✅ Updated Top 20 Checklist for Doing What You Love . . . IF you also want the money to follow 😅
Today’s post is an abridged ;TLDR version of Wednesday’s full 2,200 word piece, with a few new additions to the checklist below.
With all my personal biases and recent experiences established in the full-length version, I now offer an updated
15 18-point checklist for those aiming to do more of what you love while also paying the bills. Big thanks to those who commented on the full piece to help spark these additions!
As previously mentioned, pair this with’s post, Making the Content Math Work, and an eyeroll from anyone over 40 saying, I COULD HAVE TOLD YOU ALL OF THIS BEFORE YOU WIPED OUT YOUR SAVINGS. 🙄🙄🙄
Those who flow as life flows know they need no other force.*
* But one must do some flowing where there is an income stream.
—My Dad’s addition, written in the margins of this Ch. 8 epigraph while editing Free Time
🧐 Do what you love and the money will follow . . . if you meet more than three of the following criteria:
You are clear on what you love in the first place. You’re not still in the Tinker Dabble Doodle Try phase.
You love teaching other people how to teach other people how to make money online.
You have enough money in long-term investments—index funds and the like—to live off the interest alone, keeping the principal tucked safely aside for retirement.
You are already independently wealthy. See #4, trustafarian, or #6.
You have a spouse AND said spouse earns a robust living with solid health insurance and a thick paycheck every two weeks.
You have abundant financial runway AND you don’t mind that runway crumbling beneath your wheels as you try to get the 747 of your passion off the ground.
Your passion happens to be highly lucrative and/or
“What you love” aligns with an in-demand, profitable, thriving industry—i.e. not crypto or the arts. The income streams by what you love have not been dammed, dried up, or redirected.
Even better, what you love includes working a full-time job in one of those thriving industries. You love leading teams of AI software engineers, for example.
You excel at withstanding intense, unrelenting uncertainty and financial pressure. You are also patient and stubborn.
You love your passion more than paying your bills on time.
You are a dynamo! In this now-global economy, you possess a one-in-a-million edge in terms of raw talent. Good looks are a plus.
You absolutely love sales and marketing! L-O-V-E. It’s a fun game, you never tire of it, and you thrive on the competitive art of climbing charts. If a leaderboard exists, you are ON IT, in both senses of the phrase.
You have abundant runway and/or a large existing stream of income and/or investor funding that funnels enough paid advertising into your passion to achieve profitability escape velocity.
You are well-networked by birth (fancy parents, schooling, etc.) and/or because you love connecting with people. You will happily meet with hordes of industry peers until your passion plane takes flight. This IG reel does not apply to you.
Caveat to #16: you must be likeable, and ideally helpful to others too. Just meeting with people won’t cut it if they can’t stand you.
You are porting over a large existing platform—email and/or any of the socials—to your new passion. Your personal brand plane is already well in flight, so when you punch some buttons on the dashboard to alter your course, you can now land wherever you want. See also: celebrity book clubs (those Reese boxes make great gifts, btw).
What you think you love is also in the highest good, and/or aligned with your soul path, what the world needs, and/or what the market wants.
🍀 You’ve hit a stroke of great luck, in perfect timing for pursuing what you love and the money following! See also: Success and Luck: Good Fortune and the Myth of Meritocracy by Robert Frank.
What did I miss in this updated list?
❤️ Let me know in the comments :)
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