Sahil Bloom Gives You a Plan for 2026

Today's episode is why you're failing to achieve your goals and how we can fix it. I brought on my friend Sahill Bloom,

it. I brought on my friend Sahill Bloom, New York Times bestselling author, has invested in 100 companies because 2026, the new year is coming. And most people

drift into a new year without any real clarity. So, we're doing a different

clarity. So, we're doing a different type of episode today. We're walking

through seven simple questions that reset your direction, that clean up your priorities and give you a clear plan that you can actually follow. This is

the stuff that Sahel uses, I use, and the founders we work with use because they want a serious upgrade in their life and in their work. If you sit with these questions, the new year is going

to be a very different year. and get

your pen and papers out because we are going to do the personal annual review together in this episode. Let's get

started.

>> I'm here with Sahill Boom. Welcome to

episode 472 of Where It Happens podcast.

My co-host.

Welcome back.

>> What's going on? This is the throwback episode 4. What is it? 472.

episode 4. What is it? 472.

>> Some some crazy amount.

>> I disappeared for 440 of those. Uh, and you've you've gone and

of those. Uh, and you've you've gone and taken it to much higher heights. This is

amazing.

>> Well, welcome back for this, you know, special episode. Uh, you have a really

special episode. Uh, you have a really interesting topic. You know, what what

interesting topic. You know, what what do you want to talk about today and what will people get out of this by the end of the episode? I want to talk about why we are all failing to achieve our goals

and what are we going to get out of this. I I I hope it is the solution, the

this. I I I hope it is the solution, the antidote to that. uh to really set us up for the biggest 2026 that we've all imagined, but uh a clear structure for

how to actually get there, how to look at 2025 so that you can take whatever learnings you need to and actually march into 2026 with those new insights, new

perspectives to operate at full power.

>> Okay. So, if people stick to the end of the episode, they're going to have your framework. you're going to give away

framework. you're going to give away your framework for how you basically get the most out of the year cuz you've got a very special framework and I haven't heard I I haven't seen this anywhere and

you're you're going to let us in. You're

going to reveal it and people could take out their pens, take out their papers and while we're going through it, they can actually answer those questions.

Right.

>> Exactly. Right. We're going to go through seven questions that are going to allow you to more meaningfully reflect on the year that was so that you can actually create a real structure for

crushing the year ahead.

>> Cool. Let's do it.

>> Let's do it. First, just to set the stage very quickly, why is this important in the first place? There's a

quote that I absolutely love. Uh we do not learn from experience. We learn from reflecting on experience. This is

something that we often forget, right?

Like we we are in such a rush at the end of the year to plan for the year ahead to like, oh, okay, I'm going to create all my goals. I'm going to set all my systems. All of these things that we forget the most important data points

just happened this year that we just had. So, this entire process that we're

had. So, this entire process that we're going to walk through this seven question framework is all about reflecting. It's getting that

reflecting. It's getting that information, sucking it out of 2025 so that you're armed to use it in 2026 to go out and achieve the things you want

to achieve. I call this my personal

to achieve. I call this my personal annual review. It is seven simple

annual review. It is seven simple questions that have been transformative, really life-changing for me in my own journey. It's led to some of my biggest

journey. It's led to some of my biggest changes that I've made. And I think uh for anyone listening to this, you're going to get a ton out of going through this exercise. would highly recommend

this exercise. would highly recommend taking out a blank sheet of paper as we talk through all of these. You can write down the questions. We'll obviously have them in the show notes as well. Um, but

run through this as we talk through it.

We'll deconstruct each question. Greg, I

hope you'll share some of your reflections as we go through each one.

Uh, but let's dive right in. So,

question one, what did I change my mind on this year? The reason this question is so important is the smartest, most

successful people are not the ones who have all the right answers. They are the ones who ask the right questions. I I

have found that time and time again. And

I'd be curious if you've observed that in others that like this willingness to have software updates to your brain and embrace the software updates rather than

trying to resist them is such a powerful force for continued growth and change.

>> I agree. I think uh we're all like the smartest people I know, the most successful people I know are constantly reinventing themselves. So if you're

reinventing themselves. So if you're reinventing yourself, you have to change your mind.

Yeah, that idea of reinvention is actually really well stated, too. It's

like I feel like when you're a kid, you are told that changing is like a bad thing. Like you're, oh, it's like a

thing. Like you're, oh, it's like a flip-flopper. Like that term from

flip-flopper. Like that term from politics. People get called

politics. People get called flip-floppers if they change their minds. But that idea of reinvention of

minds. But that idea of reinvention of like new information, new evidence, and I'm going to embrace it, learn from it, and shift who I am and how I'm operating

in the world. That should be a positive.

I mean, that should be something that we celebrate. Really, reinventing yourself

celebrate. Really, reinventing yourself at any age.

If you have a business that's doing at least $50,000 a month in revenue, I've got something interesting for you. It's

called offline mode. It's a 2-day event that me and my team are putting on at a 20,000 plus foot square foot mansion.

Yes, this is what it looks like on January 23rd and January 24th in Fort Lauderdale, Florida. I'll include a link

Lauderdale, Florida. I'll include a link in the description if you're interested in coming, but it's basically for people who have a business that's kind of cranking, but they really want to put it

in rocket ship mode. They want to create a set of businesses that generate tons of money, tons of cash flow, tons of product market fit, tons of impact. Um,

but they're not just quite there yet.

