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 actually, practically invest in yourself in a way that is going to pay 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 four 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 that they should 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 whenever learning happens to them and they slowly develop into whatever person their life has made them.
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 kind of 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 (Airtable is amazing).
- A browser for research.
- A calendar or calendar app.
Step 1: Write A List Of 100 Things
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.
It took me three hours to put that list together, and it covers everything I’ve wanted to accomplish or experience since I can remember.
Here’s part of my list:
- publish a novel;
- publish a comic;
- publish a business book;
- consult on business;
- have a podcast;
- maintain a high level of fitness;
- teach an online course;
- create a non-profit .org;
- write for Forbes;
- write for the Wall Street Journal;
- appear on a panel;
- write for TechCrunch;
- go to SXSW;
- write a film;
- and a whole lot more.
Now if I can only accomplish four of those things per year, in 25 years’ time I will have worked my way through the entire list. 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 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.
Divide the list into these three categories:
- Things that I need skills for.
- Things that I can do immediately.
- Things that I need time for.
Now you have to live with it. You have to keep it with you for the next two weeks. Add to it, cut it down, analyze it. Start to hate it. Then start to love it more. Just slowly become accustomed to it and work out if it really is a reflection of who you are and what you want. Ask someone close to you if they’ll read it.
When you have a list that you’re happy with, you can jump onto the second step. It’s what drives and motivates me throughout my day. Reading it constantly means I can never forget anything from it.
Step 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.
These are the skills you’ll need to learn in order 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 four 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 pre-requisites. 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.
Step 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 now from your master list. These are the things that you could actually do right now.
There’s nothing 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 an Evernote 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 enable you to tick some things off your master list right away, and doing that is going to make 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 is going to turn into your project forecasting and scheduling.
Step 4: The Things You Need Time For
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! Yet you watched cat videos instead.
Putting aside time isn’t an easy thing to do 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 to 45 minutes on my iPhone before getting in the shower. 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.
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 of days. 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.
I’m not saying you have to be productive all day every day. I watch Netflix and read comic books and play Fallout 4 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 guide to the way you’re spending your time, in detail. 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.
Turn it all into your daily routine. Start every morning by reading through your master list. Reading your skills chart and working out whether or not you’ve progressed. Evaluating whether you’ve marked your immediate tasks from your calendar. Checking your time log.
I read my list every morning over breakfast. This is how I get things done.
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 way side.
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.
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 lost track of everything and I fall into depression. That’s the way it goes.
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, re-write it. It doesn’t matter to me, just reach out and let me know.
If you have any experience following it, I’d love to hear from you!
Jon Westenberg an entrepreneur, writer and avid learner. He advises start-ups and investors on how to build profitable companies and operate with a small business start-up mentality. For more from Jon, visit on his website, follow him on Twitter, or email him at firstname.lastname@example.org.