My Antifragile Family

By Lily Boyar with Kjartan Jansen

8 min readFeb 6, 2023


My family has always been extremely close. The talk-every-day, text-when-your-flight lands, always-in each-other’s-business kind of close. We are by no means perfect — we are messy, loud and chaotic, with plenty of arguments and over-processing (¾’s of us are therapists), but we love each other deeply, laugh a lot, and have always felt connected. I remember, growing up, people would always tell me how lucky I was to have a family like mine. They could detect this special something — it was palpable.

One year ago, my family was forever changed when my father passed away suddenly. Overnight we went from a family of four to three. We lost our dad and partner, and the person who helped root and ground us most. Life was turned upsidedown, and my mom, sister and I began our long, painful and winding journey of grief.

No one tells you exactly what happens after such a profound loss. I am sure it is different for everyone. For us, it unearthed every emotion. We’ve cried, laughed, argued, and had difficult conversations as we each process and adapt to our new reality. We knew that our family would never be the same. We feared we might never recover. Sometimes the pain felt unbearable.

As the months passed, we each began to process my dad’s death, taking turns dropping to our knees with anger and sadness. I say “began” because I know grieving takes a long time. And as difficult as this last year has been, it has also solidified the true strength of our family. Somehow, in spite of it all, we are becoming more connected and bonded than we’ve ever been.

We’ve developed new rituals; like texting each other goodnight or making plans to be together for many of the years “firsts.” We’ve witnessed each other’s pain and provided comfort and support, even when we were hurting. We’ve learned about each other in new ways we hadn’t before, and leaned on the support of our partners, family and friends. We rose to the occasion to plan a celebration of life, made incredibly difficult decisions, and attempted to fill in some of the gaps my dad left behind (even though we know this is impossible).

We just passed the one-year anniversary of my father’s passing. It made me reflect on how my family has endured this experience. Friends and family have often praised us for being “courageous” and “resilient.” However, these words don’t seem to fully articulate how I feel. Resilience refers to someone’s ability to cope and “bounce back” from adversity. But for us, there is no bouncing back. We will never return to our original homeostasis or resume to a state of recovery after losing my dad. Instead, we are challenged to adapt to new ways of being as we rebuild our family culture. And that is what we are doing.

Coming Back Stronger

In his book Antifragile: Things That Gain from Disorder, author Nassim Taleb coins the term “antifragile.” He defines this concept as the ability to grow and strengthen under stress and adversity. Taleb explains that antifragility occurs in randomness, uncertainty, and hardship. It is when an outside stressor serves as an opportunity for innovation, creativity, and connection. This concept of antifragility can also be applied to families.

A family is two or more people who are biologically related or have chosen to integrate and be connected to one another. A family is successful when they continue to choose to stay actively affiliated and deepen personal relationships with one another and also add value to their communities over time. When an antifragile family is threatened by a challenge such as an economic downturn, health concerns, natural disasters, or in our case, the death of a loved one, they are able to adapt, creatively solve problems, utilize the family’s unique skills, and eventually flourish, despite hardship. When I learned about antifragility, I realized this is the word I had been searching for.

Many families already possess qualities that enable them to rise from adversity, such as communication skills, rituals, and strong connection. And most families will inevitably face challenges and disruptions throughout the course of life. These stressors can lead to permanent fractures and serious consequences in cherished relationships but they are also opportunities to grow closer. In my own family for example, I feared that the pain of my dad’s death might put an irreversible strain on our relationships with each other. We’ve had to learn a new way of being, and how to cope and support each other when we are all simultaneously compromised. I feared we might lose each other, on top of losing such an important person in our lives. I’ve often wondered why some families become estranged or splintered after such events, while others grow stronger. What are the qualities that make a family antifragile?

Generative Families

Without an explicit intention to maintain close ties, families tend to splinter over time. Today, factors like geography, relationship stress, and competing priorities contribute to this. If they don’t want to follow this path of least resistance, families have to create a vision and a plan for getting there. The success of achieving the vision relies on the participation of the family members. In the case of my own family, I cannot see how we could have ended up where we are if anyone had opted out of our group activities. Early on, we had an explicit discussion where we promised each other we weren’t going to let the passing of my father define or destroy our family.

