8 min read

Be Wary of Life Advice, Look Inwards Instead

Be Wary of Life Advice, Look Inwards Instead

In April of 1958, Hunter S. Thompson was 22 years old when he wrote this letter to his friend Hume Logan in response to a request for life advice. Read the full text here. For me, the following blurb is most compelling:

Beware of looking for goals: look for a way of life. Decide how you want to live and then see what you can do to make a living WITHIN that way of life.

But you say, “I don’t know where to look; I don’t know what to look for.”

And there’s the crux: Is it worth giving up what I have to look for something better? I don’t know— is it? Who can make that decision but you?

But even by DECIDING TO LOOK, you go a long way toward making the choice.*

I see many young adults today looking to others for life advice, similar to Hume Logan. And I don’t blame them, outside advice is seductive – it’s faster to learn from the experiences of others than to derive everything from scratch yourself.

But outside advice is also a double-edged sword. For well-defined problems (objective, repeatable), outside advice lets you efficiently reap the rewards of other people’s knowledge (e.g. Googling which entry-level sedan to buy if you care about fuel efficiency). However, for poorly-defined problems (subjective, unrepeatable), asking for outside advice means you’re unconsciously welcoming in their biases, priorities and values. You know what I’m talking about. Think of a time you received a raving restaurant recommendation but then found yourself underwhelmed – just because your friend thinks everything is better in a burrito doesn’t mean you do too. You unconsciously welcomed in this value of theirs.

For the many inconsequential poorly-defined problems in life (like what we should eat for lunch), getting “trojan horsed” by other people’s values is harmless and occasionally surprisingly enjoyable. Thus, people don’t bother to consciously label whether a decision at hand is well-defined or poorly-defined problem.

So what happens when we run into a consequential poorly-defined problem, where following someone else’s values could set your entire life on a trajectory that makes you feel miserable at worst? You must make your own decisions in life. Asking for advice is a very human and very dangerous thing to do.

All advice can only be a product of the person who gives it. What is truth to one may be disaster to another. Only you see life through your eyes. Asking for specific advice about what to do with your life is akin to asking the blind to lead the blind.”

The decisions you, I and everyone else have to make about our life directions form the lion’s share of consequential poorly-defined problems we’ll ever encounter. And I’m here to share insights about how to better grapple with these decisions.


Look inside first when making a poorly-defined decision!

Poorly-defined decisions are subjective – a good decision for you won’t be a good decision for everyone else. In fact, a good decision for you today may not be a good decision for you in the future (e.g. younger people should be more open to taking calculated risks because they have more time to recover if things go poorly).

For consequential subjective decisions, be wary of the trojan horse.

Your main goal is to make a decision that aligns with your values. So the first step is to articulate them. This way of thinking is different than hopping on Google or asking your friends or family for advice, but is the most intentional.

But this is not to say that you should never ask others for input when making subjective decisions, especially if they’re consequential. For these decisions, look for insights and experiences from people who share some of your values, rather than their explicit suggestions for how you should act. By first articulating your values, you’ll be able to filter outside advice for relevant wisdom without distracting or outsourcing your internal decision making process. It’s like panning for gold.


As you look inside, recognize your values are always shifting!

“Looking inside yourself” is an overloaded phrase. And “values” is an overloaded term. Yet I’m going to use both of them here to respectively mean “introspect and reflect” and “your judgement of what is important in life”.

An insight I’ve gained about values is that they’re both subconscious (meant to be discovered) and improvisational (deliberately experimented with).

You should first discover values you have. These are formed through lived experiences and passed from family, friends and community. It’s like an archaeologist unearthing fossils. One important thought for another time: it’s important to delineate between values that are sincere beliefs and values that are defensive narratives, and a licensed talk therapist can help.

You should then deliberately experiment with new values you aspire to or are intrigued by. For example, maybe you admire the extroverted people in your life and wish your introverted self could taste that level of confidence. Lucky for you, I believe that “faking it till you make it” is perfectly applicable to our values since they’re derived from our lived experiences. Experience it enough and you’ll start to think of yourself as extroverted.

