Inside My Brain

Thoughts about startups, tech, marketing, and life

CATEGORY: Productivity

The two sides of “checking the box”

Checklists are really valuable. They are an extremely helpful productivity tool that can keep you on track and organized when executing projects.

For instance, when I created episodes for my podcast, I had a Trello card that included 30 checklist items that needed to be completed before launching the episode.  This checklist identified who was responsible for each task and kept me and my producer on the same page. And once all of the boxes are checked off, we can publish the episode for all the world to hear.

Checking these boxes meant that progress was being made and work was getting done.

Trello podcast episode checklist

We had to complete 30 tasks before launching a podcast episode.

On the flip side, there can be a negative connotation for “checking the box.

Someone can just go through the ropes and “check the box” so they can move on to the next thing. They can spend the least amount of time possible to complete the task, project, or job with minimal effort.

That’s where checking the box means the opposite of getting work done.

If you’re just checking the boxes, that likely means that apathy and indifference has set in, which makes it tough to do good work. At that point, something has to change, whether it’s a change of scenery, learning a new skill, or moving to a new role or company.

Are you doing the good kind of box-checking? If so, awesome! If not, what change will you make?

Three reasons why taking good notes is so important


I believe that note-taking is a very important skill, one that is often overlooked and under-appreciated.

Note-taking is often an afterthought, a mere formality. But I believe that taking good notes is even more important in today’s technology-oriented world.

First of all, meeting attendees are easily distracted by their phones and rarely pay full attention to what’s happening. I admit that I’m guilty of this sometimes. And I’d bet you’ve done this once or twice, right?

For some, checking Twitter is more important than understanding their team’s product strategy, and looking at pictures of their friend’s vacation on Facebook takes precedence over reviewing their budget. That’s why taking detailed meeting minutes is so important.

It sucks to be the scribe in a meeting, and many times this job is left to the lowest ranking employee of all the attendees. But it’s a very important task that can keep the team organized and on track, especially for those who weren’t fully present. Tasks can be assigned after the meeting, and minutes can be distributed so everyone remembers the important discussion points.

Second, in the same vein, we are constantly and continuously bombarded by information every minute. Instagram notifications, text messages, emails, and more come at us incessantly. We can’t possibly absorb all the words, images, videos, and other content that we read, watch, and listen to everyday.

By taking good notes, you won’t be forced to remember details of a phone call or meeting, and you’ll have a document with details that you can refer to later. Thus, you can dedicate that brain power to more creative or difficult tasks.

Finally, note-taking tools are better than they’ve ever been before. Whether notes are taken on a Google Doc, Evernote, or within project management tools like Trello or Asana, they can be easily distributed, organized, and tracked. Taking good notes can really help with keeping your team on track outside of meetings.

I remember when I was much better at note taking. During every meeting or phone call, I would take copious notes in a notebook or on a laptop. Then after the call or meeting, I would review the notes and file them away in a place where I can easily find them for future reference. I should go back to that process.

Maybe we should all put more thought and effort into taking good notes, instead of relegating it to a formality. It might have a big positive impact on our productivity.

Using your commute time productively

Crowded commute

Commuting sucks.

It can be stressful and draining, and you literally lose sleep because of it.

I’m pretty lucky that I only have long commutes two days a week. On Tuesdays and Thursdays, I have to drive out to Columbia, MD from DC, and half of that ride I’m with my wife because I drop her off at her job, so it’s not that bad. The rest of the week I usually work at a Cove co-working space, which is a 12-minute walk or 5-minute bike ride.

So commuting isn’t a big problem for me, but it’s a huge problem for many.

Regardless of how long your commute is, I think that it’s time that can be used wisely.

Yeah, you can listen to some morning talk show or watch that episode of Curb Your Enthusiasm (not if you’re driving, though!).

But there are many things that you can do that can make your commute or travel time more productive. Here are some of my favorites.

Plan your day

One of the things I like to do during my commute is visualize and plan my day.

