Leadership
Starting Before Certainty: Leadership When the Plan Is Incomplete
The problem often arrives before the expertise. Responsible action does not have to wait for perfect certainty.
A practical resource grounded in the current If Not for the Blast manuscript, nonprofit-building experience, speaking work, and the repeated lesson of beginning useful work before the full blueprint existed.
The plan is often late
There is a version of leadership advice that assumes the sequence is simple: know what you are doing, build the plan, gather the resources, reduce the risk, and then begin. That is a good sequence when life gives it to you. A lot of meaningful work does not begin that way.
Sometimes the problem arrives before the expertise. Sometimes the need is obvious before the organization exists. Sometimes the deadline is real, the resources are incomplete, and the person responsible has to decide whether uncertainty is a reason to stop or simply part of the conditions.
I did not know how to build a nonprofit when The Battle Buddy Foundation began. I did not know how to build a service-dog program, stand in front of rooms and tell the worst parts of my own story, write a memoir, design a professional website, or turn old Iraq photographs into a serious body of work when those projects began. That does not mean expertise is unimportant. It means expertise is not always available at the beginning.
The difference between beginning and pretending
Starting before certainty is not the same thing as pretending you know more than you do. There is nothing admirable about charging forward while hiding risks, ignoring expertise, making promises you cannot support, or treating other people as the cost of your learning curve.
The useful version is more demanding. It requires being clear about what you know, what you do not know, what cannot wait, what can wait, and who needs to be brought in before the next decision becomes irreversible.
When Battle Buddy began, the problem was clear to me before the solution was complete: veterans should not have to expose the worst parts of their lives publicly, raise huge sums of money, or wait indefinitely just to prove they were worth helping. That conviction was not a business plan. It was enough to identify the work. Structure, policies, funding, training, partnerships, mistakes, and corrections came later.
A problem can be clear before the solution is complete
Leaders often delay action because they confuse an incomplete solution with an unclear problem. Those are different conditions. You can know a customer experience is failing without knowing the perfect redesign. You can know a team is losing trust without having a twelve-month culture plan. You can know a process is wasting people’s time without having selected the final software.
That is not a license to improvise forever. It is permission to begin discovery in motion. The first responsible action may be small: document the problem, talk to the people living with it, build a reversible prototype, identify the decision that actually carries risk, separate facts from assumptions, bring in expertise where the stakes are high, and preserve a record of what worked and failed.
The goal is not certainty before movement. The goal is responsible movement that creates better information.
Make the next decision smaller
Uncertainty becomes dangerous when every decision is treated as one giant commitment. A useful leadership habit is to shrink the decision.
- Instead of “Can we build the whole thing?” ask, “What is the smallest safe version that proves whether this direction is useful?”
- Instead of “Are we ready to launch?” ask, “What must be true before one real user is exposed to this?”
- Instead of “Do I know how to do this?” ask, “What part can I responsibly learn, and what part requires someone who already knows?”
Smaller decisions preserve options. Preserved options make learning less expensive.
Reversible and irreversible are different kinds of risk
Some choices are cheap to undo: change the draft, move the button, rewrite the introduction, test a workflow, throw away the prototype. Other choices are expensive or impossible to recall: send the email, publish the claim, sign the contract, spend the money, expose private data, make a promise, put someone’s reputation or safety at risk.
Good leadership under uncertainty treats those categories differently. Move quickly where the decision is reversible and the learning is useful. Slow down where the action creates obligations, public consequences, safety risk, financial exposure, or damage that cannot easily be recalled. That is not indecision. It is risk discipline.
Use evidence without worshipping the spreadsheet
Beginning before certainty does not mean ignoring evidence. It means accepting that evidence arrives in stages. Early evidence may be lived experience, repeated complaints, a pattern in conversations, one painful failure, or a problem that keeps producing the same result. That can be enough to investigate.
As the work grows, the standard should rise. Anecdote becomes a hypothesis. The hypothesis becomes a process to test. The process produces data. The data changes the next decision. The mistake is not starting with incomplete information; the mistake is refusing to update once better information exists.
