Thank you so much for having me.
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 Sahil 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 Sahil Boom.
Welcome to episode 472 of Where It Happens podcast.
My co-host.
Welcome back.
I wanna talk about why we are all failing to achieve our goals.
And what are we gonna get out of this?
I hope it is the solution, the antidote to that, to really set us up for the biggest 2026 that we've all imagined, but 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 your framework for how you basically get the most out of the year, because you've got a very special framework and i haven't heard, i i haven't seen this anywhere and 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.
We do not learn from experience.
We learn from reflecting on experience.
This is something that we often forget.
Right.
Like we are in such a rush at the end of the year to plan for the year ahead.
To like OK, 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 going to walk through, this seven question framework, is all about 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 annual review.
It is seven simple questions that have been transformative, really life-changing, for me and my own journey.
It's led to some of my biggest changes that I've made.
And I think, for anyone listening to this, you're going to get a ton out of going through 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.
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.
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 have found that time and time again.
I'd be curious if you've observed that in others that 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 the smartest people I know and the most successful people I know are constantly 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 flip flopper, like that term from politics.
People get called flip floppers if they change their 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 at any age.
If you have a business that's doing at least 50000 a month in revenue, I've got something interesting for you.
It's called Offline Mode.
It's a two-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 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.
But they're not just quite there yet.
It's also about making your business AI first, how you can actually build not just one product but multiple products, and you're going to leave with tactical answers to your questions.
If that's you and this sounds interesting, I'll see you there.
So the goal is two to three key changes.
Yeah, identify a few things.
And two to three is a placeholder.
If it ends up being five and you had a transformative year, great.
If it's one, but it's really meaningful, also great.
The way that I think about getting under this, because when I first looked at this question it's kind of challenging.
It's like, 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 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 opportunities you were working on, some of the people you were spending time 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 habits, the people you were spending time with, the things, the ways you were thinking about the world.
Like actually go back 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 about?
That younger version of myself is making me sort of feel that, like that cringe sensation.
That to me is the most 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.
Because when I read the question, what have you changed your mind about? in the last year?
It's such a big question, right?
So I feel like people need tools to actually get to the core of that question.
That's the hard part.
Yeah and, I think, the calendar.
I'm a big believer in just the simplest tools, because every productivity guru on the internet will sell you some expensive productivity solution or some expensive second brain or whatever the thing gets called.
And What I found in my own experience working with some of those things is that you end up moving a whole lot but not actually making progress on things.
You have this complicated productivity system, but you're not actually creating progress on the things that you were supposed to work on.
And so I pull up the simplest version.
I use Google Calendar.
Go look at my calendar.
From the beginning of the year, one of my core operating beliefs in January of this year was...
So achievement is not going to change my life.
That has sort of been something over the last several years that I've grown to believe that achievements are not going to change my life in any way.
So I need to enjoy the 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 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 bemoan 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 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.
Think about you know largely in this context, like thinking about some of the relationships and some of the you know, the people, across a lot of these different questions because, in general like, the 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 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 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, et cetera.
With this.
It would be like you know, on the personal side, you know, maybe some of your routines, like you've realized you needed to shift the context in which you viewed different routines, different approaches to things, 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.
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 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, OK, so I have a question about this one.
So there are certain things I'm just reflecting on my own stuff.
There's certain things that drain energy in the short term, but the long-term benefit is created energy.
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 draining in the moment sometimes.
I don't look forward to it.
But once I'm done it, it's like a workout.
I feel amazing.
Not only do I feel 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's almost like 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, I focus on how do I feel after rather than how do I feel during.
For that exact 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 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, 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.
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.
So, on these, when you think about your energy, focus on 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?
I'm curious in your life, do you have 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...
I know you enjoy working out, but do you enjoy working out?
I mean, writing for me is definitely one.
Look, writing is my main thing.
When you and I stopped being co-hosts, the main reason was I was going to write this book.
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 so in love with writing, before and during doing it.
I find it to be a grind, honestly.
Intellectually I find it to be really challenging, but I feel incredible when I have those little breakthrough moments where something clicks in my mind.
It's like...
It's like the hard-earned win, right?
There's something about that meaningful struggle that you just endured that all of a sudden there's a little breakthrough.