Most of the time I will have my daily tasks planned out the night before. So on my commute, I’ll think more about how much time to dedicate and what resources I’ll need to complete those tasks.

If you take public transportation, you can use your commute time to write down your tasks for the day and get organized.

If you drive, you can visualize your schedule, think about your goals of the day, and better understand what needs to get done.

Then when you arrive at the office, you can hit the ground running and get to work right away.

Listen to an educational podcast

I love podcasts so much that I started one (though I’m on break now).

Podcasts are great because you don’t need to devote your full attention to consuming them, so you can listen while you walk, drive, ride a bike, or do something else.

I like to listen to my favorite podcasts during my commute so I can find some inspiration, motivation, or even specific tactics that I can apply to work.

Most of my favorite podcasts are related to startups and tech, but there are other subjects mixed in. They include:

  • This Week in Startups
  • The Tim Ferriss Show
  • Recode Decode
  • Freakonomics Radio
  • Talk Python to Me
  • Mixergy
  • Y Combinator Podcast
  • A16Z podcast
  • Here’s the Thing with Alec Baldwin
  • Bon Appetit
  • And a few others…

Podcasts are a great way to learn while you commute, and I love fitting them in whenever I have time.

Clear your mind

With a kid, a day job, and a startup on the side, life is pretty busy.

Sometimes I like to use my commute time to just disconnect and take in the world around me.

When I walk or take public transportation, sometimes I just clear my mind, listen to the sounds of the city, and watch the people and vehicles around me. I also take the time to appreciate everything I have and how lucky I am to be healthy and have a wonderful family.

This doesn’t sound like I’m being productive, especially since I’m not doing the things I just wrote about in the above sections.

But disconnecting and clearing your mind for a few minutes a day can really help in the long run. You’ll be more relaxed, more creative, and less stressed.

While I don’t do it during my commute, meditation is something I’ve been doing more often. 10 minutes of breathing and relaxation every day can help minimize stress and increase focus on what you need to get done.

How are you spending your commute time, and are you using your time productively? I’d love to hear more in the comments.


Slack, distractions, and Twist

If you read this blog, you know that I’m all about finding ways to increase productivity and minimize distractions.

And the more and more I use Slack, the more I hate it because it’s a constant stream of distractions.

I’m not alone. See here, here, and here.

Don’t get me wrong – Slack is an extremely well-designed, well-built platform. The integrations are great and the ability to build tools and bots on top of it is pretty awesome. It’s a valuable messaging tool, which is why the company is the fastest growing business app ever.

The underlying philosophy of Slack and many business communication apps – a stream of messages with little organization – is what’s bothersome to me.

My problems with Slack

Imagine you work on a remote team and you’re 12 hours ahead of most of your team members. While they’re in the middle of their work day, you’re deep asleep. Not only will you be bombarded with notifications, but you’ll also wake up to a cacophony of messages with very little idea of what subject was started where and by whom.

Another example is going on vacation. I was on a two-week trek to Thailand and got pinged with many messages that had nothing to do with me. The messages that were relevant to me were buried deep in multiple channels. I actually didn’t realize I missed messages until one of my co-workers asked me if I saw the message he sent to me.

And I know that I’ve sent many messages that were missed or unread.

At the core of the problem is notifications.

Yes, you can set certain your notification preferences – such as seeing all notifications, only those messages that mention your name, or no notifications for a channel. Those aren’t granular enough, and I find that I still miss a lot of stuff no matter which option I choose. And all you hear all day is that knock brush sound.

Another issue is that Slack doesn’t provide you with email notifications, so it forces you to use its tool to check notifications and messages, which again leads to missed messages. This is great for their engagement metrics, but not great for productivity.

Twist – a more thoughtful communication tool

I’ve been using a relatively new messaging tool called Twist, which is built by the same company who created the popular Todoist productivity app.

The philosophy and benefits of the tool are laid out nicely in this Medium post written by Twist’s creator.