It's also about, you know, making your business AI first. how you can actually, you know, build not just one product but multiple products and you're going to leave with, you know, tactical uh

answers to your questions. So, um, if that's you and this sounds interesting, uh, I'll see you there. So, the goal is two to three key changes.

>> Yeah, identify a few things and I, you know, two to three is a placeholder. If

it ends up being five and you had a transformative year, great. if it's one and but it's really meaningful also great. The way that I think about

great. The way that I think about getting under this because uh when I first looked at this question it's like it's it's kind of challenging. It's like

well well I don't really know what did I think in the past, what did I think now?

The way that I do this is I open up my calendar. So like if you open up uh your

calendar. So like if you open up uh your Google calendar or whatever you use for a calendar, go look back at your calendar from January of 2025.

Look at some of your weeks, some of the activities, some of the, you know, opportunities you were working on, some of the people you were spending time with. Place yourself in those shoes,

with. Place yourself in those shoes, like in the shoes of the person that was engaging in those activities from back then, and think about what were your

core behaviors, your mindsets, your um habits, the people you were spending time with, the things, the ways you were thinking about the world. Like actually

go back and and think about who you were in those moments.

And then think about what am I cringing at right now about that younger version of myself? Like what what about that

of myself? Like what what about that younger version of myself is making me sort of feel that like that cringe sensation? That to me is the most uh

sensation? That to me is the most uh sort of simple and fundamental way to get underneath where you have changed.

Like what have you changed your mind on?

Because it's the things that make you cringe about that younger self. cuz when

I when I read the question, what have you changed your mind about um in the in the last year? Like it's

such a big question, right? So I feel like people need like tools to get, you know, get the actually get to the core of that question. That's the hard part.

>> Yeah. Yeah. And I think the calendar like I I am a big believer in just the simplest tools because look like every productivity guru on the internet will sell you some expensive productivity

solution or some expensive like second brain or whatever the thing gets called.

And you know what I found in my own experience working with some of those things is that um you end up moving a whole lot but not actually making progress on things. you know, you like have this complicated productivity

system, but you're not actually uh you know, creating progress on the things that you're supposed to work on. And so

I pull up the simplest version like I I I use Google calendar. Go look at my calendar. Um from the beginning of the

calendar. Um from the beginning of the year, one of my core operating beliefs in January of this year was achievement is not going to change my life. like that has sort of been

life. like that has sort of been something over the last several years that I've grown to believe that um achievements are not going to change my life in any way. So, I need to enjoy the process, right? It's like a pretty

process, right? It's like a pretty common thing we hear. And to me, one of my biggest things I've changed my mind on is that actually some achievements

are so profound. Uh you've put so much towards them and worked so hard towards them that they actually do have the potential to change your life and create an inflection point and that it implies

that they are worth leaning into. You

don't need to sort of bemoone these big achievements or say that like, oh, it's not going to change me. It's not going to change who I am and what I'm about.

you can actually lean into those things and not feel bad about leaning into them because they may actually be even more impactful than you ever thought they could be.

>> Cool. So, that's question one. Question

two.

>> Oh, wow. So, you broke this out into personal and professional here.

>> I did. Yeah. So, I um I think that oftentimes people will get focused on a professional mindset when they do this kind of reflection. And I

think it's just as important to think about it in your personal life. Um think

about you know largely in this context like thinking about some of the relationships and some of the uh you know the people uh across a lot of these different questions uh because in

general like the uh people shape your outcomes and so being able to have that have that reflection on some of the people as well along the way is important. So when you say people, it's

important. So when you say people, it's like who did I, you know, was I excited about working with in January and by December I'm less excited about that sort of thing.

>> Yeah. On the change your mind question, it would be more about like, you know, what did I change my mind on when it comes to, you know, certain uh behaviors

or approaches towards certain types of people in my life. As we get into later questions in this exercise, we'll talk about like more specifics when it comes to different types of people that

created versus drained energy etc. With this, it would be like you know on the personal side uh you know maybe some of your routines like you've realized you needed to shift uh the context in which

you viewed different routines, different approaches to things um stuff like that.

Want to jump to question two?

>> Yep. Let's do it.

>> What created energy this year? So the

fundamental idea with both question two and question three which we'll come to is that your outcomes in life follow your energy. You know idea being like

your energy. You know idea being like when you are working on and leaning into things that create that lift that natural pull you create the best

outcomes. And so identifying the things

outcomes. And so identifying the things that create energy versus drain energy in your life is essential because when you do that then you're able to actually guide and make changes. so that you can

lean into the things that create and lean away from the things that drain.

This question and its inverse, which is question three, is going to have you actually look back at your calendars from the full year and use those to get underneath those trends to start

actually deconstructing what were those types of activities that created versus drained energy in your life. So, okay.

So, I have a question about this one.

