

Discover more from A Questionable Life
I have anywhere between one and seven calls each week with folks who reach out asking for advice. They ask about buying a business, or starting a business, or just generally finding some way to escape their current relationship with work.
Sometimes it’s a friend who wants tactical help. Other times, it’s someone who heard me on a podcast. Occasionally, it’s a person who sees me dropping F-bombs on LinkedIn and thinks, This guy is either a complete idiot, or he feels he has enough economic agency to sling profanity-laced tirades on the world’s largest job board. I have to find out which it is. (editor’s note: It’s both.)
Regardless, it always feels strange.
I don’t have anything to add to the colossal canon of tactical business advice that already exists. There are people who have done what I’m doing for much longer, are much more knowledgeable, and have been much more successful. Many of them also happen to have written books and filmed YouTube videos and created courses and built consulting practices on these very subjects. The number of folks one should go to for business advice before me could fill a mid-sized European country. Or Texas (suck it, Europe).
In pretty much every one of these calls, though, it becomes clear that the person in the Zoom square does not need tactical guidance. They are all very smart people, eminently capable of finding a way out of their current plight to build whatever life it is that they’d rather inhabit. There’s something else they need. And, as in most cases, it’s not tactical—it’s emotional.
If I were one of those grifters who dangles value on the other side of a paywall, this would be the part where I’d share a link to a Stripe checkout page where, for one easy payment of $299.95, you could gain access to precisely the thing you need to make your dreams come true. But alas, I am not of that breed.
Instead, I’m going to go ahead and share what I think everyone really needs:
A permission slip.
Dear Person Who Wants Their Life to Suck Less:
I, Alex Michael, by virtue of being some guy on the internet, hereby grant you permission to do that thing that you really want to do.
You have arrived at this point in your life carrying a great deal of baggage. This baggage—the various scripts and beliefs from your upbringing that you've internalized as your own—has served a purpose. It has allowed you to make sense of and navigate the world. But it's also keeping you from carving out your own path, from creating a life that is uniquely your own, one that you're excited about. If you're anything like I was, these internalized beliefs have led you to place a tremendous premium on stability, security, and safety. The thought of losing the literal and figurative insurance policies you currently hold feels like a genuine threat to your existence. When you even begin to entertain meaningful change, a voice immediately chimes in and says, That's a reaaaaaally bad idea. Here's a list of 376 terrible things that might happen, ranked in order of how badly they'll ruin your life.
This also means that your view of the potential upside of making that big scary leap is heavily clouded. You are unable to conceive of what might be on the other side of uncertainty. As such, here is a dispatch from the other side:
When you make a big scary decision to do something simply because it feels right, some crazy voodoo shit happens. You send a message to yourself that you are the kind of person who does this sort of thing. This permeates every fiber of your being. While there is no guarantee that the decision you've made will turn out successfully or serve as a path you'll be on for the rest of your life—or even the next year—it reorients the way you see the world and the way the world sees you. This is where the crazy voodoo shit happens. The universe starts to reward you with opportunities that are tailored to you. And, because you made that initial decision to act in the face of fear, you see yourself as someone who capitalizes on opportunity. This empowers you to take more action, to make more big scary decisions to do the things you want to do. Your life becomes more and more one that is uniquely yours. The cycle continues.
But wait. It gets better.
Beyond the tangible realm of material outcomes, there is a deeper, more profound benefit to making these kinds of decisions. It imbues you with a fundamental sense of agency—the feeling that you have a measure of control over your existence. This is the most powerful quality one can possess. It is the most potent life force of all. It’s what allows us to view our lives in a positive light, what makes waking up each morning something to look forward to. It is invaluable.
So yes, big scary decisions are big and scary. Bad things can, and will, happen. But the upside of making these decisions is greater than anything you can currently fathom. I promise. I've been on both sides of this.
And with all of that, I say again: this is your Permission Slip. Go do the fucking thing.
I spent the beginning of my adult life making decisions based on the scripts I had inherited and internalized. Those scripts valued security and status over all else. This led to a life that wasn’t much fun, so I doubled down on those decisions, assuming I hadn’t executed well enough on obtaining said security and status.
I took jobs with titles like Commodity Market Services Consultant because I thought they made me sound smart and would lead to the ‘right’ kind of career path. I rented a high-rise industrial loft I couldn’t afford, with exposed brick walls and stained concrete floors and floor-to-ceiling windows. I went to networking events where you got one of those stupid name tags and a couple of drink tickets.
Life got even less fun. So much less fun, in fact, that I was eventually forced to confront the reality that, unless I updated my scripts, something very bad was going to happen.
Having no other choice, I started to write some better scripts, ones that accounted for my actual beliefs and desires. This inspired some progressively scarier decisions that inched me toward a life that was more my own. More importantly, it also sent a message to myself that I was the kind of person who does scary things because they feel right.
Then I made the big, scary decision: I bought a business.
And that’s when my own crazy voodoo shit started.
The elusive life that I had dreamt about for so long started to become reality. I met, and eventually began dating, a lovely girl. I started to write. I started another business, then another one. I moved to a new city. I signed up for an EMT class. Opportunities in all areas of life started to appear. They continue to do so. My existence is now very much my own, and most of the time I wake up excited about the day ahead.
Don’t get me wrong: life is still hard. Bad things still happen. I still get scared, doubt myself, and wonder what the hell I’m doing. My utility bill still, somehow, does not have an AutoPay option.
But having a foundation of agency has transformed my relationship with all the hard stuff. Instead of believing that things happen to me, I now believe that they just happen, and that I can choose how to respond to them. This gives life a much different flavor.
None of this is to say that you should blow up your life today (although in many cases I’m a big fan of that). It may be a stupid idea to quit your sales job to become a panda fluffer or something. But if you’re unhappy with your life, there is almost certainly some action you could take to improve your circumstances that you are avoiding because you’re scared, or because you feel like you’re not allowed to, or you don’t deserve to.
Well, you are allowed to. You do deserve to. And doing so, in the face of all that fear that will never go away, changes everything.
Here’s a permission slip you can print out and tape to your mirror if you’re into that sort of thing:
It's Not Advice That You Need
I love this for 100 different reasons Alex. The permission slip is *chefs kiss*. I agree, so many people are just looking for someone to say, "hey, it's cool, go ahead and do the thing." Myself, included, still today. It's also amazing watching your growth. I grinned at the beginning to hear about all the calls you're on and interviews your doing. It's funny how quickly things change once you give yourself permission to do the thing!
Snorted at the permission slip 😂