After a string of life setbacks, here’s how I learned to rethink happiness

A mother and business leader writes that happiness is neither an intellectual pursuit nor an easily ‘hackable’ goal.

After a string of life setbacks, here’s how I learned to rethink happiness
[Photo: Noah Silliman /Unsplash]

The morning after Thanksgiving 2020, I woke to an article in The New York Times titled “Happiness Won’t Save You.” It chronicled the life of Philip Brickman, an expert in the psychology of happiness. Only hours later, I learned of the death of Tony Hsieh, the iconic founder of Zappos and author of Delivering Happiness. Brickman took his own life at 38. And while Hsieh’s death, at 46, has been ruled accidental, it is also rumored to be the culmination of a downward personal spiral.


As a career brand strategist who has spent more than 30 years studying human motivation and behavior, I was gripped by these parallel pursuits, the tragedy of their outcomes, and what the rest of us might learn from them.

What’s with our collective obsession with happiness?

Why do we chase it?

And does this chase actually mislead us down paths paved with despair?

In my professional and personal lives, I am business leader, breadwinner, spouse, and mother of four. And I have come to believe that happiness is not an intellectual pursuit. It is not something we can hack, innovate, or fast-track. It can be studied but not predicted, planned, or prescribed.


As creator and teacher of the Life Brief, which instructs my clients on how to write creative briefs for their personal lives, I’ve spent the last decade driven to understand how to create a life of meaning while harmoniously braiding and blending career with purpose; marriage with motherhood; and my self with service.

Through my own experiences, I’ve learned four personal lessons about happiness, many of which were more than surprising to me.

  1. Happiness is not a continuous state of play or positivity. It does not rise in correlation to the rise of income, job status, likes, or followers.
  2. Happiness doesn’t come from a single source. True high achievers harmonize between themselves and their most meaningful relationships, and between their work and their service to something beyond themselves.
  3. Happiness is connecting and relating to others through your truth—your innermost voice—even when it goes against conventional wisdom and the status quo.
  4. Happiness is not a goal; it’s an outcome. It emerges when we rise to face our deepest questions—with curiosity, commitment through action, and an openness to surprise and serendipity (over control or predictability).

How to define your happiness

2020 rearranged the furniture of our lives. Stripped of our usual distractions and escapes, we’ve collectively been given a pause to confront who we are, what we believe, and what truly matters.

In this space, we’re left to confront limiting and misleading stories about what we believe, about ourselves, about what’s possible and what’s not. We’re forced to face the profound and penetrating questions we avoid when times are “normal.”

What do I cherish?


What’s worth defending?

What’s worth disrupting?

What am I holding on to, and what might I let go of?

When practiced in earnest, personally and professionally, answering these questions can yield relational breakthroughs and personal triumphs.

Over the past year, I witnessed the relief that comes from admitting the end of a marriage. I also saw the acceleration that comes from demanding change instead of waiting for it. And on a lighter note, I experienced the relish in discovering that one’s “cherish list” can be counted on one hand.


For me, 2020 was spent on the relationships worth defending. My most challenging relationships this year have also been my most rewarding. As a parent of a teenage son, “defending” has meant not ignoring internal alarms or dismissing distress signals for the sake of “busyness.” It has meant inserting myself into his world, at moments when I was least welcome, pit in my stomach, loving him through accountability. At times, parenting took the form of sitting and staying in his room, usually as he screamed for me to leave, waiting for an opening to real answers. Other times, it took the form of putting everything else aside—work meetings, my attention on my three other kids—to support him without excusing him.

As a leader, I spent this year listening and learning, reconciling and redefining the meaning of management in an awakened world where equity is no longer a cause but an imperative. This required shifting from being client-centric to being employee-first. Today, more than ever, leadership is an art in relationships. It requires honesty, empathy, integrity, and grace—traits not easy to cultivate (or typically celebrated) in the demanding, deadline-driven world of business.

As we look forward into 2021, we must remind ourselves that showing love does not cancel out others; it embraces imperfection, mistakes, and messy truths. If we’re truly expressing love, we invite perspective, differences, and debate. We show up and lean in, particularly when we want to run or hide. We stay in the room even when doubt and distrust reach new peaks.

In 2021, we can make an agreement with ourselves to stop chasing happiness. Instead, let’s allow it to be an outcome—or perhaps a reward—of doing the important and necessary work on ourselves and on the relationships that we cherish, even or perhaps especially when they challenge us most.

Bonnie Wan is a partner and head of brand strategy at Goodby Silverstein and Partners and creator of the Life Brief, a practice for intentional and imaginative living.