Travel insights from Jennifer Dugan, chief family officer for Dugan’s Travels


Recently I was asked the question, “What would you tell the younger version of yourself about the lessons you have learned in the past 20+ years of owning your own small business?” Gulp. Where do I begin? I have learned so much and some of it I have not even figured out yet. When I reflect on beginning my journey as a business owner, I feel like the reason I got started was innocent enough. I saw a need and wanted to fulfill it. I enjoyed teaching others and helping them grow their own business. I feel like my intentions were in the right place, even back then.

It was also about companionship for me, because I was alone myself. This might have been part of what would become my biggest struggle though, because I got close to those who became part of the agency. Some people who then became a bigger part of the agency knew me personally and unfortunately, I feel knew how to manipulate me and prey on my kindness and openness. I grew fast and I needed help. Knowing what I know now, it’s obvious that unfortunately sometimes the people closest to you in business do not always have your best interests at heart.

 If I had to have a heart-to-heart with my younger self, I would give myself permission to be more discerning with those I chose to handle certain aspects of my business for me. I should have found people who did not want to run my business, but instead help the business. I struggled with people who looked at my business as a means to get what they wanted or needed rather than looking out for the best interests of the business or myself. I had it happen more than once I am ashamed to say. It is painful and I felt naive and disheartened each time.

I wish my younger self understood that everyone coming to you saying they can help you does not have the good intentions you might think they have. Some will use what they know about you to gain for themselves. Some will use it to help the competition. Some will cause mutiny within your business. Some get the taste of power and hope to overthrow you because they want to be the one running the show. They will go after those who are not like that and take advantage of it. They will look at it as if they deserve it and you owe them. These kinds of people also do not go away quietly. They do not take no for an answer and they do not care what damage they do. It is a hard lesson and maybe that is why it took me twice to learn it. I wish I knew that it was okay to be very selective with the people I surrounded my business with.

There will be times in your business you do need help. There will be times you want to expand and need to find someone to fill a role that will require trust. I’ve come to recognize several red flags that will hopefully prevent me from repeating past mistakes: The person who constantly asks you if you trust them is a red flag. The person who has secret meetings with others is a red flag. The person who thinks they can do every job in the business is another red flag because no one can be the expert in everything. Someone who is grounded knows they cannot be a specialist in every aspect of business.

Find people who will do their job well and not want to take over other’s jobs. Go outside for help if possible. This has been the best thing I have done for my business. I have begun to use virtual assistants that specialize in different areas. Right now, I have ten virtual assistants that specialize in different fields. I can request specific help when I need it, and this allows those who are a part of our current team to not have to do more than what is already their duty. It does not spread anyone thin and allows miscellaneous jobs to get done by people who are actually skilled in those particular areas.

Overall, I’d tell my younger self to accept there are going to be emotional challenges in owning a small business. There will be moments you want to throw in the towel only because of your heart. Be prepared for it. Give yourself time to recoup when it happens. Focus on what you can do when that happens rather than dwelling on the mistakes or how hurtful it can be. Owning your own business is a lot of trial and error, and making mistakes is how you’ll learn. Take each mistake and do not let it harden your heart. No one can teach the things that you learn from mistakes… sometimes you just have to make them to learn. I have 20 years’ experience as a small business owner and I am still giving myself the grace to learn along the way.

About the Author

Jennifer Dugan

Jennifer Dugan founded Dugan’s Travels in 1997 with the goal to have a career while being at home with her growing family. Since that time, Jennifer and her team have created a family-friendly host agency where hundreds of agents work to realize the dream of owning a successful home-based travel business. Dugan’s Travels, now a recognized top host agency in the United States, offers comprehensive education and development programs to help agents gain knowledge, establish industry relationships, and build the confidence needed to succeed. When not working tirelessly to put her agents first, Jennifer enjoys spending time in the mountains with her husband and seven children.

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