When good habits go bad


You’ve got a morning routine to start your day and another for shutting down in the evening. A routine for opening new files and a routine for closing them. A routine for interviewing new clients, writing articles, and posting on social. 

You do them the same way every day, and those routines serve you well. They save you time because you don’t have to think about what to do or how to do it.  

You just do it. 

And because you do it over and over again, you get better at it. 

But the strength of your routines and habits is also their weakness. 

When we do things repeatedly, without thinking, we typically don’t look for ways to improve what we’re doing. If what we’re doing is working, why should we? 

We should because the world changes. There are new tools and processes that can help us do things faster or better. 

And because we change—we’re not the same person we were when we started the routine or acquired the habit. 

Which is why we should periodically review our habits and routines and look for ways to improve them. 

I did that recently when I started my day re-writing my digital task list on paper, in order to be more mindful about what I was doing. I only did it for a few days before realizing I didn’t like it or need it, but I learned something about what I was putting on my list and changed it. 

I realized I was trying to fill my day with too many tasks and was often left scrambling to finish them or disappointed that I hadn’t. I put fewer tasks on my list now and have more time and energy to do important things. 

I may not have realized what I was doing had I not experimented with re-writing my list. 

I regularly try different apps, tools, and websites. I get lots of ideas that way. Sometimes, I find a better tool than the one I’ve been using and replace it.

Trying new things can also be fun. We are curious creatures and enjoy novelty. It makes the world a more interesting place. 

Yes, trying new things can also be a distraction from doing our work. But who says all distractions are bad?


You need all 3


You’ve got a new case, project, business, or idea and you want it to be successful.

You create a plan—what you want to accomplish, the resources you’ll need, research to do, the first step and the steps after that. Your plan might be a simple list of tasks or ideas, but but the process of thinking it through and writing it down helps you clarify what you want and what you need to do to get it.

“Doing” is obviously the most important part. The actions you take and how well you do them are the mechanism that delivers your results.

Most of us do the first two well enough. We plan and we do. Where most people drop the ball, myself included, is with what we do after that.

Once we have some results, we need to review what happened.

Reviewing means:

  • Noting the size and scope of the outcome. How many leads or subscribers, how many new clients, how much revenue? Did you hit the goal? Make a profit? Get what you expected?
  • Thinking about the process. What did you do well, what could you have done better, what will you change?
  • (Optional): Getting feedback from others. Talk to your client, staff, partners, and other stakeholders. What do they think about the process and the results? What suggestions do they have for the future?
  • Using what you’ve learned to create a better plan or decide to kill the idea and try something else.

The review process might only take a few minutes, but it’s key to achieving sustained growth.

Plan, do, review. You need all 3.


Pen and paper


I’m trying an experiment today. I’m taking my task list and calendar entries, which ordinarily reside in digital form, and rewriting them on a single piece of paper.

I’m going to keep that page in front of me throughout the day and when I complete something, important task or routine, that’s where I’ll check it off.

I’m not doing this to achieve an esthetic look. Nothing fancy. Just scratch paper and the first pen I grab.

I’m doing this to see how it affects my planning and execution.

By rewriting my list, my theory goes, I’ll be more likely to think about each task and ask myself questions such as, “Do I really want to do this today? Is it necessary that I do this at all? Is it aligned with my current goals? Is there anything I need to do first? Do I have all the resources I need to do a good job with this?“

The idea here is to be more thoughtful and intentional about what I do, and to consider things I should do but aren’t. It’s too easy to do things out of habit, which may not be the highest and best use of our time.

I’m also thinking that having everyone on one page that I look at throughout the day will help me focus and get everything done. That’s how we did things in the pre-digital age. We didn’t have to open an app to see what was next, just look at our calendar or the legal pad on our desk.

At the top of the page, I wrote “Today” and the date. Then I wrote “P1“ and listed my “must do’s” for today. There are two—this post and working on my latest book.

Under that, I wrote “P2”. These are other things I’d like to do but don’t have to do today. I listed some things I want to research and a phone call.

Finally, I wrote 4 routine tasks, the kinds of things I do pretty much every day.

No appointments or errands today, so that’s it.

As soon as I post this on my blog and send it out via email, I’ll check off the first “Must do” task on my list for today.

Tomorrow, I’ll write a new list and we’ll see how this goes.


Just make sure you copy the right cat


“Don’t be a copycat,” our parents told us. But we didn’t listen, did we? We copied our friends, our siblings, our parents and teachers, and people we saw on TV.

If someone did something we thought was cool, we wanted to do it. If they didn’t die riding their bike down that steep hill that scared the beans out of us, we knew we wouldn’t die either.

I’m still here, aren’t I?

We wanted to be like others. Do what they do. So we copied them.

And we still do that today.

There’s nothing wrong with that. We learn by copying. Seeing what others do, how they do it, and how it turns out.

I did it again the other day.

I watched a video about GTD and the narrator said he does his daily planning every afternoon at 4 pm. He has a ten-minute appointment with himself posted on his calendar. I’ve always done my planning at the end of my workday, whenever that might occur, but hearing how this guy does it, I had to try it.