So there's certain things, you know, I'm just reflecting on my own stuff. There's

certain things that are, you know, drain energy, red, but in the in the short term, but the long-term benefit is created energy. So I'll give you an

created energy. So I'll give you an example for me, and this might come to a shock to some people, I actually find doing episodes of the podcast to be like

draining in the moment. Um, sometimes I like don't look forward to it, but once I'm done it, it's like a it's like a workout. I feel amazing. Not only do I

workout. I feel amazing. Not only do I feel like uh amazing right after, like my brain feels amazing right after, but I also

know that the content I hope the content is going to help people. So therefore,

it's like it it it's almost like altruistic. You know what I mean? So,

altruistic. You know what I mean? So,

how do you deal with that? Like

situations like that? I always look at on the draining side in particular. Um I

focus on how do I feel after rather than how do I feel during for that exact reason. Uh working out actually the

reason. Uh working out actually the example that you brought up there is the best one in my mind for me because there's plenty of run workouts or different lifts or whatever where I'm

clearly drained during it physically and mentally, but afterwards you always feel fantastic. Or even like a cold plunge as

fantastic. Or even like a cold plunge as a silly example, right? like the fad of 2022 or whatever year it was that everyone was cold plunging. Um, you

know, clearly you're not like super enjoying being in freezing cold water.

That is draining in a lot of ways. But

when you get out, you feel incredible.

There's plenty of things like that in your life. And so on the draining side,

your life. And so on the draining side, especially when we get into question three, focus on how you feel after rather than during or even before because there will be a lot of things

like that. Um, I think that that applies

like that. Um, I think that that applies to creating energy as well. There are

certain things that maybe feel more neutral during and then you feel incredible after. Um so on these when

incredible after. Um so on these when you think about your energy focus on uh more on the like immediate aftermath effects like do you feel like you need to go run on a treadmill or do you feel

like you need to take a nap? And I'm I'm curious in like in your life, do you have like some things that create energy in your life that you really don't look

forward to during it or are you one of those people that like you know I know you enjoy working out but do you you know do you enjoy working out? I mean

writing for me is definitely one like I look writing is my main thing. uh when I uh when you and I uh stopped being co-hosts, like the main reason was I was going to write this book, right? I was

like, I'm going to take on writing as my main main thing. And I don't remember a single moment in the last several years where I have been like so in love with

writing before and during doing it. I I

find it to be a grind honestly. Like

intellectually I find it to be really challenging, but I feel incredible when I have those like little breakthrough moments where something clicks in my mind. It's like um it's like the

mind. It's like um it's like the hard-earned win, right? Like there's

something about that meaningful struggle that you just endured that like all of a sudden there's a little breakthrough. Um

and writing is definitely that way for me. And so I like I try to lean into

me. And so I like I try to lean into daily writing because I find it to be that struggle that I need to force myself to do and then I feel good on the other side. It's like the Earnest

other side. It's like the Earnest Hemingway. All you have to do is write

Hemingway. All you have to do is write one true sentence. It's like just push yourself to do that. Uh and there's this feeling of breakthrough that comes from it.

>> Cool. So what created energy this year?

Professional, personal, and people.

Yeah, I like to deconstruct the energy one even a little bit further into these three buckets. Um because on the

three buckets. Um because on the personal side, I tend to just in my own brain think about like health practices a lot within that personal bucket like

that that tends to be like routines and things like that for me. Um and so I I deconstructed that further layer because people on this one is like it's

essential to know the people that create versus drain energy in your life. I

would say if there's been one single change that has been most impactful for me over the last decade, it has been um closing off my energy to people who uh

had not earned the right to it. What

about for people like you? You know,

you're a New York Times bestselling author. You've done really well. Uh you

author. You've done really well. Uh you

probably don't even need to work if you didn't need to. What about the people who are just starting out? you know,

could you if you're in the 0ero to one phase, you know, you're in your early 20s, you know, could you like is it a privilege to be able to

say no to people who are draining you? I

think it is uh an earned privilege over time to eliminate or mitigate the energy draining things from your life. Um, but

it's an earned privilege that all of us should aspire to continue to earn over time, right? like you can make slow

time, right? like you can make slow steady incremental improvements. By the

way, I don't think anyone will ever get to the point where your calendar is entirely energy creators. Like I think there is always an element of life that is energy draining things like just stuff that you just have to do. You

don't really like it, but that's life.

That is part of living and being human.

And probably uh you wouldn't want to eliminate some of those things because they add texture and they add a layer of meaning. Um, but I think that that is

meaning. Um, but I think that that is earned over time. Like in, you know, my first job working as an analyst in a private equity fund, I was working 100 hour weeks, uh, doing a lot of like

email, Excel modeling, all of that stuff. And, uh, did I get energy from a

stuff. And, uh, did I get energy from a ton of that stuff? No. And did I have an ability to change a lot of those things that I was doing? No. But slowly over

time, you can make these little incremental improvements to it. you

know, identify one thing that you might be able to change. Like maybe it's back-to-back phone calls for a whole afternoon is really draining for you.

And maybe one of those calls could be a walking call, which you find more energy creating. All of a sudden, there's a

creating. All of a sudden, there's a little pocket of green where it didn't used to be. And those tiny changes can actually stack up and make a pretty big impact over the course of a long period

of time. Oh, I like that a lot. So that

of time. Oh, I like that a lot. So that

question leads into and is you know connected obviously to the third question which is what drained energy this year just the inverse you know you're you're looking at your calendars again you're diving in and you're

identifying what those energy draining things are um you know what was sort of the stuff that just made you feel uh

less human uh both during and and after um in in whatever format for me that is almost always every year calls and Zoom meetings. Um, you know, like I

meetings. Um, you know, like I constantly feel like uh I go through these like cycles of taking on too much and then needing a reset. Um, and again,

minor adjustments to this kind of stuff can have a pretty dramatic impact. So,

identifying what those are uh early and then learning to adjust course as you need to uh really impactful, >> dude. Zoom calls, like backtoback Zoom

>> dude. Zoom calls, like backtoback Zoom calls, nothing nothing worse. What's

your like is that your is that your big one that you feel like you need to work on?

