“WorkAnywhere”. Going beyond “Remote”

Gaping Void Remote

A wonderful depiction by Gaping Void of the core messages of  the book “Remote” 

I strongly believe in remote working. However, today let me take it a level further. For now let’s call it “WorkAnywhere”, as the idea of remote working still implies a paradigm where there is a central point of focus for a business, an office or “head office”.

We don’t need that paradigm anymore, it does not serve our thinking and so our practices. Technology has shrunk the world and enabled many of us to be able to work almost anywhere, anytime and with even more effectiveness than if we had to travel to an office or even place our focus around such a place. That said, I also believe that it is a “both/and” conversation, that often we miss the huge value of creating and building meaningful relationships by being “offline”, by being face to face with people.

So, to me, there are wonderful lessons in the book “Remote” that I will touch on later, yet my core message is that many of us can consciously operate a “WorkAnywhere” model, going beyond the idea that we can work remotely from a central office or HQ.

For us to WorkAnywhere, we then leverage both the power of remote working with online tools as well as recognising the power of actually being in the same room as people and so investing in that time (and travel to do so) as a core element of WorkAnywhere life.

Today, then, I’ll tell my own quarter-century long story of how I have evolved to my own WorkAnywhere model.

In that, I’ll share some of what I have learned along the way to support that work model, including some thoughts on the book “Remote” and the lessons from the huge success Jason Fried and David Heinemeier Hansson have had in building and running their remote business (that itself offers remote tools for collaboration).

Beginning remote working – way back in 1993

A little over twenty-five years ago, I moved into a business role with one measure, to grow the business assets of a family holding company in the Cayman Islands. I had the great pleasure of holding that role for 16 years, operating with almost total autonomy to support a Caymanian family build entrepreneurial businesses with patient capital and a family first culture. It never felt like “one job” for that period as it was so dynamic and ever-changing yet with the constancy of context of “building businesses” and a family that thought in generational terms and longer.

Now, while some of our businesses and holdings were international at that time (more were as time went by), most were in the small environment of Grand Cayman, where (at that time) one was never more than 15-30 minutes drive between any two business locations.

With no internet and need for information and data, my working life, then, involved driving around and rotating visits to all of our businesses according to need, with also a lot of working from home as I had young children and focussed on that balance.

Tech in the early days of the internet

Back in 1993, there was no internet for business. Imagine that!. To get information one had to lug a laptop around between offices and then connect. Yes, “lug”. No sleek and light MacBook weighing 2lbs, but a “luggable” Compaq that weighed 8lbs and had virtually no battery life.

Now let’s look at the tech environment beyond that. No cellphones, so I often had quiet moments driving between our business locations and landline calls. Internet access? This really only started in Cayman in 1993 and was at the time when email was virtually unheard of. I remember pulling ethernet cables for “daisy chain” networks from 1990 onwards and it felt miraculous that we could plug in and share files on a “local area network” (remember LANs and WANs? Ah, the old days!). We didn’t even get dial-up access until around 1994 and Mosaic, as the first internet browser, was a novelty only for some time after that. Wifi? Not for a LONG time yet, and in our small island with a monopoly phone provider, the idea of such things as Skype (later GoToMeeting was a staple, now Zoom and more options), Whatsapp, FaceTime etc.. gosh, we hadn’t even conceived of these for communication.

Our primary method of communicating outside of each office was (remember these?) fax machines. At one point Cayman was famous for having more fax machines per capita than any other country. Oh, the efficiency (hah!).

We need “face time” more than ever when we work remotely

Before I go further in the story and move into how I work remotely now with current technology, I want to caution that we truly need both online and offline, we do need “face time” with people to truly create and build meaningful relationships.

Now, for those who have got to know me over the last decade, I’m mostly known for being in conversation with people, often face to face, so my emphasis is on face to face communications, not the type of remote working we often think of in 2019. It is “old school”, sitting with someone and listening to them and supporting them through conversation. To do this in my role as a Sounding Board I listen intently, tuning in beyond words to energy, expression, visual cues. In short, non-verbal communications, which can (studies show) be up to 93% of what we communicate. Yes, 93%. Clearly, this works best with lots of “face time”!

Numbers and People, Online and Offline. Remote and “Face Time”

Back in the 90s, though, a lot of what I did was around the numbers. Yup, I was still using my Chartered Accountancy qualification actively, running numbers, looking to leverage assets, borrow from banks, raise equity, do deals. So, lots of spreadsheets, lots of analysis of figures, lots of time with my head down on my laptop.

