In winter of 2013 I remember trudging around in the snowy, miserable shit-hole that was Brooklyn, New York at the time, just trying to stave off death by a million crappy, cold rain pellets.
I hated my job or, at least, felt like I was actively lying to people. (Even though I made great money.)
I found myself in a romantic relationship with somebody who I was slowly falling in love with, but that relationship felt like it hung tenuously on a thread and like, at any moment, she would decide to break up with me. (Which eventually came true.)
And I’d often wake up every morning feeling totally lost, with no clear sense of purpose or vision for what I wanted to accomplish in the world.
Everything felt totally out-of-control.
Oh, and living in New York, the weather was wet, and the cold clung to you like a shower-curtain.
The weather reflected my emotional state at the time — despondent would be generous, and hopeless would be more accurate.
I’d just float through life with no clear goals or expectations for anything or anyone.
It was deep in that moment of complete despair that I’d started to write down my goals — I actually can’t recall exactly when this happened, but a cursory glance at my Evernote tells me sometime in November in 2013.
Deep in that pit of despair, I wrote down a massive list of just about everything I could ever think of wanting to accomplish over the next decade or so. The list looked like this:
I sat on it for the next few weeks but, as time wore on, found myself slowly starting to tick things off — first, a Knicks home-game, since I lived in New York at the time.
After that, a Broncos home-game, as I’d eventually moved to Denver.
After that, an adventure around Japan.
I was starting to develop momentum.
Ticking off even the smallest things on that list started to get me excited.
Even though most of them were and still are far too vague — what’s a ‘successful marketing campaign?’, even?
Even so, having some semblance of clarity around what I wanted to accomplish in my lifetime made my days far more exciting.
Science shows that even merely the act of writing down your goals increases the likelihood of you accomplishing any of them dramatically.
That can be just as debilitating as it is exciting — if you’ve always wanted to be a DJ or a YouTube personality or maybe even an Iron Chef, your success rate in accomplishing that thing over your lifetime will grow exponentially in the next few minutes, right now, just by writing that thing down.
But instead of taking a total scattershot approach towards life-planning as I did many years ago, I’m instead going to recommend something else entirely in this post — an approach that will push you to think about your core values and what things you find meaningful, so that the things you do and accomplish over the next few years don’t feel like empty, meaningless boxes on a checklist.
Instead, as you continue to check-off new goals, you’ll find that they will support who you want to become.
If you want to become a master at managing and maintaining relationships, instead of accomplishing meaningless things like earning a $1 million just because everyone in the fucking world wants to accomplish that, you might instead write down, create a sustainable, profitable business that’s centered around helping other people grow meaningful relationships.
And that will likely get you far more excited than any amount of meaningless goal-setting will.
Again, there’s research that supports this — if your values align with your goals, your rate of success is much greater than if you’re doing something purely for the sake of having goals.
Dreams that would often take months and months of consternation and procrastination are now often something I’ll knock out in a quarter.
None of these ideas have been particularly life-changing just yet but I know that, over time, many of my experiments will yield incredible rewards, both personally, professionally, and financially.
Over the last few months alone, I’ve:
- Filmed, and started to edit my first TV show.
- Launched what is effectively a global scavenger hunt with friends.
- Lived in two different continents, and two of my favorite cities in the world.
- Completely rebranded my business and what I do, and started working with some of the biggest leaders in my space.
- And started on a half-a-dozen other big ideas, including launching my first digital course, writing a book, launching a heavily produced podcast, investing in and launching businesses in Japan and Istanbul, and a bunch of other ideas.
A lot of days, I sleep in late and wallow around in a puddle of my own self-loathing, but often I’m at least making forward progress towards things I care about.
When I show people how I go about mapping out my goals and breaking them down into more manageable chunks, they’re often blown away — when you spend large chunks of your time and energy just thinking about possibilities instead of mindlessly scrolling on social media, you’ll find that you have an inordinate amount of time to plan and get things done.
That’s what I’ve set out to show you in this guide: how can you take just a few hours a quarter, and start to take serious, measurable steps towards accomplishing your dreams.
I’d estimate that, total, this should take roughly a full workday every quarter.
Step 1. ‘Dreamstorm’ a list of possibilities.
Estimated Time — 2-4 hours.
My method for ‘dreamstorming’ has evolved quite dramatically over the last few years — what used to be a rather scattershot approach towards listing shit to do has instead become a lot more focused.
