Don’t quit, or maybe do. I don’t know.

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You’ve been wanting to start a business, but you’re not sure where to start.

What if you… just quit… your job? Ah haha, just kidding. Unless…?

Wait! Don’t leave, I really am kidding. Definitely don’t quit your job, cash out your wife’s 401K, move three states away, with nothing more than an idea…

Or maybe you should. I really don’t know your situation. About six years ago I did just that. It was Thanksgiving 2014 — I was in California visiting my parents. My wife and I had recently bought a house outside of Salt Lake City, Utah and welcomed our first of three daughters into the world. She was only six months old at the time. We sat in the hot tub in my parent’s backyard for probably way too long, the heat was relaxing and probably impairing our ability to make rational decisions. As the bubbles formed and popped around us, we were formulating the plan that would turn our world upside down.

By the time we were in the car headed back for Utah, I had made up my mind. I was quitting.

Before I go further, I have to say there probably are very few people in the world dumb enough to do what I was about to do. I would never suggest doing this, unless it’s the right move for you, and only you can know that. We’ll talk here in a second about how I think you can easily make that judgement. But I digress…

I had spent five years working my way up the ladder at my job. I had gone from a commission-only, entry-level position, to an executive. I was a partner. I was in charge of every visual aspect of the brand. And I was completely stuck and entirely miserable.

My ambitions have always outpaced my skills or work ethic. I am moderately good at a large number of things, but I’m not great at anything. This is probably due to the fact that I’m aggressively lazy. I really only want to know the minimum amount I need to get done whatever needs to be done. I fully subscribe to Just In Time Learning, and I felt like I had hit the ceiling with my current job. I wanted more from life, and I wasn’t going to wait. So I made the move with virtually no preparation — just an idea.

I failed. The business I started lasted about 7 months, never turned a dime of profit and was folded up unceremoniously. I had walked away from a promising career and a steady paycheck just to eat shit for 7 months and then quit. But that was okay. It was probably inevitable.What it really was — was a stepping stone.

Now I must admit, the next step was largely good fortune and impeccable timing. When my wife got a text from a childhood friend that July afternoon about opening a candy store in Texas, it wasn’t even in my head yet to quit, but we were already going down in flames. And maybe I would have gone down with the ship… but at seemingly the last moment, I was thrown a lifeline.

After 8 months in CA, I packed up to move to Texas and start a new business with an incredible new business partner. Over the next five years we opened nine new businesses, and had a hell of a lot of fun doing it, and we’re still getting after it together today. That opportunity only came to me because I had taken a chance on something. If I hadn’t quit my job and established myself as an “entrepreneur”, albeit a pretty bad one, I would have never gotten that call.

Opportunity begets opportunity.

Now before you run off and submit your two-weeks notice — there is one thing I want you to consider.

If you quit your job tomorrow and started the business of your dreams — what is the absolute worst case scenario? What if nothing went your way and you failed in your business at every turn. What would happen to you?

I feel compelled to ask you again not to do this — or at least talk to me before you do — but if you absolutely have to do it, what’s the worst thing that could happen?

That answer for me was that I would probably have to end up living with some family for a few months while I found a new job and got back on my feet, and I’d lose some money. We didn’t have much to our name, really just the $10,000 we pulled from my wife’s 401K.

So, lose 10 grand and spend 3–6 months living with family while we picked ourselves back up. Since we were already moving in my my parents to get started, that part was already in the bag, and it was just the matter of losing a little bit of money. This was risk I could handle. If everything went completely sideways, I knew I could get us back on track one way or another.

So think about it. REALLY think about it. For a lot of you, I imagine, it would be something similar. Now, if you’re someone who doesn’t have that support structure, then do not consider this course of action, let’s figure something else out. If being homeless is a viable outcome, DO. NOT. DO. IT. But if bouncing back is in the cards for you, then maybe you can.

I mean, I don’t recommend it, but… it worked for me.




Full-time business advisor, owner, and entrepreneur. My life’s work is to help you break free from your life’s work.

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Danny Wilson | Privateer HQ

Danny Wilson | Privateer HQ

Full-time business advisor, owner, and entrepreneur. My life’s work is to help you break free from your life’s work.

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