Article - Leadership

Life has a funny way of leaving doors open if you approach it with the right attitude. Mac Olson began his junior hockey career fresh out of Detroit Jesuit High School taking him across the country, into Canada, and back. The 2016 “Babe” Kraus ‘24 Memorial award winner (awarded to the Hobart College Athlete of the Year) and Sid Watson runner up (awarded to the men’s Ice Hockey NCAA Division III Player of the Year) has persisted past numerous challenges to achieve success.

To begin Mac’s winding journey, he was first drafted by the Chicago Steel of the USHL in 2009, where he made the team as an 18 year old despite competing against established international junior players in their development camp. Admittedly, Mac confessed his first year in the USHL was a humbling experience, noting the transition from playing high school hockey to facing off against NHL prospects was no easy task. Playing with a chip on his shoulder, Mac battled to stay in the lineup for most of the year until he was traded to the Wichita Falls Wildcats of the NAHL. This was the first taste of adversity Mac would have to overcome to reach his goal of playing college hockey.

Being traded is never easy, but Mac approached the new opportunity with a positive attitude. “My personality helped me adjust well. It is difficult being inaugurated into different situations, but I think being confident in yourself makes it easier. At the end of the day, going into new locker rooms you meet new friends, and I always knew a guy in the room. The connections you make in hockey are invaluable.” These beliefs were instilled in Mac from a young age by his role model, Terry Olson (his father). Terry was an established professional hockey player and a successful businessman in his own right who put a large emphasis on never being complacent in one’s journey. “I tried my best to do everything like him and learn from him because I thought he was a successful person both in hockey and in business. I took his hard lessons to heart because I knew they would make me better.” These moral beliefs would help Mac through many more challenging times in his hockey career and professional life. The lessons Mac accumulated from his father in addition to being exposed to hardships early in his life would ultimately shape a positive outlook on handling adversity.

In Mac’s second year of junior hockey, Mac quickly excelled in his new environment. Offered numerous Division 1 scholarship opportunities, Mac was faced with more adversity when he broke his leg late in the season. Planning to go to college after the season, many of the schools that offered Mac a roster spot for the upcoming 2011 season pulled away, causing Mac to use his final year of junior eligibility. Ultimately, Mac returned to the USHL to play the first half of that year with the Des Moines Buccaneers, but finally ended his junior career playing for the Carleton Place Canadians in Eastern Canada, where he was recruited by Hobart College.

Looking back on his junior career, Mac had an experience he “wouldn’t change for the world” and three years of life experience he would never forget. “I learned a lot. Dealing with adversity was a big one. I think it's just all about patience and believing in yourself and that things will always come together. But it's also all about how you control the narrative with your positive ability.”

These early dealings with adversity would also eventually equip Mac to handle obstacles in his professional life. “The concerns I had when it came to injuries and not playing would be the same adversity at work of calling people and them saying no. How do you learn from that? How do you get better? How do you have patience and keep that belief that someone is going to say yes down the road? Having passion, having that competitive nature, things like that from playing a sport translate well into trying to win an account.”

Continuing his growth as a person and a hockey player Mac finally began his college career at Hobart College. When asked how he continued to be successful in an academic environment Mac had a very simple answer: “Success in the classroom or at the rink comes down to how much time you put in. I wouldn’t say I was the smartest kid by any means, so I had to spend a lot of extra time in the library.” Mac’s philosophy on and off the ice was quickly noticed by his teammates and coaches, earning him a leadership role in only his third year on the team. Honest with everybody, including himself, Mac took a straightforward approach in his leadership style. This style would be successful in holding his teammates accountable with a guiding hand to rally his brothers onward through the highs and lows. Learning and building as a team, Mac continued the tradition of sculpting boys into well-rounded young men.

Most of Mac’s leadership responsibilities consisted of “keeping guys in check emotionally, making sure everyone was doing their job and to ensure everyone felt like part of the team. And of course to enjoy college off the ice, but being smart at the same time.” Those were some of the daily challenges that occupied Mac’s time at and away from the rink. However, one of the hardest parts about the job was having difficult conversations. “Giving feedback on my teammates and being honest for the betterment of the program was something we had to do to lead our team to a championship.”

After college Mac took a job at Arthur J. Gallagher, an insurance brokerage and risk management consulting group. What is interesting about Mac’s journey, is that he did not get his foot in the door through any alumni or career services, but through a connection courtesy of his first billet dad from Chicago. “He is a big deal at Gallagher and those are some of the people you meet along the way [in junior hockey]. People who give up their homes for you to live in. We still stay in touch.” Career services were also a big help to Mac by helping him polish his resume and having important conversations about how to create value in the workplace. However, ultimately Mac received an opportunity through an important person he had a relationship with from years before.

As of now, Mac has been at Gallagher for nearly eight years. Largely in part because of the work he and his team do, but also because of the culture within the company. “My team is very helpful and wants to see people succeed. The other thing I like about our team is that 40-60% have been there their entire career, not to say there is any complacency, it's just that they love it here.” The other reason why Mac has stayed so long is because of the way the business works. In Mac’s role he has a book of business, which are his clients. He gets paid a percentage of his clients' paid insurance. If he were to leave he would lose his book and start from 0.

Clearly the best practice within the business is to stay put. Luckily for Mac, Gallagher is an incredible atmosphere to grow in. However, besides loyalty, Mac pointed out some important keys to climb the ladder in the workplace: “Surrounding yourself with people that are going to support you is a big one. Building long standing relationships built on trust with clients and colleagues will always help you down the road. Another key would be to understand how to take and give feedback while controlling your emotion. A lot of it comes back to being patient and finding solutions.”

Continuing on his journey, Mac is now an Area Vice President at Gallagher and is actively engaged with the Hobart community helping along the next generation of Statesmen. If Mac’s story is proof of anything, it is that any obstacle can be hurdled with the help of the people you meet along the way. His one piece of advice: “Don’t leave a stone unturned.”

Mac ended up playing one year of professional hockey after school… Just like his father.