The Singapore Law Gazette

On Work: Too Much, Too Little, and Whether It Even Matters

Editor’s note: this is the first of a bimonthly column, in which our author will explore what it means to practice well.

Perhaps you’re a young, or young-at-heart, practitioner, and you’ve been in practice for a while. But you’ve got problems.¹I mean, who doesn’t? Maybe just a few. Maybe many! And you’re getting by, but it’s not easy.

And you wonder: how do other practitioners get through these things? You’re curious, but at the same time you’re probably sick and tired of old codgers’ rambling war stories from a bygone era.

Let’s try something different. In this piece, I will share: (a) some common difficulties faced by not-so-senior practitioners; (b) why these difficulties arise; and (c) practical tips to address these difficulties.

Before we begin proper, a caveat. I recognise that not-so-senior practitioners are only part of the ecosystem, and that bosses and systems are a large part of why these difficulties occur in the first place.²I have explored this in a series since the beginning of the year – 19 LinkedIn posts and counting. I am not suggesting that these difficulties are solely for not-so-senior practitioners to fix. What I suggest, however, is that there are some practical actions that are within the control of not-so-senior practitioners, and which are likely to shift the needle even if they are not magic bullets.

“There is too much work, and too little time to do it!”

The difficulty

You’ve got a to-do list a mile long. For every item you clear from the list, your boss adds two new items. Each task takes longer than you expect. You’re working late nights and weekends. And just as you feel you’re making some progress in clearing the backlog, your boss suddenly puts you on an urgent matter that requires you to drop everything to resolve a crisis, and even as you’re hyper-focused on solving that problem you can’t help but notice that your boss is still sending out multiple conflict checks, and when you finally resurface for air you find that your backlog has ballooned even further.

And when you go to your boss, your boss sighs, looks pained, and mumbles something about this being a “happy problem”. Happy for them, maybe! Not for you.

Why it arises

This happens because, ironically, your boss is good at an important aspect of practice: bringing in the work. And make no mistake – this is absolutely crucial for any profitable practice, and you do want to be part of a profitable practice.³Your salary, CPF contributions, and bonus do have to come from somewhere.

The problem comes, however, when your boss takes on new work without a proper appreciation of, for example, (a) team capacity (how much time and energy the team has to actually execute); (b) team capability (unfamiliar tasks will take longer and require more energy); or (c) the actual size of the task (where your boss says yes to a 20-hour job thinking that it will take 10 hours, tops, to complete the task). While it’s not easy to bring in the work, it’s sometimes just as difficult (if not more difficult) to get it done well.

Practical tips

If you simply march into your boss’s office and demand that they take on less work, that probably won’t go down well. The reality is that work must be done before invoices can be issued and payment received, and cash flow is the lifeblood of any business.⁴And don’t forget that law firms are businesses.

Instead, think about how you can frame the conversation in a manner that acknowledges your boss’s interests. For example:

“You know that advice that we just delivered? Well, the fee indication you gave to the client suggests you expected that I would spend 10 hours on it, and that you would spend two hours on it. But in the end, I spent 20 hours on it. Can we discuss what I could have done better? Was I more inefficient than you anticipated? Or was the job bigger than you thought it would be? By charging what we did, did we end up leaving money on the table? And in future, do you think it would be helpful for me to give my input at the fee indication stage?”

Notice that the focus is on how you can do better, and how your boss can benefit from having this conversation (e.g. by helping you to be more efficient, or by being able to bill more). Is it fair that you have to frame things from this angle, instead of focusing on your own needs and difficulties? Maybe, maybe not. But is this approach more likely to incentivise your boss to work on the situation? Undoubtedly.