We use Twist for WinOptix. Our team is pretty small (only 3 of us, all part-time), so our message volume isn’t very high. But we’ve already seen benefits from the different approach Twist has taken to messaging.

Channels and Threads

Like Slack, Twist has channels that you can denote subjects for, such as “Design”, “Development”, “Marketing”, and more. But Twist goes one level deeper with threads within each of these channels. So under “Development”, we have a thread for “Development Task Organization”, where our developer and I discussed the best way to organize development tasks, and “FPDS data – GitLab Repo” where we talk about how to access troves of government contracting data.

These threads portray the messages in a more granular fashion so you have a better idea of what the conversation is about.

Twist's channels and threads

Twist’s channels and threads

Sender can choose who receives notifications

The next big feature is the ability for the sender to select who receives notifications. This is HUGE.

Let’s say that I just want to ask our developer a direct question. I’ll just select his name in the “Notify” field and ask away. He’ll be the only one who receives a notification. Everyone else who is part of that channel will be left alone but will still be able to view that message at any time.

This is the best of both worlds. This gives the sender the power to minimize distractions for his or her team, not just the receiver to minimize distractions for herself.

In Slack, you can type “@username” to specifically mention someone in a message, but if other employees in that channel have selected to receive notifications for all messages, they’ll still get pinged with this message.

(BTW, as I’m writing this, I just got pinged with a Slack notification that had nothing to do with me. Ugh.)

Email notifications

Everyone hates email, but I don’t think it’s that bad. I used to receive 200 emails a day, but I’ve pruned that down to less than half. Maybe I’ve just gotten less popular. :/

I might be old-fashioned, but my email inboxes are the center of my work life.

Anyway, I love how Twist sends me email notifications about messages that have been recently posted. This allows me to see if I missed anything important without having to check all of the messages in the app itself. And the asynchronous nature of email lets me review messages whenever I please.


This may seem like I’m hating on Slack, but I’m not. It’s a really great piece of software, but it just doesn’t work all that well with the way that I work.

And I’m not getting paid by Twist to write this post. I just think it’s a very well thought-out tool that focuses more on productivity as opposed to just communication.

The caveat here is that we don’t yet have a high volume of messages, but I think that the way Twist is set up, ramping up the volume won’t be as distracting.

Anyway, if you’re frustrated with the constant pinging and missed messages, I’d suggest giving Twist a shot. If you do, let me know what you think!

Reps and Sets

I interviewed David Cancel, Co-founder and CEO of Drift, for my podcast a while ago. Drift just raised $32 million from top-tier investors, and he has started 5 companies. The guy knows what he’s doing.

One of the things he always talks about is “reps and sets.”

There aren’t any secrets, hacks, or shortcuts. Being consistent, putting in the work, and getting better everyday is the only way to success.

mathhub multiplier

Getting a little better everyday can be huge in the long run. Image courtesy of MathHub.

You won’t get in shape if you go to the gym twice a month. You won’t run lose weight if you’re not consistently eating healthy food. You won’t learn to code if you’re not doing it and educating yourself everyday.

Reps and sets. It’s as simple as that.

The power of focusing on fewer tasks

I’ve been on a never-ending search to find a system that works for managing my short term tasks. I’ve experimented with different methods in the past – using my calendar as my daily task manager, writing daily tasks down by hand, and others – but they haven’t seemed to increase my productivity or made me more comfortable with my progress.

I’ve used Asana in the past, and currently use Trello to track all of my projects and tasks. Both are great tools (see the comparison article I wrote here) that certainly help me stay organized and not forget about anything that I need to do. But it’s less about logging the tasks and more about executing them to completion.

I always seem to have a bunch of overdue tasks in my Trello cards, and all I do is just keep pushing back their due dates. Shitty.

Trello Overdue Cards Blurred

Ugh. Lots of tasks overdue, and it’s usually much worse.

This week, I tried something different.

