WiFi-Money: Overworking with AI

Don't give all the upside from AI to your W2 boss, use it to build your escape

It was early 2024. The hype of AI had been in the air for over a year, and I had finally landed a project where I was excited to try it.

It was a contracting gig, 8 weeks, fulltime. I'd be coming into an existing backend project and getting it ready to launch.

All while working my big tech W2.

Previously, this would have been very difficult. Stressful even.

But with AI, could it now be possible? (It is.)

Maybe even easy? (It was.)

And now, a year later, can it still be done to double your income? (The IRS is going to love you.)

Buckle up. It’s time to share some of the tactics that have unlocked my first wifi-money - and maybe soon yours.

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What is Overworking?

Working multiple full time W2 jobs, at the same time.

Your employers don't know you are, but the IRS certainly does. When you start earning double the first year, let me know how the taxes look.

If you’re looking to ramp up consulting or contract work, I’d seriously consider setting up a corporate vehicle, both for limiting liability but primarily for tax planning purposes. Do your own research, every state/country will have slight differences.

For taking on a second W2, or 3rd, or 4th… check out r/Overwork on Reddit. You’ll see first hand some of the tradeoffs in people’s stories of success and failure.

Learn from their experience, so you can make fewer mistakes.

Lastly, you need a good kvm switch. IYKYK.

Overworking, whether contract work or multiple W2s, can work well as a short term boost to earnings.

But long term, multiple W2s isn’t for everyone. W2 is more demanding on your time than contract work, with meetings and social expectations of an employee - not a hired hand.

I also would worry about losing my primary W2, which is already well optimized to less than 2h/day and getting “Exceeds Expectations” performance reviews every quarter. There are many stories of the second W2 calling the first when they find out you’ve been overworking, and then you get fired from both.

I’ve chosen the mix that works for me, and that can change by the season.

As for you anon, you'll have to decide for yourself.

Today's post shares new strategies on how to leverage AI to max your earnings at either your primary W2 and consulting contract work or secondary W2s.

Buckle up, this could be your first step towards earning money outside your W2.

And that's when everything will change. You won't be able to stop.

Overworking with AI: Mindset & Tactics

So, how do you leverage AI to overwork?

How can you keep up with consulting expectations while keeping your "Exceeds Expectations" rating at the primary W2?

How do you double, maybe even triple your income leveraging the latest in AI tools?

This post may unlock a future you didn’t think possible.

Fundamentally, there a few major mindset shifts and key tactics that will make overworking possible, while continuing to fade effort with your primary W2.

Without some nuance here, you will risk losing your loafty, cushy W2 and be worse off than you started.

No reward without some risk. But you’ve got to be smart about this.