Facing your fears when they're valid | #53
a reflection on my career history, my mistakes, and my plan going forward
It’s remarkable how close I can get, how well I can simulate facing my fear without actually facing it.
It’s so insidious how many temptations there are, how many reasons my brain can come up with to avoid facing it.
The worst part? Some of those reasons are valid. Confronting it *is* a bad idea. There is a reason the fear exists. Doing it anyway causes unnecessary grief at best and gives the fear more control over me at worst.
But that doesn’t mean don’t confront it. Instead, I can get creative with how I confront it.
I can take inventory of when it has popped up in the past. I can look for patterns. I can narrow in on exactly what I’m afraid of, come up with a plan to mitigate any actual risk, and then bravely move forward. That way, I can properly contextualize the experience. I have a better chance at expanding my comfort zone and learning a more useful lesson.
This post is a brief-ish history of my journey towards working for myself, some of my mistakes, and my plan moving forward.
All of this is mostly for me to refer back to (and for accountability to myself), but if it interests you, here you go!
My career: a short history
W2 jobs
Contract jobs
Some of my mistakes
a lack of intentionality
analysis paralysis
over-correction
lack of agency
lack of a “winner” mentality
Positive Active vs Positive Passive vs… Negative Active
not facing my fears
The plan, going forward
What am I afraid of?
Is it efficacious? (Does it work in general?)
Is it effective? (Will it work for me?)
Is it efficient? (Is it worth doing?)
What’s the day-to-day look like?
Okay, what are the next steps?
My career: a short history
W2 jobs
2016 - 2017: Software engineer at a big company. Wasn’t clear that what I did was that useful. Got interested in doing AI, so I talked to some folks doing AI at the company. They told me I needed at least a Master’s degree
2017 - 2020: Grad school. I enjoyed the flexibility. Being in the room with professors brainstorming ideas was fun. Teaching was fun. Doing a bunch of stuff and discovering most of it didn’t work wasn’t fun. Found out that most of the value came from getting the right data and presenting it correctly. And that managing data is a lot of work.
2020 - 2021: Software engineer at a medium company. I wanted to be more obviously useful. I worked at a big company with no obvious impact. I did a bunch of things that didn’t end up working in grad school. I figured I could have a bigger impact at a smaller, more mission-driven company. The work was more useful, but varied in scope a lot more. I ended up doing a lot of different things and found it hard to build expertise. Feeling confident in what I’m doing turned out to be pretty important to me.
2022 (January - February): Software engineer at a startup. I got an offer from a company that taught people to build crypto apps. They wanted me to build software to manage their bootcamps and said I could also teach. I liked teaching and liked the idea of owning a project. It turns out they expected me to work a lot more than I was prepared to work. They wanted 50-60 hour weeks, but I wanted time to work on both my day job and my own projects. I ended up having to quit to be a care-giver for my mom, but I don’t think it would have worked out anyway.
2022 (April - October) Business intelligence analyst at a big company. I thought a lot about what I wanted and what I didn’t. I wanted a focused job with impact. One that I could get good at, but also wasn’t super demanding and gave me time and energy to work on side projects. I liked looking at data. I loved explaining things. Business intelligence seemed to be a good fit. Unfortunately, it still wasn’t clear to me that what I did mattered. In fact, a lot of my job turned out to be finding out what mattered. I was tasked with making sense of, managing, and being the go-to expert for a bunch of data. I like looking at data for specific reasons when curiosity strikes. But, I discovered that I didn’t care to learn a dataset inside and out. To go looking for problems when it wasn’t obvious that solving them would matter to anyone. I learn when I put in reps. I put in reps when the problem is obvious and solving it makes a meaningful difference to a legible person.
Contract jobs
I thought for a while about what I wanted to do next and what I wanted to work toward. I thought, wrote, meditated, took walks, talked to people, and did little experiments.