>> Um I'm actually you know I'm privileged in the sense that like my calendar is pretty pretty empty >> and you know I've

you know the reality is like I would be way more successful if I did have more Zoom calls. But I just enjoy my life a

Zoom calls. But I just enjoy my life a lot more. Like we're hanging out on

lot more. Like we're hanging out on Thursday, you and I, and like I think that's my only thing on on on Thursday.

You know what I mean?

>> It just depends on your definition of success. If you were to ask me, uh, you

success. If you were to ask me, uh, you know, according to to my logic, it sounds like you're just as successful as you want to be. You're meeting your own definition.

>> Yeah. I mean, I that's how I that's how I see it, you know. So I think um for me there are a certain set of like weekly

or monthly or quarterly calls that I am on where I'm just like it's recurring meetings. That's what it is. Recurring

meetings. That's what it is. Recurring

meetings and for that's the last thing I need to just like remove from my calendar. Um, yeah,

recurring meetings are a funny one, too, because what what I find happens is you create stuff to talk about on them that's not actually impactful. Uh, you

you're like, "Okay, I have this recurring meeting every month on the first Monday of the month. So, I'm going to have a bunch of touch points that we need to talk about, but like it wasn't actually necessary. You could have done

actually necessary. You could have done it asynchronously."

it asynchronously." >> Yeah. I also think what I want to do is

>> Yeah. I also think what I want to do is if I'm going to have a recurring meeting, there needs to be, and this is I think the Amazon approach, like there

needs to be a PDF, a deck, a prototype sent before that we're all reviewing. So

that way we're not spending half the meeting like uh just like sharing an update, you know what I mean? Like let's do that async and then let's use the meeting to

actually be constructive. This was

probably one of the most impactful lessons I learned from my years in private equity. You know, I think

private equity. You know, I think private equity funds sometimes get a lot of things wrong, but one of the things uh that I thought was profound was the

structure of board meetings when well done, which was the CEO and the board and the team would send around like maybe a week in advance a deck that was

basically the business update and all of the like key information about the business. And then the meeting itself

business. And then the meeting itself when everyone was in the room together was entirely focused on the like forward-looking most critical decisions that needed to be made and debated because what would happen in the absence

of that was you'd get into the meeting and people would just be like updating you on the metrics and the numbers for the entire thing and you'd get no time on the key strategic decisions. And it

was like that is actually totally fine to just have in an email or a deck.

Everyone reads it. Everyone's primed on it. they can ask any questions in

it. they can ask any questions in advance on anything necessary and then let's focus the brain power when we're all here on the things that are actually going to drive the business forward.

>> Yeah. So, this is the this is going to be the big change for me in 2026. I also

wish and someone this is like a startup idea. someone should figure this out is

idea. someone should figure this out is I wish there was a way to ensure that people actually >> read >> read the prep materials like you know what I mean like accountability

>> cuz sometimes I find we'll we'll implement this in in a monthly meeting or whatever and we get to the meeting and you know 75% of the people haven't

read the you know the deck or whatever it was.

>> Yeah. Yeah, I guess like with Loom you can see like or a doc send or whatever like you can see how long people were in it or I mean obviously there's always ways to hack those systems. >> Um >> yeah,

>> you do need like a little quizlet or something like that to make sure that the whole team is reviewed.

>> It's like if you haven't watched the Loom, you don't get access to the Google Meet.

>> Ooh, >> that's kind of a good idea actually.

That's how you unlock it.

>> That's how you unlock it. You have to put in like some you have to put in a response to some question from like page 27 of the memo.

>> Totally. Yeah. It's like instead of a capta prove that you're human, it's like prove that you're a good team member.

>> It reminds me of like uh Harry Potter and like the sorcerer stone when they have to go through the levels of that like maze thing to get to Voldemort the battle at the bottom and like they have to like make it through each challenge.

Like they play wizards chess and they have to like get through the different things.

>> Exactly. I like it. I like it.

>> Um, all right. So, three buckets also here.

>> Yep.

>> So, you're you're professional, personal, and people.

>> Yep.

>> And again, the people one cannot overstate this. Like, identify the

overstate this. Like, identify the people that make you feel like you need to take a shower after spending time with them. Uh, and figure out a way to

with them. Uh, and figure out a way to limit the energy you give to those people in 2026. My note is identify the shower people.

shower people. I like it. It's catchy.

>> Yeah, I'll know. I'll know what that means.

>> All right, question four. What were the boat anchors in my life? So, boat

anchor, you throw it in the water, it keeps you in place as a boat. If you try to drive the boat at full speed, the anchor is just stuck in the seabed behind you. It's going to obviously

behind you. It's going to obviously hinder your capacity to operate the boat at full power. Boat anchors using this metaphor are the things that are holding

you back that are creating drag in your life. That could be mindsets, behaviors,

life. That could be mindsets, behaviors, people, uh stories you're telling yourself, self-limiting beliefs, etc. Things that are not allowing you to operate at full power. Identifying what

those are and cutting the line, if you will, is the fastest way to make progress.

We as ambitious, high performing people automatically assume that the fastest way to make progress is to add something new. You're like, "Oh, okay. I'm going

new. You're like, "Oh, okay. I'm going

to try to make progress in 2026. What's

the new habit? What's the new company?

