How to travel and work remotely
Personal reflections having taken The Ask onto the road, alongside some life and business lessons for us all.
I’m writing from a new location today. It’s 7 am and I’m in my bed in an apartment in Lisbon, Portugal. After not too long I’ll be moving onto other new locations across the world.
With client coaching calls and admin ahead of me it feels like any other working day except for a feeling of excitement in this new reality I’ve created for myself. I feel so grateful to be able to take advantage of this opportunity that my work has afforded me.
In today’s post, I’ll share my reflections on the build-up to taking my business on the road and the lessons it teaches. Although remote work seems possible to many in theory, that doesn’t make it so easy in practice.
My own journey has required the following pillars to getting here:
A clear vision for what I wanted and my why
Calculated risk-taking and leap into the unknown
Careful planning and execution
These are the pillars to remote working in my instance but I also see them as pillars to doing anything new, exciting or scary in life such as changing careers or building a business. A client of mine has recently completed a similar life and career change, so we will look at his story too.
My vision to do the ‘nomad’ thing dates way back
For at least five years I’ve known that I wanted to travel the world and work on my own thing.
So when, in 2019, I was in a job making me miserable and quit without a backup plan, I already had a seed of hope inside of me that self-employment might be my answer. In 2020 I trained as a coach and set up The Ask®. There is more to that story obviously, which I have shared previously.
However I didn’t start my business so that I could travel per se, and nor do you need a business to travel, my point being that this travel decision is highly intertwined with the overall vision I have had for my life.
After two years working long hours on The Ask® and the uncertainties that come with running a new business, to now be able to say that it has afforded me with the opportunity to travel and earn a living from the fruits of my labour, is pretty damn rewarding. There are even some costs that I can pay for through the business. Who knew health insurance was so expensive?!
I know this decision dates back to that early vision I had for my future.
As a coach I believe firmly in the power of vision when it comes to creating the future you want. Only from a clear vision can we take aligned action.
The startup founders I’ve worked with who have the clearest visions I find have the most success in turning them into reality. That’s because vision can overcome the fears and pitfalls so par for the course in business building. (Ready to turn your vision into reality? I have a guide for that.)
In my own decision to travel, much like business building, there have been obstacles and there will continue to be more. Just as there are in any business building journey and so knowing that up top and developing a resilient frame of mind is the key to fulfilling your vision.
The leap of faith into the unknown — and what being single has to do with it
Despite the vision for this plan, it has not been without its question marks.
For example, at the stage of life I am at, one of my big goals in life (along with buying a house and starting a business) has been to settle down and start a family. In my initial travel ‘vision’, I had pictured that it might be with my husband.
But whilst we plan, God laughs.
My hard work and determination paid off enough to buy my house and build my business before the age of 30, but despite my goal-driven nature, you cannot ‘plan’ meeting the love of your life.
My newsfeed and social engagements are becoming increasingly full with engagements, weddings and babies. I share this to acknowledge my own fears in going away when others are settling down.
I’ve taken this ‘risk’ in the hope that it isn’t really a risk after all. If another year goes by without finding someone in the grand scheme of things, so what? I have a full happy life that I’ve built and am proud of.
This is not the only ‘risk’ I’ve imagined.
In fact, my questions and anxieties have been wide-ranging! Such as:
What if I’m miserable without my home comforts, favourite people and places?
What if I can’t run The Ask remotely because internet connections won’t be strong enough for Zoom calls with clients?
What if I can’t get into a routine with work and travel and the business suffers and I can’t afford my plans?
What if I’m too focused on the business to meet people and build a life?
What if I’m lonely?
What if not speaking the language is too challenging?
What if it’s too dangerous as a woman on my own and I’m at risk?
What if I’m too stuck in my own ways to adapt to a lifestyle of change?
What if new covid variants put us back into another lockdown?
What if the war in Ukraine escalates and my safety is compromised?
What if when I return home, my friends have all moved on and I have to rebuild my London social life again?
I reveal my fears with you to acknowledge how most opportunities in life come with sacrifice, risk or uncertainty. If the day comes that I decide to get married, that would be no exception to the rule.
And it is no different in business building.
For every startup success story, come brushes with failure, imposter syndrome and chaos.
We choose the type of pain we want to endure in life.
Some people choose the pain of the unknown in the hope that there is a reward on the other side, and some people choose the pain of staying still.
As a coach, I meet people afraid of change all the time. Afraid to actually make the decisions and investments that will change the game for their life and career trajectory. Many stay still because it feels safer to stay in the ‘known’ than leap into the ‘unknown’.
