Remote working tips and how to live the laptop lifestyle

Remote Working Laptop Lifestyle 1

Unlike most people who live the laptop lifestyle and are self-employed, I have this lifestyle and a boss. Not everyone who is interested in remote working wants to start their own business. I know I didn’t.

Right now, I’m doing a big lap of Australia in a caravan with my husband and 2 pre-school aged kids.
If you’d like to make something similar happen in your own life, here are my suggestions:

1. Position yourself correctly

Before you write this article off because ‘that’s nice for you, but not possible for me’, let’s unpack that.

Remote working is not industry specific. Anyone who can do their job from home is a candidate.

But some businesses will be more open to supporting remote working arrangements than others. Similarly, certain roles within each business will be better suited to remote working arrangements.

If your current role isn’t suited to remote work, think about how your role and responsibilities could be adjusted. Or ask yourself whether there is another role within your organisation (a sideways move perhaps?) that would be more aligned.

Once you’re in a role that you’re confident you can perform remotely, it’s time to seek permission from your boss and business. But before you do…

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2. Establish your value as an employee first

If you’re seriously kicking goals at work, skip this section and move straight on to 3.

If you’re new to your role or have only recently joined the business, you’ll need to establish your value before hitting your boss with your remote working proposal.

How do you do this? Work your butt off. Produce high quality work. Be reliable. Be punctual. Be the first to put your hand up. Make yourself available. Win your colleagues over. Basically, make yourself indispensable.

If the business doesn’t want to lose you, it’s more likely to accommodate your request.

3. Prepare a kick-arse proposal

Now it’s time to think of all, and I mean all, the conceivable concerns that the business may have with you working remotely. Then come up with solutions to every single one of them.When I put the proposal to my boss asking if I could work from a caravan whilst travelling Australia for 12 months, I covered the following which I saw as potential issues for her:

Australia is a big place with remote locations that have no internet or mobile signal. I addressed this by getting a Telstra coverage map and planning my big lap itinerary around internet and mobile coverage areas. I also agreed to invest $600 in purchasing RVwifi – an internet signal booster designed specifically to increase signal to the caravan it’s connected to.

Your boss needs to know that regardless of where your travels take you, you’ll be connected. There are a number of things you can do to increase coverage (like having sim cards from all the different mobile service providers so you always get the best signal) – but that deserves a dedicated article in itself.

Time zones are a consideration if you’ll be travelling interstate or internationally. I agreed to keep my working hours aligned with my boss’ time zone. I also asked for flexibility with my hours. Instead of working from 9am-4pm with a 1-hour lunch break, I now work from 5.30-8.30am and then again from 1-4pm. This gives me a 4.5 hour break each day to go exploring with my family.

Time zones are a consideration if you’ll be travelling interstate or internationally. I agreed to keep my working hours aligned with my boss’ time zone. I also asked for flexibility with my hours. Instead of working from 9am-4pm with a 1-hour lunch break, I now work from 5.30-8.30am and then again from 1-4pm. This gives me a 4.5 hour break each day to go exploring with my family.

I have my own work equipment (laptop, screen etc.) but if you have company property, I would suggest offering to buy your own like-for-like equipment to take on your remote work journey. A business doesn’t want to see its property riding off into the sunset.

And if you haven’t already got them, I’d highly recommend noise-cancelling headphones. They help you concentrate anywhere and are gold for remote working.

Businesses are generally liable for their employees’ health and safety whilst working. Give your boss information about the place or types of places you’ll be working and offer to indemnify your employer from all potential work health and safety claims.

Your employer doesn’t want this adventure of yours to cost them anything. Make it clear that any additional costs you incur related to your remote work arrangement will be covered exclusively by you.

Offer to trial the new arrangement over a probationary period. That’ll give your employer the comfort that they have an easy out if they find the new dynamic is not working for them.

Is there anything extra you can offer the business as a result of the new arrangement? Think out of the box here. For example, I offered my boss exposure on the social media channels and blog I have set up for our big lap. After she agreed to my proposal, she came up with further suggestions including me creating legal video tutorials in beautiful locations and doing client meetings whilst on the road. What benefits could your laptop lifestyle add to your employer?

Lastly put some soul into your proposal. Explain your motivations for wanting to work remotely (mine were more quality time with my family, adding adventure into our lives and making memories).

Put this all down in writing and send it to your boss. Don’t expect an immediate response, they need time to consider it. It’s a big ask.

If (and when!) you get the green light, it’s time to consider the technology you’ll need to make this thing work.

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Remote Working Laptop Lifestyle 5

4. Technology

The tech you need will be business, industry and personality specific. The key thing is to be able to get your work done and communicate effectively with your boss, your team and your clients or customers.

In my arrangement, we use Slack (for instant messaging and document sharing), Outlook (for emails), OneDrive (for document storage and sharing), Dubsado (business management software), Zoom (for video conferencing), Loom (for creating screen sharing-type videos) as well as Microsoft office and the good old mobile phone.

It’s a good idea to be able to access your tech from multiple devices (laptop, phone, iPad and/or extra laptop) and have backup power sources like an extra laptop battery and/or power bank.

5. Communication and performance

In terms of making the arrangement work – your boss needs to be confident that you’re working just as hard as you would be in the office.

Touch base with your boss and, if appropriate, other team members, numerous times throughout your work day. Instant messaging is great for this. I instant message my boss about 10 times a day. I’ll always shoot her a quick message to let her know when I’ve come online and when I’m signing off. After completing tasks, I let her know. She needs to know that I am working and what I’m doing.


Time tracking

Some bosses may be more comfortable with you working remotely if you track your work time. There are plenty apps out there which allow you to do this conveniently or you can create a simple Excel spreadsheet to populate manually.

Whether tracking your time or not, make sure your output and the quality of your work doesn’t decrease. Do what you say you’re going to do and do it to the same standard you would if you were sitting in the office.

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6. Conclusion

Over the past 5 years I’ve worked in 3 different roles (HR Officer for an ASX-listed company, Paralegal for a small traditional law firm and Lawyer for a virtual law firm) and all have been remote working arrangements. I’ve never even met 2 of these 3 bosses in person.

It is genuinely possible to live the laptop lifestyle whilst remaining employed. I’m not saying it’s easily achievable, but you can certainly make it happen if you want it badly enough.

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Courtney Bowie


Courtney is Her Lawyer’s founder and principal lawyer. Before starting the firm in 2017, she worked as both a lawyer and consultant in top-tier law firms. Courtney is passionate about gender equality, mental health and wellbeing, especially in the legal profession.

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