One email a week - something from which I hope you'll get real value. We talk about things we can build, and how to defend them. That can apply to cybersecurity, physical buildings, digital products, and .... just about anything. It gives me a lot of latitude in what I can write about, but the two concepts are important for progress - as individuals, and as society.
(I’m trying to get back to publishing on Wednesday - I got pretty close this week!)
Today's topic is: building and defending your personal board of directors.
There is a particular kind of (bad) decision that feels very clever when you are making it alone. You have thought about it for three weeks. You've read seventeen articles. You have asked an AI to give you a pros-and-cons list, then asked a different AI to critique the first AI’s list, which is the modern equivalent of consulting two fortune tellers who share a Wi-Fi connection.
Eventually you conclude that nobody understands the problem as well as you do. Sometimes that's true. More often, you are simply too close to the problem to see the thing that everybody else can see from outer space. That's why people have advisors. That's why companies have boards. They have people who are not running the business day to day, but who can ask annoying questions, spot a gap, challenge an assumption, and occasionally say, “That sounds exciting, but have you considered that it makes you seem mental?”
Most of us need a smaller, less formal version of that. Not a committee with nameplates and a quarterly slide deck. (although that actually does sound kinda cool....) A personal board of directors: a few trusted people who make you less likely to make important decisions in an echo chamber of one.
🔨 BUILD: Your Personal Board of Directors
The first rule is that this is not a collection of impressive contacts. Also, don't do LinkedIn Open Networking (LION). I did that for a while and I have 18,000+ contacts which I'm slowly whittling down. It was 21,000+. It takes A LONG TIME to remove all those people.
You do not need a billionaire investor (or maybe you do!?), a former general, an AI founder, and somebody who uses the word “synergy” without irony. You need people who know something useful, care enough to be honest, and are not so invested in your choices that they will simply tell you what you want to hear.
Start with four roles. Four is enough to make it useful without turning a decision into an episode of Family Feud.
The truth-teller. The person who knows you well enough to recognise your usual nonsense. They can tell when you are rationalising, procrastinating, overreacting, or trying to buy a new project because you are bored. This should ideally not be your spouse.
The person ahead of you on the road. Somebody who has navigated a version of the thing you are considering: a career shift, business, move, family decision, financial goal, or difficult season.
The specialist. The person who understands one field better than you do and can keep you from confidently stepping on a landmine.
The different-life person. Somebody whose priorities and circumstances are unlike yours. They are useful precisely because their answer will not be a copy of your own.
These are roles. One excellent person might fill two of them. A spouse may be the most important board member of all, although possibly not the right person to ask whether you should buy another computer because “this one only costs $20k and will be used for for local AI". I'm not knocking the value your spouse brings to your life, but they are the second closest to things after yourself. They may not be as objective as what I'm thinking of requires. That will be for you to decide though!
Write down the names privately. Beside each name, write the question you would ask them. “Am I making this move for the right reason?” “What am I missing financially?” “Will this still matter in five years?” “Is this a good idea, or do I just like the sound of it?” That is your first board pack. No PowerPoint required. Unless you want. I know people that would create a Powerpoint for this.
Give the board real work
A personal board only works if it has a job. Don't suggest that you're employing them though - but do ask if they are willing to help.
Do not call someone out of the blue every time you are in a panic and expect wisdom to arrive with the starter motor. ("Poor planning on your part does not constitute an emergency on theirs.") Create a small rhythm instead:
a walk, coffee, or call once every few months with one member
a short annual check-in with the whole idea in mind
a decision rule for genuinely consequential choices
The decision rule is simple: before a decision that affects your money, family, health, work, or freedom for more than a few months, ask at least one person who has earned the right to disagree with you.
You are still the chief executive. You make the decision. The board is there to improve the quality of the decision before it becomes an expensive learning experience.
🛡️ DEFEND: Defend Against the Echo Chamber of One
The obvious danger is bad advice. The more common danger is no advice at all.
When life is busy, we make choices from inside our own head because it is faster. We stay in the job because changing is inconvenient. We take the opportunity because it flatters us. We refuse the opportunity because it scares us. Alone, with the conversation of both voices in your head (you guys have two as well, right!?) almost every explanation sounds plausible.
A good board protects against a few predictable traps:
Confirmation bias. You do not need another person to agree that your favourite idea is brilliant. You need someone to ask what would make it fail.
Borrowed ambition. A promotion, house, business, degree, or lifestyle can be admirable and still not be yours. Ask: “If nobody saw me do this, would I still want it?”
Urgency theatre. Plenty of choices feel urgent because somebody else benefits from you deciding quickly. A trusted person can give you permission to slow down.
Advice collectors. The opposite problem is asking so many people that you never own the outcome. Seek counsel, not a referendum.
Transactional relationships. Do not treat your board like a free consultancy. The people who give the best advice are people whose lives you also take an interest in.
There is a useful distinction here: a mentor tells you what worked for them. A board member helps you decide what is right for you. Sometimes the same person can do both. Sometimes the person with the most impressive biography is the worst fit because they are still trying to turn everybody into a younger version of themselves.
And yes, AI can help you prepare. Ask it to turn your thoughts into a one-page briefing, identify assumptions, or argue the other side of a decision. But do not confuse a fluent response with a relationship. AI has no stake in whether you move cities, leave a job, buy a business, or spend the next five years chasing a goal that does not actually suit you. (Yet.) For that, you still want people.
💰 STACK: The Board Pack
Your board needs less infrastructure than a fantasy football league.
A one-page personal brief. Who you are, what you are building, what you value, and what you are trying not to sacrifice along the way.
Four names. The truth-teller, the person ahead, the specialist, and the different-life person.
A decision note. For any meaningful choice: the decision, the options, the likely upside, the likely downside, the assumptions, and the date by which you must decide.
A recurring reminder. One conversation per quarter is plenty. Put it on the calendar before life eats the intention.
A reciprocity list. Note what matters to the people on your board. Send the article, make the introduction, remember the job interview, ask how the sick parent is doing. Be a useful board member for them too.
A “not yet” list. Some choices do not need an answer today. Recording them stops every loose possibility from renting a room in your head.
The most important tool is not an app. It is the willingness to ask a better question before you announce that you have already made up your mind.
🔗 LINKS
(Amazon links are affiliate links.)
Farnam Street’s Mental Models Collection
A useful place to borrow questions that improve a decision before you commit to it.
Never Eat Alone
By Keith Ferrazzi is about building generous, durable professional relationships rather than collecting business cards like Pokémon.
Give and Take
By Adam Grant is a good reminder that the strongest networks are built through contribution, not extraction.
The Coaching Habit
By Michael Bungay Stanier is short, practical, and especially useful if you tend to give answers when a better question would help more.
💬 ONE THING
Open a note called “My Board of Directors.” Write four names: the truth-teller, the person ahead, the specialist, and the different-life person. Then send one of them a real message this week. Not “We should catch up sometime.” Ask for a walk, coffee, or call, and bring one honest question. You do not need more opinions. You need one person who can help you see around the corner.
Thanks for reading this newsletter! Feel free to respond any time.
Thomas
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