The Danger of “It’ll Work Itself Out” Thinking Hope isn’t a cash flow strategy

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The Danger of “It’ll Work Itself Out” Thinking Hope isn’t a cash flow strategy

Let’s talk about one of the most dangerous lies contractors tell themselves:

“Things will work themselves out once I land the next big job.”

Sound familiar? Maybe you’ve told yourself that once the cash hits from that next invoice or that big job finally closes, everything will be okay. You’ll catch up on bills, fix the books, and get ahead. But let’s be honest — how often has that actually worked out?

Hope is not a system. And when you run your business based on hopeful thinking instead of clear financial visibility, you’re setting yourself up for more stress, more surprises, and more sleepless nights.

Here’s the truth: the next big job won’t fix a broken system. In fact, it often makes the cracks bigger.

You get more materials to float, more subcontractors to pay, bigger payrolls to meet — and you’re still chasing checks. Suddenly, your “big break” becomes your biggest liability.

Real World Mistake & Lesson: I worked with a landscaping contractor who had just landed a $300K project. He was pumped — until three months later, he was $50K in the hole, maxed out on his credit line, and behind on vendor payments. Why? He took on the big job without a clear cash flow projection. We had to unwind that entire job, renegotiate payment terms, and put a draw schedule in place just to stabilize him again.

The lesson? More money doesn’t solve cash problems — smarter systems do.

If you keep hoping the next project will save you, you’re gambling, not running a business.

 Pick up your free copy of my new book, “The 7 Minute Conversation-How to Hear the Story Your Small Business Financial Statements Are Telling You-CONTRACTOR EDITION”.  Go to www.7MinuteConversationBook.com

Ready to find out where your cash and profits are really going? Book your free 15-minute Profit and Cash Flow Call with me. No pressure. Just real clarity. I’ll help you see where your money’s hiding — and what to do about it. Schedule at www.CashFlowCallWithLarry.com

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Larry M. Weinstein, CPA—the Cash Flow Cowboy®is a trusted advisor for tax planning and resolution strategies for business owners and contractors in Texas and beyond.

Minimize your taxes. Boost your cash flow. Keep more of your hard-earned money. 

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