I selected four big tasks that I would absolutely complete this week.

There will still other weekly maintenance tasks, like analyzing web traffic, social media, and writing this blog post, that I would finish by week’s end. But the four highlighted tasks were larger To-Dos that were either started a while ago and never completed, or an important project that needed to get done soon.

To log these tasks, I created a new Trello board, starred it, and only put those four tasks on that board. That’s it.

No other tasks or lists to distract focus from those tasks. Four tasks on a little lonely Trello island.

I have to say – so far, so good.

None of the tasks are fully complete, but they are all 90-95% done, and I still have today and Sunday (when I always put in a couple of hours of work) to finish them off.

The key here is to really focus and put more time into a fewer number of tasks.

In the past, I would start writing a blog post, get sick of writing it, then start another post, get sick of that, then go on and do something else. After repeating this process for days, if not weeks, all I would have is three or four quarter-written drafts and multiple Trello cards telling me how much work I have to do.

This week, I selected one of those unfinished blog posts and focused on completing it. Lo and behold, it’s almost ready to go!

Not only will I get to archive that Trello card, but the progress I’m seeing gives me a shot of dopamine and gets me amped up to complete the next task.

Maybe I’ve finally found a system that works for increasing my productivity.

How do you manage your daily and weekly tasks? What has worked for you? I’d love to hear your thoughts in the comments!

How is your work judged – by hours, output, or results?

There are many ways to judge how well someone is doing their job, but I’ve been thinking about three primary ones – hours, output, and results – and the impact they have on each other.


If you’re judged on hours, you likely have to show up at an office, log your time, and directly trade time for money.

Lawyers and consultants are judged this way, where billable hours and utilization are the main metrics. These firms charge their clients some crazy amount for each hour of their employees’ time, so it makes sense to maximize the number of hours worked.

Another form of being judged by hours is how big corporations do it.

These large organizations force you to work in the office from 9-5 and as long as you show your face and maybe get some work done, you’re all good. Many times it doesn’t really matter how much work has been done in that time, as long as the time gets logged. Ever see Office Space? You know what I’m talking about.


Being assessed by output is different, of course.

If you’re a sales rep, you may be judged on the amount of sales calls you make or appointments you book.

If you’re a content marketer, you may be assessed by the number of blog posts you publish.

Software developer? Your main metric might be how many lines of code you create.

Judging by output is certainly better than assessing by time spent, as there is evidence that work has been done.


Results is where the rubber meets the road.

If you’re a lawyer, did you win or lose the case?

If you’re a consultant, did your strategy get implemented, and was it effective? How did it impact your clients’ bottom line?

If you’re a sales rep, how much revenue did your sales calls bring in, and what is your win rate?

Nearly every job can be measured by results, which is the best measure of effectiveness. Unfortunately not every company chooses to do so.

The interaction between hours, output, and results

These three criteria don’t exist in their own vacuums.

High output can potentially lead to great results.

More blog posts written can lead to better search engine optimization (assuming the posts are high quality), which can lead to more web traffic and sales.

More sales calls can lead to more revenue. Even if you have a low win rate, the more calls you make, the more deals you may be able close.

While more code may not necessarily mean better software, the more code you write, the better you’ll get at software development, which will lead to better software.

And if you work hard, create a lot of output, and see good results, you may enjoy your work more and create even more output.

But more hours won’t necessarily lead to more output or better results.

A law firm can pile on the hours and still lose the case. A consulting firm can deploy a ton of consultants’ time and come up with the wrong solution.

And it’s these companies that judge effectiveness on hours worked that are being disrupted. The consulting industry is undergoing change, while the legal industry is in decline.

On a personal level, more hours may be detrimental to your output and results, as you might burn out and wind up hating your job.

So take a moment and think about how your work is being judged, and whether you want to be assessed in that manner.

If not, what will you do about it?

How do you deal with distractions from your smartphone?

driving with smartphone

Distractions are all around us, and most of them can be blamed on that tiny supercomputer in our hands – the smartphone.

