Remote working from anywhere is one of the easiest ways to get started as a digital nomad over 40. Read this guide for the low down on what remote working is and how you can move into it.
“The secret of success is getting started. The secret of getting started is breaking complex overwhelming tasks into small manageable tasks. Then starting on the first one.”
Mark Twain
Taking small steps, achievable steps towards becoming location independent is more likely to guarantee success.
Let me explain what I mean by that. Let’s say you hate your office job. Your vision is to become a highly successful business coach generating $100K of income a year. You also want to leave your your home, your family and friends to become location independent. Your intention is to run your business from your laptop in a tropical beach location for 365 days a year.
Anyone can see that that is a LOT of goals to achieve all at once. So selling everything and jumping on that plane to Thailand without any experience of business coaching isn’t the wisest idea. Without a realistic plan, you run the risk of failing, running out of money and coming home.
Another point to consider is Newton’s first law of motion:
“An object at rest stays at rest and an object in motion stays in motion.”
In other words, once you start on your journey towards location independence, you are much more likely to reach your end goal. So it’s very important to take that initial step forward.
Remote work can be the first stepping stone to other location independent opportunities
Take the example of Cris Gawlik, a 40 year old nomadic business owner who is saving 70% of her income with the aim of retiring early. Cris has been able to do this through scaling her business. She is also based in countries where the cost of living is significantly cheaper than the States (her home country).
But Cris didn’t set up her business, grow it and leave the country all at once. She took a remote role with a company first of all. This allowed her to become location independent whilst in the States. She then started her own company, before moving to Mexico a year later.
In this way she tested her proof of concept over time. This made her confident that the path she was taking was the right one for her. And she kept moving from one realistic goal to the next, gaining momentum through time.
Remote working can be the easiest place to start
Increasingly, companies are adopting ‘work from anywhere’ arrangements to retain valuable staff. If you’re 40 and above with years of professional experience, then you’re in a good position to be able to negotiate a remote working arrangement. This could make remote working an easy first stepping stone to the lifestyle you want.
What sort of remote working arrangements exist?
There’s a wide range of remote working arrangements in existence. Some employers enable home working some of the time. Others allow employees to work remotely for the majority of their working hours. From time to time they’re required to come to the office for meetings.
Other companies are supportive of ‘work from anywhere’ roles. To enable virtual meetings, they may have an expectation that remote employees work the same timezone hours as colleagues. Some companies run distributed teams where the entire company is run remotely and people only ever meet online. People can choose to work whenever they want, provided they attend the virtual meetings.
Some common roles which work well in a remote arrangement include:
- Tech and software development
- Virtual assisting
- Marketing
- Communications
- Teaching
- Website development
- IT support
- Customer support
- Business development
As technology improves and becomes cheaper over time, more ‘traditional’ roles will be suitable for remote working. For example, health care assessment, psychotherapy and counselling.
Is remote working for you?
Some people enjoy remote work because they find that it makes them much happier and improves their productivity, and others… really struggle.
If you are the sort that struggles to be productive when working on your own, this sort of work may not be right for you.
Bear in mind that location can make a big difference to your productivity levels. As a freelancer, I’ve found that I’m much more likely to focus when I’m in a beautiful destination on the other side of the world. When I’m overseas I want to spend the minimum amount of time in front of my laptop doing my work. So I ensure my time is as productive as possible.
Also, if you find you’re more productive in an office type environment, there are things you can do to emulate this as you travel around.
There are so many co-working spaces across the world now. For a fee (which varies) you can access these peaceful, air conditioned office spaces. You’ll also be amongst like-minded remote workers, freelancers and entrepreneurs who are trying to do the same thing as you. This can be very motivating.
Could your current role be undertaken remotely?
Consider whether your current role might be able to be undertaken remotely. Does your company undertake a lot of virtual meetings already?
Would your company be open to doing things a little differently? After all, this could make you a significantly more happy, fulfilled and productive employee.
Having a conversation with your boss about a different sort of working arrangement can be a little tricky. It can be especially hard if the company has not allowed this before. People don’t generally like change. That’s why I’ve published another blog post – when and how to make the case for remote working. It has a handy checklist you can run through to ‘risk assess’ the likelihood of a positive response from your employer. It also provides a business case template for making the case in the most effective way.
Where to find remote working roles
Noot convinced your current employer will agree to a remote working set up? There are some amazing websites out there that advertise thousands of remote roles everyday.
Some of these roles are contract roles where you are taxed in the normal way (e.g. it is deducted by the employer before you receive your pay). Others are freelance contract roles.
