🍕 I’m JA Westenberg. I write essays about technology, philosophy, productivity, and what it means to be human. If you like ideas that take their time, you’re in the right place.
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This isn’t a bullshit, head-in-the-clouds, “you can do it if you just believe” post.
There’s plenty of those out there. I’m not going to write another one.
This post is about how to start (start) investing in yourself in a way that actually pays real dividends.
How to take the steps today that will enable you to be a better person, a better creative, a better developer, or a better business owner tomorrow.
And how to do awesome things with your life.
It involves 4 steps. They aren’t even complicated.
This is my framework for investing in myself. I follow it every day, and I tell anyone who asks for my advice to follow it, too.
It’s not a difficult system at all, but it can have a huge impact.
I created this because I know too many people who live their lives without direction. They finish school, get a job, and then spend 60 or 70 years falling with style.
They take on new skills as they come to them.
They go through life, barely reacting as it happens to them in real time, and slowly develop into whatever person their life has made them, without ever making a decision one way or the other.
Sure, it’s fun to live life as it comes. Structure isn’t everything; achievements aren’t everything.
For a lot of people, trying to follow any guidelines like the ones in this post will be a disaster. It just won’t work for them, and that’s fine.
And then there are people like me. The people who need that structure or we freeze.
We fail. We struggle. We lose direction. If you’re in that boat, this post is for you.
Here’s What You’ll Need:
A note-taking app or notebook
A spreadsheet app (Literally any will do)
A browser for research
A calendar or calendar app
Here’s the process:
1. Write A List Of 100 Things.
First: you have to define where you want to get to, no matter where that is.
I have a list of 100 things I’m going to do in my life. It’s not a bucket list; it’s not things I wish I could do - it’s things I really am going to do. I wrote it down the day I quit drinking and chose sobriety, the day I decided I was here for the long haul, and I wasn’t going to check out early. That was 7 years ago, and I’ve been working through my list ever since. I sit down and read it every single morning.
It took me 3 hours to put that list together, and it covers everything I’ve wanted to accomplish or experience for as long as I can remember.
This is some of my list:
I will reach $10m ARR as a purely solo founder and creator.
I will publish a science fiction novel set in my own world and featuring my own characters.
I will write and hand-draw an indie comic book.
I will publish a business book. (Done!)
I will become a parent. (Done!)
I will write, produce, and direct an indie film.
I will become a board member for a tech company I deeply and passionately believe in.
I will design my own sneaker.
I will deliver a commencement speech at a major university.
I will run a marathon.
I will visit the Grand Canyon.
I will raise a small, highly selective fund dedicated to solo creator businesses.
I will build a SaaS product that replaces an entire traditional agency function and does it with fewer than three full-time humans.
I will write and maintain a personal constitution that guides my values and my time.
I will own a collection of vintage cars.
I will visit the Arctic.
I will get married. (I’m engaged!)
I will stay in Tokyo.
I will build a treehouse for my kids.
I will found a non-alcoholic distillery.
I will meet an astronaut.
I will visit and research in the Vatican Library.
I will own a first edition Dickens novel.
I will experience a multi-day silent meditative retreat.
…and a whole lot more, decidedly too private for public consumption.
A couple of things to note.
The list goes from major life accomplishments to minor; from huge leaps to small steps. But each thing on the list is weighted the same; whether it’s meeting an Astronaut, hitting $10m or building a treehouse. There is no hierarchy. These are the will-dos of my life.
“I will” is the important framing here. It’s not I want, it’s not I might, and it’s certainly not I wish. I will do these things. There’s no option. I will, because I must, because I will.
Now if I can only accomplish 4 of those things per year, in 25 years I will have worked my way through the entire list.
If I keep this up, I will have lived a life that I will be proud of. I will have lived a life with a strong, clearly defined direction.
So make a list. Don’t feel you have to copy mine - it can be full of anything.
Ever wanted to build a mobile app on your own?
Participate in a skateboarding competition?
Own a ranch?
Learn to make your Grandmother’s chocolate mud cake?
Put them on the list.
Next: divide the list into these 4 categories:
Things that I need skills for
Things that I can do immediately
Things that I need time for
Things I need money for
Now live with the list.
You have to keep it with you for the next 2 weeks. Add to it, cut it down, analyze it.
Start to hate it, start to love it more.
Slowly get accustomed to it and work out whether it really reflects who you are and what you want.
Ask someone close to you if they’ll read it.
When you have a list you’re happy with, you can move on to the second step.
It’s what drives and motivates me throughout my day. Reading it constantly means I can never forget anything from it.
2. Create a skill chart.
This is how you’ll level up and track your experience.
If you want to get through a list of 100 things that you’re going to do in your life, you need to level up.
You need to work through the Skills category on your master list. Go through it and assign the skills you’ll need to each item.
Be realistic; don’t kid yourself. You have to honestly put down exactly what skills you are lacking or currently possess but are weak in.
