Friend, how long have you been waiting to begin pursuing your goal of owning a short-term rental? Most of us get stuck in a cycle of waiting for the “perfect” moment — the perfect market, the perfect property, the perfect amount of cash, or the perfect amount of knowledge.

Here’s the truth I’ve learned after years of helping people rescue their retirement: the perfect time almost never comes. The best time is almost always right now.

Time is far more valuable than perfect timing. Waiting wastes the one resource you can never get back. As stewards of the years and resources God has given us, we’re called to move forward with wisdom and courage — not endless delay.

Why Most People Keep Waiting (and Why You Don’t Have To)

1. You’ll never feel 100% ready. If you wait until you feel completely prepared, you’ll still be waiting on your deathbed. You don’t need to know every step — you only need to know the next one. Start by simply looking at properties. The rest unfolds as you go, one step at a time, just like climbing stairs.

2. The “perfect” time will never arrive. There will always be an excuse — interest rates, the economy, family obligations, or “I need more information.” Remember the young Scrooge in the Muppet Christmas Carol? Year after year he delayed his dreams “until the time was right,” and one day the love and opportunity were gone. Don’t let that be your story.

3. The sooner you start, the sooner you succeed. Every month you wait is a month of potential income and experience you’ll never recover. The earlier you begin, the sooner your short-term rental can start generating cash flow that supports your retirement and legacy.

4. Most retirees’ biggest regret is waiting too long. I’ve asked many retirees and expats in places like Hawaii and Panama what they wish they had done differently. The answer is almost always the same: “I waited too long. I wish I had taken action years earlier.” Don’t carry that same regret.

5. Action teaches you more than information ever will. You can read every book and watch every video, but the real education comes from doing. You already know enough to take the first step. The best lessons come from owning and operating your first property — even if it’s not perfect.

6. Successful people decide quickly and move forward. They don’t wait for certainty. Give yourself a reasonable time limit to make a decision, then act. A good decision made and followed through is far better than a perfect decision that never happens.

7. Action creates inspiration and momentum. Most people wait to feel inspired before they act. The truth is the opposite: action creates inspiration, which leads to more action. Once you take that first step, clarity and motivation usually follow.

The Honest Reason We Wait

If we’re truthful, fear is usually at the root. If we never start, we can still hold onto hope that it might work someday. But the flip side is sobering: if we never begin, we’re guaranteed to miss the opportunity entirely.

Take a deep breath and remember: you don’t have to be fearless — you just have to be willing. God honors steps of faith taken with a heart of stewardship and diligence.

Start Today

You’ll never be completely comfortable or 100% ready, so you might as well begin now. Look at your first property this week. Make that first call. Run your first numbers. Take one concrete action today.

Even if your first short-term rental isn’t perfect, the lessons you learn will make the next one stronger. And every dollar of cash flow you create moves you closer to the retirement peace and legacy you’re praying for.

If you’re ready to stop waiting and start building real retirement income through short-term rentals (or other passive streams), I invite you to join my free weekly webinar every Thursday. We talk through practical next steps, answer your questions live, and help you see if our Retirement Club & Community is the right fit for your journey.

You’re not alone in this. Let’s rescue your retirement — one bold, faith-guided step at a time. The best time is now.