Websites which advertise remote jobs:
Flexjobs is the best jobs board in my opinion, with a wide array of roles and a great search functionality. It is a subscription service, but it’s worth the money.
You can explore the site free of charge but you won’t be able to apply for any until you have paid for the subscription. It’s worth exploring before going ahead and subscribing. That way you can establish whether there is an abundance of advertised roles which meet your skillset.
Some tips for using the site’s ‘advanced search’ functionality. Pop a keyword relating to your core skillsets in the Keyword field. Set the International field to ‘Anywhere – can be done anywhere in the world worldwide’. Finally, set the Remote Work Level field to ‘100% remote work’.
These criteria will give you a greater chance of finding a role which enables you to work anywhere, without restrictions. You can always adjust the criteria if nothing comes up.
The cost? It’s $14.95 for a month’s worth of access, $29.95 for three months and $49.95 for a year.
To reduce this further, try searching for a coupon code. I found one which gave 30% off the subscription price.
remotewoman.com – a great new free jobs board where you can apply directly from the site. Aims to support women to work remotely (but I assume anyone can apply for the roles). Also has a community of members.
weworkremotely.com – a wide variety of roles, many of which require you to be from North America (for tax or timezone purposes).
workingnomads.co – a straight forward site listing thousands of roles in a variety of areas. The focus is on development roles and marketing.
nodesk.co – an excellent resource which lists jobs, articles and blogs about remote working.
remoteok.io – thousands of jobs with an emphasis on tech development.
justremote.co – this site focuses on four core areas: development, design, marketing and managerial.
remoters.net – this is a comprehensive site with a blog, interviews with remote workers, co-living listings as well as jobs which focus on software development, marketing and managerial positions, amongst others.
remote.com – a similar focus on development and marketing here.
Landing your dream remote role
So you’ve never undertaken a remote role before, and you want to apply for one now. Consider how you can present yourself in the best possible way. As someone who is in their late 30s, 40s or early 50s, you are likely to have many years of experience under your belt. You can use this to your advantage in your application to land that dream role!
Many companies that advertise on remote job boards run distributed teams. In these teams, everyone works from a remote location. Communication takes place via online meetings and tools, for example Google Hangouts, Asana and Slack.
The advantages to a company working this way is that it saves on office costs. At the same time, it’s possible for the company to hire really experienced people at a lower ‘global’ market rate then their local employers’ market. For a company based in London or New York, the savings can be considerable.
Quite a lot of these companies are tech start ups. It may be that you’ve never worked for a start up before… but don’t let that put you off. Find a role where the desired skills and experience match with your CV / resume. Then articulate how your experience will transfer well. Give examples where necessary.
As a Head of Marketing for a large healthcare organisation in the UK, I had years and years of corporate experience in an office. At first, I wasn’t sure how I was going to land a remote role in a tech start up. But I knew I needed to get one.
After searching Flexjobs for some time, I found a freelance senior communications contract role. The role was for a content-sharing app called phlow. As I love photography, and they were primarily looking for a first class writer, I could see how my skills could translate. That’s how phlow became my first client.
If you’re from Europe, the UK or the States, the chances are that a remote role will pay less than what you’re normally used to. Bear in mind that if you’re travelling around SE Asia or South or Central America, your cost of living won’t be as great as it will at home. Consider that you might be able to afford to take less of a wage to live the lifestyle of your dreams.
Ensuring your remote work is a success
If you want to make your remote working opportunity a success, good communication is paramount.
I spend a lot of time ‘putting myself in the other person’s shoes’, and ensuring I’m communicating clearly. It’s easy to misunderstand people when you’re communicating through Slack all the time. I also take time to build relationships with people – particularly senior executives. Developing a win-win mindset, asking for feedback, and being clear about expected outcomes from the start of a project can also help.
Honing your ability to take the initiative and be resourceful is also important. Your colleagues want to know you have everything in hand and you can take responsibility for your own goals. Being highly flexible and adaptable is essential, too.
Of course many of these skills are expected of senior professionals in any role – regardless of where the role is based. That’s why I think “older” people make such fantastic remote workers. Their ‘soft skills’ are honed to perfection and their corners have been rubbed off. They know exactly how to get along with others so that everyone achieves the best outcome.
Which leads me to my last point – confidence and self esteem. Having confidence in yourself and your abilities will help you to move on to the next stepping stone of your location independent plan. It will also help you develop resilience in times of stress.
What are your top tips for remote working? I’d love to hear them. Get in touch through the comment box below.
Sam 🙂
P.S. Would you like to get a free copy of my new eBook, Become location independent over 40? Get yours here.
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