Help me plan my life | #22

jk, I've done the planning, but I'd still love your opinion

In the previous newsletter (#21), I took you through a tour of my job history. I elaborated on 26 lessons I learned and feelings I felt along the way.

Now, having taken some inventory of my life, I'll use this newsletter (#22) to sketch out a plan. I'll think out loud about my fears, desires, ideas, and timeline.

I hope to

1. Refer to this newsletter in the future when I'm having trouble making a decision

2. Ask for feedback from smart people such as yourself. Where do you call bullshit? What do you think I should do differently?

3. Inspire you to think about what you're up to and why

A preview of what's ahead:

• Why I'm writing this out

• What I've learned: an autopsy of what has and hasn't worked for me

  • Lesson 1: I get really into stuff

  • Lesson 2: I love explaining things

  • Lesson 3: I'm people-oriented

  • Lesson 4: I want to sharpen my voice, not my skills

• What's the plan?

  • What do I need to learn to do those things successfully?

  • In what order should I do those things?

  • What's the business model?

    • Path 1: be a CGP Grey

    • Path 2: be a CGP Grey, but with a niche

    • Path 3: Partner with a writer

    • Path 4: Be a ~~~ coach ~~~

    • Path 5: don worry ’bout it (THE PATHLESS PATH)

Why I'm writing this out

I wrote about it in the previous newsletter but, in short, my client took the work I was doing for them in-house.

That caused me to think about where my income will come from next.

Which caused me to think about what my plan was.

Which caused me to think about

1. what I wanted out of life and

2. what my assets and experiences are.

Professionally, I've done a lot of stuff. Like,

• waited tables

• life-guarded

• edited writing

• built websites

• tutored and taught math

• analyzed data

• produced videos

But if you ask me what my thing is, I can't tell you. I don't have a bread-and-butter. Only a pantry full of seasonings and condiments.

I'm getting older. I turned 31 a few months ago, and it's beginning to feel a little bachelor-y in here.

I feel like Peter Pan. Reluctant to hunker down and commit to something.

In an iMessage group chat with some friends, we were talking about how one of us needs to get rich. One friend said this:

I'm betting on OTHER FRIEND, I used to think it'd be Josh (me) but idk anymore 😅

My stomach dropped when I read that. I felt so disappointed in myself.

He was right. I felt like I had all this experience but nothing to show for it. So much potential, so little results.

I felt myself getting defensive.

Well, what if my goal isn't to get rich?? I wanted to say.

It was cope. At least, to some extent.

Sure, I don't care about having hundreds of millions of dollars. But many of my goals seem to involve being wealthy.

A few examples:

• to give my future family a comfortable life

• to take my friends on vacations for no reason

• to be a leader and active member in my community

• to be close to my friends, family, and "the action"

• to become successful and then show others how to do it

• to exercise my creativity to its full potential

• inspire others to reach their potential in meaningful ways

I know I could do all the above, and more. I know that if I stuck with something, I could reach the potential I know I have.

This is normally where I'd fall into a trap.

I'd feel fired up, pick a lucrative skill, and start planning steps to master that skill. Often that meant buying some course on the internet.

After some progress, I'd hit my first rough patch. I'd have thoughts like:

• is this worth it?

• is this me?

• is there something else that fits me better?

• if I won't keep this up in the long term, I should bail now, right?

After a few rough patches, doubt would creep in little by little. Then, I’d quit.

I've been through that cycle many times. It's time to take a good, hard look at what's going on here.

• Do I have the wrong goal?

• Do I not have a good enough awareness of what I actually want?

• Do I not want it bad enough?

• Do I need more accountability?

It's a lot to think about.

I find that getting my thoughts out of my head helps me think clearer. I also find that publishing them helps keep me honest.

Thus, I'm writing out my plan here. As a bonus, I'll have a North Star to weigh decisions against. It's also neat to have something to point to for people that ask what I'm up to.

What I've learned: an autopsy of what has and hasn't worked for me

I covered these lessons in detail in the last newsletter, but here's a summary.

Lesson 1: I get really into stuff

I love when people ask me, what's top of mind for you, right now?

Most of the time, I have something I'm obsessing over. Ideas are firing off around the clock in my mind. That's the #1 reason I write: to unclog the drain.

This is great when it matches what my day job demands of me. I'll go above and beyond. I'll take lots of initiative.

When that's not the case, it's a real drag.

I remember going camping for a friend's birthday. We were a few minutes away from arriving at the camp site. I was excited for s'mores and fire-side chats.

When we pulled up, I had the record-scratch realization that we had setup work to do. We had to build the tent, prep the food, get firewood, etc.

That record-scratch realization is a good metaphor for my relationship with 9-5 jobs. I always “forget” that I have one.

Most week days, I'd wake up excited to do or learn about something. A new blog post. An app idea.

I'd be auto-piloting through my morning routine, getting excited about the idea.

And then I'd remember: damn it, I have a 9-5 job.

With camping it was far more worth it: an hour or two of prep for a few days of fun.

