Time Off and Away as an Entrepreneur

One of the best parts of working for yourself is the flexibility - which is one of both Lindsey and I’s definitions of success. Even with that flexibility, at least in my part, I still tend to work a lot outside of your typical 9-to-5. It’s taken a long while, and having kids, to do a better job at setting work boundaries - including planning and taking dedicated time off. 

I remember early in my business, in my mid-20s, my husband and I would often zip in and out to destination weddings. Literally, we’d fly in on the morning of the big day, stay one night, then check out and head home the very next day. Sometimes I look back and wonder: Why was I in such a hurry? That made sense at the time, for a lot of reasons.

Now, one of my favorite things to do is travel - whether that’s to see family over the holidays, hit the beach or the mountains, round up some friends and their kids to share an Airbnb, going on my annual moms only trip, or even trekking across the world to see friends in Thailand. With work trips, I often try to tack on a few days before or after for some extra fun and either time alone or time with my people. 

I will admit, I feel great when booking the trip - and then when the time comes to pack and go, I usually feel a little differently. Can I really take that much time away from my clients? Will the business run in my absence? What about all of those things I didn’t finish? Maybe that’s you, too. Even still, once I’m finally settled into vacation mode, there’s no turning back. I’ve noticed that it’s easy to let everything go for a little while when my toes are in the sand, I’m hiking a trail, or I’m exploring a new place. It will all be there waiting for me when I get back. If you’re the type of business owner who needs a nudge or you’re waiting for “permission” to book the trip and go, consider this your sign. Not to mention, this is a form of protecting the asset (you) and running your business more sustainably long-term; and here's a short bit on why you should vaca from the American Psychological Association.

Here are some of the ways I set myself and my business up to be able to enjoy the time away:

Beforehand

• Scheduling clients: I consider my away time when I am scheduling clients in advance, and do the best I can to meet with folks before or after based on their session cadence. I am transparent with clients about why that time is blocked on my calendar - and I generally find that people are very understanding and accepting of time off, no matter if it’s personal or professional. 

• Updating my availability: I usually have my calendar open for clients to schedule sessions up to 30 days in advance. In preparation to be gone, I’ll double check that my availability is accurate for 30 days out from the last day of my trip, and sometimes I’ll go ahead and open my calendar out further if that makes sense. 

• Gaining awareness: As a trip gets closer, I’ll make time to look at the month before and 1-2 months after my trip - to gain better awareness of what is on my plate surrounding the trip. This helps me to prioritize anything that really must get done before I leave, versus what can wait until I return. I also use this awareness to ask for what I need from others related to deadlines and deliverables, and to start a to-do list for after my trip so that it's ready for me when I return.

• Setting expectations for myself: I clarify if a trip has any work involved, and if so, to what degree. This helps me decide what I need to bring with me. At bare minimum, I bring a tablet with a keyboard and my airpods - to have the option to take care of something quickly if I absolutely need to. Regardless, it’s worth considering: What does “work” mean on this trip, what work are you planning to do, and what do you need to bring in order to accomplish that (without going overboard)? 

• Setting my email signature: A month before I leave, I add a note to the bottom of my email signature, like: *Please note: I will be out of the office from July 3-10. People will see this - which helps to set expectations ahead of time for my clients, contracts, and colleagues.

• Setting my email vacation responder: I remove the above from my email signature when I set my OOO (out of office message), then turn my vacation responder on from the day I am leaving (or the day before) to the day I return to normal working hours (which may be after I return). In that message, I let people know what they can expect in terms of my response time, which may not be until after I return, and I thank them for their patience. Set it, and forget it.

Afterward

• Buffer time: I am not one of those people who can hop off a flight or pull in from a road trip and jump right back into a full day of work. Tried it before, hated it instantly. Now, I tend to provide myself a buffer between travel and work - which is usually 1-3 days (depending on if it’s a weekend or not). This gives me time to reset and recharge, especially if jet lag is involved.

• Reflection: For me, part of that buffer time and easing back into reality is spent reflecting. For personal trips, that might mean making an Instagram reel of the best moments and doing “high-low-buffalo-thank you so” around the table with my husband and kids (favorite moments, low points, anything funny/strange/weird that happened, and gratitude). For professional trips, it’s usually putting pen to paper and reflecting on what the trip meant to me, the best moments, things I learned, and next steps. This helps me to slow down and savor the good thing before I speed back up.

• First day back: My first day back in the office is a no-client and no-meeting day, which allows me time to GHOS (pronounced “g-hoss”), or get my head on straight. Even if I’m back-to-back the entire next day, or next several days, I’ve found that this is sacred time to reorient myself back to work, respond to emails, prioritize my post-trip to-do list, prep for clients, and feel settled and ready to roll. 

Putting these things in place have helped me to take the trip, and more importantly, enjoy the trip. Having the flexibility to travel and make memories, for me, is one of the sweetest parts of entrepreneurship and getting to work and do life in your own way. We hope you have some time off coming up that you’re looking forward to - you deserve it. Happy travels!