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How I started taking control of my own life - and hockey helped me do it.

Guest Contribution #3 with Aaron O’Callahan


Hockey has always been a huge part of my life.


I grew up in the Chicago area and played youth and high school hockey there. I played for teams like the Highland Park Falcons, Glenview Stars, and the Chicago Young Americans and went on to play high school hockey for the Loyola Ramblers. Some of my best friends to this day were my teammates from those teams.


The two years I played for the Glenview Stars stand out to me as some of the most fun years. We were bantams in middle school and played in a travel league called Central States. It was a competitive league, we were good, we all wanted to be hockey players and took practices seriously -- and my dad was the coach.


I don’t think it would have been the same without my dad as the coach. His coaching style just brought the best out of every player. We all bought in, and as a result, a lot of us got to experience being part of a special team for the first time.


My dad is Jack O’Callahan. Over the years people have asked me, ‘What's it like to be the son of Jack O’Callahan?’


I don’t always respond with this, but what comes to mind for me first is:

‘Yes, my dad had success in hockey, but when my sister and I entered his life we became his number one priority. So as a kid growing up, all I knew was that I had a loyal and dedicated father, and it wasn't until later that I learned about his hockey success.’
My dad and I after a Blackhawk Alumni Game in Chicago.

As for my dad’s hockey success: NCAA Champion, NCAA MVP, 1980 Olympic Gold Medalist, and 390 NHL games, to name a few - I couldn’t be more proud of him. But, I also know more about his life than most people, which gives me an even deeper appreciation of everything that it took for him to achieve it.

Nothing was handed to my dad. He believed in himself, and grinded for every inch. He taught me to do the same.

After the Glenview Stars I wasn’t sure what was next.


I tried out for the AAA midget team, but got cut.


Junior hockey didn’t feel like it was for me, so I didn’t go that route.


Lucky for me, I had access to Illinois high school hockey, which has plenty of strong programs, schedules, coaching and players.




Freshman year I made the second varsity team and then sophomore and junior year I made the top varsity team for Loyola Academy. Those were very fun years. I loved playing there, getting to see my teammates in the halls and then carpool to practice together.


Junior year we made it to the state finals at the United Center, but we lost to Glenview’s high school -- some of my friends from the Stars were also on that team.




Looking back, I think the idea of playing college hockey snuck up on me. I was a late bloomer in both strength and skill. So, by the end of my junior year I felt like I was the best player I’d ever been -- but that only left one more year to figure out what to do before college.

I was exposed to New England prep school hockey


In between the summers of high school I would fly out to Massachusetts for a hockey camp. A teammate of mine from the Glenview Stars - one of my best friends to this day - had moved to Mass in 8th grade, so I sort of followed him to these camps. Through these camps I got exposed to prep school hockey and even met some coaches from colleges like Trinity College and Merrimack.


After my sophomore year at this summer camp I felt like I belonged on the ice with these prep school players. And I liked the idea that college hockey could be an option for me. So, during my junior year of high school at Loyola I started touring prep schools, filling out my applications and worked with a tutor to get my score up on the PSAT.


By spring of Junior year at Loyola I found out I was admitted to Choate and Taft and both would have been great places to land. The friend I mentioned earlier had already made his way to Taft the year before. It felt right to me too, so I followed him there as a repeat junior.

It was tough to leave high school before my senior year, but it was a life changing opportunity for me that I knew I had to pursue.

At this point, I’m 17 years old, I had been getting better at hockey every year at Loyola, and now I had 2 more years of getting to play at a top prep school program for Dan Murphy - - one of the best coaches I’ve ever had. All this work, and training in the summers, landed me the opportunity to play college hockey at Bowdoin College.

Bowdoin College is where I start to noticeably grow up as a person, and start to think seriously about life after hockey.


I remember at a party during my freshman year I was talking with a senior on the team - the 3rd string goalie - and he commented on how fun it was to all hang out like this. Then, he casually mentioned that hockey wasn’t the most important thing anymore -- and that none of us were going to the NHL.


This was eye opening to me, and it clearly stuck with me.

I took hockey as far as I could at Bowdoin, but early on I was already starting to realize I needed to think about what I would do next, after hockey was over.

I started taking control of my own life at Bowdoin, and hockey helped me do this.


One story that stands out to me was in the first half of the season during my freshman year.


Every Thursday we would learn the lineup for the weekend’s games. But as I remember it, for some reason, I couldn’t wait until Thursday to find out if I was playing. The reason was that I needed to tell my dad if he should book his flights to come watch the games. Somehow I found myself in the coach’s office and told him this. I left his office for the most part ‘unscathed’ but what he told me was that:

My dad’s flights didn’t matter. I wasn’t playing hockey for my dad anymore, I was playing hockey for myself. And, I needed to grow up.

This changed my life.


And, I’m proud to say that for the rest of my hockey career I wasn’t worried about reporting the weekend’s lineup back to my dad every Thursday as soon as it was posted. Instead, I made it a point to check that lineup for myself, and no one else.


Just because I got accepted to Bowdoin, didn’t mean I was guaranteed a spot on the team.

We carried around 30 skaters on the team and only 18 would dress. I fought hard in practice and in the off-season to earn every minute of ice time I was given. I was healthy scratch in some games, but I never gave up.


The summer between sophomore and junior year is when I trained maybe the hardest ever.


I spent roughly 30 days living in Milwaukee working with some talented coaches on my skating and my lower body strength. We would do things like jog in a circle for 6 minutes, alternating jogging and doing duck walks every 15 seconds. If you do the math, this equates to 30 seconds of duck walks for every minute, so if you jog for 6 minutes it would be 3 total minutes of duck walks.


If you do things like this every day, along with on-ice training, for 30 days... you are going to get better.


My junior year at Bowdoin I was the best at hockey I’d ever been. That year we won the conference championship, and I scored the game winning goal in the championship game! Possibly my greatest hockey achievement. I am glad to say my dad and my grandfather were in the stands that day too.

After hockey, I entered the NYC business world. Even though I didn’t know exactly what I wanted to do, someone who I looked up to told me it was a great place to go to start my career.


I started in an analyst role working for a year with Aon Risk Services, and then two years with Mercer Health & Welfare.


These roles were great for experience, but I knew I needed to make a job change in order to set myself up for more happiness in my career.


In order to make sure I would get the most out of this job change, I did not want to take any shortcuts. I wanted this job change to be something I could build on for my entire career, and not just a short-term solution.


I connected with a mentor of mine and he coached me through the below exercise. He told me to think very deeply about the four headers below, write down my thoughts in each box, and then reflect on what jumped out at me.

After I completed this exercise it was clear to me that I wanted to make a career change into sales.

This was scary to me **fear**, and I wasn’t sure what others would think **ego**.


But, at the end of the day I was willing to take a risk to find a new arena where I could thrive.

Sales took the place of hockey for me. And 5+ years later after making this change, I look back and it’s one of the decisions in my life I’m most proud of.

Right now I work for OwnBackup, an exciting cloud data protection software company, and I’m proud to say that I like what I do.

Hockey has always been a huge part of my life and always will be...for the memories, friendships, wins and losses. I continue to carry what I've learned from the game into my life.

I am currently living in Saratoga County with my wife, Molly, and our dog, Gilly, playing men’s league once a week and doing a little coaching too.


I can be reached via LinkedIn for anyone that wants to connect.


Thank you to the Next Shift team for letting me share!

All the Best,

Aaron O'Callahan


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