With my 9-5 job, it was ~8 hours of prep for 1-2 hours of fun in the evening.

I wanted much more time to work on my own stuff.

Being a part time contractor has turned out to be a great middle ground. I have so much more flexibility to work when I'm not begging my brain to stop fixating on something else.

It was hard to carve out 8 hours a day of time around my projects for an employer. But it's been easy to carve out 3-4 hours, 5 days a week. Or a full day's work three times a week.

It's also helpful if the work isn't cognitively or creatively demanding. That way I have more gas in the tank when I transition to personal projects later.

It'd be great if I could work on something full-time that happens to match my interests and goals. But, since my interests are so specific and fluctuate day-to-day, I don't see that happening.

Lesson 2: I love explaining things

Out of all the jobs I've had, being a math tutor has been my favorite. That's the first job I remember looking forward to going to.

I learned that I enjoy articulating things. I love trying to explain something and realizing that it's not as obvious as I thought. I love finding the contours between what something is and what it isn't. I love taxonomies, dichotomies, flow charts, and Venn diagrams.

I love sniffing out misunderstandings. I love seeing peoples' faces when they have a stroke of insight. I love watching them get enveloped in confidence as they realize their new capabilities.

I learned that most road blocks to learning are emotional, not cognitive. I took the time to establish a rapport with students. Talking out a problem beforehand allowed them to relax and build some confidence. Often, this was all they needed.

I later learned the same thing applied to me. Most issues I had with learning, problem-solving, and project management were emotional.

When I took the time to

1. get myself in the right frame of mind, and

2. set goals and expectations correctly,

the cognitive stuff often solved itself.

I think this explains ~60% of all the stuff I've started and abandoned. I skipped a lot of planning I shouldn't have skipped. Other times I rushed myself. In both cases, Much Frustration.

Lesson 3: I'm people-oriented

I've talked to a lot of people about personal growth. A common talking point that emerges is learning to be true to yourself. To do what's best for you, the opinions of others be damned, if necessary.

This was a struggle for me. For an obvious reason and an unexpected reason (to me, at least).

The obvious reason was a fear of enforcing my boundaries. Subconsciously, I was afraid that disappointing people meant the end of our relationship.

It helped when I internalized that people respect your boundaries in healthy relationships. I'm not missing out if the relationships end because boundaries weren't respected.

But there was still another blocker, which is the unexpected reason:

I still didn't know where to draw the boundaries! (great video, by the way)

I no longer had to please people from a place of fear, but I still had the desire to do so. I enjoy seeing people flourish. I enjoy contributing. I enjoy going to places where people want me there.

Hence, decisions like, to go socialize or to work on a personal project didn't get easier.

At first, I thought this was because I still hadn't conquered my fear of enforcing boundaries.

But, I began to notice signs that... maybe I'm more people-oriented than I thought. A few examples:

• When I watch Netflix with my friends, I get more invested and emotional than they do. I feel the cringe moments more vividly. I get noticeably more excited for characters than they do.

• I'm more likely than others to read things that my friends write or recommend. I love reading things people have written to get to know them. I recall several times where people have told me, wow, you actually took me up on that.

• When I think about what my ideal vacation is, the first thing I think about is who I'm going with. When I started asking other people what their ideal vacation was, most people went into destinations or logistics.

• When I was in product meetings during my software engineering jobs, they had slides with lots of numbers and charts. Some people got excited about hitting metrics and revenue numbers. I found it hard to. It felt faceless. I never met or talked to any of our customers. It felt like the work I did never affected anyone.

Hence, I should take advantage of my conscientiousness by doing more people-facing work. I should let how much I care motivate me.

Lesson 4: I want to sharpen my voice, not my skills

It wasn't until I started editing videos that I realized what I didn't like about writing code. My frustrations with working as a software engineer boil down to 2 things:

1. the number of ways to solve any given problem is huge, and

2. if you squint, everyone has the same problems (it’s all CRUD apps and moving data around)

If you ask an engineer what the most important part of their job is, they usually say one of two things:

1. learning to find the right code on Google, or

2. learning to navigate their company's code base

Those two skills are the most important because the ecosystem is gargantuan. There are a million tools, standards, programs, versions, etc.

And every company has their specific set that you have to learn if you work for them.

Once you've mastered finding the right code and putting it in the right place, that's the whole job.

Figuring out the outcome is (theoretically) not your job. The outcome is already defined for you by the product team. It's up to you to finagle the code to make it happen.

I figured out that I'm more interested in defining the outcome. Moreover, I'm interested in doing the work in proportion to how much I helped define the outcome.

If I didn't define the outcome, doing the work to achieve it is a chore. There's nothing unique to me about accomplishing that outcome. It's just work that needs to be done. When I do work that anyone can do, that’s when I get that cog-in-the-machine feeling.

Thus, I'm not interested in developing those skills. Especially with GPT4 on the verge of being able to do it for us.

