8 Steps to Build a Life-First Business That Pays for Your Vacations

Imagine This...

You’re sipping a mango smoothie on a lanai in Maui. Palm trees sway. Your kids are laughing in the pool. The sun is melting into the Pacific.

And meanwhile? Back home, your business is quietly making money—without you checking Slack, posting on Instagram, or stressing over missed sales.

Sound impossible?

It’s not. It’s exactly what happened to us this summer.

We spent 10 days in Hawaii as a family. The flights, the hotel, the food, the excursions—all paid for by our business.

And no, it wasn’t because we went viral.
It wasn’t because of a massive launch.
It wasn’t because I pulled late nights before the trip.

It was because we’ve been intentional about building a life-first business—one that funds not just our goals, but our experiences.

And today? I’m walking you through the 8-step system that made it possible (and that you can start using right now).

Step 1: The Monthly Travel Fund That Makes It All Happen

Here’s the #1 reason we could say “yes” to Hawaii without blinking:

Every single month, we save 5% of gross business revenue into a dedicated travel fund.

➡️ Slow month? We still save.
➡️ Big month? The fund grows faster.

That consistency compounds.

So when the opportunity popped up to swap a Maine trip for Hawaii, the money was already there. No scrambling. No credit card debt.

How You Can Do This:

• Open a separate business savings account.

• Automate a monthly transfer (we recommend 5–10%).

• Treat it like a non-negotiable expense.

Tip: Even if you’re starting small, $50–$100 a month adds up faster than you think. By next summer, you could have a trip fully funded.

Step 2: Mastering the Points Game

We didn’t pay cash for flights. Instead, we strategically used credit card points.

• Chase Sapphire Preferred → Flights for four (roundtrip)

• Marriott Bonvoy Brilliant → Hotel perks + free nights

Result? Flights = $300 in taxes/fees. Hotel = covered by points + travel fund.

How You Can Do This:

1. Pick one card for business, one for personal perks.

2. Use them only for expenses you’d already pay.

3. Always pay in full (otherwise interest cancels out your perks).

4. Save points for big travel, not gift cards or cash back.

Tip: Focus on one rewards program until you can cash in for flights or hotels.

Step 3: Ask for the Upgrade (Always)

At check-in, I smiled and asked:

“Do you have any upgrades available?”

The result? Beachfront room + free daily breakfast.
That single question saved us $1,000+.

How You Can Do This:

• Be polite, confident, and genuine.

• Ask about: room upgrades, free meals, late checkout.

• Worst-case? They say no. Best-case? Huge perks.

Step 4: Find the Hidden Perks at Your Hotel

Hotels are full of secret experiences—but you won’t always find them on the website.

Before our trip, I searched YouTube: “Best things to do at [hotel name].”

That one search led us to:

• Free lei-making classes 🌸

• Hula dancing & cultural workshops

• Beachfront yoga

• Chocolate tastings

How You Can Do This:

• Search YouTube + TikTok for behind-the-scenes tours.

• Ask the concierge directly about hidden perks.

• Look for cultural activities—many are complimentary.

Tip: These perks are memory-makers. Build them into your trip plan.

Introducing a new private podcast series that’s just for you if you’re sick of all the Instagram BS! (or insert social channel of your choice). You can build a business without being a slave to the social engine. Grab the free series.

Step 5: Book Smart for Tours + Activities

We booked most tours through the Viator app—fast, easy, and review-driven.

One exception? The Road to Hana. Gorgeous but better done on your own with a rental car.

How You Can Do This:

• Use Viator or GetYourGuide for quick booking.

• Always read recent reviews (things change fast).

• Watch YouTube vlogs for first-person insights.

Tip: Don’t overschedule. 1–2 tours per week leaves space for rest.

Step 6: The Sandwich Strategy for Meals

Meals are one of the fastest ways to overspend on vacation. Enter the Sandwich Strategy.

Our breakdown:

• Breakfast → Free (thanks, hotel upgrade)

• Lunch → PB&J sandwiches + fresh fruit from local markets

• Dinner → A mix of casual eats + 1–2 splurges (like the Four Seasons 🍴)

How You Can Do This:

• Shop local grocery stores for fruit, snacks, and picnic meals.

• Save splurges for experiences (sunset dinners, local cuisine).

• Balance casual + fancy to stretch your budget.

Tip: Hawaiian grocery stores have amazing poke bowls + tropical fruit—better (and cheaper) than most restaurants.

Step 7: Our Business Ran Without Us (Here’s How)

The real win? Our business didn’t just survive while we were gone—it grew.

Here’s what we set up before leaving:

• Batched podcast episodes

• Pre-scheduled emails (1x per week)

• Evergreen funnels running in the background

• Repurposed old launch assets (holiday promos still worked!)

Results (while we were at the beach):

• 100+ new organic email subscribers

• 7 sales of Anti-Social School™

• 5 new Crush the Rush Club members

• 2 planner sales

• 1 Bot Bundle sale

Total? Five figures in revenue—with zero live launches.

How You Can Do This:

• Pick one evergreen offer (course, membership, digital product).

• Set up a simple email funnel (welcome → nurture → offer).

• Repurpose old content (don’t reinvent the wheel).

Tip: Done > perfect. Even a basic 3-email funnel can create sales while you’re offline.

Step 8: My Social Media Vacation Rule

Yes, I captured memories. But I don’t post in real time.

Instead, I:

• Save content to a Shared iPhone Album.

• Batch posts after the trip.

• Share highlights 1–2 days later.

How You Can Do This:

• Set a rule: “No live posting while traveling.”

• Use a shared album with family for photo curation.

• Batch captions + reels on the flight home.

Tip: Being present creates better content anyway. Engagement is the same—sometimes better—when you post later.

The Real Win: Moments That Matter

Here’s what I’ll remember most:

• My girls learning to make leis by the pool.

• Sunset dinners on the beach.

• Morning yoga on the lanai.

• Long walks, laughter, and quiet.

Not one launch.
Not one stressful deadline.
Not one “I should be posting” thought.

Just space. Rest. Joy. Freedom.

Your Turn: Building a Business That Funds Your Freedom

The truth? This wasn’t luck. It wasn’t a fluke. It’s a system.

You can do this too. Here’s where to start:

1. Open a travel fund account.

2. Choose one rewards card and use it consistently.

3. Batch + automate your marketing.

4. Define your vacation rules (like no live posting).

5. Give yourself permission to rest.

Because here’s the reality:

• You can hit your revenue goals and take your kids to dance class.

• You can run a business and take real vacations.

• You can be a present parent and a powerful CEO.

Next Step: Steal Our System

Want to learn how to set up your own life-first business that pays for freedom?

🎧 Join our free Ditch the Social Drama Workshop where I’ll show you:
✨ How to grow without being chained to social media
✨ AI prompts to speed things up
✨ The exact system we use to make sales—even while offline

Final Thoughts

This Hawaii trip was proof that the dream is real. You don’t have to hustle 24/7. You don’t need a viral post. You don’t need to sacrifice your family to grow.

You need a plan, a system, and permission to put your life first.

And the best part?
Your next vacation could be paid for by your business.

Cheers to your mango smoothie on the lanai.

About the author

Holly Haynes is a female business coach and business strategist who loves a good plan and flow chart. She is crazy passionate about teaching women like you how to build your dream job and scale to 6-figures without sacrificing your weekends or priorities.

Connect With Holly:

•  Ask me anything

• Work with Holly

• Find Holly on LinkedIn

• New! Check out our YouTube channel!