at it for a looooooooooooooooooooooooong time and be okay with what the lifestyle entails (lots of touring, no stability, no guarantee of success). If you’re at it for long enough you’ll get to a point where you develop a following and your own voice, and there will inevitably be some sort of demand for what you do. But like I said, that is a long road, there’s no playbook, and it’s ultimately about what your vision is.
If he just likes playing cover versions of other people’s music, that’s really a hobby. If he feels compelled to do his own music, and he’s playing all the time even if everyone says “don’t do it,” then more power to him and that’s going to be the answer no matter what you say. Frankly, if he really wants to go for it, he should do it while he’s young. You can always go to med school later in life.
BUT.
Oftentimes when people are raised with a lot of external expectation, they actually don’t know what they want because they usually haven’t been allowed the space to figure it out. If he hasn’t had a lot of time away from his mom’s pressures, or had time to develop as an individual, I would be leery of trying to push one way or another.
The biggest piece of advice I can give is for your cousin to take his time and figure out what he really wants. I don’t think one should rush into big decisions. If he needs to take some time off and try being a musician full-time for a year or so, he should do that (and try to live off what he can make doing that). If he doesn’t like performing in front of people, hustling for gigs, and all the other crap work that it takes, it’s going to disabuse him of any fantasies he might be harboring.
I would also recommend not going to medical school until he knows damn well sure he wants to be a doctor. I know too many people that have wound up as doctors simply because by the time they realized they didn’t want to be a doctor, it was the only viable way they could pay off their medical school debt. Their younger selves mortgaged their future to for something they didn’t want. Why risk it, why all the rush?
If you grow up living up to other people’s expectations, it’s hard to develop your own sense of self, and that’s the most important thing required to figure out what you actually want. I’ve never seen anyone that’s discovered what truly resonates with them pursue it wholeheartedly and not become a happy, fulfilled* individual.
But I would also add that I’ve met very few people that actually know what they actually want or what actually resonates with them in this manner — it takes time and space. Remember that if you work hard over a long period of time, you’ll likely get what you’re working towards. Why pick something you didn’t really want in the first place?
Hope this has been somewhat helpful,
j.
*not necessarily conventional success, but oftentimes they come together
jeffjlin.com 
The first advice I would offer is this: be wary of following the careers advice your college gives you. In journalism school, for example, students are routinely instructed that, though they may wish to write about development issues in Latin America, in order to achieve the necessary qualifications and experience they must first spend at least three years working for a local newspaper, before seeking work for a national newspaper, before attempting to find a niche which brings them somewhere near the field they want to enter. You are told to travel, in other words, in the opposite direction to the one you want to take. You want to go to Latin America? Then first you must go to Nuneaton. You want to write about the Zapatistas? Then first you must learn how to turn corporate press releases into “news”. You want to be free? Then first you must learn to be captive.*
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What a thoughtful reply to your friend’s question.
What I realized reading this is that the risk of taking 12 months off is much lower than the risk of jumping into an expensive grad school program. Being broke for a year is much less risky, financially, than racking up $50k in debt that will have minimal return on investment if you decide not to apply your education.
Yet somehow, parents and society in general tend to push the riskier path under the guise that it is less risky. Weird.
The broader social conversation about the value of college and the crushing burden of student loan debt seems to be our collective attempt to absorb this insight into our conventional wisdom.
Education is not always a good investment.
P.S. $5 says that the cousin’s true career fit is neither medicine nor music – but that opening up the space to ignore the ‘rents will help him figure out what’s really going to work.
P.P.S. Just subscribed to the blog. Great stuff!
Career guidance given to Glen Hansard:
…he told me that he was actually sent out to busk at the age of thirteen by his headmaster at school in Dublin. It’s an unusual beginning for a musical life, given that whenever a musician mentions career advice they received at school, it is usually a bitter story about being told to get a proper job.
“I was very lucky,” admitted Hansard. “My headmaster was also a producer on RTE Radio 2 and he really gave me my break. Cause I was the classic sort of attention deficit student, always in the office, always in trouble. He said to me, ‘Glen, listen, you can tell me the track listing of Bob Dylan’s CDs back to front, you can tell me who plays bass and who’s the guitarist, but you can’t tell me the square root of nine. So you’re a smart kid but you’re not using your education the way that we need you to. So here’s an idea. Go home today, take your guitar, go into Grafton street and start on the very bottom rung of entertainment. Start by being a busker. Come back to me in a year and if it didn’t work out, I’ll take you back into school and we’ll continue. If it did work out, come back to me and I’ll find some excuse to let you go. But for the next year, you’re still in school but you’re doing a different course.’ So I jumped on his advice. I became a busker and I felt the safety of it somehow being part of my education. I ended up hanging out with great people and I soaked it all up. Five years on Grafton street, that was the only education I’ve ever needed.”
http://blogs.telegraph.co.uk/culture/neilmccormick/4349211/Glen_Hansard_Busker_Makes_Good/
That’s great! If only there were more folks like Hansard’s headmaster, my guess is there’d be a bunch more people doing more interesting things. Providing the support to help folks in their early years is pretty invaluable.