Compare that to making videos. You use the same handful of tools (the Adobe suite + some add-ons) and the same process (pre-production, production, post-production) every time. But, each outcome is unique.

If you hire 10 different video editors, you're going to get 10 different videos. You can feel their style and voice.

I love that. I get to make my mark on everything I ship. I get to exercise that desire to express myself.

There's a big difference between "I made this" and "I made this".

What's the plan?

So, if I keep those 4 things in mind (repeated below for your convenience),

• I get really into stuff

• I love explaining things

• I'm people-oriented

• I want to sharpen my voice, not my skills

I think it's a safe bet to say I should do some combination of the following for income:

• explain things

• help people one-on-one

• create things

Helpful, but still vague. What if I combine them?

• help people create things

  • e.g. help creators edit and market their content

• help people explain things

  • e.g. creating curriculums

• create things that explain things

  • e.g. making YouTube videos

The first and third bullets resonate with me the most. Plus, they're synergistic: getting better at one means I get better at the other.

Let's get more specific, what does this work look like?

For helping people create things, I imagine

• looking at drafts and telling people

  • what would make it clearer,

  • what would make it resonate more, and

  • what the value is - thus, how to market it

• helping people identify valuable content ideas

For creating things that explain things, I imagine

• becoming interested in an idea

• learning about that idea

• documenting my learning process

• making the content I wish I had to speed up my learning process

• marketing that content to people interested in the idea

• rinse, and repeat

Okay. Now I have three questions left:

What do I need to learn to do those things successfully?

For helping people create things:

I think I'm pretty good at making things clearer and identifying value. I can identify when something resonates and when it doesn't for me.

But I'm not confident in my skill to

• identify when something does(n't) resonate for a given audience

• market content to that audience

I think if I consume 100 pieces of content while narrating out loud my thoughts, like

• what need I'm trying to fulfill by clicking this

• what I think I'll get out of clicking this

• what I actually got out of consuming this content

• how I felt

I'll have a good mental model for how to make something resonate.

As far as how to market content better (titles, thumbnails, etc), I think I'll get better by

1. making my own content, and

2. reading Ca$hvertising and Breakthrough Advertising

For creating things that explain things:

I'm pretty good at Premiere Pro. I'm okay at After Effects. I'm bad at Illustrator. I don't have a process for using them all in concert.

I also need to get better at project management and scoping. Often I don't have an answer for the question, have I learned enough about this thing?

But I think all the above will solve itself if I make a bunch of explainer videos.

To not get stuck in production hell, I should make my first ~10 videos super short. And about things I already know.

Like, proving the square root of 2 is irrational.

So I should come up with a list of those 10 things. Then go from there when I'm more comfortable with the tools and process.

In what order should I do those things?

So, here's my to-do list

• consume 100 pieces of content (vids, tweets, substacks), narrating my thoughts

• read Ca$hvertising

• read Breakthrough Advertising

• come up with 10 super short video ideas

• make those 10 videos

Not sure what the cadence will be, but I'll

• come up with the video ideas first,

• make the videos, and

• read/consume when I have extra time.

I imagine this will take me like 2 months, so I'll re-assess at that point.

What's the business model?

I can think of a few paths. It's likely I have zero ability to predict what path I'll end up on, but I still think it's worth thinking about.

Path 1: be a CGP Grey

CGP Grey is a YouTuber who makes animations explaining stuff. No real niche.

I could do something similar.

1. get interested in something

2. make a video explaining it

3. improve

4. rinse, and repeat steps 1-3 until I get enough traffic to live off the ads

Path 2: be a CGP Grey, but with a niche

Same as Path 1 except I'd pick a specific domain and only make videos in that domain. I'd probably grow quicker but I'd risk feeling boxed in and blowing it off.

Or, maybe the deeper I get, the more interested I'll get? Hmm..

Path 3: Partner with a writer

I read a lot of content written by folks on Twitter, Substack, etc, that I think, WOW, this would be an even better video.

I could be their video guy.

If I picked someone in a niche I'm interested in, that could be a good arrangement. They get more reach, I get to learn.

Down the road, I could provide this as a service to folks with mature marketing funnels and offers. Or anyone for whom I can convincingly demonstrate that I make them money and therefore they should give me a cut.

Path 4: Be a ~~~ coach ~~~

I have mixed feelings about identifying as a coach (a mixture of imposter syndrome + coming across as pretentious).

But I do love the idea of helping people with their content. I do it for free, anyway. I might as well get really good at it, help people make money from it, and take a cut.

Path 5: don worry ‘bout it

I could just assume that if I got good at

1. making videos,

2. explaining things, and

3. helping others make their content resonate,

the money part will figure itself out down the road.

The lazy part of me likes this idea. The financially conscious part of me wants more details. But maybe the conscious part will be satisfied once I get the ball rolling.

Anyway, I think I’ve reached the optimal dose of planning. Doing more feels like procrastination.

So, yeah! I hope you enjoyed reading this. Would love to hear your thoughts! Hit reply if you’re in your inbox, or if you’re on Substack, drop a comment!