Season 1, Episode 15

Work & Travel Secrets

 In this episode, I share what it’s really like to take your business on the road and work while you’re traveling. I definitely had some wake up calls when I took my first trips as a full-time entrepreneur because I didn’t actually know the best strategies to manage my time between work, travel, sight-seeing, etc. I share some of the strategies that worked best for me and also shed light on some strategies I’ve seen others use. I hope you all find this episode helpful as you prepare for your next (or first) trip as an entrepreneur!  


Episode Highlights

Hosts & Guests

Jackie Kossoff, Host


The Millennial Success Society

Connect with other millennial women entrepreneurs by joining our community on Facebook! 

Inside This Episode

(1:15) One of the reasons I started my business was so that I could travel and see all of the places in the world I dreamed of seeing and take my business with me.

(1:50) For me, traveling was a BIG factor in wanting to start my business. 

(2:20) Back in 2017, I took a two-week vacation with my family to Hawaii

  • My family goes to Hawaii every two years.
  • After I returned from this vacation, I realized that I don’t want to see the world in just two week increments once a year. 

(3:35) When I was introduced to the online entrepreneur groups, I got connected with women who were already traveling the world abroad and working. I realized that is what I wanted to do, too. 

(4:10) I am actually taping this podcast on vacation in Charlotte, North Carolina!

  • I’m visiting my sister.
  • Working while I’m traveling totally works, but it’s all about time management.
  • I have to break up work, sight-seeing, and spending time with friends and family. 

(5:33) Personally, I have found that when I take a shorter trip–a week long vacation– where I’m visiting and staying with my friends who are still in their 9-5 jobs, I go to work when they go to work in the morning, and then I sight-see in the afternoon.

  • For me these trips are much more relaxing and working, especially if I have been there to visit them in their city before.
  • I even allow myself to sleep in! 

(8:08) When I am taking a longer extended trip where there will be a lot of sight-seeing, I find that it is easier for me to break up my work days and travel days.

  • I cannot work and sight-see in the same day because I will be exhausted in the afternoon by the time I have to start work.
  • What worked best for me was one work day for every two travel days. 

(11:11) Before I realized this, I was trying to work and sight see in the same day. I was absolutely spent by the time I had to work, and it was so hard to get my stuff done for my clients! 

(11:53) Now I have realized that breaking everything up is much better for me; I even added in a rest day to recuperate! 

(13:02) Thinking of my schedule in week-long increments and having designated work, travel, and rest days makes me feel a lot better about life. I don’t feel behind at work or stressed! 

(14:22) If you’re not sure what will work best for you before you go on a long trip, take a fake trip at home and test out sight-seeing and working in the same day, or trying to break it up! That way you’re prepared for your trip! 

(17:40) Stay tuned for more solo travel episodes! I’ll be talking about other topics such as packing and making other travel arrangements when you are an entrepreneur.

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Links Mentioned
Millennial Success Society
Jackie’s Instagram