Travel is a brilliant enabler & magnifier for your ideas in so many ways and on so many levels, but that’s not the best part about it.

It’s a fabulous lifestyle for those who crave a greater sense of freedom and adventure in their life and work.

So if you want to travel more this year without ruining your career, then this episode is for you!



So I want to share with you 6 brilliant strategies that enable you to lean on your corporate skill set as a platform for financial support while you either figure out what it really is you want to do, or when you need to cash up between or in the middle of launching your ideas, projects and businesses.

You see, your 9-5 skill set is such an amazing gift that you will always have – not only can you use many of the skills & knowledge to grow your own business, but also because you can leverage the corporate world and your brilliant corporate skill set when you want to take a break or cash up for the next level of your business.

Can you imagine anything smarter than using your corporate skill set to travel more and launch your own ideas?


Can you imagine anything smarter than using your corporate skill set to travel more and launch your own ideas? #thefreedomphilosophy #travel #startup Click To Tweet


I can’t! It’s so strategic and so SMART to support yourself while you’re launching your ideas, and to use your amazing skill set to do it.

It also removes the barrier of running out of money because when you do, you just cash up again so you can continue.

It kind of removes the ‘ran out of money’ excuse (fear) for quitting on yourself before you get the results you’re looking for!

So let’s talk about the 6 epic strategies that help you leverage your hard time in the corporate world so you can begin to live & work on more on your own terms (even if you don’t have an idea yet!)


Before you read on, you can also grab the guide from my FREE Starter Kit Library.

Original Image By Amos Bar Zeev

#1: The Built-In Backup Strategy

Alternate 1-3 year corporate stints with long periods of travel.

Ideal for those who:

  • want to experiment and explore their passions and ideas, but not yet sure exactly what they want yet.
  • have some ideas but no clue how that might enable a sustainable life and business.
  • want to give themselves a fixed time frame to work on a specific idea and if it doesn’t work out, come back to re-assess the next venture.

What you need:

  • A plan for how you’ll spend your time: what you want to do and learn, and where you want to travel.
  • Adequate funds for travel and a transition fund to cover you for up to three months while you find your next job.


  • Immersive periods of exploration during which you can figure out what direction your want to take, and begin to discover your passion, purpose and vision for your life and your work.
  • An in-built ‘back-up’ plan because it builds your experience and CV over several years. {While you work half as much as your friends!}


  • After a few cycles you may be perceived as a flight risk to prospective employers.


  • Clearly articulate how the skills & experiences gained from travel/ study/ business will benefit your future employer.
  • Volunteer while you’re traveling {everyone loves a humanitarian}
  • Position yourself as a freelancer and have at least one stellar recommendation from a reliable ex-colleague from each place of work.
  • Be a superstar employee; resign with elegance, grace, and honesty, and your previous employer will probably invite you back.

Get started: The Freedom Philosophy Classes, to discover what it is that you REALLY want!

#2: The Risk-Minimiser Strategy

Pick a country or continent you would love to explore and find a job there.

Ideal for those who:

  • want a deeper real-life experience of another country or culture but loves the perks & opportunities that come with a secure job.
  • Want to startup on the side, minimise the distraction of friends & family at home, and leverage the creative expansion that happens outside your comfort zone.

What you need:

  • Strong personal and social networks {ideally LinkedIn}, head hunters or recruiters, a great relationship with your current employer {for a transfer}, or a self-starter mentality.


  • Full-time salary and more time & energy to explore your ideas on the side.
  • Minimises career and financial risk completely.
  • If you end up escalating the corporate ladder after all, many industries see international experience as a catalyst for the CEO track.


  • I don’t think there are any!

Get started: LinkedIn Jobs / Escape the City Jobs

#3: The Online-CEO Strategy

Look specifically for remote job opportunities. With a rising tide of online businesses, more and more people are growing a team of people who work ‘remotely’ from all over the world, who want to hire talented people regardless of their location.

Ideal for those who:

  • Are self-starters, have a strong work ethic and love working autonomously
  • Want a transition step between the corporate world and starting their own online business
  • Want to learn the nuts and bolts of an online business model

What you need:

  • Ideally tech, admin, support, or marketing skills, as these are typically the requirements of most remote working job specs


  • Minimises career and financial risk completely while enabling you to learn how to work on your own terms.
  • First hand experience and knowledge into what it takes to run and grow an online business
  • Learn how to work alone, master work-life balance, and work with a global virtual team before you become CEO of your own business!
  • Regular in-person company meet ups all around the world!


  • I don’t think there are any!

Get started: any of your favourite tech startups/ jobs/ career sections

#4: The Freedom-Seeker Strategy

Register yourself as a sole proprietor (freelancer) and pursue contract of any length, any time you like.