And writing is definitely that way for me.
And so 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 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.
Because on the personal side I tend to just in my own brain, think about health practices a lot within that personal bucket.
That tends to be routines and things like that for me.
And so 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 closing off my energy to people who had not earned the right to it.
What about for people like you?
You're a New York Times bestselling author.
You've done really well.
You probably don't even need to work if you didn't need to.
What about the people who...
If you're in the zero to one phase, you're in your early 20s.
Is it a privilege to be able to say no to people who are draining you?
I think it is an earned privilege over time to eliminate or mitigate the energy draining things from your life.
But it's an earned privilege that all of us should aspire to continue to earn over 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.
Right.
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 you wouldn't want to eliminate some of those things, because they add texture and they add a layer of meaning.
But I think that that is earned over time.
My first job working as an analyst in a private equity fund.
I was working 100-hour weeks doing a lot of email, Excel modeling, all of that stuff.
And 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.
Identify one thing that you might be able to change.
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 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.
I like that a lot.
So that question leads into and is connected obviously to the third question, which is what drained energy this year?
Just the inverse.
You know, you're looking at your calendars again, you're diving in and you're identifying what those energy draining things are.
You know what was sort of the stuff that just made you feel less human, both during and after, in whatever format.
For me, that is almost always every year, calls and Zoom meetings.
You know like I constantly feel, like I go through these like cycles of taking on too much and then needing a reset.
And again, minor adjustments to this kind of stuff can have a pretty dramatic impact.
So identifying what those are early and then learning to adjust course as you need to really impactful.
Dude, Zoom calls like back to back 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?
I'm privileged in the sense that my calendar is pretty empty.
The reality is I would be way more successful if I did have more Zoom calls.
But I just enjoy my life a lot more.
We're hanging out on Thursday, you and I, and 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.
You know, according to my logic, it sounds like you're just as successful as you want to be.
You're meeting your own definition.
Yeah, that's how I see it.
For me.
There are a certain set of weekly or monthly or quarterly calls that I am on.
Where I'm just, It's recurring meetings.
That's what it is.
Recurring meetings.
That's the last thing I need to just... remove from my calendar.
Yeah.
Recurring meetings are a funny one too, because what I find happens is you create stuff to talk about on them that's not actually impactful.
You're like, OK, 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 it asynchronously.
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 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, just sharing an update.
You know what I mean?
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.
I think private equity funds sometimes get a lot of things wrong, but one of the things that I thought was profound was the structure of board meetings, when well done, which was.
The CEO and the team would send around, maybe a week in advance, a deck.
That was basically the business update and all of the key information about the business.
And then the meeting itself, when everyone was in the room together, was entirely focused on the forward-looking, most critical decisions that needed to be made and debated.
And then let's focus the brainpower, when we're all here, on the things that are actually going to drive the business forward.
Yeah, so this is going to be the big change for me in 2026.
I also wish and this is like a startup idea, someone should figure this out is I wish there was a way to ensure that people actually read the prep materials?
You know what I mean?
Because sometimes I find we'll implement this in a monthly meeting or whatever, and we get to the meeting and 75 of the people haven't read the you know the deck or whatever it was.
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.
Oh, 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 a response to some question from page 27 of the memo?
Totally.
Yeah, it's like, instead of a captcha, prove that you're human.
It's like prove that you're a good team member.
It reminds me of, like Harry Potter and like the Sorcerer's 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 wizard's chess and they have to like get through the different things.
Exactly.
I like it.
I like it.
All right.
So three buckets also here.
Yep.
So you're professional and personal on people.
Yep.
And again, the people one cannot overstate this.
Identify the people that make you feel like you need to take a shower after spending time with them, 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 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 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 people, 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 to try to make progress in 2026.
What's the new habit?
What's the new company?
What's the new mindset, the new routine?
Whatever the thing is, right?
New protocol, to use the language that everyone uses now on 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 reflection question really gets under.
Yeah, this is really good.
I find that answering this question often requires a coach of some sort.
Or just a friend.
Because you really have to be honest when you're answering this question.
It's hard to get to that.
Yeah, it requires a level of like ego destruction that is really challenging.