I like explaining things. I like understanding things. I like understanding people: their motives, goals, emotions, stories. I don’t like looking for problems, but I like brainstorming solutions for problems. I don’t do well without a meaningful goal and a plan I can follow, otherwise I get distracted. I like being useful.
I like cycling between intensity and disconnection. I like being in control of my time. I don’t like being told to work on smaller problems when I feel there are bigger ones. I don’t like being told to use a bad solution when I feel there’s a better one. But, if I understand why this is the most important problem and the best solution, I’m all in. I’ll start and I won’t stop until biology rips me from the work (e.g. I have to pee, eat, sleep).
I got interested in making animated explainer videos, so I taught myself how and made a few. It turned out to be fun. As a software engineer, I spent so much effort learning, configuring, and wrangling tools. I already knew what the output should be, I just had to do the plumbing to make it happen. With video and animation, my effort went to strategizing, planning, and creating. With each iteration, the output was usually at least a little bit of a surprise. That kept it interesting.
So, I decided to make a career out of making videos.
Oct 2022 - Dec 2023: Contract video editing. I was paid to do voice-over explainer videos for AI software. I learned that
I had strong (but uninformed) opinions about what makes a good video,
I had a deficit in design knowledge,
I loved the flexibility of contract work, and
I loved being “closer” to the user. The less middle men between myself and the person whose problem is being solved, the better.
June 2023 - Sept 2023: Contract animation. I animated a minute-long segment of a video for a YouTuber.
It was fun making a visual come to life, but I had a bit of a skills gap using the tool (After Effects). It was stressful giving myself deadlines to both learn and deliver. When I’m learning things, I tend to be easily distracted because I’m going down rabbit holes and connecting dots. When I’m focusing, it’s about accomplishing the task. It’s hard to both learn and focus at the same time for me.
When I did deliver, I discovered that I structured the project wrong. He corrected it for me and didn’t seem to mind too much, but I imagine it took him a few hours. It bugs me when others have to spend effort making up for something I could have prepared for in advance.
Oct 2023 - April 2024: Contract web design. I built a lead intake site for a sound equipment company. I wasn’t looking for this gig, but it was pretty lucrative, so I took it.
I got to work with the owner and enjoyed the meetings. It was great to learn what she wanted, why she wanted the site the way she wanted, and where she was coming from.
When I felt like I had a plan and knew what I was doing, I enjoyed the work as well. When I ran into something that I didn’t know how to do, that it wasn’t obvious it could even be done, it was stressful.
Some of my mistakes
#1: lack of intentionality
I spent the first decade of my life after high school going with the herd.
I waited tables for a few years because that’s what my friend group did. I got internships at big companies because that’s what my peers in college did. And then, when I wasn’t satisfied with my first job out of college, I went back to grad school. Because that’s the only other thing I knew that people did.
Then I got on Twitter/X. I saw people advocating for thinking for themselves, and it occurred to me that I could do that.
#2: analysis paralysis
I used to be (and to some extent, still am) the type that likes to observe, understand, plan, and then try something. Some of that behavior is intrinsic to my personality. The rest is disguised procrastination. I don't know how much is each, but it is clear that most of it is procrastination.
To try to combat that tendency, I set out to “do something every day for 1,000 days” and document it on Twitter/X.
#3: over-correction
This one I didn’t learn until recently (about two years ago). I have a tendency to make one mistake, and then make the opposite mistake.
I’ll ask too many questions, then not ask enough.
I’ll under-communicate, then over-communicate.
I’ll plan too much, then too little.
My accountability thread is an example of jumping from “analysis paralysis” to no planning at all. Even though I tweeted daily for a few months straight, a lot of what I did on a given day didn’t move the needle. I woke up and, in the absence of a plan, just did whatever. As I noticed my lack of progress, my motivation dwindled.
