What Its Like to Quit Your Job to Pursue a Dream

It was about a three-year process from the time I got the idea to sail off into a Bahamian sunset to the time I actually quit my job. All the while both our careers kept getting better and better, making the idea of quitting harder and harder. Luckily both Lindsey and I were steadfast in our commitment to make it to the Bahamas.

The act of quitting one’s job is a whole lot easier than one might think. In my case it was a somewhat awkward 5 minute conversation with a boss who had taken very good care of me over the past 5 years. Was it comfortable? No way. Did I feel like I was letting down my colleagues? Absolutely. Did the thought cross my mind that this was the single dumbest idea I have come up with? You bet it did.  Was I scared? Yep, change is scary, especially big changes.

There was another thought though and it was this. If I don’t do this now, what will I think of myself 10 years from now when I look back? That is a reality I couldn’t live with.

While the actual act of quitting was fairly easy, the mental aspect was very hard to swallow. I knew from hiking that setting out into the unknown was about the scariest thing I was capable of doing to myself (also the most rewarding). As such we made plans almost a year in advance to try to the make the transition as smooth as possible. A full 6 months before departure we sold off most of our belongings, and I moved onto the boat while Lindsey moved in with her parents. To keep our sanity I would spend a night or two a week with Lindsey at her parents, and she would spend weekends with me on the boat. (Shout out to Lindsey’s parents for all the help they provided during this transitional phase).  The idea behind this strategy was that we didn’t want to be closing out our apartment and trying to prep boat at the same time. I think we made the right decision, but it was still a rough process prepping the boat and getting rid of things. After I quit my job I literally had 1 week to make final preparations on the boat before we left. It was stressful to say the least. We spent two weeks moving the boat south to New Bern NC which went pretty well despite some hiccups. I enjoyed the company of friends and the progress we were making. After the two weeks was up Lindsey went back to work, and I went to TN to flip a house with my dad.

While I enjoyed the time with my parents immensely, the insanity of our plans really started taking a toll on me. It was the first time in a long time I had a dark cloud hanging over me. I knew it was irrational and illogical but I couldn’t shake it. I felt like I was flying too close to the sun. After several days of feeling very down, I opened up and started talking to my loved ones. Nobody “solved it” for me and it didn’t just go away, but just the act of talking about it seemed to make things a bit better. A few positive words from a loved one goes a long way. During this rough time I read an interview with Michael Phelps. “It’s OK to not be OK,” he said, talking about the severe depression he would encounter after the Olympic games. Reading that quote “its OK to not be ok” from somebody of Phelps’s character really put my mind at ease.  My Dad also had great piece of advice: when you feel like shit just turn on some Bob Marley and it will be alright. Accepting that the dark cloud was there but would pass, along with a healthy dose of Bob Marley, seemed to take care of it.

Being reunited with Lindsey and Miss Fe in early February was wonderful and has been pretty great since.

I know that another dark cloud will come with my name on it. Life gets us all down from time to time. The more you ask from life the harder its going to bite back occasionally but its worth pushing through; the grass is greener on the other side.

Quitting any job is hard. Quitting to pursue a dream is really hard. You shouldn’t expect it to be all fun and games. It’s going to be an adventure and adventures always have their ups and downs. My advice: take a deep breath, talk candidly with your family/friends and maybe put on a little Bob Marley. If you’re still looking for more checkout the book section on our Things We Love Page. A lot of them have some great advice for getting out of a rut.