Knowing When Let Go: What Investing Can Teach Us About Life
Jeraldine Phneah
June 01, 2025
I recently came across a reflection by Sahil Bloom on a moment that stayed with him from the UBS Berkshire Hathaway Fireside Chat.
An audience member asked Chief Investment Officer Ryan Israel: “How do you know when to sell a stock?”
The answer was not just about markets. It revealed a powerful way to think about life decisions: when to let go of a job, relationship, or dream that no longer serves us.
He shared key signs that it might be time to let go.
1. You Have Already Been Paid Too Well
For stocks, this means the price has risen so far above its intrinsic value. You have essentially captured years’ worth of future growth in today’s price.
Most potential gains are already realized, leaving little upside relative to the risk.
In your career, it might mean you have gained most of the learning and experience it can offer. Or, already accumulated the key achievements needed to move forward.
For example, you have been a Marketing Manager for three years.
Meanwhile, a six-month Bahasa Indonesia immersion in Jakarta beckons. If circumstances allow, this could be a rare opportunity to build fluency and cultural insight.
When you have gained all you can from your current role, staying might not be worth sacrificing an opportunity that could accelerate your trajectory.
The best career move is sometimes knowing when you have already won the game you are playing, and it is time to start playing a bigger one.
2. You Were Wrong About Your Original Thesis
In investing, this is when new facts contradict why you bought the stock. The company veers off course, or trusted leadership departs.
In life, it is realising your initial assumptions no longer hold.
It could mean joining a prestigious investment bank, believing complex deals for wealthy corporations defined financial success.
Five years in, you wonder if this is truly something meaningful to you.
You pivot to an impact investing firm funding sustainable businesses in underserved communities.
Though you earn less, creating both returns and positive social outcomes feels more meaningful.
Knowing when to let go of a flawed thesis allowed you to align your skills with your values and find greater purpose.
Recognising a mistaken premise is not failure. It is wisdom. Smart investors cut losses early. We can too.