5 Takeaways on Technology, Law, Life and Hustling for Business

Pooja Sinha
10 min readJan 4, 2022

From a Singapore-based Lawyer’s Spanish Countryside Getaway

I write this while sipping coffee at a small town called Toledo in Spain- a wonderful find that is a UNESCO World Heritage site just 80-odd km from Madrid [More info is here]. I came here on a solo break — a combination of the need to rest and recover after an extremely busy work year and experience some fresh, crisp winter, countryside air which is far removed from the efficient but rather urban confines of the country that I inhabit: Singapore.

This is the splendid majesty of Toledo:

View of Toledo from a Panorama Point: Mirador Del Valle

Takeaway 1: Checking Your Privilege Never Grows Old

This trip was initially booked as a response to the Vaccinated Travel Lane (VTL) that first opened between Singapore and Germany. In its original form, it had included a reunion with old and dear friends in Frankfurt before a solo escape in the German countryside. Alas, amidst a fresh outbreak of COVID in November, it was not to be and after endless research (and accompanying stress!) around old and new travel restriction fine print [which incidentally, made even MY legally-trained brain hurt] following on from the OMICRON variant, I finally homed in on countryside Spain as a destination.

Fine print for entering Germany — and that too only for transit!

But this made me conscious (once again) of the privilege that I enjoy in its many different forms — which allowed me to execute such a last-minute change of plans at short notice. It also wasn’t lost on me that being able to afford a cross-continental holiday was a gigantic privilege in itself.

My other takeaway from my trip (and indeed 2021 on the whole) is that apart from everything else, it is luck that is also a privilege — in the context of my trip, to successfully execute a cross-continental trip and remain both quarantine-free AND COVID-free in a world of ever-changing travel restrictions.

Of course I did what I could to skew the odds in my favour: I arrived in Europe with a significant range of “COVID-avoidance arsenal” including mildly obsessive sanitization practices leveraging off this trusty little bottle that hung off my backpack for the duration of my trip..

This little sanitizer went to the market: and then flew off the shelf and landed in Spain!

…and incidentally attracted quite a few stares-Hand sanitisation does not appear to have caught on in countryside Europe other than when you’re entering a store!].

But fact of the matter is that having a “successful” trip was very much a game of chance and only partially a game of [protocol-following] skill…….I am slowly coming to accept that a lot of the thinking and planning that we do is just about giving us the illusory feeling of “control” over our universe. [Case in point: In 2021, the person in my household who had the least exposure to the outside world was the one who got COVID].

So.. my conclusion from 2021 is that Lady Luck is the only winner of the 2021 Roulette and she sure works in her very mysterious ways. And therefore, as I pondered over what direction to take my law practice, my broader takeaway was simply this: Don’t Overthink It!

Takeaway 2: “Remoteness” in a Work Context can have Many Different Hues.

The Great Resignation as it is called is well underway [In case you’ve been living under a rock, you can read more here]. In essence, it is all about professionals quitting their “traditional” jobs to pursue careers that are more closely aligned with their interests and passions.

Increasingly (including through the feedback of many of my friends who are struggling with well-paid but uninspiring and/or “energy-draining” jobs, often with toxic work cultures thrown in ], I have come to agree that this alignment is a but natural and (for most) inevitable extension of our own personal growth as individuals. Feeling mentally “remote” from work is just not a sustainable state of being.

[A side note: Thankfully, I reached my epiphany five years ago. It was not work that was wearing me down but the eco-system that goes with it and being a free bird (in my cause running my own law practice since 2017- under the regulatory umbrella of different law firms) has literally and metaphorically unclipped my wings. “Life” and “Work” have finally morphed into an indistinguishable rhythm that leaves me both content and inspired every single day -both from the people that I meet and from the fascinatingly bespoke situations that I get to advise my clients on.]

However, that brings me to the other facet of remoteness in a work context- Remote Working. And the attendant publicity given to nomadic living in exotic destinations as one of the highlights of working for oneself. I mean who wouldn't want their work desk to be ensconced in the likes of this beautiful building..

One of the many beautiful buildings of Toledo

However, it is important to be aware that like everything in life, “working for oneself” too comes with its “baggage” of the good and the bad and I was reminded of this during my break.

If you’re a lawyer like me who still prefer a very traditional work desk set-up, there is the literal baggage of carting along an external keyboard and mouse while holidaying in far-flung destinations [A portable monitor to follow on the next trip so I can “double screen”- yep, true story!] and scouring hotel reviews to determine the strength of their wi-fi signals [I was lucky to get a wonderful blend of the old and new at this wonderful royal-residence-converted-to-a-Marriott Bonvoy-hotel property. Here is a quick peek of their fantastic bar area:

The wonderful Eugenia De Montijo hotel, Toledo: Got a great deal on booking. com! [No sponsorship monies were transmitted in the writing of this caption!]

More big-picture, it meant forgoing European nightlife (luckily not a biggie in a small town) so I could wake up early and deal with the demands of the Asia business day. I got a lot of sympathy for this from friends, families and even grateful clients (bless their souls) but truth be told, this is what you sign up for when you have your own practice.

