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When To Quit Your Job (The Conservative Hustle)

Entrepreneur Ideas

When To Quit Your Job (The Conservative Hustle)

When To Quit Your Job (The Conservative Hustle)

I have been interviewed for shows, programs and podcasts more times than I can count over the past 15+ years. And one question I get over and over again is.. 

“If I were to start over again with my business and had no list, no money, no connections and no resources – what would I do?”.

Well, the first thing I’d do is get a friggen job and pay the bills 🙂

I’m kidding, but I’m not.

You can call me conservative, but I don’t believe in “burning the ships” and quitting your job before your side income replaces your full-time income.

In fact, I didn’t leave my last full-time job as a gym teacher in the South Bronx back in 2002 until my online business was generating MORE income than my salary.. for 6 consecutive months.

Why 6 months?

I wanted to be 100% sure it wasn’t a fluke. And only then did I feel comfortable about leaving that job with guaranteed salary and cushy benefits.

Anyone can make short-term money. You can sell your stuff on Craigslist or eBay. You can put together a deal. But that’s not long-term.

The idea that, “if you quit your job are under financial pressure it’ll make you work harder” is a terrible way to think.


Because here’s what really happens. 

When you’re under money pressure, your judgement is clouded and you make poor decisions. You say things and do things you normally wouldn’t do. You work with a person you should never be working with.

The money might come in, but it’s usually short-term. Because you’re thinking only about the money and not about building a long-term business.

The key is keeping your regular income coming in, while still working hard by creating internal deadlines.

Yes, create some actual goals such as, “By doing X, within 8 months I’ll create $10K per month of recurring revenue so I’ll be able to replace my full-time income with my business”.

You MUST have a deadline. Without a deadline, there’s no urgency. And without urgency, there’s no momentum.

No momentum = business death.


Ok, since we live in the real-world, what if you have a soul-sucking job you hate? And because of the brutal hours, there’s literally not enough time to work on your side hustle? Or your boss won’t let you build your side business while still working for the company?

First, you cut your expenses immediately. Try to cut it by 30% today.

Move into a smaller place. Cancel cable. Sell your car and buy a used $300 car with an cassette deck with 4 wheels (if you never had a car with a cassette deck.. I feel sorry for you!).

Then, perhaps, you look for another job with flexible hours. You put your ego in check, roll-up your sleeves and WORK.

Maybe it’s delivering pizza at night. Or hauling furniture on the weekends for a moving company. Or work at a retail store in the morning. It doesn’t matter what the job it, but you find something that’ll bring in some guaranteed income while you’re building your business.

And you spend EVERY FREE MINUTE building relationships and marketing. Building trust in your market. Serving your market. And putting every ounce of blood, sweat and tears into your new business.

It ain’t easy. But if you really want it. I mean REALLY want it. Take it from this former gym teacher.. you can do it.

Hustle. But hustle conservatively.

You got this,

P.S. If you enjoyed this, please share and, if you feel compelled, post your comments below.



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