Steve Jobs gave a famous speech at Stanford, where he told graduates that the only way to do great work is to love what you do, and that if you haven't found your passion yet, you should keep looking.

Interestingly, Mark Cuban says the opposite: don't follow your passion, follow your effort, because you'll end up loving whatever you get good at.

Who’s right?!

I think they're both right…about themselves. Jobs was obsessive; he only ever did well at things he was obsessed with, so of course that's his rule! Cuban is the kind of person who gets hooked on anything he starts winning at, so that's his.

A lot of advice is like this. Two smart people can tell you opposite things, and both can make perfect sense.

So how do you work out what actually applies to you?

Does this apply to me?

Take another common contradiction which contains good advice on each side: “say yes to everything” versus “say no to almost everything.” If your career has gone a bit quiet - you're not getting many opportunities, you're not trying new things, or you're early in your career - saying yes more is likely excellent advice.

If you already have ten things going on and can’t give any of them enough attention, the exact opposite is probably better. Engineers see this all the time. One team writes about how microservices saved them, another writes about moving back to a monolith, and each was right for its own team size and problems.

When you hear advice or someone tells you to do something: don’t copy the rule, understand why it worked for that person. What problem were they solving? What was true about their situation?

Then ask the obvious question: is that true for me too? Don’t assume something that works for someone else is what you’ll enjoy too.

Start with the boring answer

When I’m confused by a lot of different directions, I love to ask: what’s the boring, obvious answer here?

Take weight loss. You can spend months debating keto, fasting, meal timing, carbs, exercise routines, etc. But what's the boring answer? Eat less. Everyone already knows this. That's what makes it boring.

Which is why I find it pretty funny that Ozempic is arguably the biggest weight-loss breakthrough in decades - and all it does is make you…eat less. Billions in R&D, and the answer was the platitude the whole time. Ha.

I find this useful whenever I’m stuck. What’s the simplest answer here? Am I actually doing that? Why not? There's a well-known essay among programmers called "Choose Boring Technology" that makes the same argument for picking tools.

Boring advice gets ignored because there’s a whole industry built on advice, and the obvious doesn’t sell :) The older I get, the more I realize the boring platitudes are often the best advice.

Can I just find out?

Here's a habit I've ingrained in myself. You're going to have a lot of people telling you what you should do: do this, try that, you have to be doing X.

Instead of taking their word for it or ignoring it, I step back and ask: can I just find out for myself? Can I run a small experiment and get my own answer?

Quick example: a lot of content creators say (no surprise) that creating content is the best thing you can do for your career. I could see it working for them, especially for job searching. I just didn't know if it was worth it for me. So I tested it: posted on LinkedIn consistently, grew a decent following, and paid attention to what it actually did for me. My answer: useful, but not useful enough to keep putting the same energy into it. So I'm less active there now and I don’t wonder about it anymore.

Get into the habit of testing things out in a small way first! If you’re thinking of switching careers, do a small paid gig at a reduced rate first. If you want to build a company, use AI to make a prototype first and try to market it.

Before making any big decision, ask: what could I do that would give me actual data?

We trust confident people, even when they're wrong

The human brain has a pathetic flaw: we routinely mistake confidence for competence.

This is proven in the research too. There’s a 2013 study where people rated statements made with high confidence as far more credible, even when the speaker was demonstrably wrong and had no evidence to back it up.

When someone speaks with absolute conviction on a podcast or in a boardroom, your own instincts wobble. "They sound so sure. Maybe my read is completely backward."

Train yourself to develop an immune response to charismatic certainty. When someone speaks with zero nuance, try to mentally discount their certainty and look at the actual argument underneath. What do they actually know? What evidence do they have?

Use AI to argue the other side

AI can make almost any position sound convincing. Ask whether you should quit your job and it can make a great case for leaving. Ask why you should stay and it can make a great case for that too. A Stanford study published in Science this year found chatbots agreed with people asking for personal advice about 49% more often than humans did.

So I find it more useful as a sparring partner than an oracle. If I’m leaning one way, I’ll ask it to make a case for the opposite, point out what I might be assuming, and tell me what information would change the answer. It helps me stay grounded and make up my own mind!