Steve Jobs's Greatest Regret: His Family

Walter Isaacson, Steve Jobs's biographer, asked him if he had any regrets.

Jobs said, "I wanted my kids to know me. I wasn't always there for them, and I wanted them to know why and to understand what I did."


Isaacson went on to ask him if he was glad that he had kids, and Jobs said, "It's 10,000 times better than anything I've ever done."

Steve Jobs, the man who many consider as one of the greatest business innovators of our time, placed the value of having kids as 10,000 times greater than anything he's ever done. Yet, his biggest regret is that he wasn't there for them and he wanted them to know why.

Most people go into parenthood with good intentions. They want their kids to succeed and be happy and healthy. But life often gets in the way of good intentions.

Bills have to be paid and you find yourself working too hard and becoming too busy to attend your son's baseball games. You get a divorce and spend a year fighting over custody while your kids ping pong between mom's and dad's house and get in with the wrong crowd. You push your daughter to do her best in school and one day she storms out with her tattoo-covered boyfriend proclaiming you an "overbearing ogre!" You try to give your kids the kind of emotional support they need, but your parents were always cold and distant and you just don't know how to connect.

Without the right model, it can be tough. Really tough.

Still, creating a successful family culture isn't impossible. In fact, with the right structure, your family legacy can be something great. But, it doesn't happen by accident. You have to think it through, make it a priority and act in ways that are supportive to cultivating a happy, healthy family.

Benefits of Family Legacy Planning:


The aim of a solid family legacy plan is to mold family members who are:

  • Capable. Members know their role in the family and contribute to the financial, social, spiritual and intellectual health of their family and the community.
  • Connected. Members care about their ancestors, extended family and descendants. They work hard to stay connected to the family and establish effective generational governance structures.
  • Grateful. Members recognize the many blessings and opportunities they have been given and focus on empowering each family member to become the very best.
  • Responsible. Members are accountable for their actions and mistakes and embrace their responsibility to give back.
  • Competent. Members develop the skills to handle and manage money, effectively utilize opportunities, and become productive, giving members of society.
  • Components of a Successful Family Legacy Plan:


    With a little planning, a vision for the future, and a lot of love, you can turn your "mediocre" family experience into "extraordinary". Let's take a quick look at what you need to consider when constructing a Family Legacy Plan.

    Your Family Values:


    It is essential to identify joint family values and establish a home that outlines and supports what your family stands for.

    Your Family Mission, Vision and Mantra:


    This will serve as the foundation for your family—the rock upon which your children can build their decisions.

    Your Family Coat of Arms:


    This doesn't need to be fancy, but it could be. (I have access to the royal sculptor for Windsor Castle, if you want to go that route.) Brainstorm ideas about a unique coat of arms or logo that will represent your family. We've found this component, when done right, can be extremely valuable to your family because it gives them a tangible identity—something they can see and connect with.

    Documenting Family Systems:


    List traditions to be passed down from generation to generation, systems for maintaining a healthy body, systems for managing money, business systems, and other knowledge that should be passed on. We teach our clients how to get the kids and other family members involved in creating a family knowledge base.

    Your Family Constitution:


    It may seem overly formal to some, but a family constitution can help solve major problems down the road by outlining the specific principles and precedents your family agrees to follow. While the vision and mission of your family is more of an overview, your family constitution lists specific rules that will be followed and respected. This isn't about creating a "police state" family. It's about setting clear expectations and establishing accountability and responsibility—crucial skills your children need to function at the highest level as adults. When everyone knows what is expected of them and that other members of the family care about their well-being and will hold them accountable for making poor choices (also praise them for making good choices!), they have incentive to avoid foolish actions and reach higher levels of self awareness.

    Yearly Family Goals:


    Each year, I would suggest you create a family theme as well as a concrete goal you'd like to accomplish together. How you want to implement your family goals depends on how your family interacts, ages of various members and interest. This is about having fun and growing and learning in a laid back environment.

    Weekly Family Meetings:


    In his book, The Secrets of Happy Families, Bruce Feiler writes about how a simple 20-minute weekly family meeting transformed his relationship with his teenage daughters. For the first couple meetings, his daughters were emotionally closed off and non-communicative. Then, they began to open up in a very big way. A good family meeting stimulates conversation, promotes love and creates a family that is more cohesive. If done right, your family meetings can be a fun, enjoyable time everyone looks forward to. This is also a time to address the day-to-day operations of the family and establish some routines.

    Archiving and Passing On Intellectual and Character Assets:


    Figure out how you want to share memories, document experiences and stories, compile meaningful family information and save it all in a way that won't be lost or forgotten.

    Living Without Regret


    No family or system will ever be perfect, but creating a plan for your family keeps your most-important priorities from slipping through the cracks. One day, at the end of your life, someone may ask you what was your greatest regret. Hopefully it doesn't result in the gut-wrenching realization that the thing that mattered most got the least attention.