What's the new, you know, mindset, the new routine, whatever the thing is, right? New protocol that to use the

right? New protocol that to use the language that everyone uses now on Twitter." The reality is that the

Twitter." The reality is that the fastest way is to cut something that's holding you back. So, we need to identify those. That's what this

identify those. That's what this reflection question really gets under.

Yeah, this is this is really good. I

find that answering this question often requires like a coach of some sort >> or or just like a friend who, you know, cuz you really have to be, you know,

honest when you're answering this question. It's hard to it's hard to get

question. It's hard to it's hard to get to that.

>> Yeah. It requires a level of like ego destruction. Um that is really

destruction. Um that is really challenging. So, you said this at the

challenging. So, you said this at the outset, like you could do this exercise with a friend, someone you trust, could be a partner, it could be a friend, someone that knows you, um, and that is

a trutht teller in your life, like someone who is willing to tell you the truth. I think that that's an essential

truth. I think that that's an essential person to have in your life, by the way, because the downfall of many great men and women throughout history is that they clearly don't have anyone in their life who was willing to tell them the

truth. So, as they've gotten more and

truth. So, as they've gotten more and more successful, they're surrounded by people who pat them on the back and tell them they're great, tell them all their ideas are awesome, when in fact they are

not. Uh, and I have certainly benefited

not. Uh, and I have certainly benefited from having a bunch of people in my life, but most importantly, my wife who no matter what is always a truth teller.

Um, so find that person maybe to do this one with. Ask them what are some of the

one with. Ask them what are some of the things they could see from the outside looking in. And then for you try to

looking in. And then for you try to create that outsers's perspective like um you know to do that maybe ask yourself here if a third party were to

watch me for a week um what would they say are the things that are holding me back like what would they say about um you know how serious I am about my goals

or about the things that I'm going after.

What do you think about using chat GVT or something like that to help you figure out what the boat anchors are? I

think it's a great idea. Actually, I

hadn't thought of it, but I think that this entire annual review exercise could actually be something that you do with chat GPT as sort of a co-pilot. Mhm.

>> Uh I think that setting the pretext to chat GBT that you need it to be um thoughtfully critical uh and sort of a an intellectual sparring partner rather

than a uh you know just a a friendly kind partner would be important especially for this question. Uh but it could be really useful.

>> Yeah. Also you you should program it to not be positive with everything and just be like you know I like the words you use trutht teller. like being a truth teller.

Uh the truth hurts sometimes basically. So

>> should we plug it into chatbt right now and see what it tells us?

>> Sure.

>> All right. I'm going to do it.

>> Why not?

>> I don't have like uh I I haven't set the pretext, but now I'm curious.

>> So you want me to all the questions or this specific?

>> No, just this one.

>> Okay.

>> Now I'm curious what uh I'm going to do it alongside you.

So, I'm gonna say or how, you know, can I say this? Um, pretend. Okay, I'm going

say this? Um, pretend. Okay, I'm going to say my name is Greg Eisenberg.

Pretend like you are Sahil Bloom.

I am conducting an annual review and I need to get to the bottom of this question.

What were the boat anchors in my life?

What would you add to this prompt?

>> I would say explain what boat anchors are. So I would just say boat anchors

are. So I would just say boat anchors are the mindsets, beliefs, behaviors, and habits that are holding you back from operating at full power.

I just plugged it in too, so I got some interesting responses >> that are holding you back from achieving what?

Achieving at full capacity or full power.

Okay. And then I'll hit enter and see what happens. Let's do it.

what happens. Let's do it.

So, it says I'll zoom in so people can see. Boat anchors are the hidden drag

see. Boat anchors are the hidden drag forces. You don't notice them dayto-day,

forces. You don't notice them dayto-day, but they slow every decision, distort every opportunity, and compound into stagnation. I kind of like that,

stagnation. I kind of like that, actually.

Um, the core categories to interrogate.

Beliefs that shrink your aperture.

Examples: I need to be involved in everything. If I slow down things,

everything. If I slow down things, things break. That's a good one.

things break. That's a good one.

>> Mhm.

Habits that drain wattage instead of creating it. Recurring behaviors that

creating it. Recurring behaviors that don't move the needle, but consume cycles. That's kind of like what we were

cycles. That's kind of like what we were talking about. Okay.

talking about. Okay.

Incentives that point you at the wrong games. You talk a lot about that.

games. You talk a lot about that.

Emotional commitments that distort judgment. Information diets that rot

judgment. Information diets that rot your intuition.

So, the methods to extract your anchors.

Here we go. Track any area of life where you consistently overthink. There's an

anchored buried there. Track anything

you keep saying you'll fix when things calm down. Anchors hide in that folder.

calm down. Anchors hide in that folder.

Track anything that used to energize you but now feels heavy. That's an anchor disguises identity. What do you think?

disguises identity. What do you think?

>> I like that.

>> Mine was pretty good, too.

>> I got uh It actually gave me >> It gave me one that was uh the strong one complex. It says, "You often carried

one complex. It says, "You often carried emotional weight alone. You rarely

admitted when you were scared, overwhelmed, or uncertain.

You said people rely on you, but sometimes it created an invisible emotional tax.

That's a good one.

>> I like that. I like that. So, people

should basically, you know, if you don't if you don't want to share with your partner, by the way, that's a whole other thing, right? Like

>> some people just don't want to share Yeah.