Build the record as you build the thing
Uncertain projects become chaotic when the learning disappears. Someone remembers why a choice was made, then gets busy, leaves, or remembers it differently six months later. A stronger system records decisions while they are still decisions.
- What problem were we solving?
- What did we believe at the time?
- What evidence supported it?
- What was missing?
- What did we decide?
- Who approved it?
- What happened afterward?
- What should change next time?
That record turns failure into institutional memory instead of folklore. It also makes leadership less dependent on confidence: a decision can be reasonable based on what was known then and still be replaced when better information arrives.
Ask for expertise before the learning curve can hurt people
There is a point where self-reliance stops being leadership and becomes ego. Starting before certainty requires learning, but it also requires knowing which lessons are too expensive to learn the hard way.
Legal questions need legal expertise. Medical questions need qualified medical expertise. Security, accounting, accessibility, engineering, publishing, and other disciplines have places where “I will figure it out” is not a responsible substitute for someone who understands the consequences. The leader’s job is not to know everything personally. It is to recognize the boundary early enough to bring the right knowledge into the decision.
Mission can start the work. Expertise helps keep the mission from hurting people.
Do not make uncertainty inspirational
Uncertainty is not automatically good. Sometimes the work fails. Resources disappear, relationships break, momentum dies, or the thing that once carried your purpose can no longer carry all of you. “Just start” can become another slogan that sounds useful only from the finish line.
There is no guarantee that beginning produces success. Beginning produces a chance to learn what the next responsible move is. Sometimes that move is forward. Sometimes it is sideways, to stop, or to hand the work to someone better equipped to carry it. Leadership is not proving that the original idea was right forever. It is staying responsible for what the evidence says now.
A practical operating model for incomplete plans
1. Name the problem before naming the solution.
Be able to explain what is wrong without requiring your preferred idea to be true.
2. Separate facts, assumptions, and missing information.
A missing answer is not the same thing as a negative answer.
3. Identify the irreversible decisions.
Put the highest review standard around the actions that create the greatest consequence.
4. Build the smallest useful test.
Learn before scaling whenever the real-world cost allows it.
5. Keep humans in the consequential loop.
Software, automation, and AI can prepare decisions; responsibility should stay explicit where people, money, rights, safety, reputation, or public claims are involved.
6. Record why the decision was made.
Future you should not have to reconstruct the reasoning from scattered messages and memory.
7. Measure the outcome.
If the result cannot change the next decision, you are collecting decoration rather than feedback.
8. Update without defending the old version of yourself.
Better information is allowed to make yesterday’s plan obsolete.
9. Preserve what worked.
A useful lesson should become a repeatable process, not a lucky accident.
10. Stop when the mission no longer justifies the method.
Persistence is not the same thing as refusing to change.
What the Marine Corps did—and did not—teach me
Military experience is easy to over-romanticize in leadership writing. The Marine Corps gave me useful habits: responsibility, preparation, team dependence, acting under pressure, and an understanding that indecision can have a cost. War also taught me something less tidy: reality does not care how good the plan looked before contact.
That is not an argument against planning. It is an argument for plans that can survive new information. The best plan is not the one that proves the leader predicted everything. It is the one that helps people understand the objective, the constraints, the next decision, and what to do when the assumptions stop being true.
The part I keep returning to
The current memoir began, in part, because the full memoir was taking too long and becoming too large. The joke was to reduce the whole thing to a haiku. The joke became a poem, then a ballad, then a forty-eight-page book. I did not begin because I had finally learned how to be an author. I began because the story might be worth something to someone, and that had usually been enough to start the next useful piece of work.
That is the version of “start before certainty” I trust: not confidence without evidence, not speed without responsibility, and not pretending the missing pieces do not matter. Begin with what is true. Protect the decisions that carry real consequences. Learn quickly where learning is safe. Bring in expertise before ignorance becomes damage. Keep the record. Change when the evidence changes.
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