What if the risk doesn’t pay off? I hear people ask.
But what if it does?
The what-ifs on the other side of my fears are so much more compelling:
What if I have the most incredible time of my life?
What if the business benefits because of the travel?
What if I meet someone incredible?
What if I am happier, more self-aware, confident and well-rounded as a person?
I’ve had to maintain hope and be energised by my desires not my fears in the process of packing up.
And then comes the execution.
In running a business, the vision and idea stage is the most exciting.
We get energised by what we could possibly create. Spending time in the reading, thinking and learning phases.
Often the reality of building, however, is less sexy.
The same thing with my experience planning to be ready for remote work. The execution stage has been arduous (think countless calls and emails with banks, insurance companies, flight providers). I have lost count of the number of lists I’ve made, hours of research, admin and planning to make this possible.
One of the major things that have preoccupied my thoughts aside from drowning in admin, has been figuring out what I want the next period to look like. I’ve had coaching sessions with my own coach on how to juggle the fun side of the travel with with the realities of running a business.
The Ask is no longer just me, with two freelancers to pay, and a full book of coaching clients to look after, there is not the option to just wing it and see. I believe it has to involve stricter boundary setting, declining projects that aren’t a direct fit and clear roles and responsibilities. Discipline in the execution to avoid working all hours.
My first week failed already as I ended up working two of the days I said I’d take off to explore and then my weekend I was exhausted and unable to do the plans I had.
So I don’t write to you with this stuff figured out, far from it.
What is the right balance of work and play?
In ten years’ time if you were to look back on how you spend your days now, what would you think?
Finding a balance between work and play is a question we are all trying to answer; business builders or otherwise.
The topic of ambition came up at dinner last night with a fellow female founder. We asked one another: how do we know whether our ambition is what is creating a good life for us, or if we’ve idolised it at the expense of having one?
I don’t have the answer yet. But I do know that this was a pinch myself kind of moment. Sat across from someone I admire and call a friend with a successful business, chatting and drinking wine in a beautiful Portuguese restaurant. This life is the vision that I had many years back, to be owning my own destiny and creating these experiences with other people on similar journeys.
I love that I have a business to occupy me and give me a purpose with my time. The sacrifice of waking up at 7 am to write a newsletter I have to write to stay consistent with my schedule — that’s worth it. I’ve never been happier then since finding my purpose in building The Ask.
It’s a journey of finding my founder-fit that I now support my clients with. Clients who have also been afforded the freedom that carving their own entrepreneurial path creates.
Meet Simon: A digital nomad coaching case study
My client Simon just landed in Mexico City where he will work and live.
At the end of 2021 he came to me as Chief of Staff in a Series A startup (a role many would aspire to) but he was very unhappy.
Today his self-employed status has allowed him the freedom to move to Mexico and join his girlfriend who recently moved out there for a new job (after coaching with me too, might I add ;-))
Through coaching and the process of change Simon had to overcome his own fears and obstacles so that he could get where he needed to be.
I have Simon’s permission to share this from his end of coaching form:
Whenever I allowed my fears to steer me, I could not progress. Growing through the coaching process involved tackling my fears head on…There was one session halfway through the course when I was ready to quit coaching … Turns out the coaching was just forcing me to reconcile myself to some hard truths that I needed to get past on my own; no one else could solve them for me.
Once I pushed through, I realised that I was making a path for myself that I've been subconsciously yearning for. Now that I've articulated it, I can't imagine going back to anything else.
We had one session where Ellen reflected my challenges back to me in perfectly crystallised, succinct terms. In short, aspects of my past role were eroding my self-belief, which was the main obstacle towards making the necessary next steps. Once I properly diagnosed this as the blocker to my growth, I knew exactly how to proceed to extract myself from the problem and embark on a new fulfilling path. I was then able to take action (i.e., leave the role) with confidence and resolve. Ever since that session, I've felt an overwhelming motivation to follow my new direction.
Ellen does for your career what a physical trainer does for your fitness. She's going to put you through your paces, but it's the best (and smartest!) way to get the results you want.
I've never felt more pulled forward towards the future than I do now, and I have my mojo back.
The future Simon describes running towards is a future spent building a newsletter publication reporting on startup tech in LATAM. He will be interviewing Founders and VCs in the local area — using his startup knowledge, writing and foreign language skills. His perfect founder-fit.
Subscribe to Simon’s new publication here.
For Simon and for myself, there will be hard work that enables this travel and life change to happen. But when you are doing the thing you really love, the work doesn’t have to feel like such a sacrifice to play. It can even be your form of play.