So you said this at the outset like you could do this exercise with a friend, someone you trust could be a partner, could be a friend, someone that knows you and that is a truth teller in your life, like someone who is willing to tell you the 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 is willing to tell them the 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.
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.
So find that person maybe to do this one with.
Ask them what are some of the things they could see from the outside looking in.
And then for you, try to create that outsider's perspective.
Like, you know, to do that, maybe ask yourself here.
If a third party were to watch me for a week, what would they say?
Are the things that are holding me back?
What would they say about how serious I am about my goals or about the things that I'm going after?
What do you think about using ChatGPT 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 copilot.
I think that setting the pretext to chat GPT that you need it to be thoughtfully critical and sort of an intellectual sparring partner rather than a, you know, just a friendly, kind partner, would be important especially for this question.
But it could be really useful.
Also, you should program it to not be positive with everything.
I like the word to use, truth teller.
Being a truth teller, the truth hurts sometimes, basically.
Should we plug it into ChatGPT right now and see what it tells us?
Sure.
I haven't set the pretext, but now I'm curious.
Sure.
So you want me to, all the questions or this specific question?
No, just this one.
Okay.
Now I'm curious what, I'm going to do it alongside you.
So I'm going to say, or you know, can I say this?
Okay, I'm going to say my name is Greg Eisenberg.
Okay.
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 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.
So it says, I'll zoom in so people can see.
Boat anchors are the hidden drag forces you don't notice in day-to-day, but they slow every decision, distort every opportunity and compound into stagnation.
I kind of like that, actually.
The core categories to interrogate, beliefs that shrink your aperture.
Examples, I need to be involved in everything.
If I slow down things, things break.
That's a good one.
Habits that drain wattage instead of creating it.
Recurring behaviors that don't move the needle but consume cycles.
That's kind of like what we were talking about.
Incentives that point you at the wrong games, you talk a lot about that.
Emotional commitments that distort 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 anchor buried there.
Track anything you keep saying you'll fix when things calm down.
Anchors hide in that folder.
Track anything that used to energize you but now feels heavy.
That's an anchor disguised as identity.
What do you think?
I like that.
Mine was pretty good too.
It actually gave me It gave me one that was the strong 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.
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 some stuff with their partner for whatever reason.
Which I understand, by the way.
I do... It probably goes to that strong one complex that I just said.
I do carry things close to the vest sometimes because 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 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 to do something like this with your 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 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 inexperience 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?
What was that fear that held me 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 under their bed or the monster in the 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 most of us.
It thrives in the darkness.
And when you shine a light on it, when you deconstruct it, you end up realizing it wasn't so scary and you start taking action on these things.
Tim Ferriss was the first person I saw talk about this.
He had an exercise I think he called fear setting, 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 abstract and amorphous.
That's interesting.
Can you share some things that you haven't done because of fear?
Yeah, I mean, I would say my biggest one was leading up to my book launch.
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 percent because we're afraid of what would happen to our ego if we did give 100 percent and then failed.
Right.
It's like a self-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, because I didn't really promote the thing.
Right.
You know, I didn't really give everything I had.
So like, yeah, it didn't work out.
Well, whatever.
Right.
It's like this self-protection that becomes self-rejection.
That was a big one for me to get through, to just realize that if I was going to go down, I had to go down truly swinging and push and give my all towards something that I really cared about and felt was really meaningful.
I'll share a little story about this because I've been thinking about fear a lot the last few weeks.
So someone who I look up to reaches out to me actually on Instagram.
Very well-known guy.
So I look up to him.
This guy I've been following for years.
He's like, I love your content, can we hop on a call?
I'm flabbergasted, I'm so excited.
I get on the call 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, let me share.
And I could just see his eyes glazing over of three or four companies that we're working on.
And he's like, can I give you my honest opinion of what you're doing?
And he goes, it's not big enough.
It's not big enough.
And we talk a little bit more, hangs up.
And I actually told my wife about it.
I was like, am I not thinking big enough?
Am I not doing things because of fear?
In this case, I actually had to go through this exercise and I realized no, it's not because I'm actually loving what I'm doing.
It's a 10 on 10.
Fear has nothing to do with it.
But I think that the prompt of...
The fear prompt is so, so helpful in giving yourself clarity, because now, all of a sudden, I'm walking into 2026 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've had similar experiences with like my experience with sort of like assuming diversification was the 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 in like 30 different buckets and that's how I'm going to make sure that one of them is going to go well and things will go well.
