A bike ride along the Santa Monica coast turned into an unexpected lesson about how we define success. After six months off the bike, the ride out felt easy: familiar roads, the sun overhead, the ocean to one side. The ride back, into the wind and up a series of hills, told a different story, and a brief encounter near the top of the steepest climb made the point sharper than any business book has.
A Stranger’s Snapshot Judgment
By the time the third and steepest hill arrived, fourteen miles were already in the legs. The first two hills had gone well, each climbed in full and noted with quiet satisfaction. The third was longer, steeper, and offered no run-up. About halfway up, with the legs giving out, dismounting and pushing the bike seemed like the sensible call.
That was when a driver going up the same hill in her car shouted across, “Don’t be lazy, get on your bike and pedal.” For a moment the comment landed. The day’s effort fell out of frame, replaced by a stranger’s verdict, and a flash of feeling like a failure followed.
The Context the Critic Could Not See
A few yards further up, the perspective came back. From the top of the hill, the ocean was visible two miles away. The driver had no way of knowing that the bike had not been ridden in six months, that fourteen miles had already been covered, or that two earlier hills had been climbed without stopping. She saw a single moment and judged it by her own standards.
Where she saw failure, the day actually contained fourteen miles of achievement and two hills successfully scaled. The judgment was not wrong because she was a bad person; it was wrong because she had no context for what had been done before she arrived.
We All Do This to Each Other
The encounter is a small version of something most of us do every day. We size up other people based on snapshots: the role they hold, the money they spend, the house they live in, the title on their email signature, the photo on their feed. We almost never have the information that would make those judgments fair, and when we apply our own standards to other people’s lives, we usually conclude something the data does not support.
Digital platforms have made this worse. The professional and personal pictures we see online are highlight reels by design. Comparing the inside of one’s own life to the curated outside of someone else’s is a fast route to feeling inadequate about a life that, in context, is going just fine.
Reclaiming the Right to Define Your Own Success
The conclusion of the ride was simple. The third hill will get climbed in full next time, or it will not, and either way the verdict on whether that day was a success belongs to the person who lived it. Success in work and career, in personal life, in friendships, in finances, in health, all of these need a definition that comes from the inside, not from a passing observer who lacks the context to judge.
That does not mean ignoring feedback or pretending external standards do not exist. It means choosing the standards consciously, building them around what actually matters, and refusing to outsource the verdict to people who only saw a snapshot. It also means returning the favor to others: respecting that their definition of success is theirs to set, not ours to impose.
What This Means for Anyone Measuring Their Life
A useful starting point is to write down what success actually looks like in each area that matters. Career, relationships, health, financial position, contribution, personal growth. Get specific enough that progress is recognizable to you, even if it would not look impressive to a stranger driving past. Then judge yourself against that, not against the latest highlight reel from someone whose life you do not actually know.
The world gets a little better every time someone reclaims the right to define their own success and offers the same respect to everyone else. One steep hill at a time.