#4: lack of agency
A few months ago I saw Emmett Shear and Visa tweeting about learning to be more agentic. This was the first tweet I saw:
I realized that was me. That was my wake up call. Even though I was aware that it was a problem (see: mistake #1, lack of intentionality), I could still be so much better at it.
I saw Emmett Shear (co-founder of Twitch) tweet that it was teachable. He would train people by prompting them with certain questions.
I gathered those questions and put them into a flow chart that I go through to problem-solve:
I decided to post it. It’s my most popular tweet to-date.
#5: lack of a “winner” mentality (h/t Alex Hormozi)
I watched this Alex Hormozi video about 6 days ago and it blew my mind. He lays out a spectrum to measure how much of a winner mentality you have.
I realized that there were some areas I had a good mentality in, but others I didn’t. And that, in any area that I didn’t have this mentality, it was hindering me. So now I resolve to be “Positive Active” in all aspects of my life. Here are the levels:
1) Positive Active
Assume that it can be done unless proven otherwise.
Alex cites Elon Musk on going to Mars as an example:
“You can’t show me that it’s physically impossible, thus I’m going to do it. I’ll be the first to do it.”
2) Positive Passive
If other people have done it, assume that you can do it, too.
Alex talks about how people thought running a 4 minute mile was impossible, until Roger Banister did it. Then, other people (who are Positive Passive) got inspired and did it as well.
“If he or she did it, I can do it.”
3) Neutral Passive
It works for other people, let’s see if it works for me.
You’re passively accepting whatever happens.
Alex says that this is most peoples’ mentality. They place the responsibility of the outcome external to them. If something didn’t work, it was because of the tool, program, etc.
He then contrasts most people with himself. Any program he did, he intended to reproduce the results promised by the course. Then, he'd go beyond them until he hit his goal. The thing (course, coaching, whatever) is not what gets the outcome, he is. He will make it work.
4) Negative Passive
It might work for other people, but it probably won’t work for me.
This is the kind of person who half-asses stuff. They’re passively looking to prove that it won’t work.
5) Negative Active
I’ll go through your entire system to prove it won’t work for me.
This is the type of person who says things like
I have bad luck, nothing works out for me.
The universe is specifically against me.
Alex comments that these people have the highest potential to jump to Positive Active. That they have the drive, they’re just oriented incorrectly. He says these are the people who are most likely to become animals (really good at the thing) or ambassadors (people who are grateful to you).
#6: not facing my fears
When I watched that “winner mentality” video from the last paragraph, I felt a tinge of fear.
I liked the idea, but DAMN: does this mean now I have no excuse for anything anymore? There’s zero reason I shouldn’t be building rocket ships like Elon Musk??
I thought about it for a few days and then watched another Alex Hormozi video where he addressed my concern.
He calls it the Push or Pivot dilemma. Here’s how he explains it.
You have wants and desires.
You have limited resources.
You make assumptions about what’s possible with your resources to get what you want.
Your strategy is how you prioritize spending those resources to get what you want.
If you follow the logic of your assumptions, you arrive at an estimated payoff for your plan. Then you ask yourself: am I willing to do the work to get that payoff? If the answer is yes, then you get to work.
If you follow the logic, get to work, and find out one of your assumptions isn’t true, then you can reassess. If pivoting at this point is the most rational decision, that’s okay. Learning things is valuable.
I don’t care to build rocket ships, so that’s reason enough for me to not do it. The effort to reward ratio is not there for me.
But, if I follow the logic and conclude that the payoff is worth it to me, then not getting to work means I’m succumbing to fear. This is (especially) true if I have lots of unknowns in my calculations.
That’s the test for whether I’m being rational or I’m afraid: Is it still worth it to me? Do I have data to support that my underlying assumptions changed? If not, keep going.
So, now I’m going to do that for my entrepreneurial endeavors.
The plan, going forward
My plan a few months ago was pretty good. The only issue I have with it now is that it’s too “build in the dark and then emerge to look for clients” for me. The “making contact with the market” part of the plan came too late. It made me unmotivated, unfocused, and insecure.
