What Is a Weekend? The Freelancer`s Dilemma.

Sunny Morning in Tokyo
Sunny morning in Mizumoto Park, Tokyo – May 2020.

“What is a weekend?” – the best line from the British TV Show Downton Abbey, which started as one of the greatest shows to satisfy our escapism needs but went on a little too long. While the ever-wonderful Dowager Countess`s statement (portrayed by Maggie Smith) aimed to underline her lack of awareness (am I being too nice?) about the “working class”, an extended phase of working from home made me deeply relate to this iconic statement, but obviously for very different reasons.1

During the six years between quitting my full-time lawyering job at a law firm in 2017 and starting a new full-time job in Tokyo in 2023, I had worked from home (or from wherever place I was traveling to at the time) on a contract and freelance basis. I committed to monthly hours rather than full days, a set-up that allowed me the flexibility to organize my own schedule (read it as travels) and days. That was wonderful and definitely what I needed after an intense 12 years at a law firm.

But as any freelancer or work-from-homer may likely relate to, adapting to a completely different rhythm after being used to the structure provided by an office environment proved to be difficult. The lines between work and personal time got too blurred, strangely even more than in a law firm setting where the boundary is almost intellectually impossible to maintain. No one hires a lawyer for pleasant circumstances. Even in transactional work where parties aim to sell something to each other (often themselves, aka M&A) or build something together (aka Project Finance, Real Estate Development, etc.), your job is to focus on the potential rupture of the relationship in the future and make sure that your client is the one who comes out on top – so the distrust, stress of future failure (what if you missed something that could make things difficult for your client in immediate and often cases distant future) is in the fabric of the profession, something that you carry back home with you every night, and also to every vacation. At least, I did.

The lingering guilt

But working from home and still doing legal work, but in a much less stressful and consequential context, blurred the lines for me in a very different way. I lost the – admittedly often very short-lived – feeling of closure that one could experience after months of work and closing a project or reaching a certain milestone. I often felt like even when I was working, I was not “really” working (where was all the pain, all the stress, and the drama?). As a result, I felt like I did not deserve time off in the pure sense of the word. 

Things got even stranger when I started a second freelance job working with travel content companies based in Japan. I started taking assignments to travel to various parts of Japan to take photos and write articles for regional tourism promotion offices. A dream job? To some extent yes, even though it can also be challenging (I wrote more about this here – Why Do We Travel?). You can probably imagine how that kind of job made me feel in terms of not deserving real time off. After all, I was “definitely” not working but just traveling.

I lost the concept of full working days and doing “actual work” and then being rewarded with two full days off (or longer). I missed the Friday night bliss and the joy of a Saturday morning, which came with two days of endless possibilities (even if none of those came to life and one spent the entire weekend on a couch worrying about the week ahead).

The lack of separation between office space and home (my Tokyo apartment is 37m2) also heavily contributed to the blurred line between work and personal time – not being fully present in either world, a little bit like a purgatory if one existed between the office hours and the personal time.

I tried to implement various structures to imitate a more regular work life to be able to enjoy my actual days off without that nagging guilt. Not sure if any of those worked, probably not. And I sure thought of Dowager Countess many times, after all, “What was a weekend?”. 

Hello weekend, my old friend

In 2023, after six years including two full years of pandemic-life in a city, which was new to me, I had an opportunity to start a full-time in Tokyo working with people whom I already knew, and in a field that very closely relates to my job experience as a lawyer. And I took it, happily. It is not a lawyering job (and comes with a perfectly bearable level of stress, if any) but a job where a two-day “guilt-free” weekend is ensured, often 100 %. And how I love being able to have time off and not feeling guilty about it.

Now, instead of wasting my non-working hours by thinking that I should actually be working, I enjoy every single minute of my weekend. I have been living in Tokyo for more than three years but discovered so little of it. Of course, there was the pandemic, but even before and after that, I never gave Tokyo a real chance. Tokyo was home and home was a place to work in and/or feel guilty for all the work (never knew what it was) that I could be doing but was not doing.

By the Edo River in Tokyo.

My days in Tokyo were previously allocated to recovering after travel “work trips” and admittedly many solo pure pleasure trips (where I could set aside the guilt for a short few days), going to school once a week, working from home for my remote job but more importantly staying at home and feeling guilty for all the work that I was not doing. Not anymore.

Now that I cannot travel for “travel assignments” (as those require weekday travels), I still travel outside of Tokyo many weekends for pleasure trips. Sometimes I re-visit the places that I went for writing assignments and make up for those trips when I did not have the opportunity to enjoy the town/destination on my own. But I also spend, very happily, many weekends in Tokyo and enjoy one of the biggest yet still friendliest metropoles in the world. 

Jimbocho - Tokyo
Bistrot Aligot, one of my favorite eateries in Jimbocho, Tokyo.

For those weekends that I know that I will be in Tokyo, I purchase museum/movie tickets in advance to make sure that I step outside of the home. And once I am out, I make sure that I spend the better of the day out, exploring the city on foot. And when I am at home (like on this rainy Sunday), I feel no guilt about sitting on the couch, writing this post while the Crown on Netflix re-plays in the background for likely the 10th time.

David Hockney exhibition in Tokyo, November 2023

Do not get me wrong, I am endlessly grateful for the opportunities that life granted me – being able to switch to a fully flexible work schedule at age 37, my family supporting my need to step back from a full-time law firm job, being able to downsize my life without anyone else requiring to do the same thing with me (as I live alone), and, more importantly, having a job to begin with, which was financially fulfilling enough and allowing me to make such a leap at age 37 (and still providing me with the opportunity to work in a much reduced capacity and remotely – though not sure if anyone (from work, family or friends) assumed that I would take the concept of “remoteness” so seriously and move to Japan).

Nihombashi Station in Tokyo, where my daily commute takes me every day. Photo taken in March 2020.

I quit my full-time job to be able to travel more freely and for more extended periods and that has been wonderful. But at this stage in my life (and I am sure it will change again and that is okay and the current phase also has a lot to do with the loneliness brought on by the pandemic), I also feel grateful for a daily routine (I even appreciate the commute), the separation between working and non-working hours , and more importantly for knowing “what a weekend is”.

This is one of the Sunday posts that I post on Substack (app only, no separate e-mail). These are weekly posts that I post on Sundays, in addition to monthly “Letters from Japan” that are published both on Substack and also email separately. If you would like to subscribe: