USA Adventure Seeker

View Original

6 tips on how to negotiate unpaid leave for your next adventure.

Having a successful career shouldn’t mean that you can’t take time out to do the things that allow you to thrive (instead of just surviving).

If you don’t want to leave your current role and would like to return to your position once your adventure is over, here are a few tips to help you negotiate unpaid leave when you meet with your boss.

Time off work can be achieved in many ways, including:

  • Taking a sabbatical

  • Requesting unpaid leave

  • Paying for additional leave (as part of the company benefits listed in your contract)

  • Take a planned gap in between roles

When meeting with your boss, consider the six points below. Go in prepared and be ready to offer solutions to any push back you may receive. This isn’t the time to wing it.

Overall, the main objective of the initial meeting is to reassure your boss that you are loyal to the company and don’t want to leave - however you are passionate about taking a leave of absence to pursue something that you see as purposeful.

And remember, the worst that can happen is that you ask and they say no!

** A few assumptions have been made **

  • You passed your probation period and have been in your role for at least 12 months.

  • You are performing well and meeting/exceeding role requirements.

  • You don’t have sufficient annual leave to cover the period away and/or your proposed trip exceeds the standard number of annual leave days provided.

  • You know what you want to do with your time off and have tentative travel dates in mind.

  • Your company doesn’t offer unpaid leave and this request may fall outside of company policy.








My story.

Everyone’s story is different and I share mine as I have taken multiple breaks throughout my career, from unpaid leave for 4 weeks - 3 months, to planned gaps in between roles.

In doing so, I continue to experience the adventurous things I love - whilst maintaining a career in digital marketing within the travel industry.

My passion is long distance hiking and most recent extended breaks include:

  • Arizona Trail: Class of 2023 (Fall hike, October to November)

  • Pacific Crest Trail: Class of 2019 & 2022, section hiking around 1,300 miles on each trip

As a result of the pandemic, I made a shift from full time permanent roles to contract work and I haven’t looked back. I traded the security that comes with a permanent job, for the freedom I crave by working on a contract basis.

The more time I spend in the outdoors, the less I desire material things, making it easier to prioritise saving money to cover expenses whilst I am away, as well as funding the trip itself.

Much like Stefan Sagmeister, I plan to work until the official retirement age, however I will continue to take breaks in the years leading up to my retirement!

Happy trails.


Stefan has taken the unique approach of taking a year off every seven years, by increasing his retirement age from 65 to 70, reallocating these 5 ‘retirement’ years and interspersing them into his working years.

Dennis interviews 100’s of people across the globe about why they took a 6 month sabbatical, to reveal that sabbaticals can play a transformational role in how we think about ourselves, and the future of work itself.


Where will you travel?

Here is a selection of popular thru-hikes in the USA, requiring anywhere from 2 weeks to 8 weeks to complete.