To give another example:

“You know how we’re handling a number of probate matters now? Don’t get me wrong, I appreciate that they help to pay the bills and I know that they don’t require as much work as the three High Court suits that we’re handling. But I do find that it takes quite a bit of time to cross-compare all the details in the cause papers against the documents that clients provide us with, because I know you’re counting on me to get this right. I wonder if my time and headspace are better spent on the High Court matters – for example, do you remember that interlocutory matter where neither of us realised that the other side was planning to run that particular argument until they filed their submissions, and we had to scramble to research the point? Do you think, for example, that one of our teammates should start to specialise in probate matters? Or do you think it might make sense to refer probate matters to our colleagues who handle them day in, day out? I’m not trying to push away work – I’m just trying to see how we as a team can deliver a better overall product.”

In other words, don’t just whinge to your boss about being overworked. Frame the workload as a team issue to be addressed collectively, and not a “you” issue. And come equipped with potential solutions that practically take into account your boss’s needs.

I end with a caveat. You may be in a team where a heavy workload is a feature, not a bug, and the rewards are commensurate. Or maybe your boss doesn’t care, sees juniors as mere economic units to be exploited for maximum profit, and is too set in their ways to change. In either case, if you find that the objectively heavy workload is subjectively too much for you, and the rewards are disproportionate to the price you are paying, you will have to seriously consider whether this is the right team for you.

“There is too little work!”

The difficulty

You have a billing target, and you’re struggling to hit it. You have some matters, but they aren’t very intense, and don’t require that much work. By the middle of each day, you find that you have nothing else on your to-do list.

Initially, it feels great! You finally have the chance to clear some leave, read some of the new decisions published on the SG Courts website, catch up on the latest regulatory developments in your specific area of law, maybe even hit some folks up for coffee. But then this lull period continues, and it starts to feel less like a holiday and more like purgatory.

And more importantly, you’re smart and you know that there’s no free lunch. You know that this is going to lead to difficult conversations during your mid-year and year-end reviews, where you have to scramble to justify what you bring to the table. You know that whatever other value you bring to your firm – mentoring juniors, maintaining precedents, radiating sunshine and joy – is secondary to your primary responsibility as a revenue generator. You’re concerned that at some point, your boss is going to look at you and wonder why you’re being kept on the payroll.

Finally, it’s not just a financial matter. You recognise that in order to get good, you need the exposure, you need to roll up your sleeves and put in the elbow grease, and you need to learn by doing and not just by watching. You don’t gain skills and experience by merely marking time or having enough tasks occupy your day: you need to be challenged, to stretch yourself, and to make mistakes and learn from them. But you’re not getting such opportunities despite indicating your willingness and availability. And you know that if things continue this way, one day, the chickens will come home to roost. You don’t want to be a 10^th-yearer who has never led a trial or a transaction (at least a small one), and who is the functional equivalent of a 5^th-yearer.⁵Harsh, I know. But probably not a completely unfair observation if you’ve spent the last 5 years repeating the same things you did in the first half of your career.

Why it arises

This situation can happen for various reasons. Perhaps you are fairly senior, and your hourly rate has correspondingly increased over the years, to the point that your boss is reluctant to staff you on matters that can be handled just as well by a more junior (and cheaper) colleague. Perhaps this is your boss’s way of telling you that you need to get out there and find your own work, instead of being solely dependent on them. Perhaps business is just bad.⁶Unfortunately, there are some areas of practice that are sunset industries, have been heavily commoditised, or have had profitability severely affected by a race to the bottom. Or perhaps your boss wants you to leave, but they are emotionally stunted and unwilling to broach a difficult conversation with you.

Practical tips

This is a difficult situation because the solution is often dependent on factors outside of your control.

My suggestion is to grasp the nettle and have an open and candid conversation with your boss about the situation. Perhaps something along the following lines:

“Thanks for setting aside this time to speak about this thing that’s been bothering me for a while. I know my numbers haven’t been great and it’s starting to weigh on me because I don’t want to be a passenger in this team; I want to carry my fair share. But I feel that I haven’t really been getting that much work from you. So I hope I don’t come across as too forward but I thought I should speak with you and understand the situation more. Is the team just going through a dry spell which you don’t expect to last forever? Am I getting too expensive for your matters? Is it because you expect me, at my seniority, to start finding my own work out there? Or is it something else? I’d like to know so that I can better support you and the team.”

