Into the Bold Annie Sisson

Travel Designer Encourages Us to Go Into the Bold

I am so thrilled to introduce you to Annie Sisson from Into the Bold. Annie is a Travel Experience Designer and basically has my dream job (oh wait – I’m creating that right now – maybe my future dream job!) We met on Facebook group for women who love to travel and I laughed when I saw her profile photo because it was more or less identical to mine – a gal enjoying a beer in a European pub. We connected immediately and I’ve excitedly followed her journey over the past few months as she builds up the travel side of her business (during Covid she focused more on empowerment coaching – how cool is that?). She’s built an awesome website at where you can see all of her upcoming offers and resources, a new membership site, and group travel (Scotland in the spring anyone?). I absolutely love her tag line: “Life is short and the ride is fast, my friend. Go adventuring. Have fun! Eat well.”

When did you start your business, and why did you create it?

I started my first travel-related business in 2015 but that one didn’t go the way I’d thought, but it was a great learning experience! The most recent iteration began in April of 2019 and then took a long, forced break during the covid times. I created all of these businesses because I want to help more people get out and see the world! The experiences I’ve had while traveling (on my own, not with tours or cruises) have been some of the most impactful and positive things in my life. I’m passionate about making the most out of this one life I have to live and helping others do the same, especially if that means travel!

What do you feel makes your audience special?

These are strong, independent, badass women who are lit up about life and want to chase their big dreams. I just want to help create the opportunities for them to have and do everything they want! <3

If you could magically give all of your community members one thing in this world, what would it be, and why?

I would give each of them a mirror that shows them what I see in them. Then they would never doubt their beauty, strength, or worthiness again!

Has anything surprised you about starting a website?

Everything takes about twice as long as I think it will! Lol! I took some web development classes in college and have played around with WordPress as a hobby so I know just enough to think I can do it all on my own only to discover I don’t know quite as much as I thought! 😛

Did you create your own website or hire it out? Do you use WordPress?

I’ve created all my own websites using WordPress.

What advice would you give to someone who is thinking about starting their own business?

Be really clear and convicted on why you’re doing this. If it’s just to make money, that may not be enough motivation to get through the tough days. And there will be tough days. Sometimes there are many tough days in a row. You’ve got to love what you’re doing enough to keep going even when it feels like you’re fumbling around in the dark.

If you could go back in time and do something differently, what would you do and why?

I would have started building community sooner. As an only child, I’ve always been a bit of a lone wolf and didn’t understand the importance of relationships when it came to creating a business. The #1 reason my first business didn’t work was because I didn’t have a network of other entrepreneurs for support and I didn’t really talk to the people I wanted to serve. I thought if I just made awesome trips and built a great website the rest would take care of itself. I was SO wrong!

Do you have an email list? If so, did you start it when you launched?

Ooh, my email list is under 200. I totally understand the value of an email list and it’s something I want to focus on in the near future. However, the relationships I’ve built instead of the email list have been much more valuable in helping get this business off the ground than I think an email list would be. There are only so many hours in a day and energy in my body so I have to choose where to focus, but an email list is climbing its way to the top of my priorities. 😊  

Is this your only job? Did you launch your business while working another job?

Yes, this is my only job now. I launched this business while still working my full-time job as a Quality and Training Manager.

How do you promote your site?

Mostly through social media – Pinterest, Instagram, and Facebook. I’m still working on this part. I love blogging and want to make that a focus once I get a few other projects off the ground.

Who are your favorite bloggers or podcasts right now? 

Bloggers – I love following the adventures of Jordan over at Global Debauchery and Jessie on a Journey. Podcasts are usually an episode or two at a time, depending on what I’m into at the moment. Most of them are travel, mindfulness, or business related.

Is there anything else you’d like to share?

For my fellow lovers of travel, I’m going to be launching a membership community soon to share all of the knowledge and experience I’ve gained over the last 13 years of planning all my own international travels! I’m SO excited to help others skip some of the hard or expensive lessons so they can just maximize the money and time they have to spend on travel! You can sign up for emails and get all the details soon!

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