The Unexpected Vacation

Oh, Club Med...

​Today’s challenge is to write about something I’m proud to have accomplished at some point in my life. It might be strange to think of quitting a job as an accomplishment, but as I look back on my past year, or even 10 years, it ranks near the top of things I’m proud to have done.

The decision did not come easily. There were dozens of pro and con lists. The list of pros for staying was long: good company, people I liked, well compensated, travel, some schedule flexibility, and I had helped build the company. I felt like I was leaving a piece of myself behind. All of those months of hard work and pulling together as a team to create something from scratch, and I was going to walk away? Maybe, because, con: I’m exhausted. I spent a lot of time convincing myself that I was lucky to be where I was, and there were at least a million people in NYC who would gladly push their grandmothers under a bus to have my job. Probably true, but I had to admit to myself that it was irrelevant. I was feeling burnt out and run down.

After months of mental gymnastics I still wasn’t convinced, and the cycle of analysis-paralysis wasn’t getting me anywhere. This is when my inner Tracy Flick* took over and gave me my solution. I decided I could leave if I got right to work on another new venture. Yes! This was the answer. I’ll start over and build my own business this time. I’ll help women learn how to take care of their financial futures! I can use my skills and also do some good for people. Sure it’s an insane amount of blood, sweat and tears but what the hell, I like that. It will GIVE me energy. It will take a few months to sort out all of the filings and registrations necessary, but 8 or 10 weeks, tops, and I’ll be up and running with my shiny new shingle out for the world to see.

With this decision made, I chose a quit date and pulled the plug in March of this year. The day after I left my job I set off for Club Med Bahamas to meet my friend Leah from Los Angeles for a week of relaxation before I got to work on the new venture. When we arrived at the resort I was in full on New York type-A mode. I dragged her to the introductory information meeting and sat in the front row taking notes. I immediately picked up the weekly schedule of events and started planning which days to snorkel, play volleyball and take Zumba class. This was when my friend started to laugh, looked me in the eye and said, “Katherine, you can’t ‘win’ Club Med! Relax. There’s no first prize here. Just have fun and chill out.” Until that moment I didn’t realize how wound up I had been. I took her advice to the extreme and by day 3 I had lost all motivation to schedule anything. We woke up when we woke up, headed to the pool, and maybe took the water aerobics class. Prior to the trip I thought the two of us would spend hours discussing business ideas and planning the months ahead. Instead, we read magazines and bad fiction, and chatted about life, relationships and travel. I realize that this is what vacation is supposed to be about, but I had been so focused on the next step that I lost sight of the need for a break.

By the end of the week starting a business was the furthest thing from my mind. I was spending my time contemplating what I could do to support myself living in the Caribbean. I could sell my possessions and live the island life! I actually researched which islands allow you to bring a dog.  I called my attorney and told him to postpone filing the LLC documents he had prepared for a little while longer. I had to figure out a few things first.

Deep down I never thought a change that drastic was what I wanted, but I realized then that a serious break was in order. I decided to “lean in” to my new found freedom. I slept late, walked my dog miles every morning, worked out daily, met friends for happy hours and dinners, and stayed up late watching TV. I spent the month of May in Colorado with my friend Joyce who had also quit to take an extended break. We rented an apartment and lived like locals, with some gorgeous time out in the mountains. I contemplated moving there permanently to lead an easier, less expensive life, but deep down NY was home and I was ready to go back. That brought me to June, and a full three months of relaxing and figuring out my next steps.

Back in New York the days flew by at warp speed. I was never bored but always had that nagging voice in my head telling me that I should be “figuring it out.” I read a lot of books on entrepreneurship, leadership and passion. I answered surveys and built timelines and journaled pages and pages of ideas. The more I explored, however, the more I realized that I wasn't sure what kind of business I wanted to build. I was holding onto ideas in my comfort zone – what I had done in the past. The problem was when I examined exactly what I would need to do to make it successful I had to admit that I didn’t like doing a lot of those things. I knew I wanted to help women, but I wasn't sure how to combine the education part with actually making a living. Time to hit reset.

​The next few months after admitting that the business wasn’t going to happen the way I had imagined were rough sailing. I felt loss, disappointment, shame and embarrassment. I had made a big deal about building something and now I had to tell people it wasn’t happening. Even worse, when they asked the follow up question of what I was going to do instead, I didn’t have an answer. I felt guilty and indulgent about the time I had taken away from my career even though I knew on some level it was something I needed. I spent a lot of time reflecting on the deeply buried reasons I made the decision to quit.

It’s now mid-November and I’m still in the process of figuring it out, but I’ve come a long way. I grew to understand why I felt so burnt out and accept that I had legitimate reasons. The past 8 years have been filled with many of the biggest life changing events possible. I had helped start 3 new businesses from the ground up. I wrote a book. I moved cross country from NY to Los Angeles and then back again 5 years later, regularly traveling coast to coast in the interim. I had a long term relationship turn into a long distance relationship and then break up. And finally, both of my parents went through extended illnesses and eventually passed away. Until then I had never appreciated the amount of continuous energy I had to keep pumping out to power through all of these major events. Throughout these years I rarely slept through the night. I think back to the concerned faces of friends asking me if I felt ok because I didn’t look so good. I chalked it up to the life of an entrepreneur and would respond with something like, “well, we can sleep when we’re dead, right?” It took me a full 6 months to realize that this break was the best thing I had ever done for myself, mentally and physically.

The last two months have been filled with projects. I’ve tried to help other people who are working on their dreams, I’ve built a website, I started writing again and collaborating with friends who are on the same journey as me. I’m exploring job opportunities that could be about creating something new. During this process I have felt free to think creatively and explore new ideas as they pop into my head. I’ve discovered what really motivates me, and I’ve also discovered some things that I thought motivated me but actually do not. I’m learning to steer clear of these things that I gravitate toward out of habit.

Everyone I see these days tells me I look happy and relaxed, and that’s exactly how I feel despite the uncertainty of what my future holds. If I hadn’t taken that blind leap back in March I never would have had the energy to discover all of these new things about myself. I know my days of unencumbered freedom are nearing an end, but I am ready for the next chapter. I’m excited to get back to work and bring to it a new awareness and motivation that comes from being honest with myself about who I am and what I want my life to be. 

*Tracy Flick was a character in the move Election. If you haven't seen it, go stream it. 

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