Legacy Over Litigation: Designing a Life — and Practice — That Lasts

Andy Sykes, Certified Elder Law Attorney and founder of a Pittsburgh-based estate planning and elder law firm, joins Salene in a rare in-person episode to talk about reinvention, legacy, mentorship, and building a practice that serves families at their most vulnerable moments. From federal clerkship to litigation to a transformative pivot into Medicaid and estate planning, Andy shares how recognizing a knowledge gap changed his career — and gave him back control of his life. A thoughtful, grounded conversation about facing adversity, protecting families, mentoring the next generation, and why “always do the right thing” is more than just a slogan. ✅ NOTES Today on The Pivot Playbook, Salene sits down with Andy Sykes — Certified Elder Law Attorney practicing in Pennsylvania, with offices in Pittsburgh (Mount Lebanon) and King of Prussia. Andy focuses on: Customized estate planning Medicaid planning Asset protection Estate administration Special needs planning Strategic tax optimization What makes his practice unique? He began from the crisis side — Medicaid litigation — and saw firsthand how poorly drafted estate documents created devastating consequences for families. “If people have good knowledge and good advice, they get a much better result than they do without it.” That realization reshaped his entire career. ⭐ In this episode, we cover: 1. The Pivot: From Litigation to Elder Law Andy began his career in litigation after clerking for a federal judge and working at a boutique litigation firm where he was handed real cases from day one. But around the year 2000, a Medicaid case changed everything. A client had improperly sold her mother’s house while her mother was on Medicaid — costing her over $100,000. Andy discovered that with proper planning and understanding of Medicaid rules, the outcome could have been dramatically different. That moment revealed: A massive knowledge gap An underserved population An opportunity to help families proactively He pivoted fully from litigation to Medicaid and estate planning. “People don’t understand these rules. If they have good advice, they get a much better result.” 2. Why Planning Over Litigation Changed His Life The pivot wasn’t just professional — it was personal. At the time, Andy’s children were young. Litigation meant: Court-driven schedules Trial deadlines Stress that spilled into family life Planning work meant: Greater control of his calendar More evenings at home A healthier work-life balance “When your practice is planning-focused, you can control your calendar much more.” 3. Who He Serves Best Andy’s ideal clients are: Middle-class families Individuals approaching or in retirement Blended families Families with special needs children Clients open to proactive, innovative planning His work emphasizes: Asset protection strategies Medicaid eligibility optimization IRA tax deferral strategies Multi-generational trust planning “We optimize and customize estate plans far more than most firms do.” 4. A Memorable Case: Love, Marriage, and Asset Protection An older couple found love later in life — but had concerns about: Protecting assets for their respective children Nursing home risks Blended family complications Through a prenuptial agreement and asset protection trust planning, Andy helped them: Marry securely Preserve assets for their children Protect against Medicaid exposure Years later, they’re still together. “It’s great to make it possible for people to feel secure enough to build a life together.” 5. Midlife Perspective & Credibility When Andy began, he sometimes felt imposter syndrome advising older clients. Now, with grown children and personal estate planning experience — including special needs planning — he brings lived experience into client conversations. “I can relate now in a way I couldn’t before.” Midlife has shifted his focus from annual profitability to long-term legacy. 6. Legacy & Mentorship For Andy, success today means: Training the next generation Bringing on a summer associate Passing down a thriving practice “It’s more about legacy now than just this calendar year.” He emphasizes mentorship: “You don’t have to reinvent the wheel. Find a mentor.” 7. Facing Adversity Instead of Avoiding It One of the most thoughtful parts of the conversation centered on adversity. Andy’s perspective: When facing professional or personal setbacks, don’t avoid them. Turn toward them. He referenced The Sixth Sense as metaphor — what terrifies us may be pointing toward something we need to confront and understand. “If you can face adversity and learn from it, it becomes a moment of growth.” 8. Ethical, Heart-Centered Leadership In elder law, identifying the true client is critical. Often an adult child brings in a parent — but the parent is the client. This requires: Clear ethical boundaries Difficult conversations Protecting vulnerable individuals Courage to say “no” when capacity is lacking “You always have to know who the real client is.” 9. Community & Connection Andy builds community through: Live educational seminars Local referrals Community visibility Church involvement Supporting local music Hosting estate planning workshops He also shared an unexpected passion: Studying improv before the pandemic Improv, he says, improved his listening skills and presence with clients. 🔥 MEMORABLE QUOTES “If people have good advice, they get a much better result.” “When your practice is planning-focused, you can control your calendar.” “You don’t have to reinvent the wheel. Find a mentor.” “If you can face adversity and learn from it, it becomes growth.” “You always have to know who the real client is.” “Always do the right thing.” 🎯 THE PIVOT PLAYBOOK FOUR PIVOTS Pivot he’s most proud of: Transitioning from litigation to elder law and Medicaid planning. Practice that keeps him grounded: Exercise — training for a 10K (The Great Race in Pittsburgh). Principle that guides him: “Always do the right thing.” Person who changed his trajectory: (With humor and heart) Salene’s photography — which led him to meet his wife. 🌿 FUN FACTS Certified Elder Law Attorney Former federal judicial clerk Studied improv pre-pandemic Avid audiobook listener Favorite show: The Crown Favorite recent song: “Constant Companion” by Juliana Hatfield Favorite travel destination: Madrid Has a wild morning dove named Daisy who visits his deck ✅ CALLS TO ACTION Learn more about estate planning and elder law services in Pennsylvania: [Insert Firm Website] Attend a live estate planning seminar in Pittsburgh or King of Prussia. If you have aging parents — don’t wait until crisis. Plan proactively. A conversation about security, stewardship, facing hard truths, and building a life — and practice — designed around legacy rather than litigation.