However, as I already said, I was often in my car several times a day moving between businesses. This was due to technological need. I had to do that so I could find a spare desk or table near an ethernet connection to access the data on their network relevant to that business. The (not so good) alternative was people sending floppy disks around (remember those?).

What I didn’t really realise for a while, though, was that all those movements in and our of different business offices and sitting at different spots had another huge benefit, which was in creating and building meaningful relationships.

I was in my late 20s and often worked long hours, feeding off and adding to the energy of building multiple startups and scale-ups at the same time. It was often the impromptu conversations at odd hours that forged the strongest relationships.

For this young chartered accountant, it took a while, but gradually as I shifted from numbers and management to leadership (to me Leadership=People, simple as that), gradually I had the epiphany about the power of investing time in being with people in the same room.

So, for about the last twenty years, as I’ve continued to work remotely, I also have consciously invested in time face to face as a core element of what I do.

For me with my clients, this blend of offline and online has evolved into a model for creating and then building relationships that typically starts with an extended period of time together. As I outline in the “How I Work” Section of the #BeMoreYou page on this site:

“Every client engagement is different, though common elements include an introductory intensive session of typically at least a half day, followed by a commitment to calls or meetings at least twice each month for a minimum of six months.

I work with clients around the world utilizing a blend of face to face meetings and call/video platforms. For remote clients our initial intensive will typically be face to face to establish a strong platform, then we will ideally meet in person at least once or twice a year.

Your investment is based on the value you experience rather than any measure of the time we spend together. In fact, clients find that after a year or more of working together and developing deep understanding, our “face time” may decrease, but the value we create will definitely increase.”

As you can see, in this model I will drive/fly/train to a client to spend half a day or more with them to forge our relationship, often from that point on working the vast majority of the time by video, with periodic travel to meet on a regular basis.

A tip here. In my experience, once a relationship is built, video can be at least 80% as effective as a face to face meeting. However, if we start only with video, that number drops to 50% effectiveness or less.

Evolving to WorkAnywhere and how I live that now

So, I’m quite unusual in that I’ve operated remotely for over 25 years. I’m also a lifelong early adopter of technology (for unusual family and other reasons I’m a 53-year-old “digital native”), so what have I evolved my WorkAnywhere model to now using current technology?

I lived in Cayman for 27 years, though in that time, valuing face to face meetings, I travelled literally millions of miles internationally to create and build relationships.

As technology evolved more and more to serve remote work, and particularly once I moved into business and leadership coaching around ten years ago, the use of video platforms became a very powerful tool for me to augment face to face meetings.

The blend of offline and online continues to be something that evolves for me, with a major shift being to move to London two years ago. When asked why London, the answer truly is to have free access to listen to and meet so many brilliant thinkers and leaders in one city, something I craved when living on the wonderful small island nation that is Cayman.

My work remains still mostly international (outside the UK), with a lot of time spent in my apartment in central London on video calls (as well as emails, WhatsApp messages, I communicate however my clients prefer) across time zones. This is then interspersed with getting on flights or taking the train across the UK or Europe to see people in person.

To me I don’t also really think of the term “work:life balance”, I love my work, it is part of who I am, so all is integrated. A typical day for me has structure (that is a key tip from me). I wake up at the same time, am sitting at my laptop by 8am each day, then I have certain elements of my day, week and month that create rhythm both in my work and the rest of my life.

An example is that, as with this post, I write a post every day. I also exercise every day, with a routine around different forms of exercise. As to my clients, I love to create and build meaningful relationships for the long term, so most clients are with me for several years and operate on retainers with a set frequency of meetings and video calls. Those are slotted into my day/week/month by my (virtual, naturally) EA, the brilliant Katie. Hmm, that reminds me, Katie and I haven’t seen each other in quite some time, note to self to invite her up to London for lunch soon. Face to face is always of value!

Around these and other “building blocks” of my WorkAnywhere life, I leave lots of space for flexibility and spontaneity. For example, I write at different times of the day depending on client calls and meetings, so today this is being written at mid-morning (to go out the next day at 8am), then I am heading up to the RSA to attend a lunchtime group conversation led by an inspiring thought leader around the power of language. I love that I can simply “pop out” and do that in London. Oh, and working from home is so super efficient, hence the flexible time. I’d imagine the average London commuter spends upwards or 10-15 hours per week travelling to and from offices. I save so much of that time, as well as looking to break such paradigms as 9am meetings, always asking people to meet at 8am or 10am as who wants to travel in rush hour ? 🙂

I could literally work anywhere with internet access and reasonable access to an international airport, but I love London for the reasons I noted (and others).

