The Myth of “The Right Time” — Why You’ll Never Feel Fully Ready to Chase Big Dreams

Rugged Destinations
Jul 20
4 min read

If you’re waiting for the perfect moment to chase your dreams — I have some hard-earned news: it doesn’t exist.

We know because we spent years believing it did.

Before we became a full-time traveling family, we told ourselves things like:“When we save a little more, we’ll start.”“When the kids are older, it’ll be easier.”“When work slows down, we’ll have time to plan.”

But you know what we learned over 13 years of dreaming, preparing, and (finally) leaping?

There is no perfect time. There’s just now — and what you choose to do with it.

1️⃣ The Illusion of “Ready”

Our culture loves the idea of ready. We’re told to prepare, plan, and wait until we’re fully qualified, fully prepared, fully stable.

But here’s the truth most people miss: You only become “ready” by starting.

When we hit the road full time, we weren’t perfectly prepared. We had some savings, sure. We had skills we’d been building. But we also had a lot of unknowns.

We had no idea how we’d handle vehicle breakdowns, how our kids would adapt, or how we’d juggle remote work on the move.

We learned by doing. We grew into readiness, one challenge and one imperfect step at a time.

2️⃣ Why Waiting Feels Safer (But Isn’t)

Waiting feels safe because it gives us the illusion of control.

We tell ourselves, “Once the kids are older, once I get the promotion, once I have more money…” — but those milestones keep moving.

The truth is, waiting can be a form of self-protection — a way to shield ourselves from failure, discomfort, or judgment.

But here’s the kicker: while you’re waiting, time is still moving. The kids are growing.Your energy is shifting. Life is happening.

And sometimes, the cost of waiting is far greater than the risk of starting.

3️⃣ Why Starting Small Matters

One of the biggest misconceptions about chasing big dreams is that you have to go all in overnight.

You don’t.

We didn’t sell everything and hit the road on a whim. We spent years taking small steps:

✅ Learning photography

✅ Building a remote business

✅ Testing our setup on weekend trips

✅ Downsizing gradually

✅ Paying down debt in phases

Starting small builds confidence.It gives you data: Does this work? Do we like it? What’s still missing? And most importantly, it turns the dream from abstract to real.

4️⃣ Fear vs. Readiness

Here’s a question that helped us move forward:

Are we truly unprepared, or are we just scared?

Fear is normal. It’s part of growth. But fear can dress itself up as “responsibility” or “wisdom” — and keep you stuck forever.

When we realized that most of what we were calling waiting was actually fear, it changed everything. We stopped seeking permission. We stopped over-researching. We started doing.

5️⃣ The Reality of Imperfect Beginnings

Our launch into full-time travel wasn’t flawless.

We made mistakes. We underestimated things. We faced setbacks.

But here’s the gift of imperfect beginnings: They stretch you. They teach you. They reveal resilience you didn’t know you had.

And they remind you that dreams are living things — they grow, evolve, and change shape as you walk them out.

6️⃣ What the Most Successful People Know

One thing that’s been fascinating over the years is meeting other creators, entrepreneurs, and successful mentors — people who, on the surface, seem to “have it all figured out.”

But here’s what they all tell us:

👉 There’s never a right time

👉 Success is directly tied to the amount of effort, intention, and sacrifice you’re willing to make

From Alex Hormozi to David Goggins, some of the biggest, hardest-working personalities are the first to tell you what you need to hear — not the cushy excuses we often want to hear.

No matter what your goal is — whether it’s landing a promotion, mastering a hobby, launching a business, or becoming a successful influencer — the roadmap is the same: It’s filled with challenges, failures, and constant learning.

There’s no bypass. No magic shortcut. No “easy” path.

But there is a path — and it’s open to anyone willing to walk it.

7️⃣ How to Know It’s Time

If you’re waiting for someone to tell you, “Now’s the time,” let this be it.

You don’t need to have every dollar saved. You don’t need to know every answer. You don’t need to feel fearless.

You just need to:

Take the next right step
Let it be messy
Commit to learning along the way

The people who make it aren’t the most prepared — they’re the most persistent.

Final Thoughts: You Are Allowed to Begin Before You’re Ready

Thirteen years. That’s how long it took us to go from dreaming about this life to living it. Not because we weren’t capable sooner — but because we had to unlearn the myth of the right time.

Now, on the other side, here’s what we can tell you:

You’re allowed to begin before you feel ready. You’re allowed to try, fail, adjust, and keep going. You’re allowed to live the life you want now — not just in some distant, perfect future.

Whether your dream is travel, art, business, or something uniquely yours, the door opens when you stop waiting and start walking.