Digital Nomad or Virtually Homeless?

This is a difficult post for me to write. I’m going to be incredibly honest. Sometimes uncomfortably honest. But I need to get these things out of my head and off my heart. As part of my healing process and as an opportunity for you to get to the more vulnerable side of me. Not the sassy, funny or witty side. The part of me that’s flawed and fearful but willing to look at those things and grow.

Lately, I’ve been feeling scared and anxious. My summer job is coming to an end which signifies the official beginning of my life as a Digital Nomad. I returned the keys to my apartment over 4 months ago, but I’ve been living and working from a place of comfort. This is my third summer working at this summer camp so the people, my cabin, even the food is familiar. After camp is over everything will be different. It’s exhilarating and frightening AS FUCK!

I’m a self-professed planner. I like to have all my ducks in a row and plan things out ahead of time. But I’m quickly learning, that’s not always possible as a Digital Nomad. My original plan after camp was to do some housesitting in New York for a month. So I could attend New York Fashion Week and live out my dream of being the Black Carrie Bradshaw, minus Mr. Big and the designer wardrobe. I’ve not been able to find any housesitting opportunities in NYC so I’ve resorted to plan B. Visiting a friend in Miami for a week and then spending Fashion Week in New York.

Empire-State-Building-ViewsEmpire State of Mind: View from the Empire State Building.

I have to be extremely budget conscious because I’ll be traveling through South East Asia for nearly a year afterward. And although I have an incredible remote job as a Senior Fashion Stylist. I want the money from my summer job to last as long as possible. I’ve come to the conclusion that for me, the Digital Nomad Lifestyle will center around where I can get the most affordable living accommodations.

Not having a home to call my own and constantly searching for affordable housing is bringing up some childhood issues. Specifically homelessness. I was homeless as a child. I remember sleeping on couches and in cars. I remember panhandling and selling my toys on the street for money. I remember promising myself that as an adult, I would NEVER be homeless.

1980-Baby-Annette-RichmondBaby Netty Circa 1987.

My mother has been sober for over 20 years. But while she was in the streets I was being raised by my grandmother. My grandmother was also an addict. She died from her addiction. While living with her I moved from hotel to motel. From apartment to couch to car. I didn’t always have a place to call my own and having my own room was something I dreamed about. Eventually, my mom got her shit together and was able to regain custody of me and my younger brother. But during some of the most impressionable years of my life, I didn’t know where I’d be sleeping. So as you can imagine, voluntarily going into a similar situation 25 years later could bring up some unresolved issues.

I’m currently feeling like being a Digital Nomad is a glamorized way of technically being homeless. But I know that’s just my fear and insecurities talking. I know that I need to allow myself to live a more carefree and spontaneous life. Especially since I’m currently single and don’t have kids. I feel like I’m constantly fighting against the societal norms that tell me that at my age (32) I should be thinking about settling down, starting a family, buying a house and contributing to a retirement plan. And for years that’s what I did because that’s what I thought I wanted. Now I realize, I felt trapped and pressured into that cookie cutter life. Because of my unstable childhood, I wanted nothing more than to create stability for myself. But I refuse to live inside that bubble. My ambitions have changed. While many of my friends are getting married, starting families and buying homes. My goals now revolve around seeing the world and sharing those experiences with others.

Always-A-Bridesmaid-Beautiful-BrideAlways a Bridesmaid. Not ready to be a Bride.

I feel like I just spilled a family secret. But you’re only as sick as your secrets, right? I’m ready to be open and honest about this. The Crack Epidemic took a toll on my family as it did many other Black and low-income families in the 80’s and 90’s. But I’m proof that you don’t have to be a product of your environment. You can dream big, you can set goals and you can reach every single one of them. As long as you don’t let fear of the unknown hold you back.

Sick-As-Your-Secrets-QuoteWords to live by.

To hear even more of my story read My Most Personal Post Ever and listen to the podcast.

26 thoughts

  1. No need to settle down! 32 is still very young. I’m very familiar with that scary feeling of not knowing what will happen next… I moved to the US with just one suitcase, US$800, absolutely no credit, and somehow made it out alive with a college degree. The digital nomad lifestyle seems very challenging, but I have a feeling you are going to make it work beautifully πŸ™‚

    1. Thanks for your kind words Candy! That makes me happy that you moved here with so little and were able to accomplish so much. Where are you from?

  2. Really interesting thoughts. I agree it is scary and exciting at the same time. But I am sure it will be a great experience for you!