Why did making contact appear at the end of the plan? Because I was scared.
So it seems to me that the best thing to do is articulate all my fears and either
Solve for them if they’re valid, and
Bravely march forward if they’re not
What am I afraid of?
Three themes:
it’s not efficacious (it doesn’t work in general)
it’s not effective (it won’t work for me)
it’s not efficient (I could do it, but it’s not worth it)
Is it efficacious? Does it work in general?
I’m scared that there is no market.
This is obviously not true. Folks like Hunter Weiss tweet about work they’ve done for their clients all the time. There are plenty of agencies and companies whose business is making videos for people.
See Sahil Bloom and Codie Sanchez who are examples of people who buy those videos.
Is it effective? Will it work for me?
I’m scared that people won’t buy from me. I don’t believe that I will put out an offer and people will buy it.
This is an assumption that I should absolutely test. There’s only one way to find out: put it out there.
But also: what does it mean to put it out there? It’s likely that since I don’t have the skills and credibility yet, people won’t buy. But, that doesn’t mean they wouldn’t in the future.
At this point, I think it means removing the money from the equation. I think it means proving that I can add value now, and charging for it later. So, doing free work for maybe 30 people and seeing if at least a handful of people use it?
I’m scared that I can’t do it.
I’m scared that people are going to want some really complicated animations that I can’t make.
I’m scared that I’ll agree to make something and then find out I’m in-over-my-head.
I’m scared that I’ll make something that doesn’t add value to anyone (e.g. it gets no views or it’s otherwise bad).
Some responses to the above fears:
Remember the research you did on YouTube. 90% of the success of the content comes from the idea and packaging. 90% of the packaging’s success comes from psychology. At the end of the day, you don’t need fancy effects.
And if, for some reason, you do need those skills, that’s ok! In fact, that’s desirable. You want the market to direct you and give you a reason to learn stuff.
At the end of the day, it’s a sequence of pictures and some sound. If you have to, you can change pixels one by one. You’ll never not be able to make something. The question is: is it efficient to do so? And the answer is: probably.
You might be in-over-your-head at first, but
you will negotiate this in advance with mockups to avoid surprises, and
the work will be sold based on your portfolio (i.e. proof that you can do something similar).
And if all else fails: if you can’t do the job, or if you do it and it sucks… that’s okay! You can always offer alternatives. Refund them if they paid. Offer to try again. There are many ways to make it up.
I’m scared that I won’t want to do it.
This is probably my biggest fear. What if I get into it and I don’t like the work?
My response:
Historically speaking, anything that I’ve gotten very good at, I’ve at least not minded doing. For example, driving.
Also, anything that I’ve done with leverage, I’ve also at least not minded doing.
I haven’t done a lot of things that I'm good at WITH leverage, but I imagine that when I do there will be at least some joy in it. And those are two things that I can control.
Plus, historically I’ve been interested in anything that involves understanding things or people. Making videos at least requires understanding people. Even better if I can figure out a successful offer to make explainer videos, which requires both.
Plus!! I’ll be learning a lot. I’ll have a lot of fun going through content and taxonomizing stuff and adding to my swipe file.
Worst case: I get good at it, outline a Standard Operating Procedure, and hire it out. I like writing (obviously) so I'll probably do this anyway.
I’m scared of my family/friends/community finding out I sell stuff online.
Well,
'Be who you are and say what you feel, because those who mind don't matter, and those who matter don't mind.' - Bernard M. Baruch (FDR’s Presidential Advisor)
The people who would feel negatively - would you actually care about their opinion?
As long as you’re not being sleazy, there’s nothing to be ashamed of
You might even inspire others in your situation to do the same thing
Is it efficient? Is it worth it to me?
I’m scared that this isn’t efficient for me. Maybe there is a service I like performing, and maybe there is a price someone would buy it at. But what if that price works out to be something like minimum wage?
