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3 Ways to Travel More Without Jeopardising Your Career

by Stephanie Holland on September 24, 2015

Stephanie Holland


3 Ways to Travel More Without Jeopardising Your Career

As much as you love your career you have a sneaking suspicion that other aspects of life might be passing you by. Having it all is hard when you work 40 hours plus a week.

Because it’s not just the 40 hours, is it?

It’s the commuting, the running around in between, making an effort to maintain relationships, and trying to keep up appearances, manage your home, & your family (& your waistline). We arrive home, our bodies kidnapped by exhaustion. The exhaustion of life. But sometimes the call of the wild cannot be silenced. Tiredness be damned. There’s an innate curiosity about the world that pinches us from the inside.

Good news: There are a few ways to get out there and experience more of it without jeopardising your career. The following 3 strategies are frameworks only – if they tickle your fancy but aren’t quite right, keep asking ‘how’ until they are.

This is your life. Make it work for you.

1. The Freedom-Seeker Strategy

Register yourself as a sole proprietor and pursue contracts of any length, any time you like.

Ideal for: A seasoned pro or a confident 20-something whose work speaks for itself and loves short-term project work. Highly social people who can integrate fast in any culture or lone wolves.

What you need: Excellent client testimonials and a gleaming track record.

Pros: 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. In demand during recession while permanent employees are laid off. Write off your expenses.


  • You must be diligent about invoicing & receiving payments.
  • Your salary is gross so you have to factor in the cost of tax.
  • You’re not eligible for company benefits like medical, holiday & sick leave.
  • Demand for your services is performance-based.


  • Build holidays, sick leave & benefits into your rate.
  • Keep 40% of your paid salary in a high interest saving account ready for tax time.
  • Give each contract 120% to guarantee excellent testimonials.

2. The Ultimate Freedom-Seeker Strategy

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

What you need: Proof of high calibre problem-solving skills and innovative thinking.

Ideal for: Those who have achieved guru status in a specific area of expertise and feel confident charging a premium for it. Great for Millennials who master cutting-edge technologies and processes fast.

Pros: 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.


  • Forget about working 9-5. You might work long hours to meet tight deadlines.
  • If your area of expertise is highly specialised it might be months between contracts.
  • Holiday, sick leave and benefits not included.
  • Large checks for the tax man every year.


  • Establish clear rules of engagement during contract negotiations.
  • Budget accordingly: keep 6 months living expenses in easy-access savings.
  • Set aside 40% of earnings for tax purposes and factor benefits into your fee.

3. 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 …

What you need: Entrepreneurial drive and products or services that people want to buy.

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.


  • 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.

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

Featured image via Pixabay under Creative Commons CC0


Stephanie Holland - Leaders in Heels Guest writerStephanie Holland helps corporate misfits set themselves up for success before they startup. Join the revolution at

Stephanie Holland
Stephanie Holland is a digital strategist and startup coach who got the digital *bug* from the original startup rebels (yahoo!, msn), cementing a career in exploration and discovery that continues to satisfy a crazy curiosity for life in general.Launching her own brand in early 2014 she offers a *killer* combination of vision creation formulas with powerful strategic frameworks so that purpose-driven people can change the world with their own digital-savvy brands. She coaches and consults with some of the most inspiring people in the new economy — so they can change the world, one strategy at a time.
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