Instead of thinking of everything I want to accomplish over my lifetime, I’ll instead focus on one core idea that’s important to me right now, and go from there.
Often, this step will start with journaling — I’ll take my handy-dandy, leather bound notebook with my Rotring 600 pen and start with a deep, philosophical question, like, “Are farts designed to be a deterrent from predators?”
(Spoiler alert: mine are but some people’s smell like roses.)
A better question you might want to ask, is:
- What areas do I feel stuck in, and how would I like to grow in those areas?
- What are some things I could only dream of doing over the next 3-6 months?
- What is the smallest step I can take towards something extraordinary?
- Where do I feel discontent, or like I’m not doing enough?
A typical page in my notebook might look something like this:
And then often, I’ll have outcomes that look something like this:
The goal, here, is to identify patterns and maybe a potential seed for an idea that might be at the core of what I want to be doing over a few weeks or months.
I view my existence as little more than a series of brief experiments.
Eventually, after hours and hours of journaling, I might get to a conclusion that looks something like this:
If that’s my Why, and my raison d’etre, then that should be at the core of all of my decision-making moving forward.
Everything that branches out from that are simply ways of realizing that core purpose.
What I do is centered around that, and then the different paths that I take are purely extensions of that.
Troubleshooting: In most places, the suggestion that I’d normally make here is illegal, so instead of writing about that, I’ll give you an alternative: get away from your normal routine.
It is way too easy to be constantly distracted when you’re surrounded by distractions.
I barely trust myself to be in the same room as my smartphone without feeling tempted to pick it up every few minutes.
Plan an elaborate day or a weekend retreat where you don’t have access to your phone.
And, ideally, you don’t have access to any of your gadgets.
There are plenty of places that you can escape to, likely near your city, where you can find an Airbnb or a Hotel or a weekend Retreat place and just get away from the world.
Breather is a great spot to find distraction-free places.
It’s so, so easy when you’re stuck and you’re planning something for you to just pick up your fucking phone and start frittering your time away at something absolutely meaningless.
Remove the temptations by escaping.
Step 2. Pick a few ideas, and define them as ‘goals’.
Estimated Time — 2-4 hours.
The next step in this process is then breaking down what are often totally absurd, whacky ideas — launching a TV show, or a podcast series, or leveling up my YouTube channel, for example — and then breaking them down into more concrete, actionable goals.
The way I do this in Notion is as such — using a template called the Gamification 2.0 template from Conrad Lin, I come up with a list of goals under several different categories.
Finance might be one, or Relationships, or Business, or Fitness, and so on.
I develop goals around each of those things — I want them to sound dope, but also be something that has a very clear outcome that I can visualize and that I can control.
Building and selling an Oscar award-winning film sounds sexy on paper, but it’s not something you can really control.
But scripting and developing a proof of concept for a TV show is actionable, and something that I feel like is in my power if I put enough time and energy into it.
And so, that’s exactly what I did — instead of thinking about launching a TV show a few months ago, I started to develop it, hired a team to help produce it, and, voila — we now have something that, at the very worst, will serve as a proof of concept for a show and possibly lead to more interesting (and perhaps lucrative) projects down the road.
At best, it’ll help launch me into the next step of adult life as somebody who’s, uh, making shows.
My Notion template for goals looks roughly like this — and as part of those goals, I have very clear key results ie. ‘develop the proof of concept’, ‘sell the show’, and so on.
Troubleshooting: If you get particularly caught up on an idea, and find that for months and years you’ve written down several goals but often haven’t gotten any closer towards realizing them — for example, if you run a company and your revenue is often stuck at a certain point and you often lose motivation to push it beyond that point — then an exercise that I’d highly recommend trying is called ‘Fear Setting’.
Here’s an explanation of what that looks like:
Often what prevents us from moving forward with things in our lives is an immense fear of the potential consequences.
Through doing this exercise, you’ll often realize that while many of them might be founded, they’re also preventable and, in the worst case, repairable and that the short-term discomfort from your harebrained ideas going awry will often be greatly outweighed by the potential life-changing impacts of those things.
Step 3. Break them down even more into smaller projects and tasks.
Estimated Time — 1 hour.
The less obvious piece of this task is to then take your goals — those moon-shot, absurd ideas that you’ve come up with — and break them down into smaller projects and tasks.
Again, I use the Gamification 2.0 template here because it already includes a number of different formulas and equations for tracking progress and attaching projects and tasks to big-picture goals.
