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Ingrid Riley
Ingrid Riley

Entrepreneur. Super Connector.

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Ingrid Riley

Entrepreneur. Super Connector.

The Four Intentions of My Radical Sabbatical

Ingrid Riley, March 30, 2019April 3, 2024

Picture this:

It was a process that started in 2017.

I resigned from all government boards and advisory councils,

I put a hold on all startup mentorship and saying yes to startup board appointment requests,

I closed my pioneering and iconic Caribbean Startup event brand Kingston Beta in June after 11 years,

I reduced my blogging efforts everywhere especially at SiliconCaribe and

I sent an email to what was thankfully a very short list of creditors,

I stopped looking for new digital consulting projects.

In short, I was in full on selfish mode.

I wanted no responsibility for anyone or anything other than my damn self-breathing, eating, moving, being, exploring, meditating, thinking or doing absolutely nothing but staring into space.

So I hopped on a plane last July to join my bestie Marlon James in New York. I was only supposed to be there for 10 days, the time got extended by a few more days because, I got called to do a technology panel moderator gig by the Clinton Foundation in Miami on my way back to Jamaica, then I was back in New York again for my birthday in October, 2018 and my life has not been the same and I am so happy for that. And so it began. I ended up spending two months in Williamsburg, Brooklyn, ringing in the New Year with Marlon and friends – quietly, effortlessly and consciously. Most importantly…New York was so good to my headspace and heartspace and so things unfolded from there.

My radical sabbatical was over due.
 I had hit a plateau, was bored, antsy and had outgrown a lot of people, places and things in Jamaica, in my industry( Caribbean Tech). And while I knew I needed to challenge myself, to do things very differently in my life and business…I wasn’t super clear about what I wanted to be, do, have next, I did have a few ideas written down in a couple of note pads and on my phone, and I had some starts and stops with a few things also. And also, many times I thought my ideas weren’t big enough, different or worthy enough to pursue because I was comparing myself to others.

But I needed time to reflect, question everything again, seek newness in place, people and purpose, read a crap load and experiment with new platforms and ideas and most importantly, trust myself to follow through on what emerged and felt right to me and not give a flying fuck about what anyone thought.

And what emerged for me was this: that the four outcomes I want out of this radical sabbatical are:

  1. What I’m going to do next business wise – DONE. I just launched my new Cannabis Marketing and Business company Digital420.co in March 2019, while I was staying with friends in Lawrenceville, Atlanta. This is done and I am happily on that journey. I am building a business around my lifestyle, about the way I am want to live from here on it. Decided to be super focused and go deep on this for the rest of 2019 and see what happens.

2. A decision on where I’m going to live next. DONE. It’s New York. (Updated Sept 1)Which city in this amazing, beautiful and abundant world am I going to live next. I love Jamaica and will always have a base there, but I’d been craving more for a while (intellectually, socially, culturally) so I want to see which city and in which country moves me to want to live there, even for a few years. So far, New York fits where my head and heartspace it a the moment. So unless the Abundant Universe has some better city for me, it’s likely to be New York and Kingston as my twin home cities.  Now to have the best apartments in both places that are just right for me.

3. Be in a really great relationship. NEXT UP. I started dating again just over a year ago, slowly, after a conscious decision to remain single for 2 years, to heal, work on myself and redefine what the kind of relationship that I really want and deserve..and what that would look and feel like. So yes, I started dating in Jamaica…but now, that pool of choice is even more expansive as I travel and even now using apps which are not yet in the Caribbean, but mostly by attending events, dinners, shows and new fun activities that really excite me. I feel ready to meet the love of my life, fall in love and be in a relationship with my life partner – so I’ve been just open, thinking and doing things very differently in this aspect of my life. So let’s see how this deliciously unfolds.

4.  Express More of Myself. All of myself. DEFINITELY DOING, SO DONE. (Updated Sept 1) What I mean by this…is just to be more open, authentic in how I show up every day and in every situation…to speak my truth, live my truth, dress like my truth, love in my truth, show my truth, be happy in  my truth, evolve in my truth and allow the chips to fall where they may. And allow my tribe, community, desires, dreams to evolve from that position.

For much of my adult life… I showed only parts of myself to certain people..including my family because I cared too much about what people thought about me. Now, that I don’t give a flying fuck what my family, friends or anyone has to say or to think about me, it’s amazing freedom. Only my close friends really KNOW me. Added to that, I’ve been largely about my career and business and I show much of what I thought would be good for business, versus now, I only am doing the kind of business and investments that resonates with me and seeking to work with people and brands that reflect that. Plus I’m working/doing business in a way that wraps around the life I now want to live. I had always wanted to live this, but didn’t dare…until now.

I dunno what the fuck happened when I hit my mid 30s where I thought I had to tone down…hide who I was….still am – the Ingrid the lgbtq party promoter and former gay bar owner, Ingrid who loves traveling and exploring, Ingrid who smokes weed for pleasure, insomnia and bad periods at times, Ingrid the self-experimenter, Ingrid has both the spirit of a New Yorker as well as a flip flop, tshirt wearing island girl who loves to sleep on the beach and driving droptop jeeps and electric scooters, Ingrid who loves and collects Art, Ingrid the Nerd and who is highly spiritual and is a committed daily meditator. Isn’t it beautiful when you give yourself permission to be and express ALL of yourself and love the multi-dimensional spirit that you are…oh yeah.

                         One could almost describe this Radical sabbatical as the Year to Unfuck Myself!                                   And I rather like it.

“Authenticity is the state of simply being yourself, listening to who you really are, and making decisions that align with your beliefs and values. Authenticity at its core is about deeply accepting all that is ‘you’ and honoring it above ALL else. ” 

 – Mateo Sol

Send good vibes.

Entrepreneur Wellness Travel & Remote Work Maverick Mediaradical sabbatical

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Comments (4)

  1. Alistair Scott says:
    March 30, 2019 at 6:50 pm

    Wicked! And brave and honourable and so real. We all need this at some point but few intentionally do It. Sometimes it’s life itself that parks us and says ‘chill yaso’ or Detour here. So very happy you got to choose and are reaping the benefits of being newly aligned 🙂

  2. ingridjm says:
    March 31, 2019 at 11:56 am

    Hey Alistair, my choice to do this was a conscious one yes, but life was giving me a few slaps and hints before for sure. lol.

  3. Joel Dean says:
    March 31, 2019 at 9:07 pm

    You go Ingrid! Expecting nothing but greatness from you! Thanks for all the inspiration and work you have put into the tech space over the years! I know the universe will be good to you so keep on exploring & most importantly, do what is best for you because in the end that’s all that matters 🙂

  4. ingridjm says:
    April 5, 2019 at 7:39 am

    Ahhh Joel, Thanks so much for taking the time to read my blog. I appreciate it…your words really touched my heart especially coming from you. Thank you so much for your good wishes and energy. And maan it’s been a pleasure to watch you grow and contribute to the tech community and to education sector..keep rising.

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