Always happy to talk, to listen, to learn, to share ideas around this and anything else. I love meeting interesting people doing interesting things. If you are based in or visiting London, let’s meet (face to face!) for coffee. If you aren’t, hey, video works!

In closing, a final section about “Remote”, the book

“Remote” and inspiration from DHH and Jason Fried

I mentioned that I have always been an early adopter of technology. In having responsibility for multiple businesses at one time starting in the mid-90s, I was always looking at how to make that easier using technology.

In the mid-90s that often meant, for me, becoming more and more expert with tools to measure and manage businesses and projects. Excel was one for sure (to this day I’m a spreadsheet geek!), another, used often by our businesses for construction and development projects, was Microsoft Project. Walk into any construction trailer and for decades now you will see Gantt charts on the wall with visual timelines and milestones. Yup, Microsoft Project is the mainstay for creating those.

By the mid-2000s, though, I found that MS Project was getting really “bloated” and was way beyond the needs of all but our largest and most complex projects. It was also expensive and didn’t have much online capability.

I then discovered the early days of an online software called Basecamp. It was simple, focussed on the 10% of MS Project that was all that 90% of users would ever need. It was not free, they charged for it from Day 1, then constantly reinvested into evolving the software based on feedback from customers.

I didn’t learn all of this right away, I simply started using Basecamp for our business. I did, however, get curious about the business behind it, called at that time 37Signals.

Think about it. Back in the early to mid-2000s, their company was:

  • Building a product based on only what clients needed – could that now be called a Minimum Viable Product or MVP?
  • Iterating that product after launch based on client feedback. Perhaps they were being (cough) “Agile”? (the Agile Manifesto was launched well after Jason and David got rolling).
  • Charging from day one for their product and not taking VC money – nowadays we call that Bootstrapping. Back then it was called “building a business”. My own bias is absolutely towards investing in businesses that always have their eye on revenue, profitability and cash flow, as that has always been the way I have done it! 37Signals lived this from the start. As DHH often rails about on Twitter (and I totally agree),  too many startups and scale-ups are only in the business of raising money, not making money! (Uber, anyone?).
  • They shared what they were learning as they went through blogs (Signal vs Noise, running since 1999), public speaking and then a series of books, all of which I devoured voraciously in my quest for continuous learning and improvement.

Oh.. and their workforce was remote from the very beginning.

So, having deployed Basecamp, and later their similarly deliberately “thin featured” CRM, Highrise, I naturally bought their books, I highly recommend them all.

Re/Work (2010)

  • Simply so, so much in this book about rethinking work itself, as well as leadership, culture, how to run a business. I read it in first in one shot on a long flight and was overwhelmed by how many transformative ideas were in it. This also arrived at a perfect time for me as I’d left the role above after 16 years and was starting out helping others with their businesses. Then and now I am known for encouraging and supporting those who seek brave and transformative change. This book is full of ideas to get you thinking as well as to utilise for yourself

Remote (2013)

As you can see at the top of this post, Hugh McLeod of Gaping Void has captured key learnings of this book in an image. I also love that he sets out at the top a philosophical anchor of “Be More” for each of these elements.

In this book are some great ideas, tips and tools for working remotely, though I highlight that at the heart of it the only way this works if you have a culture that believes in and supports your team to make their own choices, offers them space to contribute, to do meaningful work.

Remote work will ultimately only work if Trust is present. The company must trust team members, the team members must trust themselves. Once that is present then responsibility and accountability can happen fluidly, including the remote worker creating structure and accountability for themselves more easily as they know that the work they do has impact and meaning.

It Doesn’t Have to Be Crazy at Work (2018)

Their most recent books hit hard at the culture of “busyness” and “do more” in the world of work. As we’ve had more and more technology at our fingertips, it seems that instead of this meaning we can work fewer hours while being more productive, instead so many businesses create a culture where their people have to work even longer hours.

At to this the hold that constant emailing and other messaging platforms have on us, plus meetings after meetings after meetings, it is simply crazy at work.

It just doesn’t have to be that way.

WorkAnywhere can mean you can add more value for yourself and your clients/employer in less time with far less “busy work”.

As a collection of three books over eight years, this is a hugely valuable library that David and Jason have generously shared with us all to learn from.

I encourage you to read them all and am sure everyone will take some learnings of great value.

I also hope that my own story and thoughts this (much) longer than usual post are also of some value to you too in making your own potential possible.


Also published on Medium.