>> some stuff with their partner for whatever reason.

Um, which I understand. By the way, I I do um >> it probably goes to that strong one complex that I just said. Like I

do carry things close to the vest sometimes because I I personally am probably carry a dated and somewhat traditional belief that like my responsibility to my family is to do

that and shoulder the burden of certain things. Um and I take pride in that in a

things. Um and I take pride in that in a lot of ways, but I think it's it's a double-edged sword like most things in life. So I understand if you don't want

life. So I understand if you don't want to do something like this with your partner. Um, and it's great that there

partner. Um, and it's great that there are AI tools that might be able to be useful in this way.

>> Cool. Should we go to question five?

>> Let's do it.

Question number five. What did I not do because of fear? So, this is a natural outflowing from the boat anchors one and

similarly requires a level of ego destruction. I think the most common or

destruction. I think the most common or upfront observation that I would have here is that fear is really about inexperience, not

incapability.

You're afraid because you haven't done it yet, not because you can't do it.

And that inexperience then is the problem to be solved. And you can solve that in experience as a problem through action.

So, when we look at fear, what we're trying to really get underneath is why did I not take action on this thing?

Like, what was that fear that held me back? What did I not do? And how can we

back? What did I not do? And how can we shine a light on that monster, if you will, to realize that it actually wasn't quite as scary as we really thought?

Like, you imagine yourself as a kid or maybe some of the people listening have children. They're afraid of the monster

children. They're afraid of the monster under their bed or the monster in the closet. And then you open the door and

closet. And then you open the door and you turn on the light and you realize there's no monster there and now you're not afraid. That is what fear does to

not afraid. That is what fear does to most of us. It thrives in the darkness.

And when you shine a light on it, when you deconstruct it, um you end up realizing it wasn't so scary and you start taking action on these things. Tim

Ferrris was the first person I saw talk about this. He had an exercise I think

about this. He had an exercise I think he called fear setting. uh where you deconstruct a fear by saying what were the downsides if I had taken action and what were the upsides if I had taken

action and it gives you this balanced sort of objective perspective on the thing that was previously uh you know abstract and amorphous >> that's interesting could you share like

some things that you haven't done because of fear >> yeah I mean I um I would say my biggest one was leading up to my book launch uh

this is late 2024, very early 2025.

My real fear around it that I uncovered was I was afraid of giving 100%

towards this thing and failing. So, one

thing that often happens to us is like we don't give 100% because we're afraid of what would happen to our ego if we did give 100% and then failed. Right?

It's like a self-p protection mechanism.

you build in the excuse. So, you've

probably done this at some point in your life, Greg, or anyone listening, you know, you've you've basically said like, "Oh, well, it didn't work out, but like, yeah, cuz I didn't really promote the thing, right?" You know, I didn't really

thing, right?" You know, I didn't really give everything I had, so like, "Yeah, it didn't work out. Well, whatever."

It's like this self self-p protection that becomes self-rejection.

That was a big one for me to get through to just realize that like if I was going to go down, I had to go down truly swinging and and push and give my all towards something that I really cared

about and and felt was really meaningful. I'll share a little story

meaningful. I'll share a little story about about this. Um I was cuz I've been thinking about fear a lot the last few weeks. So, someone who I look up to

weeks. So, someone who I look up to reaches out to me actually on Instagram.

Well, very well-known guy. Uh, so I look up to him. This guy I've been following for years. He's like, "I I love your

for years. He's like, "I I love your content. Can we hop on a call?" I'm like

content. Can we hop on a call?" I'm like flabbergasted. I'm so excited. And

flabbergasted. I'm so excited. And

he I get on the call and he's and he's like, "I want you to walk me through the businesses that you're running." So, I share my screen. I'm like, "I'm a screen share. I need I need to let me sh let me

share. I need I need to let me sh let me share share my thing and and I could just see his eyes like glazing over of the you know three or four companies

that we're working on. And he's like can I give you an my honest opinion of of what you're doing? And he goes it's not big enough.

It's not big enough. And

like you know we talk a little bit more hangs hangs hangs up. And I was thinking you know I actually told my wife about it. But I was like, am I not thinking

it. But I was like, am I not thinking big enough? You know, and am I am I not

big enough? You know, and am I am I not doing things because of fear? Um, in

this case, I actually had to go through this exercise and I realized no, I'm not it's not because I'm actually like loving what I'm doing. So, it's a 10 on

10 that fear has nothing to do with it.

Um, but I think that the prompt of, you know, the fear prompt is so so helpful in giving yourself clarity cuz now all of a sudden I'm walking into 2026 and

and I'm like, "Yeah, actually the stuff I'm doing I totally 110% believe in."

>> So, you kind of got pushed and like the question pushed you to reassess on it.

Yeah. I um I've had similar experiences with like my experience with sort of like assuming diversification was the approach. Like I would say for the three

approach. Like I would say for the three four years leading up to this year, I was always like, "Oh, I'm going to be diversified. I'm going to have my hand

diversified. I'm going to have my hand in like 30 different buckets and that's how I'm going to make sure that, you know, one of them is going to go well and things will go well." And I've um gotten pushed on that by several mentors

who said something similar. you know,

it's like it seems like you have your hand in a bunch of small stupid stuff that you don't really care about and rather than just leaning into the couple things you do care about. And it led me

to a fairly painful like one full year of like unwinding a bunch of things that I had my hand in that really made no sense. I was like, why am I involved in

sense. I was like, why am I involved in these things? To the point where now I'm

these things? To the point where now I'm heavily concentrated in like two to three things, but they're two to three things that I really care about. And I

feel like I'm at a similar place to you.

like I've been inspired by you on this regard of having those fit within my own parameters and definition of success, not needing to feel like I'm playing other people's game and uh you know living true to your own definition does

feel good.

