How do I convince my boss to let me WFO (work from overseas)?

Each week, Dr Kirstin Ferguson tackles questions on the workplace, career and leadership in her advice column “Got a Minute?” This week: asking to Work From Overseas, re-entering the workforce, and competition among new staff.

I am 25, have no family responsibilities, and I am really keen to see the world. I have a job I love in tech, which I primarily do from home. My workplace allows us to work from home no issues at all, but I want to take it one step further and work while travelling overseas. I can see how I can make it work, although I am not sure my boss will be as keen. How am I best to get him on board, so I can pack my laptop and go?

It sounds like you are keen to become a digital nomad (and it is easy to see why given this is probably the best time in your life to do so). You are right in anticipating that there is a big difference for some organisations in agreeing to have people work from home – somewhere in Australia – to having you work from the road in a remote corner of the world.

You are definitely going to need a well-thought-out argument and detailed plan for how to make this work. I would then ask to meet with your boss and talk about how your current remote setup is working well for both you and the organisation. I would reaffirm your commitment to the business and explain how you would like to be able work from anywhere, not just from home. Be prepared to explain what your work schedule will look like on the road and how you will track and report your progress. You are also going to need to understand any tax or company policy issues your plan raises.

You will need to be prepared to address how you will manage timezones. If your work is something you largely do alone, timezones may not be much of an issue. However, if you have to attend online meetings, presentations or even collaborate with your work colleagues online during Australian work hours, there will be some concern about how practical this will be so make sure you address those concerns upfront. Hopefully, safe travels.

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I have been on a career break for five years, and I am contemplating re-entering the workplace. I still have two young children at home, so I don’t think I am ready to go back to work just yet, but I am starting to think about my options. I don’t have a formal career path and so am open to what I do, but that is actually pretty scary because I don’t really know where to start. What do you recommend?

It is a great idea to be thinking ahead about and starting to plan for what a possible return to work might look like. Don’t be scared though – this is a wonderful opportunity while you are planning to think about what you love to do and how that might look as you balance work and family in the future. Fortunately, the workplace has changed a lot over the past five years with most employers now offering a range of virtual or hybrid options to give you more flexibility than you may have had before. Depending on the work you choose to do, flexibility could open up many new doors you hadn’t thought of previously.

One option you might want to look into is a program called Jobs Academy. It is a free, year-long virtual program designed to help women return to work after a career break. It is run by Future Women and funded with assistance from the federal government. Since the program is run online, it may be a helpful way to start investigating and thinking about an approach to take for re-entering the workforce when you are ready.