Obviously, work is where you can be most distracted.

Constantly checking your phone for emails, text messages, Facebook, Twitter, Snapchat, or whatever app du jour you’re using can be so detrimental to completing your tasks. Push notifications make concentrating nearly impossible.

One second, you start a task in the morning. The next second, your friend sends you a message on WhatsApp about the slate of NFL games played yesterday.

Next thing you know, you’re checking on how your fantasy teams did. Then you’re researching a trade for a running back. Then negotiating said trade with other owners.

Oh man, it’s 5PM already? Time to go home!

What did you get done that day? Maybe a fantasy football trade, but maybe not even.

(BTW, that’s not me I’m talking about, it’s a hypothetical story, I swear).

I’m not only talking about work, though.

I walk my dog everyday and many times check my phone while doing it. Next thing I know, she’s eating some food scraps off the ground, and I have to worry if she’ll make me pay for my lack of attention by pooing somewhere she isn’t supposed to.

Sometimes when I play with my daughter, I’ll get distracted and check my phone. While I’m not looking, she’ll run toward our deck and lick the screen door. Or go to my dog’s water bowl and stick her hand in it. Or do something else she isn’t supposed to do.

And of course, we can’t leave out the distractions of the smartphone while driving. Dangerous.

As magical as the smartphone is, it is probably the biggest distraction ever created.

We can turn on airplane mode to avoid any incoming communications, but do we?

We can leave our phones at home when we go out for a short amount of time, or place it in another room so it’s not always with us. But do we?

How do you deal with all of the distractions that the smartphone brings? Do you ever put your phone in airplane mode, or leave it in the other room? Talk to me in the comments!

I hope you found this interesting! If so, please share this article with the share buttons on the left! That’d be awesome of you.

3 ways to set artificial deadlines to get sh*t done



As an entrepreneur, you may not always have a boss breathing down your neck, client demands to meet by certain times, or hard deadlines that you need to adhere to.

Many times, it’s up to you how much work needs to get done and by when.

Thus, there may be times where you slack off every once in a while.

What’s the worst that can happen if you don’t finish that blog post by the end of the day? You’ll get to it tomorrow, right?

So what if you don’t work on your online course today? It’s not due until December!

Does it really matter if you don’t take that programming lesson today? That shit is too hard anyway, and you’ll never become a good software developer.

We’ve all been guilty of that mindset every once in a while (I hope I’m not the only one), and it really sucks when that happens.

You miss one deadline, then you do it again the next day, and then it’s a slippery slope.

So I’ve learned a few ways to set artificial deadlines to be more productive and get shit done. Check out these techniques that I’ve used.

The Pomodoro Technique

I’ve written about the Pomodoro Technique in this blog post and in my productivity ebook. It’s a great technique to enhance productivity.

The Pomodoro Technique is a time management approach where you concentrate solely on your work, with no distractions, for 25 minutes. This is one Pomodoro. After that 25 minutes is up, you take a 5 minute break and do whatever you’d like. You then repeat this throughout your work day.

I try to complete one task by the time one Pomodoro expires. Then I do it again and again for other tasks. If I have a large task to complete, I break it down into smaller tasks that I can fit into one Pomodoro.

For instance, I write a blog post like this one every morning. On most mornings, I try to complete the entire set of blogging tasks – which includes writing on this site, finding an image, including outbound links, republishing on LinkedIn and Medium, and posting to social media – all within one Pomodoro. It’s tough and I sometimes rush in the end, but it gives me that artificial deadline to meet.

For a longer blog post like this, I will split it up into one Pomodoro + 10 minutes, or  two Pomodoros, depending on my progress.

However many Pomodoros it takes, having that 25-minute deadline and countdown clock (I use staring you in the face helps immensely. Setting that artificial deadline and meeting it feels awesome and gets me going for my next task.