>> I love that. I love that one. This is a really this is a really powerful one.

Okay, so this is the Tim Ferrris exercise.

>> Yeah. So sketch out what the fear is and then like if you would take an action, what were the downsides and what were the upsides? Uh, and you know, typically

the upsides? Uh, and you know, typically it's like you've overestimated the downsides and underestimated the upsides. So, what you're doing here is

upsides. So, what you're doing here is you're really what you're really trying to do is clarify what these upsides were. Uh, because your mind your mind

were. Uh, because your mind your mind overstates what the downsides were throughout. That's why it feels so

throughout. That's why it feels so scary. That's probably why you didn't

scary. That's probably why you didn't take action.

>> Cool. So, I think we have two more questions right?

>> Yep. Two more.

Question number six. What were your greatest hits and worst misses? And the

secondary piece of this is why did the hits hit and why did the misses miss.

This is so important because your own natural bias skews how you view your year and the way that you reflect on your year. A lot of highly ambitious,

your year. A lot of highly ambitious, high performing people are overly critical of themselves. They'll see a whole lot of the misses. They'll see the to-do list of stuff that they didn't get

to at the end of the day and very easily and readily ignore all of the good, all of the things that they hit on. So

you'll look back at your year and say, "Oh, I didn't accomplish anything. I

need to really get going. I haven't

gotten a lot done." Or the, you know, crazy optimist will only see the good and will ignore the things that didn't work out and as a result not improve on the basis of those failures. So laying

them both out and being really explicit about what those hits were and what the misses were and and why, trying to get underneath the why behind each side of

that um is a pretty powerful exercise.

Could you give me an example of a great greatest hit and worse miss?

>> Yeah, I mean on the hit side, my biggest thing this year was the success of my book launch. I mean I I said it at the outset, but one thing I've changed

my mind on is like certain achievements have the power to completely change your life. That was one for me that did

life. That was one for me that did completely change my life. Um, you know, in terms of like the trajectory and the inflection point of my ability to impact and reach people, the rooms I I'm able

to be in, the people I'm around, it was a three-year in the making pursuit that I fully leaned into once I got over the fear of it not working out. Gave

everything I had to it. And uh, and it hit and it clicked. And I was mostly really proud of the fact that I did confront the fear and lean into it. And

when I say why did the hit hit, part of it was all of the work that went into it. Um, and the other piece was just

it. Um, and the other piece was just like it hit because there was no other option. I was just like I I didn't leave

option. I was just like I I didn't leave any single thing on the field. And um

that feeling is one that I haven't had since maybe my athletic days of like truly giving every single thing I had to something. Uh and so it was a pretty

something. Uh and so it was a pretty profound lesson for me.

It's sort of like ask yourself, are you really allin?

Like for your book, for example, you were really allin and I mean, you had years of like there's a lot of reasons why it was a success, but you know, the

fact that you were really allin, I think played a big role in why it worked.

>> Yeah. And it's the all-in thing is so funny cuz everyone says they're all in, but then they're not. You're like, you know, a lot of people I'll talk to about book launch stuff. I'm like, um, and

then they'll say they don't want to like shamelessly self-promote it or they don't want to like text people. I'm

like, look, dude, you just spent three years doing something. If you are insanely proud of the thing you created, you should be happy to talk to your friends about sharing it. And if they don't want to, that's totally fine.

Like, it's not like you force anyone to do anything. But if you're proud of the

do anything. But if you're proud of the work that you put in and you know it's going to be impactful for the world, if you're not willing to shamelessly self-promote your thing, why should anyone else be willing to to share it?

Um, and I think that that is I mean that's the key insight here is like truly being allin is a very rare thing and you can't be allin on five different

things over the course of five years.

Like you you get a couple of these missions in your life and you pick and you choose really well and wisely about which ones they are

>> 100%.

So greatest hits and then reflecting.

>> Mhm.

And by the way, we can share this PDF out with people like in the show notes or whatever it might be um so that folks have a place to download it if they want to use it to go through. Yeah, it'll

it'll be in the show notes. And lastly,

the final question. So, this brings everything together. Uh, you know, the

everything together. Uh, you know, the idea here is to zoom out, think about the prior six questions, your responses that you've written down, all of the notes, and synthesize

3 to 10, 5 to 10 core learnings from the year. What did I learn this year? What

year. What did I learn this year? What

are the big picture learnings that I'm going to carry with me into 2026 and beyond?

I'm curious what your uh what your couple would be from this year. And I'm

happy to share a couple, too.

>> Um what did I learn this year?

Let's let's let's write a few out actually >> on my notes cuz I'm actually going to go and do this after. Yeah. Like after this this podcast, I'm just going to answer all this stuff for myself.

>> And by the way, I can also turn it into content which is great. You can share it.

>> Totally.