And I've gotten pushed on that by several mentors who said something similar.
It seems like you have your hand in a bunch of small, stupid stuff that you don't really care about, 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.
It was like why am I involved in these things to the point where now I'm heavily concentrated in like two to three things, but there are 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, you know, living true to your own definition does feel good.
I love that.
I love that one.
This is a really powerful one.
Okay, so this is the Tim Ferriss exercise.
Yes.
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?
And you know, typically it's like you've overestimated the downsides and underestimated the upsides.
So what you're doing here is you're really what you're really trying to do is clarify what these upsides were, because your mind, your mind overstates what the downsides were throughout.
That's why it feels so 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, 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 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 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 why, trying to get underneath the why behind each side of that, is a pretty powerful exercise.
Could you give me an example of a greatest hit and worst 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 completely change my life, you know, in terms of like.
The trajectory and the inflection point of my ability to impact and reach people the rooms 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 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.
And the other piece was just like, it hit because there was no other option.
I was just like, I didn't leave any single thing on the field.
And 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.
And so it was a pretty profound lesson for me.
It's sort of like, ask yourself, are you really all in?
For your book, for example, you were really all in.
There's a lot of reasons why it was a success.
But the fact that you were really all in, I think played a big role in why it worked.
Yeah.
And it's the all in thing is so funny because everyone says they're all in but then they're not.
Like you know a lot of people I'll talk to about book launch stuff.
I'm like 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 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 share it?
And I think that that is – I mean that's the key insight here is like –
Truly being all in is a very rare thing, and you can't be all in on five different things over the course of five years.
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.
Mm-hmm.
And, by the way, we can share this PDF out with people, like in the show notes or whatever it might be, so that folks have a place to download it if they want to use it to go through.
Yeah, it'll be in the show notes.
And lastly, the final question.
So this brings everything together.
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 three to 10.
Five to 10 core learnings from the 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 couple would be from this year.
And I'm happy to share a couple too.
What did I learn this year?
Let's write a few out actually on my notes.
Because I'm actually going to go and do this after 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.
What did I learn this year?
One sort of miss that I had this year was I met an entrepreneur that I believed in.
I really, really believed in.
I thought he was exceptional and I knew he was going places.
But he brought to me a business that I didn't believe in.
So he said, hey, I'm working on this business, but I want to work with you.
I want to work with your agency, LCA.
And we turned him down.
And we turned him down because we didn't like the business.
And he offered us significant equity in his business.
Lo and behold, that business is a $3 billion business.
And we got offered, call it just simple math, 1% of $3 billion.
So we said no to, conservatively, what is that, $30 million?
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 can't say yes to everything.
But the biggest thing I learned was there was a reason.
My gut was telling me there's something with this founder.
Just because the business wasn't right.
So basically, what I didn't tell of the story is he pivoted the business.
He spoke to me.
I'm not saying I helped him pivot the business at all, but he spoke to me and, just by chance, 30 or 60 days later pivoted the business and then it's a rocket ship.
One of the fastest growing companies of 2025.
Yeah, it's like I mean, if I have one reflection on startup investing, I'm by no means some savant at this.
I've probably invested in 100 companies, but I have no 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.
When I focus on the idea, honestly, I think I'm wrong 10 out of 10 times.
I'm like, oh, but 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 focusing on 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 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 and don't worry about 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 went through their product I was like this isn't going to work.
Therefore, I can't be involved in this.
I feel like I've read a few things recently of like People doing this, like 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 want to 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.
And I think it applies to people that you want to build things with or invest in or whatever that might be.
But 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 the dating market too.
I definitely can't speak to that one, but...
Cool.
And that's your year in review.
That is your year 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.
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.
Thank you for sharing it with us.
I'll include links where to follow Sahil in the show notes, as well as the PDF, if you want to do it yourself.
Until next time, you've got to be our frameworks guy.
I think what the show has become is Very tactical and tactics are great.
But sometimes you have to kind of look at what you're doing from a 40000 foot perspective and be like am I sailing in the right direction?
And that's why having you come on here I think is really important and 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 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.
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 ya.
See ya.