The “Don’t Bring Your Computer Battery to the Coffee Shop” technique

If you have a task that you really need to complete within a 2-4 hours (depending on how long your computer battery lasts), head to your local coffee shop with your laptop, but leave your charger at home.

Need to write a blog post you’ve been putting off? Do you have to crank out that research report? Gotta finish that proposal or presentation?

Leave your home or office with your laptop sans charger and head to the coffee shop, library, or co-working space.

Without a charger, you will be absolutely helpless when your battery runs out, so you’ll need to complete your task or project in the time before your charger conks out.

Even though this deadline is “artificially” set by you and your computer’s battery life, the desperation and helplessness you feel when your battery gives you a warning is as real as it gets.

I love this technique.

Paying up for missed deadlines

This is one that we’re trying here with our team at Thorn Tech.

We each set reasonable deadlines for content that we need to create, such as blog posts, tutorials, case studies, whatever.

If I don’t meet my deadline for the first draft of my piece of content, I have to pay $50 to the pot.

I then reset my deadline, and if I don’t meet that one again, I owe another $50. And so on and so forth.

We are paying cold hard cash if we slack off.

Proponents of positive reinforcement will shit all over this idea. But those who understand Prospect Theory and loss aversion will understand that many people will choose to avoid losing something of value than gaining something of equal value.

The money will go to something fun, like a company happy hour or new toys for the office, so it’s not all bad.

The idea behind this experiment is to see how fear can be a motivator, and how the deadlines that we set can be held up with consequences.

We’ll see how it goes!

Combine all three!

You can combine all three of the above to create one super-powerful artificial deadline.

Pick a task that will take under 4 hours (your laptop battery life), come to an agreement with someone to pay them some money if you don’t finish the task, head to a coffee shop without your laptop charger, and use the Pomodoro technique to crank out your work.

Give it a shot and let me know how it goes!

What do you think of these artificial deadlines? Are there techniques you use to get shit done? Talk to me in the comments!

I hope you found this interesting! If so, please share this article with the share buttons on the left! That’d be awesome of you.

How do you create your To-Do list?

to do list

I still haven’t figured out the best way to organize my To-Do list. How do you organize yours?

I’m not just talking about the apps that you use. I’m talking more about the process in which you lay out what you need to do each day or each week.

I use Trello to organize all of my projects, tasks, and ideas. It’s very visual and flexible, and has everything I need to stay on top of all of the tasks that I need to complete.

But when it comes to those tasks making it to my daily or weekly To-Do list in a way that I get the most done, that’s where things sometimes fall off.

I just haven’t found the right process to stay as productive as I can on a daily or weekly basis.

I’ve tried creating a “Today’s To-Do” board on Trello, and listing only the tasks that I need to do that day. That seemed to work for a while, but it didn’t help me see the bigger picture of what needed to be done that week. And there would be times where a larger task due that week wouldn’t make it to my daily to-do list until the day before it was due, when it was pretty much too late.

I’ve also tried creating a “Weekly To-Do” board that had a list for each day of the week, and the tasks due each day. In this case, I would overload each day with too many tasks that I couldn’t accomplish in time. Thus, I would move the incomplete tasks back each day. This would actually be pretty discouraging, as my Friday would have a list of 10-20 tasks that I didn’t get done, and probably won’t.

So I’m trying something new. I am going to create a “Weekly To-Do” board, but instead of having a list for each day of the week, I am just going to have the typical “To-Do,” “Doing,” and “Done” lists. Then for each day, I am going to input and assign a specific time slot for each task into my Google Calendar.

I think this may provide a balance between daily and weekly To-Dos, and put more of a time structure around each task. This will also help me schedule my day around meetings and calls and makes sure that I’m not overloading my To-Do list for each day.

I’ll report back in a week or so to see how this works.

How do you create your to-do lists? What are the process and tools that you use to stay organized each day? Talk to me in the comments!

I hope you found this interesting! If so, please share this article with the share buttons on the left! That’d be awesome of you.