Gregory R. Sheehan, AIF®, CFF

Managing Partner / Financial Advisor

About Gregory

After high school, I knew I wasn’t ready to be a serious college student, so I entered the full-time workforce. It was during this year that I learned if I wasn’t going to further my education, I needed a skill set that would be in demand and transferable throughout my life. That’s when I decided to join the United States Air Force. After serving in support of the First Gulf War, I came back to Western Massachusetts with a renewed purpose and direction. Having been trained and licensed as a heavy equipment operator, I now had a skill set to fall back on as I pursued my college education. I had begun working full-time on the third shift at a paper mill, simultaneously becoming a full-time college student during the day. Shortly before I was set to graduate, my mother was notified that she was going to be downsized after 25 years with the same company. Her plan before that was to work five more years. Unfortunately, we all know that things don’t always go as planned. This news created immediate stress in my parents’ household.

Thankfully, my mother had saved in her 401(k) plan. There was also a profit-sharing plan that was quite robust until hard times hit the company. My father was an entrepreneur who had expanded his business into commercial real estate in the late ’70s and early ’80s. The housing collapse in the late-1980s nearly wiped him out. Shortly after my mother was downsized, she was notified that she needed to do something with her retirement plan. I could tell that these major life transitions were worrisome to them both. Never having really engaged an advisor, they didn’t know if they had properly planned for the future. They were referred by a friend to a trusted advisor, where they learned that although not a planned life event, past years of disciplined saving and modest lifestyle would allow them to maintain their independence in retirement. I could tell there was a sense of immediate relief associated with what had been the stress of the unknown. It was at that point that I decided I wanted to work with people in a similar fashion. I began looking for opportunities in the financial services industry.

I transitioned from college graduate to a position with a MassMutual General Agency. During this time in the agency, I learned the ins and outs of life and disability insurance. I also discovered the importance of life insurance in financial planning. Wanting to learn more about the industry in general, I transitioned to Cigna Bank & Trust. It was at CB&T that I began working with beneficiaries of corporate-owned life insurance policies. In most cases, widows, and widowers. Most times, these people had no direction for moving forward. This is where I learned to appreciate a solid financial planning process. I truly enjoyed the gratification of helping people during one of the most difficult times of their lives. Although I thrived during my time at Cigna Bank & Trust, the one-hour commute each way began to take its toll.

Wanting to help business owners and families develop solid financial plans, I began looking for opportunities closer to home. After a short search, I transitioned to assistant vice president of investments and insurance for Peoplesbank in Holyoke, Massachusetts. This allowed me to work close to home and become more involved in my community.

Having formed many meaningful relationships with bank staff and clients, I was still searching for that missing piece. My entrepreneurial mindset gave me the confidence to transition out on my own. I had formed SFG, Inc, and began working in partnership with Pension & Benefits Associates, Inc. (PBA). It was during this transition that I would meet the love of my life and future wife, Heidi.

Heidi was an operating room nurse and had spent many years at Massachusetts General Hospital as well as at Mass Eye & Ear before accepting the same position at Cooley Dickinson Hospital in Northampton. Heidi and I would marry one year after meeting and begin our lives together. We began making plans for our future, and for the next seven years, we would both excel in our chosen professions. Life was good, and everything was progressing as planned.

We sold our condominium and bought our “forever home” in South Hadley. We rescued our dog, Maximus, from a shelter, and he became family right away. On June 2, 2017, Heidi was terminally diagnosed with cancer. On August 13, 2017, Heidi, my best friend, soulmate, and partner passed away in our home.

During the previous decade, my practice had expanded from wealth management to advising business owners on their fiduciary duties associated with their company 401(k) plans. In partnership with Pension & Benefits Associates, we were providing advice and education to more than 60 business and 3,000 participants.

To say Heidi’s passing would make for my most difficult transition to date would be an understatement. Tragedies often lead to an internal audit and review of priorities. I have spent the last year evaluating what is most important to me going forward. Where will I find the most purpose in my life? I’ve sought counsel from mentors, trusted colleagues, and close confidants. From this came an idea—and a decision. I would narrow my focus back to where it all began. From my parents’ kitchen to Heidi’s passing, I have been reminded of the good work we do for people in transition. Whether it’s a wedding, a new home, a first child, a career change, or the passing of a loved one, we are always in a state of, or planning our next, transition.

Heidi decided on nursing after caring for her grandmother who passed from ALS. I decided on financial planning after my mother’s unexpected downsizing. Perhaps that’s why Heidi and I were drawn together, to help make people’s lives better through our chosen professions.

Heidi and I had hoped for the best but planned for the worst. Proper planning is why my next transition is possible. It’s why I can share my story with you, and countless others, now and in the years to come. Planning for life’s ups and downs is why The Wealth Transition Collective was created. We hope you will think of us when you are planning for your next transition.

Warmest regards,
Gregory R. Sheehan, AIF®

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