When I relaunched my company from scratch last year, I received one piece of advice from my friends and colleagues over and over: follow your gut. My intuition, they told me, would be my saving grace, a flashlight in the dark — the hatchet that would clear the brush of my uncertainty, and show me the path forward.

And it was. Over the last two years, I’ve learned to listen to my instincts, trust my gut, follow my joy, and all those cheesy sayings you’d find on a decorative wall sign at the gift shop of a  California wellness retreat. As much I cringe at these easy concepts, I know I’m where I am because I’ve learned to take that inner voice seriously.

But it wasn’t easy. Not for me, anyway. I’m not exactly a “go forth and sing your song with all your heart” type. I’m more of an “apply decades of experience and dramatically overthink things” type. My heart’s fine, but my head’s better. My head, after all, is what helped me escape being kidnapped (twice), led me into (and then out of) the legal profession, and taught me how to build and scale multiple companies. It helped me overcome imposter syndrome and find my purpose. It taught me how to keep going and make meaning out of suffering.

For most of my life, my head was where it’s at. Until I was forced to relaunch.

Suddenly, I found myself in a situation where the path forward was so difficult to navigate — impossible to even see — that my head literally didn’t work anymore. I couldn’t apply my decades of experience to this one, because I didn’t have that experience yet. I couldn’t run every possible scenario in my head over and over, because there were no scenarios.

One day, I had a company. The next, I had no company. How do you intellectualize your way out of that?

You don’t. Because you can’t.

You can only ask yourself some really basic (and pretty scary) questions. What do I want? What do I care about? What kind of person do I want to be? What pieces do I have on the board, even if I don’t know how to use them? What would I do if money and stability didn’t matter?

Then, as best you can, you try to answer them. Not with your head, which is about as useful as a screen door on a submarine, but with (and I hate myself a little for saying this right now, but here I go) your heart. Which is really just a poetic way of saying your intuition — that inner voice that tells you what to do, where to go and what you want when the heady part of yourself throws up its hands and says, “Honestly? I don’t know. I just don’t know anymore. Someone else take the wheel.”

It’s then, in those powerful and humbling moments, that intuition doesn’t just become important. It becomes essential. It becomes the only compass that’ll get you home.

And if my last two years have been any indication, following that compass leads you into some pretty incredible territory.

If you listen to your intuition the right way, it can tell you which direction to head, which people to bring along and which decisions to make, long before you know where that direction actually goes, long before you know what role those people will play, and long before those decisions will pay off.

It’s a blueprint for living based on your unique specifications — your goals, your values, your passions, your personality — before you know what the structure will ultimately look like. It’s the way forward, basically, before you even see the way.

But here’s the thing. That special intuition? It’s not a tool in and of itself. It’s not some magical life force that turns out right no matter what. It can get you into trouble as often as it leads you to success.

Trusting your gut can make you believe a seductive lie, trust a shady person, ditch a valuable relationship, turn down a great opportunity, or make a risky bet. This happens all the time. Following your intuition doesn’t come with a guarantee that things will turn out well; it only comes with a guarantee that things will turn out in a way that reflects your instincts, your choices, your beliefs. As powerful as it is, following your intuition is a risky proposition.

Of course, trusting your gut might also be the most authentic thing to do. It might be the most honest. It might even be an expression of your innermost truth (whatever that means for you).

But if you’re authentically irresponsible, or you’re honestly a narcissist, or your innermost truth is that you should ditch your friends, blow 10 G’s in an underground poker game and tell your business partners they’re full of shit and you’re branching out on your own, then sure, you might be “following your intuition,” but you’re probably following it to a pretty dark place.

On the other hand, if you spent five years honing a killer poker game, and your intuition told you to leave your cushy job, risk losing your significant other, and pursue a career as a professional gambler, that intuition could lead you to a prosperous and exciting place.

But in that scenario, you wouldn’t just be following your intuition, full stop. You’d be listening to a voice that is grounded in experience and eager to capitalize on your skills. If you succeeded, it wouldn’t just be because you listened to your gut. It would be because your gut was drawing on concrete ability, rational decision-making, and five years of relevant experience.

When your intuition works out, it’s not because your intuition “has your back” no matter what. It’s because that intuition is rooted in other qualities and skills that give that intuition shape, meaning, and power.

We have to remember that when we preach the gospel of intuition.

