The Spark: From a Conventional Path to a Global Mindset
Celeste’s story didn't begin with a grand plan for entrepreneurship. Growing up in the 90s, the concept of a fully remote business was almost unimaginable. However, a trip to Jamaica in 1998 planted a "travel bug" that never left. Years later, married to her high school sweetheart and with their first child, the feeling resurfaced. That simple yet profound question—“What if there’s more?”—was the catalyst. Three months later, they sold their possessions and moved to Sydney, Australia.
This initial leap profoundly changed her perspective. Living abroad exposed her to new cultures and ideas, solidifying her belief that stepping outside your comfort zone is essential for personal growth. While they eventually returned to the US and expanded their family, the desire for a life of freedom remained. Five years later, they took an even bolder step: they sold everything again, bought an RV, and began a seven-year journey across 49 US states.
Building a Location-Independent Business: The Unconventional Path
Celeste’s transition to business owner wasn't a sudden leap but a gradual, strategic evolution born from necessity and desire. Her story is a perfect example for anyone who thinks they need a perfect plan before starting.
The Evolution from Employee to Entrepreneur:
The Catalyst: Her employer offered 100% remote work, but only if she became an independent contractor. This meant giving up a salary, benefits, and a predictable schedule for hourly pay.
The Proving Ground: Initially, the remote work was limited, and her pay decreased. However, over two years, she proved her value, earning more remote responsibilities and trust.
The Pivot Back (and Forth): Needing health insurance, she briefly returned to full-time employment. But the rigidity of being “on call 9-5” clashed with her desire for creative freedom and time to write.
The Final Leap: She requested to return to independent contractor status “for good.” This time, she didn't just work for one client; she launched her own consulting business, celesteorr.com, to manage her database work while also building her passion project, Togetherness Redefined, a platform for adventurous parents.
Her key lesson? The road to time and location independence is rarely linear. It's a journey of trial, error, and persistence. As she says, “it’s possible for anyone who wants it, no matter their background, gender, color, or creed.”
Strategies and Tools for a Thriving Remote Business
How did Celeste scale her business while traveling full-time with a family? She focused on two key areas: continuous learning and smart-tool implementation.
Investment in Growth
Celeste credits her success to a relentless focus on personal and professional development. Completing her Master's degree online and enrolling in programs like Marie Forleo’s B-School gave her the skills and confidence to build a sustainable business. She learned the art of relationship marketing, email list building, and effective copywriting—skills she still uses to grow her client base and pursue her passion for writing and speaking.
The Digital Nomad's Tech Stack
Managing a business on the road requires a streamlined set of digital tools. Here's what Celeste relies on:
Project Management & Productivity: Evernote and Slack for daily tasks, project organization, and team communication.
Website & Sales: SquareSpace for its user-friendly interface to build her website and manage sales.
Audience Growth: MailChimp for managing her email list, which she emphasizes is crucial for business growth.
Social Media: MeetEdgar for automating social media posts, ensuring a professional presence even when she's off-grid.
Hardware: Apple products, which she believes make the creative process “faster, easier, and prettier.”
Financing the Dream: Mindset and Practicalities
A major hurdle for many aspiring nomads is money. Celeste’s approach combines an “abundance mindset” with practical financial strategies.
Initially, their journey was funded by cutting expenses and taking on low-paying “work-camping” jobs. However, an unsafe experience led them to pivot. They realized that low-budget travel wasn't sustainable or fulfilling. Today, their income is varied and robust:
Celeste's Consulting: Her remote database consulting business now earns double or more what her traditional job did.
Husband's Skills: Her husband leverages his construction and trade skills for location-flexible work.
Rental Income: They now rent out their Airstream to help fund future international travel.
Her advice on debt is refreshing. She has carried debt since age 18 but doesn't let it stop her. She viewed student loans for her master's degree as an investment and chose to buy a new, reliable RV as their family home rather than skimp. Her philosophy: if you have marketable skills and a willingness to work, don't let fear hold you back from investing in your education or quality of life.