However, where in the past, I used to be resentful about carrying work “on holiday”, on this trip, I was reminded of how different it is when you’re effectively working for yourself AND you enjoy what you do. i.e. Pardon the pun but I find myself rather happily resigned to my fate in this regard!

Takeaway 3: Hustling for Business sometimes Needs a Fresh Perspective

For those who have read my previous piece (available here), you will know that the topic of hustling really interests me. In part, it is because it is such a big part of my life as a lawyer running her own practice — but also because it is fascinating in itself, being such an intriguing combination of an art and a science.

[A side note: While on the topic of hustling, one of my guilty secrets from my trip is enjoying the American show “Selling Sunset” (Available here: okay, the last season led too much personal drama but is otherwise a masterclass in hustling in a tough market. Hats off to those go-getting, badass, self-made ladies!).]

The new hustling in the pandemic era is a mix of the old and the new. Advertizing things as “disinfected” is the new hustling as is “COVID-compliant” cleaning practices and branding around “keeping you safe”. I think the jury is out there on whether the services actually deliver what they say on the tin (particularly given the many unknowns of the virus) but my larger takeaway was that hustling for business is all about adapting to changing times.

Rural Spain has its own brand of hustling — which is generally not to hustle or over-sell at all. Given my rather “off-peak” working hours, I was often searching for food during what turned out to be Spanish Siesta hours for restaurant kitchens but I struggled to find restaurants that were willing to be flexible with their kitchen-opening hours [The ONE exception was the one below which I only stumbled onto on my last day].

Keep the marketing simple!

Their “Take It or Leave It” approach was their version of “bring your authentic self to work” in the (tapas) flesh.

It was a good reminder to me (and indeed us all) that we need to be firm and set our own boundaries and not get too caught up in the hustling — Bending over backward to adapt to client demands all the time (“some of the time” is, of course, an inescapable part of life as a transactional lawyer) can come at a huge cost to our mental and physical health.

When you order a “double” and get TWO coffees explained away as a miscommunication .. [Did I just get hustled?!]

Takeaway 4: Harnessing the Power of Technology is Both Easier and Harder Than it Appears

I find myself having a new, unique window into the world of tech-enabled services courtesy the range of clientele that I have in this industry. I’ve been extraordinarily privileged to observe my clients (and indeed an increasing number of my friends who are becoming entrepreneurs) harness the power of technology on a commercial scale in many different ways (a key theme being disintermediation): from successful traders in the crypto-economy (by definition, a disintermediated economy) to companies looking to marry brand engagement with social media in a more ethical way than current platforms to new tech-enabled platforms changing both the content and the delivery of traditional financial services including through a form of what I would describe as crowd-sourcing (Of course, some particular legal nuances apply to the last one, as I have previously covered here).

[A side note: IMHO , crowdsourcing for information via digital platforms is the greatest thing since sliced bread- even in its simplest form of an information-sharing tool. As an example, for my trip, information on pandemic rules and regulations from “official government sources” only got me so far- My most reliable source of timely and “on-the-ground” feedback was fellow travelers provided through a Facebook group set up precisely for this purpose.]

Surrounded as I am by all this technology-related inspiration, I took my holiday as an opportunity to reflect upon how I could better harness technology in my own practice- to serve my clients better AND to free up more of my time.

Within the legal services industry, digitization is now a well-trodden path with a range of solutions available -from automated production of documents to AI-based document reviews. But the sheer range of technology use cases that I have now come across has had the opposite effect of leaving me somewhat overwhelmed in terms of choosing which exact path to follow for expanding my own practice.

But what became clear to me is that in 2022: It is a path that I MUST fully explore, no matter which destination it takes me to.

Takeaway 5: The Greatest Battle Will Always Be the One Within

We all know about mindfulness. Staying in the present and also conquering your demons.

Sometimes, it takes a while to understand what those demons even are.

The extent of COVID paranoia and travel-related stress that I was carrying in my head was brought home to me when I walked into a chemist and asked for something as simple as a strip of STREPSIL to soothe a throat that was somewhat irritated after a long flight amidst the newly unfamiliar confines of a pressurized air cabin for 10+ hours.

This innocuous packet was a key “bad actor” in the drama that unfolded in my head

The very sweet lady behind the counter asked me if I had a dry cough — to which I responded yes- As the word left my mouth, my heart sank at the (supposed) enormity of what I had done. I had a sudden vision of her pressing a secret button below her desk to call Spanish quarantine police to take me away for COVID testing.

Of course, she was just being solicitous. But my larger takeaway is that it is only by having time “away from it all” that you really understand what is going on inside your head and take the first steps to conquer it.

It is therefore not surprising that the trip also helped me to clear some of my own mental cobwebs in a professional context- which is to lay aside my reservations and make a decision to seriously look into harnessing the power of technology in my law practice.

Watch this space for more updates- COMING SOON!



Pooja Sinha

A global deal lawyer running her practice from Singapore. Recently caught the lockdown writing bug. LinkedIn: https://sg.linkedin.com/in/pooja-sinha-singapore.