It’s possible to intuit yourself into pain, ruin, and unhappiness. It’s also possible to intuit yourself into success, adventure, and fulfillment. There’s no guarantee that you’ll enjoy one or the other when you listen to your gut. But there is a guarantee that the outcome will depend on how those instincts interact with what you know about yourself and the world.

If intuition isn’t grounded in something concrete, then it’s probably not intuition. It’s just programming.

And programming, as we all know, rarely makes us right. It only makes us consistent. Programming follows a pattern of conditioning — a set of unspoken rules created over the course of your life, starting in childhood, which govern everything we think and feel and do.

In most cases, when we “trust our gut,” what we’re really doing is “obeying our programming.” We think we’re listening to a profound inner voice, but it actually turns out to be a scared little whisper, repeating the same thing over and over: Avoid pain. Seek pleasure. Minimize risk. Stay alive, no matter what.

We then interpret these conditioned programs as important messages from our innermost selves, thinking that any voice inside us must be correct, simply because it comes from within.

It’s not.

For an inner voice to be true intuition, it has to attach to something else — something concrete and objectively reliable — like knowledge, expertise, training, insight, and talent.

That’s why I can’t just open up a TD Ameritrade account, scan a list of stocks, and use my gut to pick the right ones to buy. I might have a hunch about Chevron, but if I don’t know the fundamentals of that company, I’m probably not going to do very well. In reality, I’ll just be following some ancient programming in my mind — my fear of financial loss, my approval (or disapproval) of the company, my need to make a quick buck, and so on.

Whereas if I took the time to truly study the markets, my instincts about which stocks to pick would become a lot more meaningful. (Not automatically correct, of course, but far more useful.) If I’m diligent and self-aware, I might be able to use that knowledge to rise above my programming and actually, you know, make some money.

Intuition alone does not guarantee success. Success ultimately depends on the relationship between intuition and these other assets.

We never just “have intuition.” We have an intuition about something. And we have an intuition based on something. How we approach those things — how we value them, how we pursue them, how we build our relationships and choices and intentions around them — that’s what creates the fruits of our intuition. Intuition is just the compass. We still need to walk the right way.

“Intuition is like reading a word without having to spell it out,” wrote Agatha Christie. “A child can’t do that because it has had so little experience. A grown-up person knows the word because they’ve seen it often before.”

We have to remember this if we’re going to embrace intuition in our lives.

If we behave as if our intuition is all that matters — that it’s always right just because it’s ours — then we’re probably not going to get very far. How many heart-centric people do you know with money problems? How many intuitive people do you know who can’t maintain a relationship? How many instinctive people plateau when their training falls short?

But if we listen to our intuition as a guide that helps us capitalize on the resources we have, then we can follow it into greater authenticity, freedom, and joy. Not just because we’re listening to our gut, but because our gut is telling us to listen to something else: the other important assets we possess.

So if intuition and programming look so similar, how do we know when we’re actually listening to a meaningful inner voice, and when we’re just following some ancient pattern?

How to Know When to Trust Your Gut

Luckily, you can “test” your intuition by asking a few key questions. The answers will give you deeper insight into your inner voice, and help you parse true intuition from rote programming. This isn’t a perfect science, but it will give you a ton of data to hold alongside your instincts, so you can make the best possible choices.

(As per yooz, I recommend writing down your own answers to these questions. That’ll make them more real for you.)

Have I had this intuition before?

As we’ve seen, programming often masquerades as intuition. And since programming is a set of recurring patterns, conditioned thoughts tend to pop up again and again.

So when an inner voice appears with a message — quit your job, pick up the cello, commit to the fantasy novel, leave your husband, fight to keep your job, hoard your money, sell all your furniture and move to Bali, or whatever — ask yourself if this is a familiar message or a wholly new one.

If it’s a familiar message — if the thought has been recurring for months or years — then it could very well be a piece of programming.

That doesn’t necessarily mean it’s wrong, of course. If your intuition is telling you not to cut through that obviously sketchy park at night, and you realize that your intuition is actually reflecting an innate instinct to stay alive, you probably shouldn’t ignore that. You’d probably want to thank your intuition for obeying your programming, and take a different route home. We need that programming — especially in matters of survival — as much as we need intuition.

But if your intuition is serving up a brand new message — if the thought in question is creeping up for the first time — then it’s probably an intuition worth exploring.

That doesn’t mean it’s automatically right. It just means it’s meaningful. Part of its meaning is that it’s new. It’s not some ancient script running for the 10,000th time because it’s been programmed. It’s a message that deserves some investigation. From there, you might get curious about this new thought. Where is it coming from? Why is it popping up now? What is it trying to teach you? What does it want you to do, understand, and become?