These are the skills you’ll need to learn to accomplish this part of your list.
Take those skills and build a spreadsheet. It doesn’t matter what it looks like, so don’t waste your time on the design.
All you need is 4 columns.
A column that lists the skills you have to learn
A column for Research
A column for Action
A column for Progress
In the Action column, you’re going to be listing every step you can think of towards learning that skill. Think of it as the prerequisites.
Finding a course, signing up for it, taking on small projects, reading books - whatever it takes. Research this. It doesn’t have to be hard to put it together.
For almost anything you want to learn, there will be a hundred step-by-step guides online somewhere.
In the progress column, put down an estimate of how near you are to completing each of those steps. Again, be brutally honest. I won’t know if you’re kidding yourself, but sooner or later - you will.
This spreadsheet is now your guide to gaining those skills. Read it every week. Decide which steps to work on every week. Work on them. Update your progress. Repeat. It’s that simple.
3. Take immediate action.
By ticking off a few things from the list immediately, you’ll store rocket fuel for later.
We’re in the “things you can do immediately” category on your master list now. These are the things that you could actually do right now.
Nothing is stopping you, but for some reason you’ve never actually done them.
You need to make a plan. There’s no spreadsheet for this part.
Just grab a sheet of paper or a text file or Notion and write down which of those immediate things you’re going to accomplish over the next month.
Remember, they might be small. They might not take much effort at all.
Some of the immediate tasks from my list include “start reading The Infinite Jest” and “get a tattoo.” Extremely manageable, highly doable.
Why do you want to have some instant actions? Because it’s going to motivate you.
It will let you tick some things off your master list right away, making the whole project a lot less intimidating.
That’s a good thing.
Once you’ve mapped out your immediate tasks, set some dates. Put them in your calendar. Get them happening. You’ll be able to mark them off your calendar and make room for more items from the other categories on your master list.
Over time, your immediate action list and calendar will become your project forecasting and scheduling.
4. Dedicate 1 hour each day to your list
Deciding that the things you want to do are worth your seconds, minutes, and hours.
For me, that includes finishing a novel. Doing a podcast.
Those things that I absolutely have the skills and the abilities and the resources to do — but I just haven’t got around to yet.
If you didn’t accomplish anything on your list, and you looked back on your life, these are the things you’d feel the worst about.
Because they were so possible! They were within your grasp!
…And then you watched cat videos instead.
Setting aside time isn’t easy anymore. We all have so much shit going on that it feels damn near impossible to squeeze a little more time out of our days.
But I promise you, it’s possible. If you were pretty ruthless, you’d be able to find things you’re doing every day that are wasting the time you could use to do something incredible.
I realized a few weeks ago that my morning routine was spending 30–45 minutes on my iPhone before getting in the shower and just reading random crap online.
I turned that into my book time. Now I spend roughly half an hour every morning working on my books before I start the day.
It’s awesome.
The best way to work out where you’re wasting time doing things you don’t even enjoy is to spend a day taking detailed notes about what you’re doing. Put these in your notebook or app for an entire week. Examine what stands out and what you could be swapping for better ways to spend your time.
Once a month, do it again. Take stock of your habits and the way you spend your time. Notice if anything is changing, and why. This is your evolving time log.
Note: I’m not saying you have to be productive all day, every day. I watch Netflix, read comic books, and play Diablo IV as much as anyone else.
What I am saying is that everyone does some pretty pointless crap that they don’t even enjoy but has turned into a habit.
They do it regularly. And if they cut it out, they’d have time to do something they really give a shit about.
So you have your master list, the 100 things that you’re going to do. You have four categories. You have a spreadsheet that lays out all the skills you need and how you’ll learn them. You have a detailed guide to your time. And you have a calendar full of things that you’re about to do, immediately.
This is where we get to my favorite part of the system.
Make it all part of your daily routine.
Start every morning by reading through your master list.
Read your skills chart and work out whether or not you’ve progressed.
Evaluate whether you’ve marked your immediate tasks from your calendar.
Check your time log.
I read my list every morning over breakfast.
When you make it a part of your morning routine, you’ll never lose sight of anything. You won’t let your master list fall by the wayside.
A final word.
This framework has been great for me. I’m mindful, more so now than ever before. I’m focused, I’m driven, and I know where I’m going. I’ve even built a coaching and consulting business just around this framework, helping people through it.
That works incredibly well for me. I know what my life is like when I don’t take the time to invest in myself. I lose track of everything, and I fall into a deep depression.
That’s the way it goes.
I don’t let it go that way.
When you want to accomplish anything, the best way to do it is to stop dreaming. To focus and treat it like a project you’re being paid to do. A project that your job depends on. A project for the biggest asshole you’ll ever work for - yourself.
Treat this framework like an open source document.
Modify it, change it, re-use it in whatever way you want.
Publish it yourself, rewrite it.
It doesn’t matter to me; reach out and let me know.