Articulating your values through discovery and improvisation is a continual process, as long as you are living, breathing and experiencing. Thus, your values are always shifting, and that’s a good thing!


As you make decisions according to your values, think of your life as a map, not a ladder!

When you face a consequential poorly-defined problem like a major life decision (e.g. what career path to pursue, where to live, who to marry), make your decision according to your values as you currently understand them. Some life paths prioritize exploiting your known values, and others prioritize exploring new values. The decision is yours to make. The only bad decision is one that blatantly violates your known values. Think of your life as a map.

Living according to your values is different than chasing pre-defined goals and outcomes (e.g. landing a prestigious job, living in Manhattan, marrying a celebrity). Pre-defined goals assume your desires/values are static. They may wilt or lose their charm as you progress through life, and slowly but surely you'll find yourself more and more out of touch with your desires. Don’t think of your life as a ladder with a fixed goal. Don’t see your life as a series of decision nodes where you maximize happiness or wellbeing ahead as best you can.

Before charting a route through life’s map, you should consider what type of journey you will enjoy the most:

  1. Who should you ask to come with you on the journey? (friends and lovers)
  2. How should you treat your fellow travelers? (interpersonal values)
  3. How might you experience your journey if you come up with an itinerary based on the group’s shared desires and not just what you want? (ensemble mindset > center of universe mindset)
  4. What values are you interested in exploring and how might you implement them on the journey? (faking it till you make it)
  5. How do you make room for serendipity and recognize the unexpected is to be expected? (optimizing for unplanned lived experiences)
  6. Do you have the courage to let the path emerge and unfold without having full control? (live like an artist; let the destination be shaped by the journey)
  7. Do you have the courage to let your identity emerge as well as something organic instead of mechanical and planned? (lessen the weight of societal expectations)

These questions are not problems to be solved, but mysteries to be experienced, tasted and savored.

A quote from Jason Shah on Lenny’s Podcast:

There's the framework I like is ladder versus map, and I think that you can be either person that any point in your life. Sometimes there's a bit of a set mindset that somebody might have one way or another, but I like ladder versus map. Ladder is about moving up. It's more influence, more power, a higher title, things like this, whereas map is I just want to go wherever's interesting, right? I literally think of it, I think of my career very similar to travel. I want to go to Greece. I want to be hungry, walking around in India, sweating in a hundred degree weather. I want to go to Australia and kind of get locked out of my hotel and see what that's like. I'm okay with discomfort because it's interesting. Sometimes, for better or worse, maybe this is a privilege, it's certainly a privileged thing to say, but I care more about living a really interesting life than let's say a good or comfortable life. I think that's where the growth comes from. That's where the stories come from. That's to me the things that I'll remember the most.

As you explore life’s map, don't get stuck on a decision or else it will be made for you by circumstance.

Sometimes in life, it is more important to make a decision than the "right" decision (especially in poorly-defined problems). If none of the enumerated options in front of you feel compelling, you must find another option. Otherwise, if you procrastinate on making a decision, your choice will be made for you by circumstance.

If you’re paralyzed by the fear of “settling,” your decision making approach may be that of a Maximizer rather than a Satisficer. Click here to read more!

“Your time is limited, so don't waste it living someone else's life. Don't be trapped by dogma, which is living with the results of other people's thinking. Don't let the noise of others' opinions drown out your own inner voice. And most important, have the courage to follow your heart and intuition; they somehow already know what you truly want to become. Everything else is secondary.” – Steve Jobs

Enjoy our blog?

Forward to a friend and let them know they can subscribe (hint: it's here).

Have requests or feedback? Hit reply to suggest topics, send feedback or say hello.

Feeling mediocre or directionless? Explore our "Inner Compass Building" protocol that helps ambitious people build internal conviction, make urgent decisions, and minimize regret.