The freedom of constraints
The challenge with optionality and the case for carefully designed constraints.
"Your scientists were so preoccupied with whether or not they could, they didn't stop to think if they should."
– Ian Malcom
"Constraints" feels negative. It implies restriction, limitation, being stopped from doing something you might want to do.
Likely the product of our early experiences in life. Don't do this. Don't touch that. Study hard. Follow the rules. Constraints feel like shackles.
We carry that baggage into adulthood. And so, we often try to avoid things that feel restrictive, a one-way road, or a corner. We love optionality.
What I’m going to argue here is that constraints are incredibly positive when introduced to help you make progress towards an outcome.
Sure, most of us live with constraints already — diets, career paths, financial limits. But these are often inherited or reactionary, shaped more by social pressure than personal intent. These constraints feel like burdens, sources of resentment and resistance. In contrast, intentionally designed constraints feel liberating. They clarify priorities, eliminate distractions, and create momentum.
It takes time to configure optimal constraints. Most aren’t great at doing it (including me). Here’s a collection of mental models, examples, and methods you can use.
Use inversion to create constraints
"It is not the present which influences the future, thou fool, but the future which forms the present. You have it all backward."
― Frank Herbert, Children of Dune
In other words, how you perceive the future informs how you organise the present. When you want to achieve something, be that a relationship or a career outcome, we often consider the things we need to do in order to get us there. We organise the present into actions we think we should take.
However, a hugely underutilised method is actually to invert how you organise the present. Consider the actions you shouldn’t take. Instead of asking, 'what should I do to succeed?' ask 'what behaviors would guarantee my failure?,’ then systematically avoid them.
This is inversion thinking. It's a mental model where you flip a problem around. Rather than struggling to identify every possible action that might lead to success, you define clear constraints that prevent failure. Constraints won’t solve all your problems, but they’ll help you avoid failure and navigate decisions more effectively.
Examples of great constraint designers
Derek Sivers captured this idea perfectly in his "Hell Yeah or No" principle – if you're not saying "HELL YEAH!" about something, say no. It's a simple constraint that eliminates the merely good to make room for the truly great. By limiting our commitments to only those that genuinely excite us, we focus our limited time and energy where they'll have the most impact [0].
Hemingway became Hemingway by deliberately limiting himself to short sentences and minimal adjectives. Haiku poets create depth within just seventeen syllables. The sonnet's fourteen-line structure hasn't limited poets but pushed them towards a different kind of excellence. Constraints kindled creative friction.
Maya Angelou rented a hotel room where she would write from 7am to 2pm. She removed all artwork from the walls and wouldn't let the hotel staff touch her notes. Constraints to keep distraction at bay.
Charlie Munger, Buffett's business partner, said: "It is remarkable how much long-term advantage people like us have gotten by trying to be consistently not stupid, instead of trying to be very intelligent." This is inversion at its finest [1].
Rather than chasing brilliant investment moves, Munger and Buffett constrained themselves by avoiding obvious mistakes. No investing outside their circle of competence. No following market fads. No complicated businesses they couldn't understand. Constraints that created downside protection.
When we lack constraints, we drift. We either continue aimlessly in whatever direction we were already moving or, worse, bounce randomly between options like a pinball.
Carefully designed constraints provide direction. They help us focus on what matters and give us space to develop our craft.
Poor Charlie’s Almanack from Stripe Press — a book I gift regularly.
Optionality makes our constraints brittle, so you have to actively limit options
But we face a contemporary challenge when it comes to designing our constraints. Two thousand years ago, if you were born a poor farmer, you stayed a poor farmer. Your options were limited.
Today, you have more influence over how you navigate life and who you do it with. Optionality is great, but it complicates decision-making.
Look at romantic relationships. That poor farmer might have had half a dozen options in their local community (across their entire life), a few more if they uprooted to a larger village. Modern society is very different. The internet gives us the perception of endless romantic optionality, and urban living facilitates it.
In romance or business, we're taught that life is a numbers game. It's about shots on goal. Making mistakes and iterating. 50 failed relationships don't matter if that 51st is a winner. It only takes one business to hit it big to make up for previous failed ventures.
We glorify optionality and reject forms of restriction.
But endless optionality has unintended consequences. When everything seems possible, it becomes increasingly difficult to commit to anything specific. Our self-imposed constraints become brittle — you can date anyone, move to Australia, start a new business, chase the next trend, leave your company — why limit yourself? We're constantly tempted to change course.
A portfolio approach to life means we make shallow progress in several domains, rather than deep progress in few. Creating options at the expense of outcomes [2].
