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How I narrowed 33 options down to 4 (and why I'm running them simultaneously)
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Last week I made an AI interview me before it ranked a single side hustle. Turns out the useful part wasn't the ranking. It was what the interview dug up about me.
What changed everything
Four facts about me blew up the plan.
I get obsessed with a thing for about three weeks, then go cold. You can blame it on the ADHD (which, apparently, everyone else and their mom also has).
An autoimmune disease benches me for days with no warning. So whatever I build has to keep running while I'm flat on the couch.
My dog, Tula, is half my life and a part-time job's worth of hours. Weekends are sacred. So I've got far less time than the spreadsheet assumed.
I am excruciatingly risk averse. I hate losing money and would rather waste my time than my money… but I can’t commit a lot of time either given the previous three “aha” moments.
I call myself “lazy,” and this is kind of showing me how much I have to overcome to even get to the table. Maybe you do too.
What I'm betting on
So here's where I landed. Four small bets, all at once. Here’s the slate:
This newsletter, because I talk for a living and can knock it out in 20 minutes, and I am convinced that Claude is obsessed with newsletters.
Consulting, with the cold-outreach I hate automated away so I only handle warm replies
Two boring Amazon products that runs itself
One thing I can build in a weekend and sell
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Why all four at once
The AI wanted me to build these sequentially. But, you know, I get bored easily (ADHD) and I have that big, expensive MBA that taught me a thing or two about business stuff. Namely, rapid iteration is the key to success. Don’t over analyze. Move, move quickly, and learn as you go. Setting up sequential bets would have me burned out before I got to bet two (and doubting myself - reference issue 2).
So, I pushed back. Then, the parallel, unhinged bet was born. I wanted to rapidly test various ways of making money as quickly as possible to quickly deprioritize or re-calibrate my strategy in real time.
This way, yeah, I am burned out now, but I won’t be burned out for the next two years. I will already know which income streams worked best for me.
But like any good experiment, you need to know your guardrails, constraints, and success criteria.
Let me introduce you to my bail criteria
Newsletter: under 200 subscribers and no real revenue by month 6, I change the format. Over 200 and growing, I put money behind it.
Consulting: 150 emails and zero warm replies by month 3, the offer's wrong, scrap it. First paying client, I raise my rate.
Amazon products: not profitable by month 6, kill the first two products and swap in the next one. Profitable, add a second.
Digital Product(s): under 3 sales in 30 days, reassess the funnel strategy. Over 5, I will do a dance.
What I'm committing to
So that's the deal. Four bets, each with a deadline and a number that ends it whether I'm feeling brave that month or not. I'm putting it in writing so you can hold me to it, and so I can't quietly move the goalposts when a favorite starts to flatline. Which to be honest, are already my digital products right now. I think they rock, but I have not cracked the sales funnel yet.
But let’s talk about you
Because I want you to learn from what I have already learned.
Do one thing, tonight. Pick the one thing you keep meaning to start. You know what it is. Before you do anything else, consider what metric is meaningful to you. If it is a side hustle, this could be subscribers, dollars, views, etc. If it is something else, this could be anything. Now, write it down.
Where that number has to be for you to keep going.
Where it has to be for you to quit.
The date you check, and not a day sooner.
Now, text your friend that you are committing to this. Hold yourself accountable.
And if you want the actual tool I built to run this interview on yourself, that's this week's bonus issue. Stay tuned.
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