About Us


Legacy LifeLines

No two families are alike; every family and their individual circumstances are unique to them. Why would you settle for an estate plan that is exactly the same as your neighbors? There is not a set of cookie cutter, word processed forms, regardless of what you are told, that will serve each and every family, while considering their personal hopes, dreams, and intent, both for disability planning and ultimately, death. (By the way 100% of Americans die, we just don’t know when!)

That is why we consult and partner with our client families using our unique Legacy LifeLines™ approach thus, ensuring cooperative client and attorney participation and “team” estate planning – Your family is unique – shouldn’t your estate plan be unique? It should, and NEVER will be with cookie cutter, fill in the forms type of estate plans!


As an avid history buff, Milford attorney Jack W. Bolling is passionate about keeping the past alive for future generations. He is just as interested in preserving your family's legacy by helping you make decisions that will keep your memory alive through your children and grandchildren. With a deep respect and passion for history, Bolling is pleased that his practice can help families see their past and plan their future. "History comes alive to me while conducting my practice and learning about my client families," Bolling said. "It gives me a sense of the past and a vision for the future - exactly what I want to bring to my clients."

Jack has trademarked his approach to the estate planning process and accompanying legal services as Legacy LifeLines™. His unique Legacy LifeLines™ process consists of three steps:

  • Personalized, individual counseling and estate plan design. We have a lasting relationship with our client families - not simply a transaction! Don’t just fill out forms!
  • Important funding of your revocable living trust. If your assets aren’t owned correctly your estate plan will fail, or produce undesired results, when you need it the most!
  • Lastly, and the most unique part of the attorney/client relationship at our firm, is a client update and maintenance plan that is unique to Jack's practice, promotes on-going and usually no cost constant communication. Jack likes to say that unlike a nice wine, estate plans don’t get better with age!

Jack encourages his clients to think beyond their financial matters and look into their own life's fulfillment by planning for their life, not just their death, by asking themselves questions like:

  • What and who really matters most to me, and why?
  • What legacy do I really want to leave behind? Can I leave my non-financial wealth too!
  • What if I become disabled before I die and unable to make life’s decisions? What should I do to protect my family and myself?

"Through proper planning, it is possible to provide for your long-term care while preserving assets for you and your loved ones," Bolling said. "Why should you give up what you've worked your whole life for just because you or your spouse becomes ill or disabled?"

These important life questions are all the more reason that Jack’s practice includes Medicaid planning, as he helps families with their trust and probate estate settlement.

Be a partner! Your initial consultation is at no cost and no obligation to you as it allows us to determine what your family needs are, based upon what your family demands will be.