Ronald G. Wayne is the unluckiest man you’ve (probably) never heard of.

In 1976 he joined two youngsters named Steve Jobs and Steve Wozniak to found a computer startup called Apple. Just twelve days later, Wayne got cold feet and sold his 10% share of the company – a whopping 800 dollars – and walked away. He had already lost a small fortune in a failed slot machine business and was afraid of being on the line if Apple went sideways. Instead, it went on to become a juggernaut that made Jobs and Wozniak millionaires (and later, Jobs a billionaire). 

Wayne has described his life as being “a day late and a dollar short.” On one occasion, after a reunion with Jobs and Wozniak at an Apple event, he decided to dust off his old Apple contract and sell it to an autograph collector. Several years later, the contract sold at an auction for $1.6 million. On another occasion, Wayne’s life savings – locked in a 2.5-ton safe in his Florida home – were stolen. He was forced to sell his home as a result.

Today, Wayne lives in the small town of Pahrump, Nevada. Do an internet search and you’ll find images of a pot-bellied old man with a good-natured expression, puttering around in front of a faded yellow mobile home in the dusty desertscape. He lives off social security checks and the money he makes selling stamps and coins.

You’d have every reason to think that Ronald G. Wayne is a bitter person, paranoid after a life of losses and missteps. I’m happy to report this couldn’t be further from the truth.

Hindsight Bias Is the Thief of Joy

Hindsight bias is the instinct to see past events as more predictable and controllable than they are. We even assume others see the past the same way we do. ¹

The natural thing for someone in Wayne’s shoes is to assume that he could and should have known that Apple would have turned into a multi-billion dollar enterprise. This sort of thinking puts unrealistic responsibility on our shoulders, adding insult to injury: “Not only did you blow it – you should have known better.” Most people who know of Ronald G. Wayne remember him not for being a resilient, independent-minded individual and talented engineer, but for being the “world’s unluckiest man” who walked away from the chance to be ultra-wealthy. 

It takes real strength of character to shrug off people viewing you as a blunderer. Wayne is used to being asked in interviews how he feels about his decision (morbid curiosity is a stubborn thing), and always his response is cordial. 

He once explained it this way:

“Look, I live my life step by step, event by event as it happens. And by the way I [was] extremely fortunate to have been at a turning point in history and the establishment of Apple was indeed a turning point in history. Although at that time of course, nobody really knows this. It takes [the] perspective of history to do that.” ²

Rather than focusing on the money he “lost” (assuming all other factors held equal in this alternate universe), Wayne focuses on the chance he had to be a part of history for a brief moment. He doesn’t beat his past self up or hold his past self to unfair standards. He’s at peace with his limited understanding of reality.

“The Richest Man in the Cemetery” 

Hindsight bias is tied to another pernicious joy-stealer: counterfactual thinking. The downside of having a brain with a hyper-developed neocortex is that we can question our choices. We can’t test different outcomes in different universes, so all we’re left with is our imaginations. Counterfactual thinking is the parent of that double-edged sword we all grapple with at some point: regret.

On the one hand, regret can be good for us in helping us course correct our life mistakes. But too much dwelling on “what might have been” is a recipe for the worst kind of regret. And it’s the latter that Wayne is wise enough to avoid.

“Do I regret selling my share of Apple?” he once asked rhetorically in an interview. “No, and that has been my answer ever since day one and will be my answer until I die.” ³Hindsight bias aside, why would he (or anyone) want to opt out of an exciting enterprise? There are plenty of good reasons.

Wayne understood the ancient maxim of the Delphic oracle, “Know thyself.” He knew he wouldn’t be happy in a backroom dealing with paperwork for the rest of his life. His passion was in engineering and designing things (especially slot machines) and he didn’t have the energy to keep up with a couple of hungry 20-somethings and settle all of their squabbles. ⁴ “If I had stayed at Apple,” he concludes, “I would have wound up the richest man in the cemetery.” ⁵

It’s a tongue-in-cheek reminder of a sobering truth: we’re all going to be dead sooner or later. Money is great, but focusing on our deepest drives and interests is more important because time is short. A lucky few of us will get both; all of us will have to make trade-offs.

When Wayne’s life savings were stolen overnight his friends asked him why he wasn’t “screaming up the walls.” Taking a note from the playbook of the ancient Stoics (in modern parlance) he answered, “What am I supposed to do? Make myself sick over the sides? I mean, the situation has happened. I’ll deal with it. When something happens, you just deal with it.” ⁶

Hopefully, most of us won’t have the spectacular, ironic type of bad luck that Wayne has had. But if we do, it will save our sanity to keep both counterfactual thinking and hindsight bias at arms’ length. There’s no way to have a mistake-free past; agonizing over our choices will only hamper our future.

Or in the more eloquent words of Søren Kierkegaard: “Life can only be understood backward, but it must be lived forwards.”

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Read Next: Why We Can’t Predict What Will Make Us Happy →

1. Hom, H. L. (2023). Perspective-taking and hindsight bias: When the target is oneself and/or a peer. Current Psychology, 42(5), 13987–13998. https://doi.org/10.1007/s12144-021-02413-z
2. Luo, B. (2013, September 12). Ronald Wayne: On co-founding Apple and working with Steve Jobs. NextShark. Read here.
3. Moitozo, M. (2017, July 11). Apple’s third co-founder has never used an iPhone and has no regrets. Vice. Read here.
4. Jobs first brought Wayne on board because he was good at mediating between Jobs and Wozniak. Quite the honor, but I’m sure it would have grown tiring.
5. Ibid.
6. Dormehl, L. (2014, December 3). The oddly uplifting story of the Apple co-founder who sold his stake for $800. Cult of Mac. Read here.