Ideal for those who:

  • are seasoned pros or a confident 20-somethings with excellent skills and love short-term project work, highly social and can integrate fast in any culture.
  • want more control of your time as you alternate corporate projects with your own projects while you build your business.

What you need:

  • Excellent client testimonials and a gleaming track record.
  • Flexibility across industries and categories.


  • Work on a project by project basis which keeps life interesting & builds your experience and portfolio quickly. You can establish a name for yourself and high demand for your services fast, which can transition into your own business over time.
  • Massive demand for your services during recessions while permanent employees are laid off.
  • Work remotely for previous clients in your country of residence while traveling.


  • Getting back into a permanent role might be challenging


  • Assess the pros of your short term contracts from a career perspective, the pros of a permanent position from a personal perspective, and present these as an business advantage to your future employer.

Get started: Register on Upwork, sign up for the Freelancer Course

#5: The Ultimate Freedom-Seeker Strategy

Position yourself as a consultant when you’re a bonafide expert in your field.

Ideal for those who:

  • have achieved guru status in a specific area of expertise and feel confident charging a premium for it.
  • master cutting- edge technologies and systems fast.
  • want to work less and earn more so they can invest in their own ideas.

What you need:

  • Proof of high calibre problem-solving skills and innovative thinking; or,
  • A unique philosophy, system or process that you use to create transformation for your clients business.


  • Freedom to choose who you work with while charging a premium.
  • You can charge value-based fees for your services because of the high-impact nature of your contracts which means you can work less and have more time on your own ideas
  • If you love this work it might become your sustainable life & business model.


  • You might work long hours to meet tight deadlines.
  • The highly specialised nature of your work might mean it takes time to find clients and negotiate contracts


  • Establish clear rules of engagement during contract negotiations to ensure you’re still able to work on your own terms
  • Budget accordingly: keep 6 months living expenses in easy-access savings.

Get started: Read the incredible collection of books by Alan Weiss who tells you how to set yourself up as a consultant

#6: The-Make-Money-While-You-Sleep Strategy

Transform your expertise into digital products & services that people can buy online from anywhere in the world while you sip margaritas from your hammock.

I know what you’re thinking: I can’t leave my job! Hear me out

Ideal for:

  • Self-starters who love the opportunity & challenge of starting up and being their own CEO.
  • Those who have valuable knowledge or expertise that they can package, or creators & makers who have a product to sell.

What you need:

  • Entrepreneurial drive and products or services that people want to buy.


  • Complete control over your time and business size & direction. Outsource everything outside of your zone of genius. Breathe life into your ideas and have an impact on the world around you. Complete control over work-life balance over the longer term.
  • You career and your job will ALWAYS BE WAITING FOR YOU if you want to go back. Fact: It looks pretty cool when you have your own business on your CV.


  • Work-life balance is hard at first; fledgling entrepreneurs work 24-7 which quickly becomes a lifestyle.
  • No control over size or timing of commercial success; threat of failure can be paralysing.
  • Startup cash flow can run out fast.


Set work-life balance parameters that maintain physical & mental health from the outset.

  • Outsource/ grow your team before you feel.
  • Have a vision larger than this project so you can move beyond failure.
  • An emergency fund to cover six months living expenses; crowd source funding for your project; maintain good relationships within your industry so you have a back-up plan.
  • Lean on your corporate skill set to take breaks and cash up

Get started: Grab the startup guide The Freedom Philosophy or join the Freedom Philosophy Classes so you can build a business around the life you want, the impact you want to have, and the legacy you want to leave behind.

Just Get Started

Ultimately you can start with the level of risk you’re willing to take and slowly increase it to move closer towards absolute freedom.

How do you feel about traveling more and working less?

Which of these appeals to you?

I hope this inspires you to think about how travel might give you more freedom and adventure in your life and work.



Do you have a dream, goal or decision to make but tend to get overwhelmed or flustered when it comes to taking action?

Stephanie Holland Marketing Consultant

Hey, I’m Stephanie. And I’m your greatest ally.

I have a unique gift for simplifying complexity, powerful perspective shifts, uncovering hidden opportunities, and crafting the immediate next steps that fast track your goals.

Find about more about my mentoring sessions here, or send me a note and we can connect for a 15 min call to discover how I might be able to work with you to achieve your goals.

Find out more


Other posts in this Life Planning Series:

How To Write Goals That Manifest Miracles (and a FREE Planner To Get You Started)

6 Epic Travel Strategies for Solo Entrepreneurs and Corporate Misfits

5 Ways to Plan More Freedom Into Your Career

13 Life Hacks that Amplify the Impact of Your Life and Work

What Kind of Life Do You Want? Practical Lifestyle Design in 3 Simple Steps


Image: Monikia Geble via

Stephanie Holland
Stephanie Holland

I'm a strategist & traveler obsessed with thriving on all levels and helping fellow entrepreneurs launch their ideas with more ease, vision and likelihood of success.