If this strikes a nerve, you're not alone. Dan Hockenmaier's essay "Generalist Disease" [3] (which I’m sure many of you have read) diagnoses a condition that plagues many knowledge workers. The common symptoms include ambitious people hoarding impressive roles from big company logos that look good on resumes but never develop into genuine expertise. Each prestigious "door-opening" opportunity perpetuates the cycle. Hockenmaier's remedy aligns with our concept of constraints — at some point, you must deliberately take options off the table. Real growth demands committing to a direction and closing other doors. This is precisely what well-designed constraints provide — the structure to commit rather than endlessly explore.
“To pick out a mission and honour it with real focus is the trick”
— Something Ophelia from Tiny VC sent to me via email 3+ years ago - safe to say, it stuck.
How to design good constraints
When it comes to designing good constraints, the trick here is to avoid being too general. “Don’t die” is a catch all, yes, but it’s not all that helpful in daily decision making.
A good constraint should be:
Useful enough to guide immediate decision-making
Specific to your goal (healthy relationship, investment outcome, learning French)
Binary or measurable (yes/no or clear threshold)
Your constraints can start broad if you’re new to an opportunity space, but they should get more specific as your expertise grows.
Take angel investing as an example:
You’ll notice how the “ambition-level” of the failure pattern changes with expertise. Basic constraints focus on avoiding failure. Intermediate ones attempt to avoid mediocrity. And advanced constraints pursue exceptional outcomes. The baseline changes with experience.
If you don’t regularly revisit and update your constraints, they’ll quickly get out of date and lose their usefulness. It could be as simple as asking yourself a different question:
What guarantees failure?
What leads to mediocrity?
What prevents excellence?
Constraints are particularly useful when you find yourself at a new frontier of knowledge. When something hasn’t been done before, it’s easier to configure what you know you shouldn’t do, versus what you think you should do [4].
—
*a few investor friends rightly pointed out that there’s a strong argument for not doing follow ons, particularly if you’re investing at the early-stage. Power law, spread bets, following on offers diminishing returns — I get it. I’d also argue that we’re going to witness a lot of crappy companies being started over the next 10 years (an order of magnitude more than the last decade) thanks to it being easier to build software. There’s going to be more noise, less signal. When you find signal, and get deeply convicted on a founder, hold on.
Design your constraints before the world does it for you
If I had to wrap up this long thought in a sentence or two it would be; Just because you can do something doesn’t mean you should. Designing intentionality around what not to do is a useful way to navigate endless optionality.
The future you want to create requires constraints to reach it. Not the external ones imposed by circumstance or authority, but the internal ones you choose deliberately. A life without thoughtfully chosen constraints is chaos. It's “making a millimeter of progress in a million directions instead of meaningful advancement toward what matters” [5].
"In a few hundred years, when the history of our time will be written from a long-term perspective, it is likely that the most important event historians will see is not technology, not the Internet, not e-commerce. It is an unprecedented change in the human condition. For the first time—literally—substantial and rapidly growing numbers of people have choices. For the first time, they will have to manage themselves. And society is totally unprepared for it"
— Peter Drucker [6].
I don't think we humans are very good at self-management. Constraints are a focus mechanism. One way to reduce the aperture, narrow our field of view in exchange for depth. Arguably, constraints are low hanging fruit in the world of self-management because anyone can run a short thought experiment and deploy them — but few do!
What constraints should you deliberately introduce? What activities are keeping you from your most important goals? What boundaries might you need to establish? What systems could make the essential inevitable and the nonessential impossible?
Parting thought - “Freedom” doesn’t mean the absence of constraints. Freedom is the privilege to choose them for yourself.
Constraints enable you to pursue depth. To say no to most things. To focus.
[0] - https://sive.rs/n - Sivers is fantastic. He has several excellent audiobooks. This simple framework is designed to protect your time so that you can invest it into the opportunities that are most meaningful/inspiring to you. We often get drowned by saying “yes” to things we’re not that keen on.
[1] - https://fs.blog/avoiding-stupidity/ - if you do nothing else today, I would consider a subscription to fs.blog a successful day. Shane is 🤌
[2] - anyone that worked closely with me earlier in my career has likely heard me claim that I’m behaving in ways that “preserve optionality”. I think there’s an argument for doing so earlier in your career/life (try many things, learn what sticks and what you’re good at), but there has to come a point where you pursue depth. Otherwise you sort of bounce around in mediocrity. Dan Hock’s Generalist Disease (see below) also shares this sentiment.
[3] - Dan Hock’s essay
[4] - https://www.paulgraham.com/greatwork.html
[5] - https://heream.wordpress.com/wp-content/uploads/2017/12/greg-mckeown-essentialism-the-disciplined-pursuit.pdf - I like this book, but feel it could actually just be a blog post.