What’s in My Briefcase: Essential Tools for Business Executives

The briefcase has become the modern rucksack for busy executives, so having the right tools and technology is critical for maintaining productivity. 

For an executive on the move, what separates a hectic workday from a seamless one? For executives like me, it all starts with having everything I need in my briefcase.  This article will share my philosophy on deciding what to carry, as well as the executive travel essentials I keep in my briefcase (weather traveling or in the local office). 

Briefcase backing philosophy to balance having the right kit while staying light

My philosophy on what to pack in my briefcase harkens back to my days in the military.  A couple of memorable phrases stick out from that time and still influence how I pack my personal briefcase:

Design your briefcase kit specifically for how you travel

Using the above aphorisms, I’ve honed my personal briefcase packing philosophy over the past ten years as a management consultant and traveling executive.  The following lists have worked for me, but you will want to modify for your own situation and preferences. 

A few examples of how you might modify the below list:

Annual check-in on your briefcase contents

At the beginning of 2025, I followed my own advice and dumped everything out of my briefcase.  This served two purposes: (1) look for items that were damaged or expired and (2) identify any gaps that should be filled for future travel. 

Executive's briefcase with all of the essentials for modern business travel

Choose the right work bag style for your work

I believe there are three basic kinds of work bags – briefcases, backpacks, and messenger bags.  Each of these bag styles can have a place in our professional journey.  But it is important to identify which bag type is right for you, based on how you work and travel.

Messenger bag: urban hip and bike mobile

When I was attending graduate school, I absolutely used a messenger bag.  The modern version of what I used is the Timbuk2 Classic Messenger Bag (in medium & blend in black). 

These bags gobble up everything you need for a day in school and are easy to bike with.  If I still had the ability to bike commute, I would absolutely consider a messenger bag. 

Backpack: utilitarian and functional

I also think that backpacks have a place in the modern workplace.  My favorites over the years have been GoRuck and Brown Buffalo (which is currently down for maintenance).

Working in factories and/or traveling a lot – the right backpack can be a godsend.  Backpacks with their two shoulder straps are perfect for hauling a bit more weight (think overnight trip) or for longer amounts of time (think long walking commute). 

If I were looking for a new workback back today, I would consider the Bellroy Transit 20L pack or Troubadour Apex 3.0.

Briefcase: upscale and easy to carry on

These days, my go-to work bag is a briefcase.  Not because it’s a classic in the workplace for executives (though it is).  But because it just works well and looks great. 

When I was traveling every week in consulting, I heard that the way that you know a bag is a Tumi is that you can reach under your seat on a dark flight and still find what you’re looking for.  There’s something to that.  That the bag is designed in a way that your items naturally go into usable pockets.

I’ve been using a Tumi Alpha bag for about a decade and it’s still going very strong.  I know it like the back of my hand and it fits perfectly over my rollaboard suitcase when flying. 

Tech Essentials for Productivity on the Move

Technology essentials in an executives briefcase

Technology makes the world go ‘round and executives are no exception.  The traveling executive needs the right tech to keep them in communication and productive while on the move. 

Key technology items for all executives

Obviously a laptop is the most essential piece of technology that any business person carries.  This core piece of computing can allow you to be as productive on the road as you are in the office.  My go-to is the Lenovo X1 Carbon.  What I think is more interesting (and important) is the accessories that enable your laptop while traveling.

I carry a small felt pouch to organize my technology accessories inside my briefcase.  I’ve been using an older version of the Nidoo technology case for many years and it’s just the right size to hold everything by my laptop charger.

Technology accessories every executive should have in their briefcase

Health care items for every executive briefcase

Go to medicines for business travel - always carried in the briefcase

In addition to being your own communications officer, you should also be ready to be your own medic.  Ailments happen on the road more often than when home, likely because of the exposure to new environments and people.  You should be able to get through the day with what you have in your briefcase.  Always check with your physician before using any medicines, below are just what works for me.

Digital Notebook (& Analog Tools) For Note Taking

While the standard advice is to always carry a notebook and pen, I take a more digital approach to that advice.  For many years, I carried the standard Black Moleskine (first in 3.5×5.5” to fit in my uniform pocket, and then in 5×8.25”).  But in 2021, I started using the reMarkable 2 digital notebook and I haven’t looked back. 

Digital notetaking tools for the executive on the move

As mentioned above, I have completely converted to taking written notes digitally on the reMarkable 2.  I have tested the device in a number of contexts (at work, traveling internationally, at conferences, for non-profit work) and continue to be pleased with the tool.

To keep myself organized while traveling, I utilize many different ‘notebooks’ within my reMarkable 2 to organize various projects, meetings, and my daily smart sheet.  This reduces the number of separate paper notebooks in my briefcase while still having specific sets of notes to easily refer to.

In mid-2024, reMarkable introduced the reMarkable Paper Pro as an upgraded version of the reMarkable 2, featuring a color display, backlighting, and increased writing responsiveness.

Regardless of the reMarkable model, there are a couple of items in my briefcase that maximize my ability to use my reMarkable:

Paper notetaking materials for executives in a digital age

For those that haven’t converted to digital note taking, carrying analog notebooks and utensils is still critical.  When I started at West Point, we were told to always show up with “something to write with and something to write on.”  That adage still applies to the modern executive.

Writing utensils

Notebooks

Fuel and water essentials while traveling

Staying hydrated and properly fueled are critical to maintaining productivity while traveling. I like to reduce my reliance on outside sources because sometimes meetings and other requirements can make eating well difficult.

Therefore, I always carry a water bottle in my brief case (which I can fill up once through security or taking with me throughout my day). I’ve been using the Camelbak Podium 21oz water bottle and it fits very well in my briefcase. I’ve not had issues with it leaking, as it has a lockout on the nipple. Additionally, this type of water bottle is great for getting runs or gym workouts in at your hotel.

Additionally, I like to carry a healthy snack or two in my briefcase so I can avoid going to a dreaded vending machine during a long day. Barbell protein bars have been a recent go-to as they taste great and pack 20g of protein in each serving.

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2 Responses

  1. Heya just wanted to give you a brief heads up and let you know a few of the images aren’t loading correctly. I’m not sure why but I think its a linking issue. I’ve tried it in two different internet browsers and both show the same outcome.

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