Again, notice how the issue is being framed – not from the perspective of what you want and need, but rather, from the perspective of a team leader who needs to get the most out of their people. Sure, this may rankle a little. You may even think that you have a divine right to be doing the kind of work you like to be doing.⁷After all, you are brilliant and graduated from law school. Never mind that others did so as well – objectively, you deserve it. But I guarantee you that focusing the conversation on your boss’s needs is a far more effective way of getting answers and pushing for change. And if this is what it takes to get the answers you need, then needs must.

And of course, when broaching this topic, do have a think about the timing. On a Friday at 5:00 PM when your boss already has one foot out the door? The day before a big filing or a transaction closing? The afternoon after a gruelling morning session in Court? Maybe not. If you want your boss to take the conversation seriously, be at their best, and have the psychological safety to tackle difficult topics, then do what you can to ensure a conducive environment.⁸Believe it or not, bosses are also human. And yes, you can’t control whether they are in a bad mood because they just had an argument with their spouse or got into a fender bender. But you control what you can.

But sometimes, your boss simply does not have the answer or a solution to this problem, or does not see it as a problem they need to solve. Maybe they are just a few years from retirement and are starting to check out mentally. Maybe they are trying their best to find the work but they find it impossible in this business climate. Maybe they think that you screwed up a big matter some time back, the trust is irretrievably broken, and they simply cannot bring themselves to rely on you anymore. Perhaps you think your boss is wrong, weak, or not trying hard enough. You might even be right! But you being right brings you no closer to a solution.

If you do not see your boss as being able to proffer or be part of a solution, then the only logical move is to get out. Maybe it is time to move to another team or firm, roll the dice and strike out on your own, or even try moving in-house or into the public service. You decide. But the point is to do something, rather than stay put and hope that things get better. They might! But I wouldn’t bet on it. And please don’t think for one second that such a pivot reflects weakness or is a cop-out: when you hit a roadblock, a detour is often more logical than trying to bash through the obstacle.

Finally, the longer you stay in practice, and the more you intend to stay in practice, the more important it is to build your own book of business. I will go out on a limb to suggest that this is one of the few long-term solutions to the problem of having too little work, and that you cannot rely on your boss forever.⁹After all, they will probably retire some day. And even if they never formally retire, they will likely start to slow down at some stage. So it is unlikely that your boss can always be the solution to this problem – unless, perhaps, you are an adherent to the FIRE movement and plan to retire at the same time as your boss. And as for how to build a book of business, that’s a topic for another day.

“I’m not sure what I’m doing.”

The difficulty

Perhaps you’re in a situation where you’re being kept sufficiently busy with work, and the days are occupied, but you’re just… not feeling it? You don’t really have a sense of purpose, and are just going through the motions. Sure, you’re not completely checked out because you don’t want to screw up the work, but you’re just doing what needs to be done, because you have to do it, and not necessarily because you want to do it. You’re not barely surviving, but you’re not thriving either. You’re just… there.

Let’s call this the ennui problem.

And when you speak with some of your peers, it seems like everyone else has bigger problems. Maybe they are overworked and are on the verge of burning out. Maybe they do not have enough work and are seriously concerned about being asked to leave. Maybe they have problems outside of work – interpersonal problems, family issues, financial woes. So your discomfort seems to pale in comparison. You wonder if you’re making a mountain out of a molehill. Perhaps feeling this way is just part of the human condition and you should just suck it up.

And yet the feeling persists, is all-pervasive, and is a constant weight at the back of your mind.

Why it arises

I wish I knew for sure. I only dare hazard some guesses.

