This post is an excerpt from my weekly paid newsletter, “How I Wrote This.”
In my early 20s, my boss and mentor said something to me that ended up changing the way I lived my life.
“Cole, you can’t steer a stationary ship.”
The first time he said it, I didn’t really get it. But then he would see me sitting in the office at the end of a long day, hovering over my notebook, clearly “stuck” on something.
“What are you working on?” he’d ask.
We had a great relationship, and he took an interest in my personal development. He didn’t just want me to succeed at his own company, but to succeed in the ways I felt were most important for myself in life.
“I’m trying to figure out what I should work on,” I’d answer. I had book ideas. I had music ideas. I had tech ideas. My early 20s was a never-ending journey of me trying to figure out who I was, and what I should build first/next.
Grabbing his backpack and getting ready to head out of the office for the day, he’d say, Well, can’t steer a stationary ship,” and then shut the door behind him.
It wasn’t until I started writing every day on Quora that I really understood what that phrase meant.
Writing on Quora every day made me realize that I never really “knew” what I was going to write that day.
And the more days I let go by where I thought about writing, but didn’t actually write, the longer it took for me to make any real progress.
But once I start writing on a daily basis, I realized that it became easier for me to come up with more things to write about because, well, I was used to writing every day. In addition, the more I wrote, the more feedback I got from readers. The more feedback I got, the easier it became for me to write things I knew would resonate. Until all of a sudden, my writing flywheel was spinning so fast, I felt like I couldn’t be stopped.
When other people would see how much progress I’d made in a single year, they would ask, “How did you start?”
And I would reply, “You can’t steer a stationary ship. You just have to start somewhere, and steer from there.”
*Relevant Reading: This Is How Much Your Life Can Change In 1 Year
Since that revelation in my early 20s, I have since applied the “you can’t steer a stationary ship” thinking to every aspect of my life.
- Specific goals (writing, personal finance, etc.)
- Lifestyle goals (eating healthy, working out, etc.)
- Relationships (relationship building, conflict resolution, etc.)
- Anything that involves “progress.”
For example, one of the things I do at the end of every year is reflect on the year prior and really determine whether or not I’m “steering” in the right direction.
After all, it’s one thing to START a journey.
It’s entirely another to KEEP making meaningful progress in the direction you desire most.
1. Coffee With Cole ☕️
So, if you can’t steer a stationary ship — then the first question you should ask yourself is, “Am I moving yet?”
Everything becomes easier as soon as you take the plunge. The moment you commit to a writing routine, the moment you dedicate yourself to a daily habit, you unlock an entire wave of new questions you can ask yourself.
- “How can I do this better?”
- “How can I do this faster?”
- “How can I do this smarter, with more leverage?”
- “How can I do this more often?
The truth is, these questions aren’t really on the table before you start. Before you start, the questions you’re asking are more like, “Which direction should I go?”
If you can’t decide, pick the first one that jumps into your head and start there.
You can always turn your boat around, or steer it 45 degrees to the right or left.
But until your ship the leaves the harbor, you’re going nowhere.
Since we’re coming up on the end of the year, these are the 5 questions I ask myself every year to determine where I’m headed, and what new decisions I need to make in order to get to wherever it is I want to go.
1. “Am I spinning my wheels? Or am I actually moving forward?”
It’s one thing to be busy. It’s entirely another to make meaningful progress.
The reality is, I have found over the years that whenever I feel “CRAZY BUSY,” that usually means I’m spinning my wheels. Meanwhile, it’s the times when I feel like my life is almost TOO-SIMPLE, that I find my entire focus has been placed on one thing and one thing only — and that’s when I see the most meaningful progress.
Another way of thinking about this is whether you are stuck in the habit of ADDING to your schedule or SUBTRACTING from your schedule.
- When you are always trying to ADD things (“I have to do THIS, and THIS, and THIS”) you are diluting your focus more, and more, and more.
- But when you are always trying to SUBTRACT things (“I’m NOT going to that, and I’m NOT going to do that”), you are exponentially increasing your focus on the things that matter most.
2. “Am I moving in ONE direction? Or are each of my goals forcing me to move in DIFFERENT directions?”
I am so bad at this.
Guilty as charged.
I am someone who has so many different goals, and different TYPES of goals, that choosing “one” direction feels like an existential crisis.
Unfortunately, time has also shown me that living life this way isn’t exactly the most effective path forward. When you have different goals, you have different North Stars. And when you have different North Stars, well then one part of you wants to go North and the other part of you wants to go South — which means you end up spinning your wheels going one way, then the other, and so on.
The older I get, the more I am learning how beneficial it is to pick ONE direction at a time. It doesn’t have to be forever. But for a period of time, choosing one direction gives you a tremendous amount of clarity around what you should and shouldn’t do — which impacts question #1.
