Over the holidays, I sat down with a friend whose job had taken a turn for the worse.
For four years, the work had been fulfilling and productive. Now there was a real possibility that the job might not exist in a few months.
She had been thinking about going out on her own and finding a way to make money independently. Part of her wanted to make the leap before the decision was made for her.
But she did not feel ready.
“If only I had more savings,” she said. “Then I could take some time off and figure out how to make money on my own.”
I understand this instinct.
When the path in front of us becomes uncertain, we start looking for ways to eliminate the uncertainty. We tell ourselves that we need more savings, a better plan, another client, or a clearer signal.
But sometimes the preparation is not really preparation. It is an attempt to make an uncertain decision feel certain.
That kind of certainty may never arrive.
As we talked, I began thinking about the difference between the downside she imagined and the downside she would actually face.
She was not choosing between total security and total ruin.
If she tried working for herself and it did not work, she had skills. She had relationships. She had professional experience. She could look for another job.
The landing might be uncomfortable, but it would not necessarily be catastrophic.
The net was closer than it felt.
This is not true for everyone.
Some people support families, carry debt, have health concerns, or lack a dependable safety net. Risk should not be romanticized. The distance to the net is different for each person, and part of making a good decision is being honest about where yours actually is.
But I have noticed that founders and would-be founders often calculate risk in only one direction.
They carefully imagine everything they could lose.
They are much less specific about what might become possible.
The downside is made vivid. The upside remains abstract.
The difficult thing about a new path is that its opportunities are usually invisible from the starting point.
Before you begin, you cannot know which customers you will meet, what skills you will develop, or which version of the business will finally work. You cannot see the introduction that will change the company, the idea that will emerge after six months, or the opportunity that does not exist yet.
You can see what you might lose because you already have it.
You know the salary, routine, status, relationships, and comfort attached to your current life. The potential loss is concrete.
But you cannot fully see what you might gain because that life does not exist yet.
The upside is made of people you have not met, places you have not gone, ideas you have not had, and opportunities you could not have planned for.
I first heard a version of this idea from Kyle Cease:
He said,
“You can always know what you might lose, but you cannot know what you might gain.”
That, in investing, is what we call asymmetry.
I eventually came to picture it this way:
The net is one foot below you. The sky above you is infinite
It does not mean that every risk will work out.
It does not mean that everyone should quit their job.
It means that some decisions are more asymmetric than they first appear. The realistic loss may be limited and recoverable, while the potential gain is open-ended.
For a founder, the gain is not only financial.
You might gain a business. You might also gain a new sense of agency, a network, a body of work, a clearer understanding of what you are good at, or a life that fits you better.
Even an attempt that fails can change the opportunities available to you afterward.
I wish I could tell you that everything went perfectly for my friend after she made the leap.
There were still difficult periods, uncertainty, and moments when the safer path probably looked appealing.
But she is now making more money than ever.
More interestingly, her life opened up.
She traveled way more. She met new people. She found herself in surprising situations that neither of us could have predicted during that original conversation.
Before the leap, her life had become relatively stagnant, comfortable, and known. Afterward, there was a rush of new experiences and possibilities. Her life became drastically more interesting.
Take the Next Right Step
At the time, I did not tell my friend to quit her job.
I told her that she did not need to solve the entire future before moving toward it.
She could take one step into the unknown, into the infinite.
Talk to a potential customer. Offer a small service. Test whether someone will pay. Put aside a specific amount of runway. Go to an event.
The choice is rarely between staying exactly where you are and making one enormous, irreversible leap.
There are usually smaller moves that reduce uncertainty without requiring certainty.
Fear naturally directs our attention downward. It asks us to protect what we already have.
Sometimes that protection is wise.
But sometimes we become so focused on avoiding the fall that we never look up.
xx David
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