why you should imagine more
you haven't reached the end of your history yet
What if the secret to living well isn’t predicting better, but imagining more? Humans suffer from an inability to forecast change, but more precise and scientific prediction isn’t the answer to this. Instead, cultivate the ability to imagine more.
The end of history illusion, described by Dan Gilbert in a 2014 TED Talk, is a psychological bias where we think at every age we’ve finally arrived and won’t change anymore going forward. Though we can recall changing over the past ten years—and over every previous era of our life—we think that our values, personalities, and preferences will remain largely the same going forward.
Gilbert and his colleagues conducted a survey study in 2013 showing that people, at every age from 18 to 68, reported significant changes over the previous ten years. Yet, despite recalling those changes, participants believed they would remain mostly the same over the next decade.
This illusion can shape and sometimes distort the plans you make for the future, whether around careers or relationships or personal finances.
Gilbert suggests this happens because imagining future change is harder than remembering past change. You can easily recall how your values, personalities, and preferences have shifted. But when you try to picture future transformations, you struggle, not because they won’t happen, but because you can’t predict exactly how they’ll unfold. Gilbert calls this a failure of imagination.
imagining helps you break free of your old ways of winning
In The Last Word on Power: Executive Re-Invention for Leaders Who Must Make the Impossible Happen, Tracy Goss writes that each person develops a Winning Strategy for their life, and their career. This strategy “defines your reality, your way of being, and your way of thinking.” It guides and shapes your actions, limiting you as much as it helps you succeed.
The Winning Strategy is reinforced by the end of history illusion. You think that your winning strategy will continue to work, because it did work in the past.
Instead, it just keeps you stuck.
When I was a data scientist and artificial intelligence leader in various startups, my winning strategy at work was to identify some radical way the world could be better (using AI/ML of course), sell this idea to the people around me, and then move out on it. I didn’t always bring the radical new world into being, but I was able to get hired, get promoted, and get funding to put together teams to build the future I had described so compellingly.
Now that I’ve left my technology career, that winning strategy won’t work anymore. I now seek to create value individually through my own creative efforts, not via a team I build and lead, funded by someone else’s business and someone else’s ability to raise funding or sell stuff. I can no longer rely on marketing and selling my big picture thinking. I have to find ways to market and sell small batch creation.
You could say, “you are giving up on imagination” because I’m letting go of the big picture thinking and selling I used to do. But instead I’m imagining that I can be different, that I can earn income in another way, that my (career) future can be wholly unlike my past.
So I’m creating step-by-step. I created the painting above, Do You Remember What Happened? Its sister paintings will be exhibited in a show soon. I’ve sold a painting now. The painting process is slow, laborious, and manual. Selling those paintings is even slower. Meanwhile, I’m writing everyday, both on my 100-day project personal finance blog, and on a screenplay I have in the works.
If I sat down and tried to predict how this would all come out, looked at the probabilities of succeeding as a painter and writer and individual creator, I would probably shut this effort down. Instead I’m imagining worlds where I successfully, step by step, turn these creative activities into a new career, radically different from the one I left. I’m dwelling in possibility.
the end of history illusion in investing
I started thinking about this in the context of managing my investments. I was trying to figure out how to get myself to think long term, when it’s so easy (and dangerous) to get caught up in short term thinking around personal finances.
I realized: in investing, imagination is better than prediction.
Economic regimes change, sometimes in drastic ways. But as investors it’s easy to think that things are going to continue indefinitely the way they are, and that you will have experiences similar to the experiences you’ve recently had investing. This is an end of history illusion similar to the one that people have about their selves.
Any prediction you do is rooted in what you experienced before, whereas imagination isn’t limited like that.
The best investors recommend against prediction. Prediction relies on probabilities, but as Howard Marks said in The Most Important Thing: Uncommon Sense for the Thoughtful Investor:
There’s a big difference between probability and outcome. Probable things fail to happen—and improbable things happen—all the time. That’s one of the most important things you can know about investment risk.
The current end of history illusion for many individual investors says that there is a way to succeed with investing. It’s worked for the past fifteen years and it will continue to work in the future, to the tune of 10%+ annualized returns. All you need to do is buy and hold the S&P 500.
It’s easy to get stuck with a “winning strategy” in investing that won’t serve you in the coming years, because the future could look so different than the recent past.
One way to break out of this is by developing your imagination. Don’t think about what is likely to happen, because you aren’t good at judging how the future will evolve, and prediction ties you into your perception of what’s probable, which ties back to your own past. You base it on what you have experienced.
Train yourself to consider outlandish outcomes, not the ones you think are likely. Imagine a wide range of possible futures including that China takes over as the world’s most popular stock market, the US and the rest of the developed world go “full Turkish”1, or, yes, American exceptionalism continues.
Where could you use more imagination in your life?
recent writings
I’ve committed to writing daily(ish) for 100 days about personal finance for GenXers like me, preparing for retirement or maybe for a new career.
Recent posts:
Day 9: Dirtbag rich (inspired by
work)
Anne Zelenka is a Gen X data scientist, artist, and writer who shares her observations on living successfully at midlife here and in other places around the web. You can follow her on Twitter or on Bluesky, check out her yearlong reinvention blogging at The Reinvention Project, or visit her website, currently focused on her abstract art but could change any time!
Going “full Turkish” would mean keeping interest rates down, even as inflation soars. The currency would collapse. Capital would flee US Treasuries. But US stocks might continue to do well in nominal terms.