How to Plan a Productive Workcation & Make Travel Fit Into Your Business

Let me start off by saying... I am no tax or financial professional nor do I want to be one. I hire a professional bookkeeper (he's not accepting clients, sorry) and CPA and while their services are tax deductible, not all of the ones I talk about in this bulletin are 100% deductible. You'll have to consult your financial team on how to best manage your tax liabilities.

Day THREE of THIRTY days of writing something every day to tell you...

I NEEDED TO FLY AWAY.

It was 2022, Evan and I had been trying to conceive for a hot minute, the world was opening back up after COVID and I just needed to get away. Not from him but from the internal pressure that was stifling my creativity.

I had always imagined being a mom by then and with our failed attempts to grow our family naturally, Evan and I were beginning to walk into our new path together. Honestly, quite happily too. We had finally moved on, grieved the loss of a vision and then embraced the opportunity of building a life wearing a fresh set of glasses.

We didn't know what exactly that would look like but I knew it would include traveling. And I knew I didn't want to wait until everything was "just perfect" to start doing it. We had tried that method growing our family and I'll be damned if I wasn't going to learn my lesson and not take charge.

I wouldn’t be wasting time waiting for the perfect time to travel.

Content photoshoot in Montana, preparing to launch AHC

Looking back, I realize the lesson, again, wasn’t about faith. I never doubted we could adjust our perspective, reimagine our lives together, and make travel a reality.

My issue has always been patience.

If there is a bump in the road, I will build a bridge, tunnel, or sidewalk before most people have finished identifying the problem. (Evan says this is both my greatest strength and the reason I text in lots of short messages.) I have that faith in my problem solving.

But moving quickly is not the same thing as moving sustainably.

The problem with solving everything immediately is that you rarely stop long enough to recover before the next thing needs your attention. Travel became such a big part of my job, I realized I was burning through energy and resources for something that was supposed to be personal anyway.

I DON’T REGRET THE INTENSE TRAVELING I DID.

Those trips gave me photography experience, business knowledge, and educational inspiration (not to mention friendships and connections).

They also taught me that wanting something badly is not the same thing as planning it well.

When we adopted our son in 2025, I knew solo travel needed a different standard. I didn’t want to stop traveling— I just wanted every trip away to have a clear purpose.

Now I use a simple rule of thumb. A trip should accomplish at least one of the following, and ideally two. 👉

• Generate money (ex. photography session)

• Allow for incredible work output (ex. develop an entire funnel)

• Deducted from airline miles (I use the AAdvantage Business Program)

• Share expenses with other business owners, friends, or family

The first three bullet points are clear. The fourth is where it gets hairy.

If the primary purpose of the trip is relaxation, it is a vacation. If the primary purpose is business activity and the leisure happens around it, you are much closer to a legitimate Workcation.

View from our rental vehicle outside the Great Sand Dunes National Park, Colorado. The tickets to the photography workshop were so cheap, we paid personally for Evan to attend it just because it was at the top of a sand dune and the workshop included admission to the park & swag. I used miles for my plane ticket/accommodations and Evan paid his way for tickets and food. The entire trip cost the business maybe $500 and skyrocketed the confidence I had to charge premium pricing in my photography business.

HERE'S HOW TO PLAN YOUR NEXT WORKCATION WITH YOUR BUSINESS BESTIES

1. Decide when you want to go & for how long.

   
   

   You're the one planning the dang thing, you get to choose the date but keep in mind any "must have" besties and their ability to step away from their personal and professional lives.

I have found two nights to be the minimum and three to be the maximum. One night doesn't give you much time to work outside of the hours you'd normally be working so it's hard to justify it as a necessary trip for anything besides inspiration or personal fulfillment. Two nights is fine but really only allows for one complete day at a rental unit so you're going to be less fulfilled socially.

More than three nights is usually my limit. By day four I start missing my personal bubble.

2. Decide where you want to go.

If you're planning to drive over four hours, you're going to want to stay at least three nights. This gives you a solid two days to work and play so you don't have to cram as much in to feel productive. You're also less likely to cave, say "screw it" and take a vacation detour.

If you're planning to drive over 6 hours, you're going to want to fly.

And if you choose to fly, you will probably eliminate the bulk of besties who can join you. That could either be good or bad, possibly strategic 😅

3. Choose a rental.

I have used AirBnb, VRBO, and private rental management companies to rent.

