My Biggest Lesson From a Month in Silicon Valley
Entrepreneur Office Hours - Issue #285
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Right before writing these words, I finished drafting the final lesson plan for the four week entrepreneurship class I’ve been teaching in Silicon Valley. Tomorrow is the last day, and… well… I have thoughts.
Thoughts about Silicon Valley.
Thoughts about teaching a four week, intensive entrepreneurship class.
Thoughts about being away from home for a month.
Thoughts about In-N-Out.
In short, I have lots of thoughts. But your time is valuable, so I’m going to condense all of those thoughts into one core message that’s my key takeaway from this experience: Try things.
Simply put, that’s what Silicon Valley is all about. It’s not about certainty. It’s not about polish. It’s not about always getting it right.
It’s about trying.
Trying to build something new.
Trying to learn faster than you’re comfortable with.
Trying to live in a place that doesn't feel like home… yet.
That’s what I watched my students do for the past month. They didn’t start companies or launch apps. They didn’t need to. They tried something harder.
They tried living with new people.
They tried showing up every day in a new city.
They tried asking questions they didn’t know how to answer.
I tried, too. I tried teaching a class I’d never taught, in a place I don’t live, surrounded by tech I don’t worship. I tried being a different kind of professor — not just the kind with lesson plans, but the kind who can sit next to a student on a bus and chat for an hour about nothing related to what he’s teaching.
To be clear, none of it was perfect. (Far from it.) But the point of trying isn’t perfection. The point is learning.
And that’s my biggest takeaway from a month in Silicon Valley. I realize everyone has an opinion about what makes it a special place (or why it’s not a special place), but my opinion — for what it’s worth — is that this is a place where trying is celebrated almost as much as succeeding. And if more places operated with that kind of mentality, I suspect we’d all be living in a better world.
-Aaron
This week’s new articles…
The Mayor of San Francisco Is Teaching a Startup Lesson Most Founders Learn Too Late
Is the city that’s been making headlines for the wrong reasons using some startup hustle to get back on track?
Apple’s Eddy Cue Just Taught Me the Most Important Word in Entrepreneurship
One of Apple’s most senior employees took an hour to teach me and my class a lesson I’ll never forget.
Office Hours Q&A
QUESTION:
Hi Aaron – This is maybe a weird question, but I’ve been running my startup for about a year now, and one of the strangest challenges I didn’t expect is how lonely it feels. I’m constantly surrounded by people in terms of work with customers and employees, but I still feel like I’m doing everything alone. I don’t really have peers I can talk to, and I’m starting to wonder if this is normal? If so, what do you do about it?
Thanks,
Jordan
Actually, it’s not a weird question at all. In fact, it might be one of the most normal questions a founder can ask. (And maybe that’s the weird part.)
From the outside, entrepreneurship definitely looks like a hyper-social, high-energy thing. You're emailing, Zooming, Slacking, pitching, hiring, selling. It’s constant motion and constant interaction. But, on the inside, it’s wildly lonely.
So yes, the question you’re asking is normal. I’d go so far as to tell you it’s painfully normal. Even worse, the more responsibility you carry, the fewer people you can talk to about it. After all, it’s not like you can be fully transparent with your employees or your customers. And even if you’re lucky enough to have a close cofounder, that relationship can come with pressure to keep yourself together when things start wobbling.
Unfortunately, loneliness is just… kind of the way things are naturally structured. But here’s my question for you: What if loneliness is more of a feature than a bug?
Remember that founders are, in a sense, what we might call “scouts of isolation.” They’re constantly venturing ahead of the crowd, trying to build something that doesn’t exist yet. You’re walking paths before they’re paved, explaining visions no one else can see, so of course you feel lonely. That’s what trailblazing is.
What if the goal isn’t to fix the loneliness? What if the goal is to understand it?
The best founders I know don’t eliminate the feeling; they learn how to work with it. They turn it into a kind of signal telling them: “If this feels hard and strange and alienating… I might be on the right track.”
To be clear, I’m not encouraging you to wall yourself off. I’m just reminding you that a founder’s job isn’t to be surrounded. It’s to be ahead, and being ahead is lonely. But it's also the point.
So instead of asking, “How do I stop feeling lonely?” maybe ask, “How do I listen to what my loneliness is trying to tell me?” That’s where the good stuff is.
Got startup questions of your own? Reply to this email with whatever you want to know, and I’ll do my best to answer.