For Seven Years I Wanted to Leave Chicago

For seven years, I wanted to leave Chicago. For seven years, I passionately spoke about my need to be elsewhere and toiled with trying to leave but the doors just not opening.

For seven years, I wondered if I’d get stuck and never be able to get out. I tried to do my best to grow, be better, dig deep, embrace the present, and be thankful for what I had. 

For seven years, I wrestled with the idea that “the grass is not greener on the other side” when I believed that sometimes it was.

And then suddenly, that all changed. 

It was the start of 2018 and I had just enjoyed a nice long week off of work for the holidays. I was a new CEO with a vision to lead the company, I was thoroughly enjoying my new little baby, my kids were doing well, my partner and I were thriving in love and in our work together, and I had set very clear intentions and goals for the new year that felt really good. I was quite optimistic and excited that despite all the ups and downs of 2017, this was going to be a good year and I was going to make it through.

However, I couldn’t keep myself from feeling a deep inner turmoil. Tears kept welling up and I felt heavy. “What is going on?” I thought.

It was as if the undercurrent got a hold of my feet and began slowly pulling me towards the center of the ocean. 

Do I fight it or do I yield? 

Although I’d lived in Chicago a lot longer than seven years, it wasn’t until I went to Baja California Sur, Mexico for two and a half months that I realized what I needed to thrive as a human being. I left everything for those months, including my two young kids. No Facebook. No phone. For that time, I backpacked, sea kayaked, and sailed in the Sea of Cortez in search of peace and direction while mourning the loss of my mother. I found a part of myself I didn’t know existed. A happiness that sits grounded at the center of my belly.

It was the first time I experienced what it is to have a quiet mind and it changed me forever. Since 2011, I yearned to get back to that.

And now, here I was, seven years later feeling like despite my best efforts to “look on the bright side”, as I’d been conditioned to do, my wild woman was wrestling me to the ground until I listened. She had something to say.

I went in my room, closed the door, and tried to listen for 45 minutes. Alone. Not an easy feat with a five month old.

“Okay, I’m here.” I said. 

“What is it?” 

“What’s going on?”

“What wants to emerge?”

“What wants to be uncovered?”

“Why do I keep crying?” 

“Why do I feel heavy?”

“What the fuck.”

I spent some time reading journal entries from a pertinent moment in 2016. 

I pulled some cards from a mother’s wisdom deck.

And I wrote ferociously.

I didn’t know what wanted to surface and I didn’t know what I was writing. I was simply trying to channel what I was hearing and allow whatever was buried deep inside to reveal itself.

I’m usually pretty self-aware and in tune to my gut and intuition. However, in 2016 I took a job with a company after working for myself for two and a half years. I tried to justify it but for the entire time I was there, I couldn’t reconcile that I’d given up the freedom and autonomy of working for myself. It never felt totally right. Not because I don’t enjoy working and learning in a company setting, in fact, I think there are things I learned that I would have be unable to learn on my own. 

Instead, it was more that I’d felt I’d done so much work in those two and half years to learn about myself, find my rhythm, own my power, and live a life that holistically supported all that I was. I felt I was realizing my potential as a person. By taking the job, I knew I was putting all that on the back burner because it was nearly impossible to maintain that level of self-care, mindfulness, and flow in a job.

Work became my main focus and caused a lot of unnecessary stress. I got completely out of balance. There was drama, my relationship was going through its hardest time ever, and three months after getting the job, I was pregnant with my third child. 

I slowly got disconnected from me and started to lose track of myself, my voice, my creativity, and my mission. 

I reached heights I didn’t know I could by becoming the CEO during my maternity leave. However, I could no longer hear my intuition clearly and be decisive, and for me, that was a serious problem.

So as you can see, while I was happy about the new year, there was a sea of happenings that needed navigating. What was emerging in my room was a result of nearly two years operating in a space that was not ideal for me to thrive in but I was trying. While what was unfolding in my room that day wasn’t totally transparent, one thing came out that I was able to latch on to. 