I try to break them down into small, achievable chunks — if they feel like month-long projects, then they’re probably too big.
Each project shouldn’t take longer than a few weeks at most, and should have a clear picture of what finished looks like.
From there, I’ve built out a view in Notion called ‘My Daily Digest’ that effectively has a breakdown of current posts and articles I’m writing, current projects I’m working on, things I need to delegate, and short morning + afternoon check-ins.
Here’s a quick overview of what my day-to-day view typically looks like:
You can copy that view, with clear instructions on how to set up each area here.
Step 4. Take the smallest step towards accomplishing those things this week.
Estimated Time — 2 hours.
The last piece is critical, in that it takes all of these things from theory into reality — for example, a big Mission of mine over the next 6-12 months is to get back to Japan, and find a long-term Visa so I can live there forever.
In the short-term, it’s actually impossible right now — even permanent residents aren’t allowed back into the country due to travel restrictions, at this very moment.
But in the long-term, it’s completely possible — plenty of entrepreneurs and business-owners are building amazing lives in Japan, and they even have Visa programs centered around helping people who wants to start businesses in Japan actually launch those businesses.
Beyond that, they also have an Artist’s Visa that’s centered around giving artists an opportunity to practice creating and selling their work in Japan.
So the first, easiest step for me is to either…
A. Talk to a business-owner who has already created a business in Japan, or…
B. Talk to an immigration attorney in Japan who is familiar with the different Visas in order to identify potential opportunities.
I took option B., since I have a number of friends who are business-owners in Japan who I’ve already connected with about this, and they’ve basically suggested the Startup visa.
After having that conversation with the attorney, I now have a clear picture of what exactly I need to do in order to create a more long-term Visa in Japan, and it seems very manageable (albeit a bit expensive).
Step 5. Reflect on your wins, highlight things that aren’t working, and iterate your plans.
Estimated Time — 1-2 hours.
Let’s assume that the show that I’ve launched doesn’t work — that nobody is interested in buying it and producing it and turning it into anything more than a series of videos that I might post on my YouTube channel.
That’s okay — for me, I learned so much in that process about what TV production looks like, what components go into it, and how to execute on those things that, for me, it was totally worth it if the idea completely goes to shit.
In the worst case, I have tons of great video content that I can use to later sell me and what I’m building.
It’s never entirely useless.
Often you’ll find that many of your experiments don’t work — the point isn’t to guarantee success here, it’s to simply try things.
In a separate database in Notion, I’ll often take an hour or two at the end of every month to write down wins, highlights, what went well, things I’ve procrastinated on, and so on.
Here’s what one of those pages will typically look like:
This works to remind me that, often, I do a lot in a given month even if it feels like I haven’t done shit.
But beyond that, if I see that I’m often procrastinating on something that I say I’ll do, it forces me to either take even smaller steps to bring that idea into fruition, or to simply give up on it.
That’s huge — executing on your dreams and visions is as much about eliminating things to focus on as it is choosing which areas to focus on.
Years later, that list that I’d created in Evernote now looks something like this:
It’s alarming how much can change in just a few years.
Most of the things that I’d accomplished often happened unconsciously — they were simply a by-product of relationships I’d built, luck, or circumstance.
Many of the goals just happened because of some strange turn my life had taken due to unforeseen circumstances — I never planned to live in Europe, for example, but Covid sent me here to Istanbul since my Visa was about to expire in Japan.
And there are dozens of other dreams and things that I’ve accomplished over the last few years that I didn’t even include on that list, too — epic, 200+ person parties that I’d organized with friends; a pivot into filmmaking; beautiful photography; amazing, life-changing mentorships and romantic relationships, etc.
Recently, my life has felt like a video game — I just level-up every quarter or every year or so, and not every hour.
And a lot of those accomplishments simply stemmed from that act of actively writing down my dreams.
Several weeks ago I went on a wonderful date with someone who was kind, thoughtful, who I connected with, and who was absolutely beautiful, in the middle of one of my favorite cities in the world.
It was one of those moments where you just think, somebody wake me up from this beautiful dream, please.
I looked up into the sky as we were holding each other’s hands and just smiled and said out loud, “What. Is. My. Life?”
“What do you mean?” she asked.
“I just mean… this is great.”
And I looked at her and I smiled and that was it.
The sad thing about life is that, at some point, if you want to, you will get everything you’ve ever wanted and more.
That’s also the beautiful part, too.
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