Well, let’s do a quick estimate and work backwards. Let’s use Videospark’s pricing, which is $2,500 for a 45 second video.
Could I make 4x 45 second motion graphics videos a month? So a 45 second video a week.
My answer is: right now, no, I don’t have the skills, but I think I could get the skills down the road.
Boom. That’s $10k a month in revenue.
Maybe $2,500 for a 45 second video is too ambitious. Maybe the market price for that kind of video is less.
I’ll mark this as an assumption I should test out.
Another rebuttal I’ll throw out there is: think about the long tail. There are so many niches. Once you have the basic skills, you can likely niche down and charge more.
I’m scared I can’t be productive enough to do all this stuff at once (marketing, content, fulfillment, etc) at an acceptable level of monthly revenue.
Well,
It’s not obviously impossible. Plus, other people run similar businesses, there’s probably a way you can do it, too.
With proper planning and expertise, I know that I’m very productive. So the bottleneck is not productivity. It’s planning.
But I also admit those two arguments aren’t airtight - you’ll have to find out. Remember: you can hire people, too. But this fear is about the pre-hiring phase.
What’s the day-to-day look like?
Well, once I get my video sales letter and website up and running, it’ll have 3 components: learning, practice, and outreach. And those aren't mutually exclusive!
Learning will involve going through courses, tutorials, and books like
Internet Money’s videos
Metaphors We Live By by Mark Johnson & George Lakoff
Visualization Analysis and Design by Tamara Munzner
This Is Personal by Brendann Dunn
etc (I have a big list)
Practice might involve tasks like
Breaking down the packaging of a video (title, thumbnail, hook)
Breaking down the content and retention of a video
Breaking down a creator’s profile or channel
Creating some recommendations for video ideas for their channel
Editing a video they’ve already published
Making a video for them using their voice over or splicing some of their existing videos (adding animation, motion graphics, VFX, SFX, etc)
Outreach might involve tasks like
Cold Emails, DMs, etc
“Hey what problems do y’all have?” or
“Hey I did this thing for you, feel free to use it!” or
“Hey, I could do one of these things for you, interested?” or
“Hey, here’s my offer.”
Generally making content (what I learned, what I made, what I’m practicing, what I did for people, stuff I like/dislike etc) on Twitter/X/YouTube/Newsletter etc
Commenting on other peoples’ social media
And of course there is auxiliary stuff like
Updating my dream 100
Updating swipe files (e.g. views and retention Figma boards)
Posting in the accountability channel on Internet Money what I’ve done in the above categories
Okay, what’re the next steps?
Step 1: Make a dream 10 list. I eventually want to get to 100 but not moving on until that’s done would block me. I want to get 10 right off the bat so I’m not blocking myself from doing outreach.
Step 2: Draft an outreach DM/email. It’ll be something like, “Hey, what problems do you have when it comes to making content? I want to solve a real problem. I don’t think I have the credibility or skills yet, but if I did, which of these seems the most useful to you?” and then list out the tasks from the “Practice” section.
Step 3: Make some kind of offer, based on the feedback I get.
Step 4: Make a Video Sales Letter around that offer
Step 5: Make a website or landing page around that offer.
After that, every day, do something from one of the 3 buckets:
Learning (Internet Money videos -> Storytelling course -> After Effects course -> Content OS -> etc)
Practice (Packaging/Retention/Profile breakdowns, editing a video, making a video)
Outreach (ramp up to: 2 YouTube vids a month, 3 tweets a day, 1 tweet thread a week, 20 comments on other accounts a day, 1 Dream 100 outreach a week although maybe more frequent is feasible, 1 Newsletter a week, and 20 DMs a day once I have a more solid offer)
And tweet about it + post in Internet Money about it. That’s it!
Time to get started!
I enjoyed reading this post. One thing I noticed: I feel like you're trying to counter fear with logic.
you can do it josh!!