The paradox of choice, why running four ventures taught me to want less optionality
Running four companies taught me I want less optionality, not more.
The old me, starting out, would have said the opposite. Entrepreneurship meant freedom. Freedom meant options. More options meant more leverage, more upside, more ways to win. That was the story, and I believed it.
The operator me knows better. The most valuable thing a multi-venture career has taught me is how much anxiety, rework, and lost compounding comes from keeping options open that should have been closed months ago.
The original idea
Barry Schwartz wrote The Paradox of Choice in 2004. The central finding: more options do not produce more satisfaction. Beyond a small number, more options produce more anxiety, more second guessing, and more regret about the paths not taken. The research was done on consumers in grocery stores and retirement plans, but the framework applies cleanly to operators and founders.
Schwartz’s subtle point is often missed. He is not saying options are bad. He is saying that beyond a modest threshold, the marginal option adds more decision cost than decision value. The curve inverts. Once it inverts, adding options makes the decision maker less satisfied, less confident, and less likely to commit. That is the paradox.
Four ventures is a cap, not an opening
If I keep four ventures running, I cannot have a fifth. The discipline of that constraint is what makes the four good.
Every conversation about a new venture starts with the question: which of the existing four would I shut down to make room for this? Usually the answer is none. Usually the conversation ends there.
That sounds limiting. It is the opposite. Without the constraint, I would keep adding. Each new company would be a little worse than the last because my attention would keep getting thinner. Within a decade I would run twelve mediocre businesses instead of four serious ones. The four are serious precisely because they are four.
Inside each venture, the same discipline
Scentpression could offer two hundred fragrances. We offer a curated dozen, drawn from a larger library but brought to a customer as a considered set. Clients routinely thank us for the curation. What they are actually thanking us for is the absence of paralysis.
Vanbert could quote every available aircraft on every route. We present three to five options per trip, chosen carefully. Clients make decisions in minutes that would take them hours on a pure marketplace. The marketplace is technically more comprehensive. The curated quote is more useful.
BOM could sell every billboard we have to every advertiser who walks in. We build a media plan and present it. Our job is not to maximize a client’s optionality. Our job is to remove the options that would waste their money.
In each case, the curation is the product.
Choice architecture is the product
That is the counterintuitive operator lesson of the paradox of choice. What you sell is not just the service. It is the arrangement of options around the service. A smaller, better arranged set of options is worth more than a larger, unstructured one.
This is why the curated restaurant menu outperforms the diner menu. Why a three tier pricing page converts better than a custom configurator. Why a good consultant is worth the fee over a raw report. In every case the operator is not adding information. They are removing it, and the removal is where the value sits.
Clients do not usually notice that this is what they are paying for. They notice that decisions feel easier. They notice that the outcome they chose feels right. They give you credit for the service. The real work was the subtraction.
On the other side of the desk
I hold myself to the same standard. When a decision has more than a handful of real options, I treat that as a sign that the problem has not been framed well yet. The framing is where the options get cut from twenty to three.
If I find myself in a room with a spreadsheet of fifteen vendors, I do not ask which is best. I ask what was wrong with the initial brief that produced fifteen survivors. Usually the brief was vague. A tighter brief produces three survivors. A choice among three is a decision. A choice among fifteen is a procrastination mechanism with a filename.
Three practical disciplines
Three habits I try to enforce for myself and for the teams I work with.
Constraints before options. Define what you will not do before you consider what you could do. A decision made inside hard constraints is almost always better than the same decision made in open field. The constraints do the work.
Reframe decisions with too many candidates. If a decision has more than five real candidates, the problem is not that you cannot pick. The problem is that the field is too wide for picking to be useful. Go back to the brief and narrow it.
Close the door after you decide. Once a decision is made, close the door. The cost of keeping an optional door open is not zero. It is a quiet tax on attention and a standing invitation to second guess. Closure lets the decision compound. Openness lets it drain.
The compounding case for constraint
Running multiple ventures looks from outside like the expansion of optionality. From inside, it is the discipline of repeated closure.
Every morning I start with a short list of things that will get real attention today. Everything else is either delegated or declined. The list is short by design. A short list, executed well, outcompounds a long list executed partially. This is unglamorous math. It is also true.
The paradox of choice is one of the most useful ideas I have come across in a decade. Not because it tells me to want less. Because it tells me that wanting less is not a concession. It is a strategy.
Further reading: First principles thinking · Contrarian thinking from the Caribbean