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See Behind The Scenes: How We Work and Travel

It’s taken us a few years of trial and error, but we’ve figured out how to run our businesses efficiently no matter where we are.

The life of an entrepreneur is a funny thing. Some days you find yourself not being able to remember the last time you ate a meal or took a shower, feeling exhausted and creatively drained. The next you’re on a plane headed to some huge meeting or event, brimming with excitement and nervousness.

But what does the life of an entrepreneur actually look like? Hang on tight, I’m about to share a slice or two of it with you!

Work and Travel, Jason Zook and Caroline WInegeart

This year marks the ninth year that I’ve been unemployable. Oh wait, I mean self-employed. Since 2007, I’ve worked for myself and owned or co-owned my own business. My girlfriend Caroline, who will be joining the fun in this article, has been living the entrepreneurial life with me since 2011. In that time we’ve managed to figure out ways to work at our maximum efficiency levels, at home and on the road, while still enjoying a life of flexibility.

Working at home: our desks

Let’s start with where the majority of the entrepreneurial magic happens: The desks. You’ll notice some stark differences between Caroline’s desk and my desk, but that’s because we work very differently. Caroline is always doing something with her hands, usually creating a beautiful piece of art through multiple mediums. And me, well, if I’m at my desk, I’m usually typing away on my keyboard (actually, 99% of the time that’s exactly what I’m doing).

I’m not exactly sure when it happened, but at some point after college I became a little bit of a neat-freak. Okay… Truthfully, I’m a little OCD with how tidy I like my workspace. But hey, there’s a reason for this. When my workspace is clean and free of clutter, I can easily get in the zone (my zone is kind of like when Bugs Bunny drinks “Michael’s Secret Stuff” in Space Jam).

Jason Zook Desk

Jason Zook Working At Desk

As you can see, I don’t use an overly expensive setup. And yes, this is what my desk looks like almost all the time (like I said, I’m OCD, deal with it). Here are my desk essentials:

If the cleanliness of my desk soothed your inner-OCD-monster, then I want to forewarn you about Caroline’s desk: It’s a creative jungle! But in the best of ways obviously… Caroline has learned that having a tidy desk is not conducive to flexing her creative muscles. Being overly organized actually hinders her ideas from flowing freely from her imaginative mind. Trust me, I’ve tried imposing my organized will on her and it didn’t work out so well for either of us. I’ve come to appreciate her workspace because of the work it allows her to create. Just as long as her stuff doesn’t touch my desk (hah!).

Caroline Winegeart Desk

Caroline Winegeart Working At Desk

I’d run out of bullet points if I let Caroline rattle off all the stuff on her desk, but there are a few key items that she simply can’t live without:

Working on the road: travel fun

One of the things Caroline and I value most about working for ourselves is the flexibility to be able to pick up and go at a moment’s notice. Over the years we’ve become very efficient when it comes to packing for trips.

The things we carry with us at all times

Much like the limited amount of things I keep on my desk, I don’t travel with a ton of stuff. I used to bring lots of extra things along as just in case items. But I always found myself never actually using those items and have challenged myself to travel with much less.

Jason Zook Stuff

Jason Zook Samsonite Duffel

Fun and random, huh? Pretty much a visually organized representation of who I am as a person. Here’s the breakdown of what I keep in my travel bag:

You might be shocked to see what’s coming next, but Caroline doesn’t actually just slide all the items from her desk into a plastic bag to bring with her (I’m so happy she doesn’t!). The items she brings with her vary based on her current medium for creation or the current projects she’s working on.

Caroline Winegeart Stuff

Caroline Winegeart Samsonite Tote

Crazy organized, right!?! I know. So proud. Here’s what she keeps close at-hand in her travel bag:

The things we pack

I won’t bore you with each item we put in our suitcases, but I will share a couple packing tips we’ve learned over the years.

Tip #1 – Wear your biggest pair of shoes, pack your smaller pairs.

This is more for me than Caroline, but it’s amazing how much room a slightly larger pair of shoes can take up in your suitcase.

Tip #2 – Roll your clothes.

If anyone reading this has a family member in the military, then you know the beauty of rolling your clothes. This is an absolute must and actually helps keep clothing wrinkle-free-ish.

Tip #3 – For the ladies: Pack basics that you can mix and match.

From Caroline: The key to making sure you have an outfit for any occasion when you travel without including your entire closet is to make sure you have neutral and versatile basics (like a gray cotton dress) that can be dressed up or dressed down with shoes/accessories.

Tip #4 – For the gents: ExOfficio makes the best men’s underwear ever.

I know, I said I wouldn’t bore you with suitcase item details, but this is a type for my dude-readers. Buy a pair of these and tell me I’m wrong!

Bonus Tip – Never check bags. Ever.

This is a hard-and-fast rule for a couple reasons. One, it makes the travel process way more efficient (leave me and my idiosyncrasies alone!). Two, it forces you not to empty your entire closet into a suitcase that becomes heavy, that you have to pay to check, and that causes you to wait in baggage claim watching the conveyer belt of hope (hoping that your bag made it safely, that is).

Packing Awesome Clothes

All The Clothes, And Plaxico

Caroline Winegeart Rolling Clothes

Jason Zook Rolling Underwear

Caroline Winegeart and Samsonite Luggage

You’ll notice we only travel with Samsonite luggage. Full transparency, they reached out and offered to hook us up with luggage and we couldn’t say no to fancy new bags. Especially Caroline, whose previous rolling suitcase looked (and sounded) like it squared off in a gladiatorial arena with a disgruntled airline crew worker. Seriously, you could hear that thing and its bum wheel coming from an entire terminal away.

The bags we own are as follows:

We recently went on a trip and as we were walking out the door, with the exact stuff you see above, we realized how much of a minimal lifestyle we’ve established. We could easily travel for weeks on end bringing only what you see above (and we have!).

Where we enjoy working

When we aren’t at home, our favorite places to work are unique coffee shops. There’s just something about the smell of fresh coffee, the vibe of the place, and the people coming and going that creates an atmosphere we love.

Caroline Winegeart, Holsem Coffee San Diego Jason Zook, Dark Horse Coffee San Diego

It’s taken us a few years of trial and error, but we’ve figured out how to run our businesses efficiently no matter where we are. Whether we have to hop on a plane at a moment’s notice (yes, it’s happened before) or we just need a change of scenery to get the creative juices flowing, our work process is a well-oiled machine. No matter where we are when our next big ideas hit, we’re ready to make them happen.

Note: Some of the links in this article are affiliate links. You pay the exact same price if you buy something and we get a tiny bit of money to spend on underwear and coffee.

This is the end of the yellow brick road. If you want to read more articles mosey on over yonder.