My job came to an unexpected end almost two years ago, without warning.
Suddenly, I was among the ranks of the unemployed after a 20% staff cut.
At 48, I had to face a harsh reality: replacing the closest thing I’d ever had to a dream job after 30-ish years in the workforce.
I looked for ‘normal’ jobs but couldn’t land an interview.
It didn’t matter if it was for part-time work or entry-level positions; nobody seemed to be interested.
The Freelance Plunge
Reluctantly, I returned to the freelance marketplace that I hadn’t used in almost six years. I had put off looking for work there, but my financial runway was quickly disappearing. I needed to start earning.
Fast forward a few months, and I had landed a solid, recurring freelance gig and was starting to feel good about myself again. I was nowhere near earning enough to replace the income I lost, but it felt good working for clients and getting paid again.
Becoming a freelancer seemed to be my only alternative to competing in the soul-destroying job market, so I embraced it.
Learning to Work with AI
As a new (reluctant) freelancer, I had to be efficient.
My time was my money. That’s what finally pushed me to seriously explore AI, a tool I had initially resisted.
I started by dipping my toes into working with AI. It helped generate cover letters and proposals in record speed and my guess is that the flood of AI-generated applciations explains why landing an interview was such an uphill battle.
If everyone is churning out resumes, cover letters and proposals… then you need to do something different to stand out.
But that’s a story for another day.
While I was a little apprehensive about AI (it seemed to be decimating marketing teams everywhere) I began experimenting with it more and more.
What did I learn?
AI can be one hell of an assistant and a teacher. But it’s up to you to verify the output.
ChatGPT broke onto the scene in late 2022, so I’m sure I don’t have to tell you that AI is known to “hallucinate” or fabricate information in 2025.
There’s even an infamous story about a lawyer who used ChatGPT to form his legal defense and how he came to regret that choice.
To put it another way: AI isn’t an easy button.
You need to monitor it. You need to steer it and direct it.
You need to tell it if it did a good job or failed miserably.
Bad things happen when you don’t validate what AI gives you.
This happens most often out of either laziness (AI = easy button, am I right?) or when you know absolutely nothing about whatever you’re asking AI to do. In that case, you’d do your own research or ask an expert to check if ChatGPT is shoveling you a steaming pile of BS.
Or, roll the dice and hope it doesn’t come back to haunt you later.
The Allure of the Easy Button and the AI ‘gold rush’
It doesn’t help that almost everywhere you look, someone is selling some kind of “silver bullet” AI software that promises to do all the heavy lifting while you sleep / party on the beach / completely ignore whatever AI is doing.
That’s right, the AI gold rush is in full swing.
And just like the original gold rush, the people getting rich are the ones selling the tools and equipment, not the ones out panning for gold.
Remember, if it’s easy and has a low barrier to entry…then everyone else is doing it too. Sort of like those jobs I was applying to and couldn’t land an interview with.
So resist the ‘easy riches’ AI software, because without a strategy, some expertise, some effort and understanding of a specific audience and the problems they have – whatever you pay for the AI software (no matter how cheap) is likely to cost you more than you’ll earn back.
“But Mike,” you say, “what should I use AI for if it isn’t the easy button like all the ads are telling me?”
Let AI assist YOU.
Let it amplify YOU.
Realign your expectations. Don’t expect perfect results, zero effort and maximum profit.
If your offer is garbage. If you don’t have a clue, if you’ve never helped someone to do whatever it is your selling to them then AI is only going to amplify that garbage signal.
Why “Free” AI costs more than “Paid” AI
If you have a computer and access to the internet, you can access AI for free.
Whether it’s ChatGPT, Gemini, Claude, Manus or whatever other flavour-of-the- month AI you’ve heard of, they all seem to have a free version.
You just need to create a login and go to work.
But there are limits built-in.
If you use AI occasionally, you might not brush up against those limits.
You might even assume there’s no reason to pay for AI…ever.
But if you’re a freelancer and you built AI into your daily workflow, you’ll likely need to start paying for it.
Because nothing sucks worse than being 2/3rds into a task whenever you’re told that you’re out of free usage and need to wait 4-6 hours to try again.
(Ask me how I know).
Whether you pay for AI via cash (most seem to start at $20 per month USD) or whether you pay with your time…AI is going to cost you.
Typical freelancers will value money above their time. But this is a mistake.
Time is the one thing you’ll never get back.
Starting with free is fine. But once you get comfortable and build it into your workflow…
OR once you start hitting those limits…
plan to upgrade to paid.
Not only will you gain back time, you’ll also unlock more powerful and faster versions of AI and be able to enter the world of AI agents which will take you to a new level.
And for you completely cash-strapped freelancers who’d rather keep the $20…answer this question.
If, five years ago, I told you that you could have a virtual assistant that:
- had an encyclopedic understanding of almost the entire internet
- could help with editing, researching, writing, analysis, coding
- was available 24/7
- never took a vacation, never called in sick
- would cheerfully accept $20/month without ever expecting a raise
Are you telling me you wouldn’t hire them???
Even if you had zero dollars to invest and you had to cash in all your empties???
Hey, all “silver bullet” and “gold rush” BS aside…
if you can’t earn $20 per month online with a virtual assistant who can do all that?
My guess is you’ll be hard pressed to ever make $20 without one.
Prove me wrong.
Freelancing with AI
Wrapping things up, freelancing with the assistance of AI is better than freelancing without it.
But you still need to use your brain.
There are obvious and hidden costs to using AI.
If you’re lazy, mess up and break things? AI can help you do that at record speed… to your own detriment.
If you want to make a million dollars selling vibe coded software and can’t even write basic HTML, AI ain’t gonna save you.
I decided to use it to be faster at what I do, to increase my capacity.
Not to let it think for me.
Not to spam out garbage to the masses.
Well, I need to stick a fork in this thing and get back to helping my actual clients, but I’d love to hear from you.
- Are you a reluctant freelancer?
- Have you given up on finding a ‘normal’ job?
- Are you using AI to expand your capacity and to learn new things?
- Or do you have an embarrassing AI story (like that lawyer I mentioned?)
If so, I’d love to hear about it in the comments.