The Only Honest Career Advice
Entrepreneur Office Hours - Issue #345
Inside the Office
It’s orientation week at Duke, which means I’ve spent the past few days bouncing between lunches, receptions, panels, and other events welcoming freshmen to campus. And across all those conversations, I keep getting some version of the same question:
“How did you get to the career you have now?”
To be fair, students have been asking me this question for years. But until recently, I mostly assumed it was polite small talk… basically the career equivalent of discussing the weather with a stranger in an elevator because neither of you knows what else to say.
But, this year, I’m starting to think I’ve been wrong because I’ve noticed the question isn’t happening during awkward silences. Instead, I’ll be having a perfectly delightful conversation about classes or Duke basketball or where someone is from, and suddenly the student will redirect everything toward my career.
“So… how did you wind up doing what you do?”
To be clear, I don’t mean they’re being rude. They’re not cutting me off mid-sentence or anything like that. But they’re definitely being urgent, and they seem to think I have some secret treasure map to career success that I’m playing coy with by refusing to share it immediately.
Not that I can blame them. These students are showing up at college at a time when the entire world seems to be warning everyone that AI is eliminating all the entry-level jobs, reshaping every industry, and, in general, ruining whatever career aspirations they might have been carrying since second grade. Surely that feels terrifying.
Unfortunately, the only answer I have for them is wildly unsatisfying. I basically just tell a rambling story about my own career journey, which is really just a very long way of saying the only honest answer…
Time.
Sure, I have a career now that I’m proud of and enjoy. But it’s not the career I had when I graduated. Nor does it look anything like the career I imagined.
Instead, I’m officially old enough that I graduated from Duke before the freshman I’m meeting this week were born, which means I’ve been working on my career longer than they’ve been alive. And, on Day 1 of that career — the day after I graduated from Duke — it didn’t look like much of a career because I graduated without a job.
I’m not recommending that strategy. But I like to think it does a good job of making my point.
Simply put, careers don’t get “figured out.” They accumulate and evolve. You take a job, learn some stuff, meet some people, discover what you like and don’t like, and slowly but surely you move to another opportunity, then another, and another until gradually, and usually without realizing it, you build something that appears coherent and linear from the outside.
For what it’s worth, the same thing happens with startups, too. New entrepreneurs tend to imagine a startup journey as a linear path with a clear instruction manual. But that’s not how it works. Even the famously “fast” entrepreneurial successes took years. Heck, being fast is a big part of what makes them famous… the speed is the notable aberration.
That’s also true for everything important in life. Careers work that way. So do companies and relationships and families. All the most important things in life grow strangely and almost always a lot more slowly than you think or hope. But, eventually, and if you’re lucky, they grow into something you’ve enjoyed.
More importantly, there’s no instruction manual on how to get there. Or, if there is, I’ve certainly never seen it. All you have is time and your willingness to keep pushing forward.
While I realize that’s not a particularly helpful answer for an 18-year-old staring down an uncertain future, it’s the most honest one I can give.
-Aaron
Worth Your Time
For the past however-many-years, whenever I go to the gym I listen to a podcast. However, I’ve recently pivoted toward audiobooks. Maybe it’s because I got tired of listening to people in their 500th episode struggle to fill the space. Or maybe it’s because I discovered I could download free audiobooks from my local library. Whatever the case, it’s been a fun change.
Or rather, it was fun until I made the mistake of listening to a book called When Breath Becomes Air, which also happens to be the book I’m recommending this week.
I can almost hear you through your screen: “But Aaron… why are you recommending this book to us if it was a mistake for you?”
The mistake wasn’t choosing the book. The mistake was where I chose to listen to it.
When Breath Becomes Air is a memoir written by a young and highly promising neurosurgeon who, around 35 and right as he was about to approach the pinnacle of his career — the one he’d spent so many years working toward — suddenly developed stage four lung cancer.
I don’t think I’m spoiling anything by telling you it doesn’t end well. Now, imagine what I looked like trying to lift 80 lb dumbels over my head while weeping.
Despite that challenge, it’s an incredibly moving story, absolutely worth a read (or listen), and I thought it was a particularly relevant text to share alongside my above story about new Duke students feeling anxious over their careers.
Yes, careers matter. But some things matter more. And When Breath Becomes Air is a good reminder of that very important lesson… even if it’s a lesson you probably shouldn’t try to learn while doing curls.