With new intuitions, it’s also important to give them some space and time. For many of us, what seems like an urgent intuition often turns out to be just a passing obsession. We hit a little roadblock at work, and suddenly we’re Googling “how to join the New York Philharmonic” and emptying our bank account to pay for cello lessons. We get restless in our relationships, and suddenly we’re looking at beach shacks on Pinterest and outlining an ebook about digital nomading. A few weeks later, these inner voices subside, and we realize that they weren’t meaningful intuitions at all, just temporary impulses.

But if an intuition sticks around — if you find yourself exploring an instinct for months, or at multiple points in your life — then it’s worth taking a closer look at it.

In my experience, intuitions that linger for a while tend to be more meaningful. Again, that doesn’t mean they’re “right.” It just means that they matter. And anything that matters deserves some more investigation.

Is my intuition feasible, rational, and responsible?

If your gut is telling you to pursue a certain course, play out the path in your mind. See if the broad strokes of your goal actually make sense in practice. Hold them up against your abilities and commitments, and get a good handle on what the journey will require.

If you’re a middle-aged M&A banker at Goldman Sachs, for example, and your gut is telling you to quit your job and learn the cello so you can play in the Philharmonic, ask yourself: Is it actually possible for a 45-year-old to learn the cello from scratch in time to be a professional musician? Is it rational to believe that you have the talent and drive to master the instrument? Is it responsible to quit your job — given your commitments, financial and otherwise — and pursue music?

The answers to these questions might be yes or no. (I’m not taking a stance here — just asking the questions.) Maybe you’re one of the few people who does have the means to leave a career and pursue art later in life. Maybe you have 20 years of experience with another instrument to draw on, and that gives you a foundation for the cello. Maybe the relationships you’ve built in finance can help open doors in the music world. This is all possible.

It’s also possible that your programming is telling you to leave a stable situation and pursue a romantic goal because you’re feeling stifled and unfulfilled, and you haven’t found a way to reconcile this contradictory programming. That could also be true.

These are excellent questions to ask of any goal, but the answers can get tricky when the data is mixed.

Your intuition, for example, might be telling you to leave your job and start a company while you still can. That goal might be feasible, but by no means guaranteed to succeed. It might be rational in one way (it’s perfectly reasonable to want to chart your own path) and irrational in another way (you’ll probably struggle to survive for some time). It might be responsible in one sense (you’re building a life that is truly your own) and irresponsible in another sense (you’re risking your time, money, sanity, and health). In spite of all that, your inner voice might still be telling you, Go do it, while you still can, this is your chance! — and it might not be wrong, even if starting a company will cause you a lot of stress and heartache.

Like I said, this isn’t a perfect science. Life be complicated. Choices be nuanced. But we have to ask these headier questions to make sure that our big, romantic, touchy-feely inner voice makes sense in reality.

Have other people walked this path?

Another helpful approach is to study other people’s stories. Is your intuition calling you to a path that has been walked by other people before? Or is it calling you to a path that is completely unprecedented, and maybe even impossible?

Imagine, for example, that you’re an account executive at an ad agency, but your gut is telling you to quit your job and go all-in on your epic fantasy novel. It’s an ambitious goal, but it’s not a completely unprecedented one. You could read up on novelists who had corporate jobs, reach out to writers online who have made the transition, and talk to teachers who have worked with people in your shoes. You can validate the path you’re considering before you make it, so you know it’s not completely delusional.

Now imagine, for example, that you’re a professional gambler $50,000 in the hole. Your intuition is telling you to borrow 100 grand from a loan shark, make back the money, and use any extra winnings to fund your next run. Is that possible? Sure. Have tons of people successfully done it? Probably not. That sort of thing worked out pretty well in the movie Rounders, but in real life, most gamblers have walked a very different path — into serious trouble.

Once again, this question might kick up some mixed data. And case studies are only useful up to a point.

The fact that some people leave their jobs and become successful novelists doesn’t mean that you will. The fact that most gamblers fail to dig themselves out of debt doesn’t mean you can’t.

Walking a familiar path doesn’t guarantee success, just as walking an unfamiliar path doesn’t guarantee defeat.

In fact, it’s sometimes these unusual paths that pay off the most. Sometimes they pay off precisely because so few people walk them.

