John Diamantis,
J.D., M.B.A.

My path to becoming an elder law attorney was probably not a typical one. Although I’ve known for a long time that I wanted to be an attorney, it took me an even longer time to figure out what that meant or what I wanted to do once I became one. As early as my first year of law school I already knew I didn’t want to grind out endless billable hours for a traditional big law firm. I needed some sort of work-life balance and autonomy. I initially looked outside the legal field for careers where I could leverage my law degree.

My first job out of law school was as a trust officer. In a way, it was my first introduction to estate planning and elder law since I didn’t take those classes in law school. I reviewed hundreds of estate plans and worked with aging spouses, special needs individuals, and families after someone had passed away. Inevitably, I saw the good, the bad, and the ugly, as some of my clients did a really good job taking care of their families, while others left a mess. As much as I loved the job, I wanted to help my clients earlier in the planning process when I could help them the most.

I finally made the switch to practicing elder law and estate planning once I found a mentor I believed in. I didn’t have to reinvent the wheel trying to figure out what the best strategies were, or how best to grow my book of business. I was working in a practice where hard work was rewarded, but you were never a slave to the clock. We were flat fee so instead of tracking hours, we tracked revenue—I never had to worry about charging my clients in 15-minute increments or sending them a bill after a phone call. My clients really appreciated knowing the total cost and what we could accomplish from day one. And, since it was results that mattered, and not time, I didn’t have to adhere to a strict 8-5 schedule or track PTO, so my family didn’t have to take a backseat to my career.

I’ve always been responsible for my own business development, whether as an associate or as an owner, and I’ve always done it in my own way and at my own pace. I’ve centered my business around referral relationships. It’s been the best way I’ve found to connect with the people who need my help the most. I spend a lot of my time traveling or meeting remotely with people in the rural Midwest who wouldn’t otherwise have access to an elder law and estate planning specialized attorney. And, after Covid, working remotely has really taken off and allowed me to connect with and help more people than ever.

I love what I do. It’s kind of a happy accident how I ended up here, not ever directly setting out to do this, but I wouldn’t change a thing. Each experience I’ve had leading up to this has better prepared me for this role, whether I knew it or not at the time. I love that I practice happy law, helping people, and I love that I have freedom and control over my career.