In thinking about this concept, I began to wonder what would need to happen in families where shared financial assets were part of the difficult or chaotic situation that tested them. In his book, Borrowed from Your Grandchildren, Dennis Jaffe studies what he calls “generative families.” This refers to families who are connected by blood, but also through a family business or enterprise for more than 100 years. Through many interviews and conversations, Jaffe aims to understand what makes these families thrive. He argues that after three generations, it is safe to assume that it isn’t just the procedures and process of a family business that keeps a family connected and successful. Instead, they must have skills, qualities, and ways of being that contribute to their family culture. Jaffe cites five factors that contribute to building a generative family, that stays connected over time:

  • Individual resilience growth and development
  • Shared values and core purpose
  • Cross-generational engagement and support
  • Governance policies and structures that guide development and decisions (a set of agreements that outline how a family or a family business operates, such as a family council or a business ownership agreement)
  • Commitment to community beyond the family

When we think about antifragility, it makes sense to us that generative families would also be antifragile. In our experience, these elements help to develop mutual respect within and across generations, which is critical for family success.

What Can Families Learn From Empires?

If we think about nations as being made up of groups of people, then perhaps we can make some parallels to families. In his book Principles for Dealing with the Changing World Order: Why Nations Succeed and Fail author Ray Dalio explores the rise and fall of empires and what makes for a strong nation. Dalio presents extensive research and exploration into the rise and fall of empires as it applies to global investment strategy. However, we see his themes as also pertinent to families and cultivating antifragility.

Based on his research, Dalio explains that countries that rise to prominence after crisis invest heavily in, among other things;

  • Education
  • Infrastructure
  • Leadership

While articulated differently, we view Dalio’s ideas as being in alignment with Jaffe’s five factors for generative families.

Education is essential for developing ourselves as people. We learn how to share, collaborate and have civilized conversations with people with whom we disagree. We work in teams and develop critical thinking skills and creativity. Education supports us in developing our character and solving problems. Antifragile families allow for each individual to enrich the unit by bringing their own skills, intelligence and solutions to problems. Investing in education helps cultivate these skills and strengthen the family’s ability to cope with change and adversity.

Like countries, families also have infrastructure and governing policies. By “governance” we mean a set of explicit agreements that define the ideas, relationships and activities that support the group’s well-being over time. A few examples are family constitutions or rules for the owner or use of family assets. As families become larger and more complex, and especially in family enterprises, governance becomes critical to the thriving of both family and business. Most disagreements in families, whether they pertain to family or business, happen because of missed expectations. Once effective governance is in place, families have a playbook that supports them in setting expectations and managing difficult situations.

Dalio’s characterization of strong leadership is also applicable to families. Effective leadership is charismatic, dynamic and appropriate for the time. Once leadership is in place, it is imperative that the next generation stewards the country forward. This is also true in families. Leadership must be representative of the family and this changes as it grows. Appropriate mentorship and succession planning in families is critical for multigenerational thriving. It is important for families to train the next generation so that one or more family members can be willing and ready to step into a leadership position when necessary.

A New Perspective

While the aftermath of my father’s loss is not “over” and probably never will be, we are starting to carve a path forward as a family. I would like to say we are “coming out the other side stronger” but anyone who has lost someone knows there is no final destination or “other side” to get to. In some ways we’re just at the beginning. However, this year I learned what my family was made of, in a way that life’s hardest events seem to do.

Learning about this concept of antifragility gave me a new perspective on myself and my family. It helped me create a vision that integrated this tragedy into our new collective identity. It hasn’t been an easy road. However, I felt moved to share this story, and the perspectives in the field, in hopes that other families feel inspired to build a culture of antifragility and feel more empowered in difficult circumstances.

On the one year anniversary of my dad’s death, we initially weren’t sure how we wanted to spend the day, but we decided to be together and do something intentional to honor him. We sat together around the dinner table, read letters and well-wishes from friends and family, expressed gratitude for one another, told stories, and wrote a letter to ourselves to be opened on the second anniversary with hopes and wishes for a new year. My sister had cleverly suggested this idea, starting what may be a new family tradition. There is a bitterness to new rituals and traditions because they are signs of moving on without my dad. However, on that day, I looked around at my family, unified and engaged in letter writing and I knew we were going to stay connected. After all, we’re antifragile.

This piece is dedicated to my dad, Alan Boyar.




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