This is especially true of entrepreneurship and art, which weed out people who don’t have the grit and talent and drive to stay the course. Of course, these challenging paths can only be navigated by listening to your intuition, which is why that inner voice is so important.

Is this intuition trying to keep me safe?

As we’ve discussed, programming is designed to keep us safe. Conditioning is basically a set of scripts that help us seek pleasure, avoid pain, and do so with as little risk as possible.

So a helpful way to separate intuition from programming is to ask whether a specific intuition is primarily designed to keep you safe.

If your inner voice is telling you to do something that protects you, it’s probably just programming. If it’s telling you to do something that puts you at risk — emotionally, physically, or financially — then it’s probably more than just programming, and deserves a closer look.

Of course, “safe” means different things to different people.

For one person, staying safe means hanging onto a dead-end job and staying in a loveless relationship to maintain stability. For another person, staying safe means fleeing a great job and ditching a healthy relationship to avoid close attachments. But both people are making choices that are safe for them.

We’re all conditioned differently by our childhoods, values, and templates. But our brains and bodies are all essentially conditioned to pursue familiarity over uncertainty, stability over change, safety over danger. So this is a very useful litmus test for intuition — to ask if it’s in service of safety or in service of something greater.

If you find that an intuition is telling you to stay safe, then you can usually categorize it as simple programming.

Maybe you’ll find that your conditioning and your gut are in healthy alignment, which is a wonderful discovery to make. Or maybe you’ll find that your programming is trying to keep you stuck in place, and that your true intuition is telling you something else.

At that point, you might start to hear a voice beneath that programming, a voice that goes deeper than the conditioning. And that will be the intuition you were looking for.

On the other hand, if you find that your intuition is not telling you to stay safe — that your inner voice is telling you the opposite of your programming — then there’s a good chance that you’re in touch with true intuition.

Why? Because the inner voice beyond your conditioning is not concerned with safety and security. It’s concerned with truth and meaning. It wants to lead you beyond the comfortable confines of your programming, into something riskier and scarier but more purposeful and fulfilling. The fact that it’s not concerned with your survival is what makes it so meaningful.

In fact, when your intuition and your programming seem to conflict, that’s when you know it’s time to pay attention.

Again, this is not a straightforward rubric. I’m not saying that all intuitions are reckless and that all programming is safe. I’m not saying that your intuitions and your programming need to conflict in order for you to live an authentic life. I’m not even saying that you have to follow your intuition when it arises.

I’m just saying that you can learn a lot about your innermost desires and values by asking what role they play in your life. By figuring out that role — stability or growth — you can parse these messages to find the ones that are truly intuitive.

Interpreting Your Inner Voice: The Gift of Calibrated Intuition

If you separate your programming from your intuition, you’ll find yourself listening to your inner voice in a new way. You’ll know when to ignore those inner voices that are fleeting, irrational or simply conditioned by the past, and you’ll begin to take your intuition more seriously, without becoming a slave to every impulse.

That’s how you merge intellect and gut, rationality and instinct, analysis and intuition.

It’s how you bring together the full suite of faculties — heady and emotional — that are available to you, and make sure they’re in healthy conversation. It’s also how you ensure that your intuition isn’t running wild, serving up wild thoughts and absurd goals that have no connection to reality. It’s how you ground your intuition in something concrete — experience, logic, ability, and self-awareness. I call that calibrated intuition.

In my view, calibrated intuition is where intuition becomes truly powerful — when it doesn’t just exist in a vacuum, speaking its own strange language and obeying its own weird logic, but helps articulate deeper goals, truths, and needs based on our unique assets.

I’ve interviewed thousands of people over the years, and the most successful ones all have this quality in common. They all know how to listen to that inner voice when it matters, and use their other faculties to assess, interpret, and act on that inner voice the right way. They all have calibrated intuition. And they all calibrate it in a way that makes sense for them, that capitalizes on their particular interests and talents.

“If science is to bring happiness and real progress to the world, it needs the warmth of man’s heart just as much as the cold inquisitiveness of his brain,” said Franz Winkler.

You could say the same thing about intuition. That marriage of “warmth” and “cold inquisitiveness” is the stuff of effective intuition.

That’s what allowed me to relaunch my show and rebuild it even bigger than it was before in under two years. It didn’t just guide me because it was there. It guided me because I listened to it, because I had the ability to understand and act on it. Not just with my heart, but with my head, and with all the skills and experience and awareness I had to make sense of that mysterious, compelling, absolutely essential inner voice.

[Featured image by Maksym Kaharlytskyi]


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