“What would it look like to go to Hawai’i for a month?” I wrote.

I know. It seems so random.

But “what would it look like to be there for one month? Just to visit.”

What I was discerning was that if I’m going to be working so hard and if I’m going to be the CEO, I have to do it my way. I have to be true to who I am. I’m no good as a leader if I don’t care for myself or if I try to succumb to some false idea about what it means to be a leader. 

While I didn’t want to give up on this new commitment I made to lead the company, I also knew I couldn’t keep things as is. So I tried to figure out how I can be and do better. 

“What do I need to thrive?” 

“What do I need to be my authentic self and lead this company?” 

“How can I honor my wild woman and be a CEO?”

“How can I be a present mother to a new infant and be a CEO?”

“How can I be a faithful partner and honor my wild woman?”

“How can I lead differently, as a woman of color, and maintain boundaries?”

“How can I be a CEO without compromising my values, my priorities, my sanity, and my soul?”

“Is all of this even possible?”

I came out of my room and said to my partner, “Babe, what if we went to Hawai’i for a month?”

He looked at me like a true Virgo would.

I was relieved that he was open to my insightful yet very much unplanned revelation.

Over the next few days we talked a lot about it, looked up flights, researched islands, and tried to book accommodations. The angst I had been feeling lightened up which made me wonder if it was just a fad and perhaps we don’t actually need to go. Maybe I just needed to get it out.

But, my now fiance, encouraged me to keep with it and make it happen. He went full Virgo and booked our flights and accommodations. In just three weeks, we’d be in Hawai’i and I was beside myself.

While I knew this trip wasn’t the full answer to all those pressing questions mentioned above, I did feel that I had just done something major. For myself. I prioritized me, my truth, my wild woman, and my intuition and I was going to Hawai’i. For three weeks. I shifted my focus from putting so much energy trying to understand things I couldn’t to focusing my energy on what was clear. To a place where I had control and power versus where I didn’t. 

In 2017, I gave into drama, worry, fear, over calculation, doubt, and other people’s shit. In 2018, I was making space for abundance, flow, intuition, gratitude, joy, trust, and #nodrama. I truly wanted to thrive this year. To realize greatness.

To make this decision despite all I didn’t know, was life-giving, liberating, and inspiring. It was just the beginning but I felt like Tiff was making a comeback.

It’s been four months since that day and in hindsight, I can clearly see how that moment of decision was a real catalyst for all that was to come after. The floodgates literally opened.

Two weeks later, I resigned from my CEO position, completely unplanned.

Four weeks later, I was on a flight to Honolulu for three weeks.

While in Hawai’i, we got engaged and decided to move to Honolulu within six months.

A week and a half after returning to Chicago, we ate at our favorite sushi place where we usually hashed out major life moments and made the decision to execute on the “fuck it” plan. We’d move to Hawaii in two weeks.

Yes, this is real life y’all.

That Sunday, David took a plane back to Honolulu to find us a place to live. 

By Thursday, he found a place and signed a lease.

Two weeks later, we’d sold all our belongings, said our goodbyes, and piled into our Blue Honda CRV with eight suitcases for a four day road trip across the country to LA. We’d ship our car from Long Beach on April 3rd and fly to Honolulu on my 33rd birthday, April 4th.

How could I have possibly known that day in my room, that three months later, we’d move the entire family across the ocean? Without a job and without much savings.

The truth is that I couldn’t have known.

Each moment in life, we’re given these opportunities to listen and respond. You never know if one of those moments will be a life-altering, shape shifting, epic moment but nevertheless, you do the best you can to make the best decision you can. Then you trust it.

For seven years I wanted to leave Chicago because I knew it wasn’t the right place for me. But during those years, I learned the importance of working in partnership with the universe to make life happen. That everything comes in its right time and it’s my responsibility to focus on what I can control, own my power, and strive to always align my life to my values.

Four months later, I now call Hawai’i home and am utterly amazed at just how fast everything can change.

This story is also published on Medium.

Tiffany HintonComment