So now, don’t try to contact me at 4 pm. I’m busy.

He mentioned something else I liked. He schedules his weekly review on Fridays at 3 pm.

Why not, I thought?

I’ve been experimenting with different days for my weekly review. For a long time, it was every Sunday morning. I recently tried Saturday, but something about doing it Friday to close out the week (and keep my weekends open) appealed to me, so I’m doing that now.

It’s okay to be a copycat. But don’t copy blindly. Do what makes sense to you and for you.

If you hear about a lawyer who built his practice by sending unsolicited email and cold calling 12 hours a day, that’s one cat I wouldn’t copy.


How long will it take to do it?


“How long will it take to complete that project?“ I hate that question because I never know the answer. I estimate one hour and it takes three. I think I can get it done in a week and two months later I’m still working on it.

Turns out, humans aren’t good at estimating how long it takes to finish things. So I usually avoid estimating. I tell myself it will take as long as it takes and don’t think about it.

Unless there is a deadline. And then I think about it a lot and get the thing done, usually on time, thank you.

If I’m forced to estimate, and it’s not something I’ve done many times before, I usually pick a figure and then double or triple that number, to give myself extra time. But I’m still usually wrong.

Sometimes, I choose a target completion date and calendar it. But I usually ignore that date because I know it’s an artificial deadline and there is no penalty if I miss it.

It’s hard being me.

It’s better for me to schedule a “start date” and/or dates to work on the project. Short deadlines, even of my own making, work better for me. They allow me to make progress without worrying about missing a day because there’s always tomorrow.

We all have our own ways and means of working and we all seem to get things done. Sometimes because we have to, sometimes because we want to and we keep working at it until it’s done.

Instead of asking, “How long will it take?“ I think a better question is the one asked in GTD: “What’s the next action?“ We may or may not work on the project, but at least we know what to do next if we do.


If you want to be prolific, you have to do this


If you want to be prolific, build more relationships, deliver more presentations, write more books or blog posts or articles, more than anything, there’s one thing you have to do. You have to let go of the need to make things perfect.

Perfectionism has been my “issue” for as long as I can remember. When you’re wrapped up in it, you’re wrapped in a straightjacket of your own making and artificially limit your accomplishments.

More content, more relationships, more good habits, usually lead to more good things happening in your life. Even if the things you create aren’t perfect, but merely good.

Remind yourself that you don’t have time for perfect. You have deadlines and goals and people who depend on you.

Set a different standard for yourself. Instead of going for 90% allow yourself to do 70%. Because unless you’re performing surgery, 70% is usually good enough.

In fact, remind yourself that “good enough is good enough” — because it has to be if you want to get more done.

If you want to be prolific, develop the habit of launching things before you think they’re ready.

That’s what I do. I want quality, but I’m willing to exchange some of it for quantity.

But here’s the thing. When I re-read something I wrote and thought wasn’t up to snuff, I usually find that it’s a lot better than I thought.

Here’s the other thing. Most people aren’t as critical of your stuff as you are. They either don’t notice or don’t care. (They’re worried about their own stuff.)

Another strategy I use is to push things out the door (before I think they’re ready) telling myself I can fix it later. What I often find is that by the time I’m ready to fix it, it’s not as important to me because I’m busy with something else.

Look, at our funeral, nobody is going to say we led a good life and helped many people but could have done a few more rounds of editing. They’ll look at the big picture, and we should too.


Planning your day


Some people say they don’t need to write a to-do list, they can remember everything they need to do for the day.

Maybe they can. Maybe they have just 3 or 4 things they need to do and they do pretty much the same things every day.

But most people are busier than that.

Can you remember all of the calls you need to return tomorrow? Do you know what your email inbox will bring, which new cases or clients will show up, which issues you will have to deal with?

Every day may be basically the same, but every day is different. And if you don’t write things down, you won’t remember.

The value of a written list, however, isn’t just the list itself. The value is in the process of making the list.

Writing a to-do list forces you to think about your goals and obligations and choose your priorities for the day or week. Thinking and writing leads to clarity and clarity leads to commitment, and what good is a goal or obligation if you’re not committed?

Writing things down also decreases anxiety. You know what you will do that day, and what you won’t do. You know you won’t forget something important, or be overwhelmed with too many boxes to tick.

You’ve already thought things through and you can focus on execution.

When do you make this list? You make it before your day (or week) begins. When the current day is over and you are no longer “executing,” you plan the following day. Give yourself ten minutes each afternoon or evening to review your calendar and your other lists and decide what you want tomorrow to look like.

And write that down.

Now, here’s the million dollar secret to making your list work for you instead of the other way around.

When tomorrow begins and you’re working your way through your list and calls and emails and letters come in, when you remember other things you need to do, don’t do them.

Write them down on the list for tomorrow or later in the week or next week.

You have a list for today. Work on that list today.

If you finish today’s list and you have time, you can look at tomorrow’s list and start working on it. But only if you want to.

It’s your decision. Your list works for you, not the other way around.


