9 Reasons I Decided To Take a Career Sabbatical at Age 28
Updated: Feb 25
For context, I wrote the following piece in June 2019, but decided not to share it publicly at the time. The main reason is that I didn't want any of the message to be misconstrued and damage the morale of anyone at my old company. Many coworkers were surprised when I left, and although it didn't have much to do with the company itself, I felt uncomfortable posting a long form piece about why I quit my job, out of respect for the leadership (and the value of my stock options, haha). If anyone else decided to leave for their own reasons, I didn't want to be known for starting a movement of quitting. Now enough time has passed and the company seems to be doing well enough where I feel comfortable posting it. Looking back, I'm very happy that I decided to take the career sabbatical, and figured it might be helpful to people out there in a similar spot to see my thought process at the time.
10 days ago, on the plane ride back from my first real vacation of 2019, I realized I had to leave the company that has consumed my life for the last 3.5 years. Honestly, I’ve thought about quitting once or twice in the last 3.5 years, but something in my gut just told me this time was different. I listed all the pros and cons of leaving in my journal.
The only real reason to stay would be for the steady paycheck. In my soul, I didn’t want to be someone who loses their motivation and becomes an obstacle to progress. I can’t stand working with people like that who do the bare minimum for a paycheck. That’s not me. I wanted to leave on a great note and preserve my working relationships I worked hard to build.
The first day I got back from vacation, I met with my boss to tell him how I felt. He was very supportive of the decision, made me feel less guilty about leaving and came up with a transition plan.
Here’s what I realized on the plane ride:
1. My life had become too soft and comfortable. I didn’t feel alive enough. I felt a yearning for more adventure, more risk-taking, more creativity and more growth. Even though my job allowed me to work remotely, it started to feel like I was just going through the motions with the scenery of a different city in the background. If I was at the office, I hardly ever sat at my desk because it had become so uninspiring. For a few years, I was learning an incredible amount of new information about product development and growing a startup everyday. At some point in the last year, I stopped learning as much and could rest on my laurels to get by.
2. I’ve been living in Charleston, SC for almost 10 years and have hit a ceiling Charleston is an amazing place, but it doesn’t have the same type of opportunities as cities like New York City, San Francisco, Los Angeles, and Austin. Being a big fish in a smaller pond has given me a ton of advantages in launching my career, but at age 28 those advantages are morphing into disadvantages. The only reason I’ve stayed in Charleston for the last 3.5 years is because my company is headquartered here and I had the flexibility to travel. Many of my more ambitious Charleston friends have either moved on or are in the process of moving on to other cities. I feel like I’ve built an amazing network in Charleston, but am probably done meeting most of the people I want to know. I’ve hit a ceiling.
3. I eventually want to be around family and the energy of Austin I have zero family in Charleston. For the past 10 years its always felt like a large missing part of my life. My sister and several cousins and their families live in Texas. Austin has an amazing energy, and many of my internet idols are moving there.
4. I want to explore what’s possible with the free time and mental space that comes without having a job I’ve become so effective at 'GSD' that I’m curious to see how that energy can manifest other things when it's not mostly going towards a job. Instead of having my mental energy chained to slack, email, and meetings from 9-5, I’m excited to see what I can do with a true blank slate.
5. I have several projects and adventures to work on. I’m not just quitting my job to sit on a couch and blast my resume to 100’s of companies. I have several passions and adventures I want to work on. My job started to impede my ability to focus on these projects.
6. Limited career upside The opportunity cost of leaving didn’t feel like much. I didn’t see an immediate opportunity to switch roles and continue to grow in the company. My stock options were 75% vested. My salary had been stagnant for a while.
7. I need an extended break from working The standard advice you get from conservative, traditional adults is “You’re crazy. Never leave a job before having another one lined up.”I’ve put a lot of my heart and soul into my job the last 3.5 years, and I can’t imagine jumping into another job right away. It would be like jumping into another long-term relationship a week after breaking up with you ex-girlfriend. I haven’t even updated my resume or tapped any connections at this point.
8. Sense of Urgency to See More of the World I know I want a family and kids in my 30’s. As I’m about to turn 28, that time seems like it's rapidly approaching. I want to experience more of the world in an authentic way before its time to settle down and have kids. I feel like if I don’t make it a priority, it won’t happen. Life is precious and nothing is ever guaranteed. I don’t want regrets
9. Now just feels like the right time in my gut
I believe the purpose of life is to fulfill your potential.I have no wife or kids. As my 28th birthday approaches, I feel the pressure of time to make a big change in my life. I’ve been able to save money the last few years to afford to take time off working a full time job.