The Permission Slip Is Never Coming

How to uninstall the Compliance OS and authorize your own life.

Your Permission Slip Is Never Coming

You think your problem is time.

You tell yourself (and anyone who will listen) that you’d love to pivot. You’d love to start the podcast, write the book, or finally take your health seriously.

But you simply can’t right now. You’re swamped with work. You’ve got a mortgage. Kids. A boss whose favourite word is “URGENT”.

And what makes this dangerous is that it is true.

You aren’t wrong. You are busy.

And because there’s truth in the story, you treat it like a law of nature. Something immutable. Something you can’t challenge.

But let’s be honest.

If your boss told you that you had to fly out of town next week for a critical client meeting, you’d figure it out. You’d clear your calendar, find childcare, and make it happen.

If you got the flu and were off for a few days, the world wouldn’t end. You’d cancel some calls, push a couple of deadlines, and the machinery would keep grinding along without you.

So, it’s not that you can’t make space. It’s that you haven’t authorized yourself to do it.

You aren’t suffering from a lack of resources. You’re suffering from a lack of permission.

The Compliance Operating System

Most of us have spent our entire lives perfecting what I call the Compliance OS.

We were trained to be good students, then good employees, then good, responsible adults. In that system, the rules are clear:

• Do what’s assigned.
• Follow the process.
• Don’t get ahead of yourself.
• Make sure you have the budget, authority, and approval before moving forward.
• Wait for external validation to confirm you’re “ready”.

In a job, this operating system works. You’re executing on someone else’s vision, within their constraints, on their timeline. Acting without approval in that environment makes you a liability.

The Compliance OS isn’t broken. It’s just optimized for obedience, not authorship.

The problem is that you’re applying those same rules to your Work—the contribution you are actually here to make.

You are waiting for a permission slip to start living your real life. You’re waiting for someone to tap you on the shoulder and say, “Okay, you’re qualified now. Go ahead.”

But that person doesn’t exist.

Your Job is Your Investor, Not Your Parent

It’s easy to feel like your job is getting in the way of your life. That it’s draining all your energy and leaving nothing for the things that actually matter. Maybe you’ve even started to resent it.

But the mistake isn’t having a job. The mistake is treating your employer like your parent.

We unconsciously look to our jobs to provide us with a sense of safety, identity, and “readiness.” We want them to authorize our worth. But your employer can’t give you purpose. They can only give you a paycheque.

Here’s a better reframe: Your job is your angel investor.

It provides the capital—the salary, the benefits, the stability—that allows you to do your real Work.

When you see it this way, the dynamic shifts. You stop resenting your job for not fulfilling your soul, and you start using it strategically. Not as a source of meaning, but as fuel.

The Real Fear Isn’t Failure

If the constraints aren’t real, why are you still stuck?

Fear. But more specifically, the fear of losing your status.

You’re good at what you do. You’re competent. Respected. You’ve optimized your life to be efficient, impressive, and safe.

Your Work threatens that identity.

Doing your Work usually requires being a beginner again. And beginners are awkward. Messy. Unimpressive.

You tell yourself you’re “waiting for the right time,” but what you’re really doing is protecting an identity built on competence. You’re imagining a future where you can start something new without looking foolish.

That future is a fantasy.

Sign Your Own Permission Slip

So, how do you move forward?

1. Grant the Authority. Stop waiting for your schedule to magically open up. It won’t. You decide what matters and what gets protected. No one else can do that for you. The difference between the people who do their Work and the people who only fantasize about it isn’t talent—it’s that one group stopped waiting to be authorized.

2. Lower the Stakes. You don’t need to launch a business. You don’t need a certification. You don’t need to “fake it till you make it” (which quietly assumes you’re a fraud). You need the next smallest step. What’s the one thing you are avoiding because you feel unqualified? Do that.

3. Get on the Hook. We’re excellent at honouring commitments to our bosses and terrible at honouring commitments to ourselves. Externalize the promise. Not because you need a babysitter, but because your Work deserves the same respect as a client deliverable. Tell a friend your deadline. Hire a coach. Post publicly that you’re starting. Pick whatever creates real stakes.

The world doesn’t need more people who are good at their jobs but dead inside. It needs people who stop waiting for a green light that is never coming.

You are the bottleneck. Which means you’re also the solution.

Authorize yourself.

Quotation I’ve Been Pondering

— Anaïs Nin

Journal Prompt

Until next week!! Work and live well. Tim Did someone awesome forward you this email? Sign up here to ensure you get my latest content. Do you know someone who would benefit from this content? Please pass it along! ♻️ Let's fix what your job broke. If you're finally ready to take control of your work life and build something that works for you, here's exactly how to start: ​Book a Free 30-minute Clarity Call. Not sure where to start? Let's talk. We'll look at where you are, where you want to be, and whether working together makes sense. No pitch - just an honest conversation. ​Book a 90-minute Strategy Session ($175 CAD). You've got a specific problem. Let's solve it. One focused session to diagnose why you're stuck and map out your next moves.

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