On Leaving Behind a Life You Love

A few months back, I was feeling unsure about my direction. So I read my tarot cards.

The first card I pulled was a hierophant. It read, “You may be struggling with an issue and are unsure about what is “right” for you to do. Know that the answers are within you.”

At the time, I was considering quitting my job and moving to Uganda. Naturally, I was conflicted. Do I leave behind a wonderful life to move to a continent I’ve never visited? I wondered. Or do I be grateful and stay the course?

Then I read a post on Elizabeth Gilbert’s Facebook page called “START KNOWING”. It read, “Anytime I am faced with a dilemma, and I start to feel very small and confused, and I hear myself saying, “I don’t know what to do!”, some voice from deep within me rises in full power and says, “START KNOWING.”

I’m not sure I believe in signs, but these two small events, especially so close together, felt like an indication.

Finally, I realized that I knew the answer to the question I had been asking for months. It was time to go to Uganda. It was time to leave Boulder.

But that didn’t mean that it was easy to decide to leave. I’ve carved out a home in Colorado. I have a roommate and a dog and an insanely comfortable bed.

More importantly, I’ve made friends here. Really good friends. Friends who will help me move or co-host dinner parties or help me run lines for acting class.

I have friends who come over every Tuesday to drink wine and laugh until we cry. Friends who I will miss, and who are sad to see me go.

It feels strange, almost irresponsible, to choose to leave a place I love. To discard the things that I wanted so fervently when I was younger: a paycheck, a group of friends, an apartment to call my own.

But I know how fortunate I am to have the opportunity to live in Uganda, and it’s not an opportunity I’m prepared to pass up.

And as my dad said, “You’ve got to find a deep harbor to launch a big ship.” For me, Uganda is that harbor. There’s so much I want to do in the next year that wouldn’t be possible in Boulder.

And though I’m sad to leave a good life behind, I’m beyond excited for what’s ahead.

I also wanted to thank so many of you for filling out my 2017 reader survey! It’s given me lots of insights on what I will post going forward. If you haven’t filled it out yet, take it here.

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About Ashley Fleckenstein

Ashley is a travel and lifestyle blogger who lives in Ann Arbor, Michigan. Since college she has au paired in Paris, backpacked the world solo, and lived in Uganda. Her work has been featured by Buzzfeed, Forbes, TripAdvisor, and Glamour Magazine.

22 thoughts on “On Leaving Behind a Life You Love”

  1. I think your decision to go to Africa is the right one. You are listening
    and knowing this is right for you. It is another adventure and
    Learning experience. I can hardly wait for your notes on a completely
    new country ( continent? ). Tell us all, for I will be traveling with you
    Vacariously, and feeling I am along with you even though I am sitting
    In my comfy chair in my morning room!

    Love❤️ Gamma

  2. Your father is a smart man. Life is a journey, live it. Just use common sense every day and get back in time to vote in 4 years. Wink.

  3. Good for you for making such a brave call! It’s not easy to leave family, friends and the place you love behind but life is a journey! You will learn so much and have an amazing time in Africa. Travel is such a great way to grow and learn about yourself. Wishing you the best with your journey Ashley! xo


  4. This article really hit a soft spot for me. I’m leaving the country I’ve lived in all my life to go to England, and it’s the scariest decision I’ve ever had to make. I still have doubts ever day, but I guess only time will tell whether it is the right decision or not. Good on you for your courage to leave behind Boulder as you head to Africa. I’m sure you will love it and feel inspired by your bravery!


  5. Ashley – This was a great post! I felt really similarly about a year ago when I decided to leave behind my amazing life in Chicago to travel. It was so difficult to leave behind friends, a great job, and a life I loved for something that wasn’t guaranteed, but I couldn’t ignore the voice that kept telling me to go! Of course, it ended up being the best thing that I ever did. Funny how that happens when we listen to the voice!

    I look forward to following your adventures in Africa!

  6. Good luck on your new journey Ashley! I’m sure it was a hard decision but I promise you’ll never regret it, so many adventures and life experiences are waiting for you and I think I’ll speak for all your readers we’re excited to read about them :)

  7. These decisions are always so hard to make, but I am sure whatever you decided the outcome is always a lesson. May Africa bring you joy just as Boulder did.
    Funny thing is that Boulder is a place me and my hubby have been talking about in the past year. =D
    Who knows maybe one day we will meet there?
    Good Luck Ashley!

  8. I feel as Ive gotten older it has become harder to ‘know’ what the right decision is. Good luck with Africa – do you have a job lined up in Africa? If so what do you do? As someone has said below, you will not regret it – life is an experience!

  9. Hi, Ashley. Hope you’re well. I just came across your blog and it’s not all the time that I would subscribe to blogs but I did with yours simple because you’re an inspiration. Loved your blog, simple yet inspiring. xx

    I’m currently in Dubai, been here for almost four years now and yes i’m working here. I’m originally from the Philippines. It would be lovely if you would visit my country someday, there’s the best island in the world (Palawan and Boracay) and of course a lot of other places to visit too. We are in the same situation because I’m also planning to move to Africa (South Africa to be exact). Where are you exactly planning to stay in Africa though? Dubai is nice it helped me grow in so many ways but i just felt like i needed more, i wanna try something else. Now that I have turned 25 (just recently haha) all i wanna do is to go to another place, meet new people, find a new job and simple take risks. I’m so glad you finally made your decision, as for me, I still have to think things through i guess. But i hope whatever my decision would be, i hope that it would be the best for me. Kindest regards from Dubai xxx

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