First, I suspect we are more susceptible to such thoughts when we struggle to see meaning in what we are doing. Take, for example, two different lawyers who both do transactional work. One of them is genuinely excited about the work – even though there are tedious and challenging moments – because they love seeing a plan come together, they find satisfaction in completing a difficult task, and they enjoy working their brains to come up with solutions. For them, the game is the point, and brings fulfilment.

On the other hand, the other lawyer might feel that the transactions are just the process by which the rich get richer, may struggle to see how the completion of these transactions makes a meaningful impact in the life of a fellow human being, and may see the process as just ticking off boxes mechanically towards an arbitrary goal. Both lawyers have every prerogative to hold wildly different subjective views about the same subject matter, but the latter is more likely to face the ennui problem.

Second, and this is a related point, we may find ourselves in this situation if, for too long, we have been chasing Key Performance Indicators set by someone else – society, our families, our friends, our peers, and the list goes on – without first stopping to think whether we even agree that these are our personal indicia for a life well lived. Perhaps we have been seeking validation in the form of prestigious roles, pay bumps, or opportunities to work on high-stakes matters, not necessarily because we want them, but because everyone around us seems to want them. Perhaps we are scared that there is nothing else that we can do relatively well, that we will be caught out as pretenders if we try our hand at something new but do not succeed wildly. And so we go with the flow, only to wake up one day to find that we’ve found ourselves at a destination that we were never really seeking in the first place.

The ennui problem is the outcome of the dissonance between what we are actually doing now, and what we think we should be doing (even if we haven’t quite figured out yet what that is).

Practical tips

There is no shortcut: we need to do the inner work.¹⁰Speaking from personal experience.

We need to dig deep and ask ourselves the difficult questions: who are we? What is important to us? Why do we do what we do? How do we want to live our lives? What are our values? Who are we, really?

We may want to seek some professional help,¹¹And in this day and age, there’s absolutely no shame in that. deliberately form peer support groups, or seek mentoring. There may be other options available. Some may work for you; some may not. What I suggest, however, is that wallowing and hoping that the ennui problem simply goes away on its own is a gamble, and not a strategy. Feelings are part of you and me, but we are more than just our feelings.

We will also need to be prepared for the process to be an uncomfortable one. We may be forced to admit that we’ve been headed in a suboptimal direction for a while now. We may have no choice but to ask ourselves whether we have been making poor decisions, and if so, whether this means that we’re not as wise, intelligent, or street-smart as we thought we were. We may feel that we are undermining our own sense of self-worth. We may not even like the person that we find that we are, as opposed to the person that we thought that we were. At some point, the discomfort may cause us to question why we even decided to go down this rabbit hole in the first place.

And since these questions that go to the core of our being tend to rise unbidden at the most inconvenient times,¹²Such as, say, at 3am the night before a filing deadline and you’re footnoting a 200-page set of written submissions. all the more there is value in grappling with them more consistently, to train that muscle regularly, so that we can better sit with that discomfort without triggering a fight-or-flight response.

Managing that discomfort is unavoidable because pain is a necessary part of the process. Introspection is not easy. And change – which requires us to act on the introspection – is even more painful. But it is the pain that tells us we are trying something new, that we are moving out of our comfort zone, that we are wrestling with uncomfortable concepts that our minds are recoiling from due to unfamiliarity. And it is the pain that tells us that we are breaking the cycle, instead of just defaulting to whatever it is we have been doing all along.

Look, I’m not a shrink, and I’m woefully inadequate to expound on the workings of the human mind. I will however stick my neck out to suggest that the unexamined life is not worth living.¹³If that was good enough for Socrates, it’s good enough for me.

Conclusion

This has been a heavier piece than I expected, and I certainly do not claim to have all the answers.

However, if you have encountered any of the difficulties I have identified, know that you are not alone, your feelings are valid, and you have the agency to change things.

I wish you the very best as we continue on the journey of practice.