>> Yeah. What did I learn this year? One

sort of myth that I had this year was I met an entrepreneur that that um I believed in. I really really believed in. I thought he

believed in. I thought he he was exceptional and I knew he was going places. Um but he brought to me a

going places. Um but he brought to me a business that I didn't believe in. So he

said, "Hey, I'm working on this business. Um I want to work with you. I

business. Um I want to work with you. I

want to work with your agency, LCA. Um,

and we turned him down. And we turned him down because we didn't like the business, you know, and he offered us significant equity in his business. Lo

and behold, that business is a $3 billion business. And we got offer, you

billion business. And we got offer, you know, call it just simple math, uh, you know, 1% of of three billion.

So, >> we said no to at conservatively, what is that? $30 million.

that? $30 million.

>> 30 million bucks. Yeah.

>> Yeah. Conservatively, so I would say anywhere between 30 and $60 million we said no to. And

part of me is like, well, don't feel bad. You know, you can't say yes to

bad. You know, you can't say yes to everything. Um, but the thing, the

everything. Um, but the thing, the biggest thing I learned was there was a reason my gut was telling me there's something with this this

founder. You know what I mean? And just

founder. You know what I mean? And just

because the business wasn't right, he so basically what what I didn't tell of the story is he pivoted the business.

>> So he spoke to me. I'm not saying I helped him pivot the business at all, but like spoke to me and just, you know, by chance 30 or 60 days later pivoted the business and then it's a rocket ship. One of the fastest growing

ship. One of the fastest growing companies of 2025.

>> Yeah. It's like

>> I I um >> I mean if I have one reflection on startup investing, I'm by no means some savant at this. I I've probably invested

in a 100 companies, but I have no like good frameworks. I'm not I'm not

good frameworks. I'm not I'm not proclaiming myself to be good, but I have had a few lucky shots. And the

lucky shots are almost entirely because all I focused on was the founder, not the idea. Like when I focus on the idea,

the idea. Like when I focus on the idea, honestly, I think I'm wrong 10 out of 10 times. I'm like, "Oh, but the, you know,

times. I'm like, "Oh, but the, you know, this idea is so great, whatever, because the business ends up being something different than whatever the original idea is." So, I'm better off just

idea is." So, I'm better off just focusing on like who is an absolute killer founder, who is going to be a talent magnet, who want, you know, who's going to be able to attract the best

quality people. Um, those people end up

quality people. Um, those people end up finding some idea that really works.

>> Yeah. So, I think my my lesson for 2026 is like, you know, find the three to five extremely talented

people you want to work with them and just figure out how to work with them.

>> Like, don't worry about the the what and don't get too super attached. Basically,

I got super attached to the idea and I got super attached to their product and when I when I went through their product, I was like, "This isn't going to work. Therefore, I can't be involved

to work. Therefore, I can't be involved in this."

in this." I feel like um >> I feel like I've read a few things recently of like people doing this like

um I think like maybe Josh Kushner was one of them at Thrive who is like exceptional at just sort of like staying in touch with people that like aren't really building anything right now, but

it's sort of just in the vein of like someone that I want to work with. Like I

just I just like I wanna I want to spend time I want to find things to work on with this person. So, I'm just going to like hang around the hoop and be in the room when the thing happens so that I can be one of those calls. Um, and I

think it applies to people that you want to build things with or invest in or whatever that might be. Um, but I I like that framing.

>> I like that a lot. Hang around the hoop.

Yeah, hang around the hoop was one of my favorites from like private equity days of like you'd put in a bid on a company knowing that you weren't going to like be the lead bidder, but you just like hang around the hoop so that if it doesn't work out with the lead bidder,

you're like standing there waiting for the rebound.

>> Totally.

>> Probably applies to applies to uh applies to the dating market, too.

>> I definitely can't speak to that one, but >> Right.

>> Um, cool. So, that's and that's that's your year in review. That is your year in review. So I hope that by the end of

in review. So I hope that by the end of that people have a good frame of reference and ideally jotted down a bunch of notes to kind of arm you to go and do this or

maybe you've started as we've been talking during this session. Um, but

this is really going to leave you in a position where you're going to feel like you've drawn a level of insight out of your 2025 that

you're not used to. And that insight and that depth and the richness of that insight is what's going to arm you to make 2026 your most extraordinary year yet.

>> I love it. Well, thank you for sharing it with us. I'll include links where to follow Sahil uh in the show

notes as well as the PDF if you want to do it yourself. And uh until next time, we'll have to you know, we got to you got to be our like our frameworks guy, you know.

>> Frameworks guy. I like it.

>> Yeah. No, I think uh you know what the show has become is very tactical and tactics are great, but sometimes you

have to uh kind of look at what you're doing from a 40,000 foot perspective and be like, am I uh sailing in the right

direction? And you know, that's why you

direction? And you know, that's why you know, having you come on here, I think is is really important. And uh so I want to thank you. Well, I think this podcast is actually a meta reflection on the

exercise we just went through, too.

Because I think for both of us, like our own reflections when we were doing it together back in 2021 or whenever that was was like the version of it that we were doing was energy draining for both

of us. And our ability to uh talk about

of us. And our ability to uh talk about that and still be friends and have you take it in the direction that created energy for you in the long run and have me to go off and work on things that

created energy for me. Uh it's really a perfect example and the success of what you've built with it is uh is a testament to that fact.

>> I appreciate it. All right, man. Well, I

can't wait to eat some meat and drink some wine with you on Thursday.

>> Eating some meat. Looking forward to it.

>> I'll catch you later.

>> See you.

>> See you.