Assume only one person will sleep in each bed, no one will sleep on a couch, and no one will sleep on a top bunk. While there my be outliers, we want to assume the least invasive footprint of the rental so we can give realistic estimates to our bestie friends.

You need at least two bathrooms, one balcony/porch, and one thing for entertainment-- my favorite is a pool, hot tub, or lake to look at. I recommend a proximity of no more than 15 minutes to the nearest restaurant/market.

If you are using your rental to bring clients to (ex. a photoshoot) you will want to get approval from the renter first. If you are using it to take your own photos or your friends' photos, a courtesy is nice but not necessarily required. Either way, content should be on your to do list so make sure there's nice decor and natural light. This alone is worth its weight in "reasonable business expense."

Make sure there is a compatible refund/cancellation policy. While your besties understand their commitment is not refundable, shit happens and sometimes the trip has to be cancelled.

4. Contact the Besties

When sending a pricing estimate be sure to give a deadline for payment along with the total and how best to send the reimbursement.

Once I have the minimum beds filled, I ask the group if they would like to extend the invite to anyone else. If someone else is willing to co-sleep, or other, and all core attendees are on board, we discuss who we could invite. If people add after the core group, everyone's total still shifts and we utilize the "over payment" towards communal food.

Lunches at the last Workcation in Gulf Shores, AL was a rotation of cold cut combinations. Pictured is a hot honey pimento grilled cheese with turkey lunchmeat & avocado, pinwheels, and a pasta salad.

Communal food includes water, coffee, continental type breakfast, easy & repeatable lunches, 1-2 quick and easy dinners, ice and paper goods. This usually comes out to $30-60 per person for the entire trip and includes delivery straight to the front door. Everyone brings their own beverages, snacks, and special diet items and pays for their own meals out and any extra meals they choose to grab alternatively.

5. Nail down your timeline & tasks.

Remember, this is a business trip. Albeit a really fun one with your business besties. What you do on this trip is completely dependent on why you needed it in the first place. A general timeline ensures you are honest in saying you simply cannot get the same quality/quantity/type of work done outside of this trip.

For me, that's a combination of work and play. Here is an example of a Workcation Timeline, though I don't usually prepare it so rigidly for driveable trips 👉

7:00-8:00 Coffee, Breakfast, Chatting

8:00-12:30 Locked In Work (record BTS content)

12:30-1:30 Lunch

1:30-3:30 Locked In Work, New Location

3:30-5:00 Swim

5:00-7:00 Dinner

7:00-10:00 Locked In Work, with movie

10:30 Bed

Here is an example of a portion of a Workcation Task List. I usually include way too many items on here but I want it to act like a productivity option bank that's been compiled in the weeks leading up to the trip 👉

• Record footage talking 1:1 with a model

• Take new headshots in 2 outfits

• Build free guide for women business owners

• Schedule out 2 weeks of reels

• Write blog about xyz

• Refine website copy

• Build new customer workflow

• Plan out Q4 workshops for small business owners in Baton Rouge

I still love to travel. I just don't feel the need to chase it the same way I did through 2024.

Back then, traveling represented possibility. It was my way of choosing to move forward after letting go of the life I thought we'd have. I wasn't willing to put living on hold while waiting for things like PTO to fall into place.

That decision changed me.

I traveled to Minnesota for my very first official branding photoshoot. I met Katie Hammond of Katie Hammond Photography at the Texas School of Photography and loved her work so much I couldn't not have her do my kickoff branding.

Today, our life looks different than I could have imagined back then. We have a son. My business has grown. My vision has shifted, once again. Flying across the country every chance I get isn't practical for this season, but that doesn't mean I've stopped making room for adventure.

It just looks different now.

These days, I'm more likely to pack up the car than board a plane for work. I'm more intentional about where I go, who I invite, and what I hope to accomplish while I'm there. The destination matters less than making the time to step away from my everyday routine, think creatively, and return home with something meaningful to show for it.

Maybe that's the real lesson.

Don't wait for things to become perfectly aligned before you start enjoying life. For me, that once meant booking the flight. Now, it usually means planning the Workcation to get some serious work done alongside some great women in business.

In the comments, tell me where you want us to go on the next Workcation! The Collab Lab members always have first dibs on their bed!