Five No-Brainer Strategies to Work Less and Travel More

AKA The Corporate Misfit’s Incremental Guide to Freedom

Quitting your job without some kind of game-plan might sound exciting to some, but for others it brings on palpitations and hives.

The perfect solution for you exists somewhere along a sliding scale where risk is directly proportionate to the degree of freedom you desire.


msn travel

Here are five strategies to help you decide on the right one for you.


#1: The Built-In Backup Strategy

Women with backpacks in airport.

Ideal for: 20-somethings not yet sure what they want to do with their lives but not yet willing to risk throwing away a corporate career.

What you need: Adequate funds for travel and a transition fund to cover you for up to three months while you find another job.


  • This strategy has an in-built ‘back-up’ plan because it builds your experience and CV over several years.
  • Build a portfolio of experience more quickly without being typecast.
  • You gain a level of maturity and wisdom beyond your years.


  • After a few cycles you may be perceived as a flight risk to prospective employers.
  • You never know how fast you’ll get another job when you come home.


#2: The Risk-Minimiser Strategy

Young woman taking notes while volunteering.

Ideal for: Anyone who wants a deeper real-life experience of another country or culture but loves the perks & opportunities that come with a secure job.

What you need: Strong personal and social networks, head hunters or recruiters, a great relationship with your current employer {for transfer}, or a self-starter mentality.


  • Minimizes career and financial risk completely.
  • It can lead to citizenship or a fast tracked savings plan when you depart. {Claim back pension & tax refunds if you can’t retire there.}


  • It can cost your friends and families to visit you.
  • If your company sponsors your business visa, one wrong move or lost client and you could be back on the plane pronto.


#3: The Freedom-Seeker Strategy

Two men drinking tea in Middle Eastern country.

Ideal for: A seasoned pro or a confident 20-something who 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.


  • Work on a project by project basis; build your experience and portfolio quickly.
  • You can establish a name for yourself and high demand for your services fast.
  • You’ll be in demand during recession while permanent employees are laid off.


  • 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.

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#4: The Ultimate Freedom-Seeker Strategy

Businessman talking on cell phone and walking through St. Mark's Square in Venice.

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.


  • 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 specialized it might be months between contracts.


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

Woman working on laptop at villa.

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

Ideal for: Self-starters who love the opportunity & challenge of starting up and being their own CEO.


  • Complete control over your time and business size & direction.
  • Breathe life into your ideas and have an impact on the world around you.
  • Complete control over work-life balance over the longer term.


  • 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 paralyzing.
  • Startup cash flow can run out fast.

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

As Emerson said:

All life is an experiment. The more experiments you make the better.

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