Aspireship: My Pursuit of Fulfillment
Several years ago around 2014/2015, I found myself starting to lose motivation. My mentors and I noticed that something was wrong, but could not quite pin point the root of the symptoms. If you are keeping score, this is what lead me to exit PayPal after 10.5 years the first time around in 2016. At that time I was arguably at the height of my career and financial success with somewhat of a guarantee for a stable future. I was also a freshly minted father of two, ages 1 and 2 so naturally this played a significant role in my mindset, that only makes sense in retrospect.
I joined Symantec in 2016 to build and run their cloud thinking something new, with new technology was just what I needed. Boy was I wrong. Symantec was in fact a great place to learn new technology, I learned tons and that was great, but it had nothing to do with the root cause of my motivation challenges, and thus my motivation continued to get progressively get worse. In the fall of 2017 I was in a really low mental space. I read a post on LinkedIn about someones struggles with depression and a light bulb went off in my head. “Could I be depressed?”, “Me, happy go lucky Jason? No way”, I thought to myself.
According to the Internet quizzes I took I was mildly depressed, but you know you go searching for trouble and you’ll find some. Perhaps it was confirmation bias…regardless I needed to make some changes. I still didn’t know what was bothering me I just knew I needed a change again, and I needed help figuring this out, I needed support. My old boss/mentor and friend Kyle Towle extended me an olive branch of an opportunity back at PayPal and I took it. I’ve got a whole post on that, but the summary is I thought having an office ( support system ) and mentors ( to help me figure this out ) was the right strategy to employ, and it was! However, shortly after returning many of my mentors left the company and while the office support system ( my friends there) are nothing short of fantastic, something was still bugging me and my motivation was still off!
Man oh man, how I struggled. Then finally it happened. I met my Co-founder Corey. At first we were just two fathers in the same boat (no literally our second time meeting we were on a boat together lol). As we got to know each other better through our families we started to connect more and more on a personal level. We realized we both wanted to help people, we both wanted to be entrepreneurs (he already was one) and we both wanted to have a huge impact on peoples lives in a positive way. Finally, the day came when he shared the vision for Aspireship and I started to get butterflies in my stomach. Here I was back at PayPal, everything was going great from career perspective, I had a new rock solid amazing team, a great boss, and again a great future with the company, and I love PayPal everyone knows that, it’s got a great culture and great leadership. Was I really going to leave again!?!? But this opportunity was just what I needed, just what I had been looking for.
You see my entire life, I wanted to be a great father, like my father. I would be heard saying things like “I’m not MLK or Mother Teresa. My greatest achievement will be how well I raise my children so they can have that kind of impact”. Well once I had children and they started to grow I started to see who they are take shape and I realized something. I am going to be a great father, no matter what, and that will be my greatest achievement, but it will not be my only great achievement. I don’t need to exclusively focus on only that achievement, I thought I did and that was my mistake. You can be a great a father, AND you can pursue all of your dreams still no matter how big or small. The voice in my head said “Take the risk, live for today and tomorrow.”, or perhaps that was the voice of my supportive wife! Either way we were in agreement.
The motivation? I’ve always wanted to help people. It is in my nature, it is core to who I am, helping people is my favorite thing to do. When I lost my way, it was because I thought I could only help my children, and couldn’t possibly be a great father taking care of them, and helping others. But again, I was completely wrong. I now realize I was selling myself short, I am a great father, I will continue to be, AND with Aspireship I am aiming to start the second half of my life trying to fulfill my other dream, of helping as many people as I can in this life.
Thanks for reading, I know it was long. I appreciate your feedback on the evolution of me, we humans are complicated and connected. If you or someone you know is looking to make a career change to software sales please check out what were doing with https://aspireship.com.Thanks for your help!
This article was originally published on LinkedIn on October 30th, 2019. If you enjoy my content please follow me on LinkedIn and Twitter. Also check out my YouTube channel for video tutorials.
