Three Types of Business Pain You Can Avoid (And How to Stop Hurting Yourself)

Some business pain is unavoidable—markets shift, competitors emerge, circumstances change. But much of the pain businesses experience is entirely self-inflicted. Here are three categories of avoidable suffering and how to stop creating your own problems.

Category 1: Snatching Defeat from Victory

You have done the hard work. The sale is almost closed. And then you blow it.

On The Buck Stops Here podcast, David Maples identifies the common ways businesses snatch defeat from the jaws of victory:

Sales Process Failures

  • Over-talking during closures: The sale is made—stop selling
  • Payment friction: Make it easy to pay (checks, credit cards, whatever they prefer)
  • Missing contracts: Always use them
  • Slow lead response: Responding within 5 minutes increases close rates 60x versus waiting a day
  • Phone handling: Ensure humans answer promptly
  • Billing handoffs: Do not transfer new clients immediately to billing departments

Hiring Paralysis

Waiting for the perfect candidate means losing good candidates who accept other offers. Jeff Bezos advises operating at “70% knowledge” rather than waiting for complete information.

Fortune favors those who act.

Category 2: Self-Inflicted Wounds

These are non-forgivable errors—deadlines you knew about but missed anyway:

  • Tax deadlines: Penalties are not tax-deductible
  • Sales tax filing: Hard deadlines with hard consequences
  • Legal filing deadlines: Missing these costs cases
  • Collection limits: Each state has timeframes for pursuing unpaid debts

“Death and taxes are two things you can never avoid.” Calendar everything. Set reminders. Create systems that make missing deadlines impossible.

Category 3: Driving Without Headlights

Risky behaviors you engage in despite knowing better:

Warning Signs to Watch

  • Client relationship changes: Stilted emails, sudden legal language, altered communication patterns
  • Employee behavior shifts: Excessive time off, job-hunting indicators, disengagement
  • Vendor vetting failures: Taking partners at face value without verification

Risk Mitigation Actions

  • Check business references and credit reports
  • Review contracts for personal guarantees
  • Audit profit/loss statements and cash flows
  • Monitor employee performance trends
  • Research vendors and clients online before committing

The 20-30% Opportunity

Maples estimates that addressing these avoidable problems can increase revenue and bottom line by 20-30%. That is not growth from new strategies—that is simply stopping the bleeding from self-inflicted wounds.

Five Minutes That Could Transform Your Business

Take five minutes right now:

  1. Audit your sales and hiring processes: Where are you losing deals you should win?
  2. Calendar critical deadlines: Tax, legal, filing—all of them
  3. Identify risky behaviors: What are you currently doing that you know is dangerous?

The pain you can prevent is the most expensive pain of all—because it was entirely within your control.

This article is based on Episode 5 of The Buck Stops Here podcast: “Getting to Grandma’s House.”

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