We’re excited to introduce you to the always interesting and insightful Lisa Pleasant. We hope you’ll enjoy our conversation with Lisa below.

Lisa, looking forward to hearing all of your stories today. How do you think about vacations as a business owner? Do you take them and if so, how? If you don’t, why not?

When I first started my company, I would have answered, “What is this ‘vacation’ of which you speak?” I used to take my work everywhere with me. On family vacations I would work half the day then join for the other half, though I did still feel very fortunate to be able to get up and go without asking permission or for PTO. Even when I was with my family, I would still check my phone every hour and answer emails or text messages as they came in. With weddings as our main focus, I was working the usual Monday through Friday at all hours, plus late into the night, then typically had events on Saturdays, with catching up on Saturday’s emails on Sunday. For the weekends when I didn’t have an event, I found myself giving into clients who “couldn’t make another day work for them.” I was not seeing my family or my friends enough, and I missed it.

Then Covid hit. Suddenly, my weekends were free. I hung out (socially distanced) with neighbors, and I had Zoom and yard hang-outs with friends and family. My girls and I came up with creative ideas for things to do on our Saturdays, and we had more time together. I also found that my clients became more flexible with their time, which allowed me set boundaries. Instead of opening every evening up to them for meetings, I cut it down to two or three a week, and otherwise they were able to find time during the workday for a quick call instead. My Saturdays became sacred to me. Covid was a time not only for reevaluation of my company; it was a time to reassess my own work-life balance.

Given the nature of our business, we actually grew during 2020 as a larger flood of clients booked to begin their planning process for 2021 and 2022. I was able to hire even more staff, and most importantly a personal assistant, which allowed me to work a more reasonable schedule. Instead of 80 hours a week I was down to about 60. Covid also made my already-travel-heavy-heart anxious and hungry. Not only had I decided to prioritize my own time for family and friends, but I also appreciated the fact that we only live once, and what better time to make memories and have experiences than now. After all, what else are we working for?

I hit life hard, going to places on a whim like a last-minute trip to Colombia with close friends, taking my daughters separately to Italy, Ireland, and London, or again taking my Mom to Ireland as well. I went to an EDM festival with friends in Belgium and visited Amsterdam while we were there, and I have many more adventures planned coming up soon. To most of these, yes, I took my computer to monitor emergencies, but I purposefully spent no more than an hour a day checking in. There was one exception, my first trip to Ireland, in which a new client did not respect my boundaries, but I also learned from that experience that I need to be more firm in setting those boundaries, and most of my clients have been amazing when given a heads up.

All in all, I will say that, as long as I set my company up in advance and have boundaries set up front with my clients, I have now truly been able to fully enjoy my vacations.

Lisa, before we move on to more of these sorts of questions, can you take some time to bring our readers up to speed on you and what you do?

I came from a mathematical finance background to starting up a planning company. Life sometimes has a way of directing you to what you were meant to do, and I was fortunate enough to understand that. I had just decided to take over another company when my older brother got engaged. “You plan things. Why don’t you plan our wedding?” Long story short, within a couple of months of starting the planning process with him and my amazing sister-in-law, I dropped everything else, started my free website on Wix, and dove right in. I have never looked back. That was twelve years ago.

Most of our business is wedding-related, but we also plan corporate and other social events, and we are in the process of growing that side, especially with corporate events. We are well known for being one of the most organized groups of planners you will find and have been fortunate enough to be voted top 2% nation-wide by our clients. We are so blessed!

Someone asked me what I like most about my job, and I told her “everything.” I love the people I get to meet and truly come to know and call friends, the problems I get to solve, the logistics and architectural programs I play with, and that rewarding feeling when everything comes together in the end, like one big, coordinated dance. It makes me smile to think about. And did I mention the amazing new friends I have made?

I can truly say that my job is part of who I am, and I don’t see that as a bad thing but a very rare and special thing.

Any stories or insights that might help us understand how you’ve built such a strong reputation?

We have been absolutely blessed with a great, supporting community of vendors and industry professionals who have been nothing but accepting and loving from the start. The comments from other vendors that we received most from the beginning were praise in how organized we were, and oddly, how nice we were. It always pays to simply treat others as equals and with respect, and the more successful events we planned, the bigger and better our reputation grew.

Any advice for managing a team?

With each team member comes a new and unique set of personality traits and emotional sensitivities, and a different source of motivation. Understanding these can be tricky, but this is key in being able to manage a team on their level. Some of them are motivated by financial incentives, while others are fueled by praise and appreciation. This, I admit, has been challenging for me at certain times. Though I do have one of the most bubbly personalities you’ll meet, I am at the same time not someone who naturally shows much emotion when something upsets me, and if I do, I give myself a few seconds then move on. I am a fixer. Therefore dealing with an emotional team member can be very uncomfortable, and I’m sure a team member with a different emotional makeup would say the same thing about my natural tendency to encourage someone, even my kids, to “just get over it, pick yourself up, and move on.” I have had to try very hard to keep in mind that each of us is wired differently, and this is something that I still work on every day.

Contact Info:

• Website: www.lisapleasant.com
• Instagram: @lisapleasantevents
• Facebook: facebook.com/lisapleasant

Image Credits
Wilder Weddings Co. Alexander South NC Beautiful Life Films Critsey Rowe Photography The Wedding Traveler