You're Not Ready to Quit Your Job
And that's not an insult. It's an invitation.
I had a two-hour coffee last week with someone who wanted to pick my brain about starting a business.
By the end of it, I wanted to tell him to stay at his job.
Not because he wasn’t talented. Not because he didn’t have a good idea. But because he was about to make the same mistake I’ve watched dozens of people make.
He thought the leap was the hard part.
It’s not.
The conversation that made me nervous
Here’s what he told me:
He’s been working for another company for a few years now. Creative differences with the owner have been piling up. He’s no longer fulfilled. He wants to branch off and do his own thing.
Sound familiar?
He’s been doing freelance work on the side, but he’s never actually run a business. Never hired a team. Never had revenue targets. Never had to figure out where the next client was coming from when the pipeline was empty.
He asked me how I found my first customers, how I figured out pricing, how I put systems together, and how I knew I could make it work and still take care of my family.
Good questions. All of them.
But then he told me his plan.
He wants to go from making four thousand dollars a month working for someone else to landing ten and twenty thousand dollar contracts on his own. Immediately. No prospects. No leads. No network. No partnerships. No visibility.
He showed me what he called his “SOP.” It was a list in his Apple Notes.
That’s when I got nervous for him.
What I didn’t tell him
I didn’t tell him he was delusional. I didn’t tell him to give up.
But I did push back.
I asked him why he wanted to start this business.
“Money,” he said. “I’ll make more money.”
That answer worried me more than anything else.
Money is a reason. We all need it. But money won’t get you up at five in the morning when you’re exhausted and your kids were up all night. Money won’t help you push through when a client ghosts you, or a deal falls apart, or you’re three months in and wondering if you made a terrible mistake.
You need a why that’s deeper than your bank account.
Mine has always been the same: to help creative entrepreneurs live the life of freedom they started their business to achieve.
That statement isn’t something I put on a website to sound good. It’s personal. I am that creative entrepreneur. I started my business because I wanted freedom, and for years I almost lost myself trying to get it.
I am my own ideal client.
That why carried me through seasons where the money wasn’t there yet. That why still carries me now.
What I actually did before I left my agency job
When I decided to leave, I didn’t just wake up one morning and quit.
From the moment I had the idea to the day I actually walked out the door, three or four months passed. Months of early mornings, planning, and preparing before I ever gave my notice.
I had a mentor during that season. We met at five in the morning before my day job started. Every session followed the same rhythm: Where are you at? What did you get done? What’s next?
We’d talk through what I needed to put in place, set goals together, and check in on progress. We’d read the Bible and pray. That accountability kept me honest, kept me moving, and kept me grounded in something bigger than ambition.
Those mornings weren’t glamorous. I was tired. I had young kids at home. I was still working a full-time job during the day.
But I knew that if I wanted this business to work, I had to treat it like it mattered before it paid me anything.
So I started putting things in place.
I created a website, designed a logo, and mapped out a content strategy. I did the hard work to figure out my pricing and how I would deliver my service. I reached out to people I had met through my agency work and through my community. I started speaking at local business centres to educate people on what I did and why they might need it.
I wasn’t waiting for clients to find me. I was making myself visible before I had any reason to be.
By the time I left my agency job, I had four thousand dollars in monthly recurring revenue. That’s it. Four thousand dollars.
But that money was mine, those clients were mine, and it meant that when I walked away, I wasn’t walking into nothing.
The HST number that changed my mindset
I also got my HST number before I needed it.
In Canada, you don’t need an HST number until you’re making more than thirty thousand dollars a year. I wasn’t there yet. I had four thousand.
But I registered for that number anyway.
Not to check a box. To hold myself accountable.
Getting that HST number was me saying to myself: Of course I’m going to need this. I’m going to hit thirty thousand dollars by month three. I have to. I don’t have a choice. My family needs me to make this work.
If I did anything less than thirty thousand that year, it would mean I had failed and would have to go find another job.
That number became accountability. It became motivation. It became the pressure I needed to show up every single day like my livelihood depended on it.
Because it did.
The books I wish I’d read sooner
I recommended three books during that coffee conversation. All of them shaped how I think about business.
The E-Myth by Michael Gerber. I read this one before I left my agency job. It taught me that most small businesses fail because the person running them is a technician, not an entrepreneur. They’re great at the work, but they don’t know how to create a business around that work. That distinction changed everything for me.
Traction by Gino Wickman. I wish I had found this one sooner. It’s about the Entrepreneurial Operating System, a framework for running a business with clarity, accountability, and structure. When I finally discovered Traction, it gave me language for things I had been feeling but couldn’t articulate. If you’re serious about creating something sustainable, read this before you leave your job. Not after.
Vivid Vision by Cameron Herold. This one helped me understand the power of painting a detailed picture of where you’re going. Not just goals or metrics, but a vivid description of what your business looks like three years from now. What it feels like. Who’s on your team. How your clients talk about you. That kind of clarity keeps you anchored when distractions come.
And the distractions will come.
The questions you need to answer first
I know a lot of people who want to do what my wife and I did: leave their jobs, start their own thing, become their own boss.
But they’re scared. They think they can’t do it. They look at people who’ve made the leap and assume it happened fast, or easy, or with some advantage they don’t have.
It didn’t happen fast for me. It wasn’t easy. And the only advantage I had was that I was willing to do the work before I got paid for any of it.
You can do this. I believe that.
But you have to slow down first.
Ask yourself:
Do I have clients? Even one or two people who are paying me for what I do?
Do I have a way to find more? A network, a community, a platform, something?
Do I have a website or some kind of presence where people can discover me?
Do I know how I’m going to price my work and deliver it consistently?
Do I have someone in my corner who can hold me accountable and help me see what I can’t see on my own?
If the answer to most of those is no, you’re not ready yet.
And that’s okay.
Being not ready yet is not the same as being incapable. It just means there’s work to do first.
Start now. While you still have a paycheck.
Start preparing now, while you still have stability.
Use the mornings. Use the evenings. Use the weekends.
Treat your future business like it deserves your attention before it can afford to pay for that attention.
Find a mentor. Someone who’s done what you’re trying to do. Someone who will ask you hard questions and not let you off the hook.
Get clear on your why. Write it down. Revisit it. Let it evolve as you evolve. But don’t skip this step. Your why is what keeps you going when the excitement fades and the grind sets in.
Read the books. Not to check a box, but to learn from people who have been where you’re trying to go.
And when you’ve done the work, when you’ve prepared the runway, when you’ve got clients and clarity and a plan that’s more than a list in your Notes app?
Then you take the leap.
Not before.
The brave part isn’t what you think
The jump feels like the brave part.
It’s not.
The real courage is in the preparation. It’s in showing up before anyone’s watching. It’s in doing the work before anyone’s paying. It’s in believing in something enough to invest in it when the return isn’t guaranteed.
That’s what separates the people who make it from the people who just talk about it.
I’ve been running my business for years now. It’s grown into something I’m proud of. But none of it would exist if I had skipped the preparation. If I had jumped without a runway. If I had let impatience win over discipline.
So if you’re sitting in your job right now, unfulfilled, dreaming about what could be, let me say this clearly:
You can do this.
But slow down. Prepare first. The leap will still be there when you’re ready.
And when you finally take it, you won’t be falling.
You’ll be stepping onto something solid.
