One of the best parts of writing this newsletter is the replies. People send all kinds of stuff — nice messages, career wins, questions they're wrestling with. I try to address them when I can, either by replying or working them into future essays.
But there's an interesting pattern I see a lot in questions I get:
A lot of people are not really asking for advice. They're asking for permission to do what they already know they should do.
For example:
"I hate my job, my boss is toxic, and it's affecting my mental health. I’m not sure what to do. Help?"
→ Answer: Look for another job
“I REALLY want to start a side hustle, but I don’t feel I have the time. What should I do?”
→ Answer: Make time for the side hustle.
“I want to grow my network on LinkedIn, but I don’t know what to post about. What can I do?”
→ Answer: Write what you know about and love.
(oh and side note, optimize your LinkedIn first using this free tool)
The answers are often surprisingly simple. If a friend came to you with these problems, you'd tell them the answer immediately. So why do we struggle to tell ourselves the same thing?
🧿 The Trust Issue
I used to do this constantly. For every decision — even small ones — I'd ask everyone for their opinion. But looking back, I knew what felt right each time.
When we ask these questions, we usually already know the answer. We just want someone else to confirm it because:
We don't trust our own judgment.
It’s a big problem.
If we need other people to make decisions for us, are we ever really in charge of our careers?
Worse, when we're always looking for input from others, we often end up stuck. You ask one person, then another, then another... get conflicting opinions, and end up more confused than when you started.
What should you do instead?
👥 The Friend Test
We're great at solving other people's problems. But terrible at solving our own.
This is actually well-documented — it's called the Solomon Paradox: we give wiser advice when we have distance from the situation.
The solution:
Pretend that your best friend’s in the situation that you’re in. What advice would you give them? Your ideas will probably be bang on.
(Try this now so you remember this technique: What's something you're stuck on? If your friend came to you with the same thing, what would you tell them?)
👨🏻🏫 Act as your own mentor
Putting yourself in the shoes of a mentor can often be much more insightful than asking the mentor themselves.
Here's what I mean. Pick someone whose thinking you admire — could be a past manager, a podcaster you respect, a famous founder, your wise grandmother, whoever. Now ask yourself: if I brought this problem to them, what would they tell me?
You'll probably have a decent answer with that simple question. You've absorbed more of their thinking than you realize.
But there's a way to make this even better: use AI.
I do this a ton. If I wanted to ask Jeff Bezos a question, I can just upload a bunch of his writing (i.e. he wrote a lot of shareholder letters as CEO of Amazon) to ChatGPT, and ask: “Based on how you think, what would you tell me to focus on?”
The answers are ridiculously specific. You can upload books, podcast transcripts, and even YouTube videos (on Gemini), and ask questions as if the author is coaching you directly.
🥷🏿 YOU are the expert
Why do we turn to others for answers?
Because we assume they know something we don't. And sometimes that's true—your doctor knows more about medicine, your mechanic knows more about cars.
But when it comes to your own life and career, you're the one with the full picture. You know your situation, your goals, your fears, what you actually want.
Even your best mentors are working with incomplete information. They're giving advice based on what you've told them, filtered through their own experiences.
You are the expert on your own life. Trust that.
🫀 Trust (and train) your gut
Gut instincts are usually right.
Why? They're not coming from your conscious mind with its limited processing power. They're coming from your subconscious, which draws on everything you've ever experienced, and pattern-matching you're not even aware of.
So ask yourself: what does my gut say? What feels right, even if it scares me a bit?
That last part is key. Often what we interpret as fear is actually our gut pushing us toward growth.
And trusting your gut is like a muscle. The more you use it, the stronger it gets.
🙋 So should I never ask for help?
Not at all! Definitely ask for help. Getting input is valuable, especially for big decisions. Multiple perspectives will broaden your thinking.
But use advice to supplement your judgment, not replace it.
The more we outsource decisions to others, the weaker our own judgment becomes. We start needing permission for things we're perfectly capable of deciding ourselves.
And most of the time, we already know the answer. All we're missing is the courage to act.
I hope that gives you a toolkit to handle pretty much any decision you’re faced with. And that you got a few laughs along the way.