3. “Am I doing what I enjoy? Or am I in a perpetual state of depriving myself of enjoyment in pursuit of some end goal?”
This is a tricky one.
I firmly believe that accomplishing meaningful goals in life means doing things that might not be all that enjoyable in the moment but are required in order for you to get to wherever it is you want to be.
HOWEVER, that doesn’t mean you should stay in that place forever. Then you’re no different than the banker who hates his life working in a cubicle all day long hoping by the time he retires, he’s “rich.”
That’s no way to live.
Making sure you are doing things you enjoy, but also pushing yourself and doing the “hard things” required in order to advance, is a careful but important balance. Another good question to ask here is, “Am I doing these things only for some sort of end goal? What am I doing simply because I enjoy doing it in the moment?”
I can say for myself there are some types of writing I do simply because the work pays well. Sure, I’m still writing, but the TYPE of writing matters — and impacts how fulfilled I feel in the process. As a result, if I am ONLY writing things for money, well then I’m not very happy. But if I am writing things I enjoy that ALSO generate a profit, well that’s amazing.
Sometimes, you won’t be able to link the two (“I love this” x “This pays me well”), so until that becomes the case, I encourage you to make separate time for both.
4. “Am I playing an iterative game?”
This has been a newer question for me, but it has been a powerful one.
I think the first time I heard this idea articulated this way was in reading The Almanack of Naval Ravikant: A Guide to Wealth and Happiness. But I’ve since heard it/spotted it from a wide variety of sources.
The idea is that everything in life benefits from compound interest. The more time, energy, and resource you pour into a direction that can be iterated and improved upon over time, the more you are going to benefit from it.
For example, writing articles online is an “iterative” game. When I was first starting to write online, each article I wrote allowed me to internalize lessons and principles that could be applied to my next article — and so on, and so forth. And it’s being in this iterative state that ends up leading to compound interest.
What DOESN’T compound interest (aka: being in a non-iterative state) is when you are constantly changing what it is you work on. For example, when I first took the leap from my 9–5 when I was 26 years old, I offered a handful of different “services” to make money. I did content writing projects. I did brand strategy projects. I did personal branding projects. I did ghostwriting projects. And what I started to realize, very quickly, was that every time I “changed” the game I was playing, I was essentially starting over. I wasn’t iterating, which means I wasn’t taking action today that was going to compound and lead to 10x more effective action tomorrow.
Being in an iterative state, and letting your progress compound is one of the most under-discussed and yet most powerful growth principles in life.
So ask yourself: are you playing an iterative game? And if not, how come?
5. “Where did I say I wanted to end up this year? Did I get there? If not, why?”
We always seem to know where we want to GO in life, but do we remember where we said we wanted to go last year?
The reason this question is so important is because unless you are “arriving” where it is you said you wanted to be, something is going wrong. There is a breakdown in your process. Either you are setting goals that aren’t achievable (yet), or you are making mistakes rooted in the above (Questions 1, 2, 3, and 4). For example, maybe last year you set your North Star, only to spend the whole year questioning whether or not that was really the best direction.
Well, you can’t steer a stationary ship. So now you know: zero progress gets made when you don’t START.
If you didn’t end up where you wanted to this year, first remind yourself of why you set the goals you did.
- What were the motivations behind those goals?
- Were those goals realistic in the context of your current habits?
- Of all the goals you set, which one did you feel was most important to you at the time?
Then, ask what happened and where things went wrong.
- What got in the way of those goals?
- Did you choose too many? Were you trying to move in too many different directions — leading to you spinning your wheels but not actually moving?
- Did you set opposing goals at the same time? (Example: “I want to make more money” AND “I want to be less stressed, have more free time, and spend more time painting.”
Learn from your mistakes, so that this year when you set new goals, you know exactly what needs to happen in order for you to be successful.
2. The Pulse 🚀
Here’s what you need to know this week:
- If you are thinking about writing a book with the goal of driving more business opportunities for yourself, here’s a Forbes piece about why entrepreneurs should self-publish.
- Another great reminder of how self-publishing can lead to serious careers for authors (and why I think the future of sci-fi storytelling is going to accelerate like crazy).
- Interesting thought piece on the “Whiteness” of the publishing landscape.
- Another interesting thought piece in The Atlantic about the big publishing houses, and how “the bigger the houses, the more boring the books.”
3. What You Should Be Reading 📖
Currently reading Invent & Wander, which is basically a compilation of shareholder letter excerpts from Jeff Bezos over the years building Amazon.
Like him or hate him, the guy is a world-class entrepreneur, and worth learning from in a business context.
- I was a guest on the Outliers podcast recently, and it’s definitely one of my favorite podcast episodes I’ve ever recorded. Give it a listen here.
- I’m sure you’ve noticed some changes to this week’s letter. I’m going to be trying some different structures out for the next few letters based on sections I feel are most valuable on a consistent basis. “Can’t steer a stationary ship!”