    1. Thanks for the positive vibes Liz! I’m pretty confident in my decision. I just had to express some of the fears that are popping up. I think once I get them out I feel stronger.

  3. Love this post. Can totally relate as am in the process of doing the same thing (I move out of my house tomorrow!). Definitely agree it is exciting and terrifying at the same time!!!! We are starting in SE Asia in November – where are you starting?

    1. Thanks so much Catherine! Good luck with the move. That was a difficult part…getting rid of all my stuff. Nice! I’ll be in Thailand around the end of September, early October. Let’s stay in touch. I’d love to meet up! Bangkok will be home base and I’ll travel about once a month to different countries.

  4. What a raw and honest post! Honestly, I say follow your heart and do what makes you happy. It’s not going to be an easy road and tons of sacrifices will be made, but it’s better trying and knowing, than not trying! Good luck on the future endeavors!

    1. Thanks, Jin! It wasn’t easy being so vulnerable. But I had to get that off my heart. It’s part of my process and one of the reasons for this blog. I’m looking forward to what’s to come. Good, bad, all of it!

  5. You’re very brave to share this, and I believe you will be very successful in all your endeavours, you will love SE Asia I’m sure

    1. Thanks so much Ciara! That means a lot. I’ve been to SEA, I loved it so much that I didn’t want to leave, but had this work contract.

  6. I love how honest and raw you are in this post. And I especially loved your statement “you don’t have to be a product of your environment. You can dream big, you can set goals and you can reach every single one of them. As long as you don’t let fear of the unknown hold you back.” So true. We all come from different backgrounds and have different experiences. Thank you for sharing this!

    1. Thank you for your comment, Rachelle. Those are some of the words I live by. I agree we all come from different backgrounds and circumstances. I find the more that I travel the more I understand the world and that we’re all experimenting with life, trying to create the most worth while experience. And sometimes goals and dreams change and we should listen to that, instead of trying to suppress and fit into a box.

  7. I am 32 as well and I feel more settled than some married dudes hitting on me or married ladies and mothers eager to taunt me πŸ˜‰ Your blog is awesome and you’re doing fine πŸ™‚

  8. Wow you’re so brave to share your story, and so inspiring! You’re definitely doing great girl!! While being a digital nomad is anxiety-producing at times it can also be incredibly worthwhile. Just remember that if it doesn’t work out you have serious skills to fall back on! All the best to you!

    1. Thanks so much Sarah! One of the things I’m most grateful for is my remote styling job. I don’t know if I’d have the courage to do it if I didn’t have such a flexible job. I also have seasonal jobs and freelance work, so I have all those things lined up (Type A personality much..?). It’s just all the little things, like where I’ll be going, when, where I’ll be staying. But it’s what I need. I’ve planned so many aspects of my life because I didn’t want to make the same mistakes as other people in my family. But I’ve been light-weight nomading for a few years and it’s about time I go full on!

  9. Hi Annette. I’m so excited for you! A gap year at 30 was one of the best things I’ve done. I’m thinking of starting a business helping others kick start their long term travel… would you be interested in sharing with me more about your journey to making the decision to go & what support you got (or needed) to plan?

  10. Hi Annette – I know how you feel. The Unknown scares me too – I sometimes suffer from panic attacks and anxiety. But early this year a friend recommended me the book: Ask And It is Given by Esther Hicks and it totally change my life. πŸ™‚

    1. That sounds like an incredible book Mariella! I will look into it. I am just wrapping up a seasonal job and will have a little more down time. Looking for a book. Thanks for sharing and thanks for the comment!

  11. I teared up a bit reading your post! You are a survivor and you’ll make it. I am currently transitioning to this lifestyle and I have the fear of the unknown as well but I can’t settle for what society thinks I should be. Please keep being brave for upcoming nomads like me πŸ™‚

    1. Kareemah! You don’t know how much that means to me. It wasn’t easy to write. But I feel so much lighter now that’s I’ve shared what’s REALLY going on inside this brain-o-mine! I’m feeling much more confident thanks to feedback like yours. I also know that when I put my mind to something, there are no limits besides the ones I set for myself. Thank you for your comment. I’m excited that you are taking risks and following your dream as well. Thanks for the comment!

  12. Great post!!! Thank you for writing it with such honesty. It puts a unique human perspective on the dealings of the nomadic life. It tends to be glamorized as this fantasy forever perfect life. Again, wonderful post!

    1. Thank you for your feedback James! It is highly glamourized and with everything there are many ups and downs.

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