Adventures in dictationland


I’m not a dictation-only kind of guy. I enjoy typing and do most of my writing that way. But there’s something liberating about being able to sit down, flap my gums, and have the words appear on the page, and when I dictate, I’m able to crank out a lot of them.

For a long time, I used DragonNaturally Speaking to dictate on my Windows desktop. I recently retired that computer in favor of a new laptop and haven’t installed Dragon. When I want to dictate, I’ve been using Google Voice Typing, which is fast and accurate, at least for me. The only drawback is that you can only use it via the Chrome browser and I use Brave as my default.

A few days ago, I downloaded a free app called LilySpeech (Windows only) and have been trying it out. It uses Google’s servers for transcription and seems to deliver equally impressive results.

The advantage of LilySpeech is that I can use it anywhere on Windows—in any browser or app, including Scrivener, which is something I wasn’t able to do with Dragon. Right now, I’m dictating this into Obsidian, and it works like a charm.

On iOS, Siri dictation works well but times out after 30-40 seconds. I tried Google Docs Voice Typing, both the app and via Safari, and it also times out. But who knows, I may be doing something wrong.

The Drafts app (iOS, Mac, Android) does dictation well. I just tested it on my iPad and it didn’t time out, even after several minutes of continuous speaking. (If you get different results, try launching a new document via the widget instead of the app.)

When I started practicing, I would dictate and record and have a secretary transcribe it. Today, many attorneys record and upload to a transcription service like Rev.com. But unless human transcription is required, I’m a proponent for letting technology do it.

There are many other options for each platform that seem to deliver varying degrees of speed and accuracy. If you’d like something that’s cross-platform and can be used via the web or an app, I recommend giving Otter.ai a try. They have a generous free plan and the paid plan is reasonable.

Otter has a couple of killer features to recommend it. It allows you to transcribe a conversation, identifying each speaker by time stamp. Very handing for interviews and meetings. Otter also adds punctuation (at your option), meaning you don’t have to dictate it.

So, over to you. Do you use dictation? What apps or process do you use on desktop, web, and mobile?

I’m all ears.


When you don’t have time for deep work


Schedule large blocks of time for deep work, we’re told. An hour or 90 minutes a day to work on our most important projects and do things that require focus and concentration.

But our work doesn’t always allow us to schedule large blocks of time. Not consistently, anyway. Our days are often fragmented with appointments and calls and other work that needs to be done as and when it needs to be done.

The good news is that you can get a lot of work done in the spaces between calls and appointments.

Throughout the day, as you go from one task to another, there are many unused chunks of time. We often waste that time, telling ourselves there isn’t enough of it to do something meaningful.

Sure, you need breaks. Time to clear your mind, think, or get another cuppa. But don’t assume you can’t also do something valuable when you only have a few minutes.

You’ve got ten minutes until the next appointment? Make a few calls and leave messages (since most people don’t pick up these days). Write the first draft of an important email, or bang out one or two-word replies to several emails. Highlight key paragraphs in a pdf or organize your notes from a recent meeting.

You’ve got five minutes? How about brainstorming a few ideas for your next article or post, or doing a quick edit of your last one?

In five minutes, you might review a file you haven’t looked at in a while and dictate instructions to your staff. Check your email and clear out the spam. Or skim a few saved articles and decide which ones to read next, when you have another five minutes.

Five minutes here, ten minutes there, and you might get a lot done. Maybe enough to let you block out time for deep work.


Work-work balance?


The world is coming to realize that working too many hours is counterproductive. You can’t do your best work if you’re always exhausted, or win friends and influence people if you’re always grumpy.

We all need time off. Which is why folks are talking about and starting to implement a shorter work-week.

That might be a problem for those who bill by the hour, which is why I stopped doing that years ago and have urged you to do the same. A lawyer’s value is (should be) measured by the value you create for your clients, not the time it takes you to create it. If you can create that value in a four-day week instead of five (or more), why wouldn’t you?

But there’s more to work-life balance than the number of hours worked. Creating balance can also be achieved by changing how you do what you do.

The CEO of Doist, creator of the Todoist app, manages his time a bit differently:

Amir Salihefendic, CEO of Doist, prides himself on having a nearly empty calendar. “Being in meetings all day long, resolving things via meetings, that’s not really an effective way to scale and grow,” he said. Instead, he’s become a loud evangelist over the last year of the idea that remote and asynchronous work — or async — are the future. Async boils down to this, Salihefendic said: “When you send a message, you don’t expect a response right away.”

So what does a truly async day look like? For Salihefendic:

A couple of hours with his kids in the morning before walking over to a co-working space.

He tries to do deep work all morning, take time in the middle of the day to recharge and then spends the afternoon catching up on messages and the rest.

If there’s something hugely time-sensitive — which Salihefendic bets is true less often than you think — he turns to Telegram, or (gasp) a phone call.

Since nobody expects Salihefendic to be around every second, he said, nothing bad happens when he’s not.

Source: https://www.protocol.com/newsletters/protocol-workplace/remote-work-wars?rebelltitem=6#rebelltitem6

A non-traditional approach may work for some (enlightened) corporations, but would it work for lawyers?

Show of hands: Who wants to find out?