Make your next big decision well.
Answers are abundant. Judgment is scarce. I help founders, leaders and professionals make important, high-stakes decisions well, the kind where the cost of getting it wrong is real, and where AI can hand you a thousand answers but never make the call. You leave with clarity, sharper trade-offs, and a decision you can stand behind.
- 30 years of high-stakes decisions: corporate, startup, investment
- From intern to General Manager, leading multidisciplinary teams
- Startmate mentor, advisor and founder
The decision is never the point. The life it builds is.
People don’t buy a framework, or even a decision. They buy what a good decision makes possible: a life they are proud to call their own. Deciding well, in an age where answers are abundant and judgment is scarce, is how you get there.
build a successful company without destroying themselves.
create a career they actually want to live.
spend more time on what matters, and less time regretting choices.
stay the author of your own time.
Do you have an important decision to make?
The Captaincy Decision Scorecard is a free, five-minute assessment of the decision in front of you. It scores that decision across ten dimensions, from clarity and risk to how much AI is quietly shaping your thinking, and shows you where it is strong, where it needs work, and where you are exposed.
Free · five minutes · your full scorecard on screen, nothing to sign up for.
People inside a real decision.
Not open-ended coaching. This is for high-responsibility people in a decision window: a high-stakes call, real uncertainty, and a genuine cost to getting it wrong. The kind of moment where a good answer is not the same as the right decision.
Founders and investors
A funding round, a pivot, a co-founder call, an acquisition or a shutdown. The decisions where the whole company turns.
Executives and senior leaders
A promotion, a transition, an AI transformation, a role you are not sure you want. The calls that set your next decade.
Specialists and practice owners
Going private, taking on ownership, restructuring or stepping back. High-responsibility decisions with no obvious playbook.
You are not short of answers. You are short of judgment.
You have AI, advisors, podcasts and ten open tabs, all confidently telling you what to do. None of them carry the weight of the call or live with the consequences. That part is yours. Any of these sound familiar?
- Every option looks defensible, and you cannot tell which one is actually right for you.
- AI gives you a confident answer in seconds, and you are not sure how far to trust it.
- The stakes are high enough that getting it wrong is expensive, in money, time or self.
- You are surrounded by input and still cannot find the signal.
- You have outgrown the old playbook, and the new one has not been written yet.
- You need a thinking partner with real judgment, not another generated answer.
Answers are abundant. Judgment is scarce.
AI has made answers free and infinite. Strategies, analyses, second opinions, all on tap. But an answer is not a decision. Someone still has to weigh what matters, carry the risk, and live with the result. As answers get cheaper, that judgment becomes the rare and valuable thing. The gap between having answers and making good decisions is the widest it has ever been.
“AI gives answers. Humans make decisions.”
The real question is no longer what does the data say? It is the human one underneath: given everything I now know, what should I actually do? That is where this work sits.
A clear decision, not more noise.
The aim is not to hand you an answer. It is to help you reach a better one, and a way to act on it. Whether the decision is a career move, a business call, or how to stay valuable as AI reshapes your field, the work is the same: get clear, then act.
Find the real decision
We name the choice underneath the choice. Most of the weight is in a question you have not asked clearly yet.
Map the options and trade-offs
We lay out the real options, the costs of each, and which fears are data and which are just noise.
Choose, with your whole life in view
We weigh the move against your values, your commercial reality, your health and the people who matter, not just the career line.
Design the way forward
You leave with the next practical move, the smallest safe experiment, and an operating rhythm that protects the life it is meant to support.
The Decision Review Session.
One focused, productised session for the important decision in front of you. Not open-ended coaching. A structured working session with a clear output and a recommendation you can act on.
The Decision Review Session
For someone carrying one high-stakes decision, under time pressure.
- You complete focused prework on the decision
- We work it through live: the real issue, the options, the trade-offs, the risks
- We pressure-test where AI and others are quietly shaping your thinking
- You get a written summary, the analysis, and a clear recommendation process
- Book a free fit call.
- We scope the decision and I quote by complexity.
- Complete the prework, then we meet for the 90-minute session.
- Receive your written analysis and recommendation.
Want a thinking partner beyond a single decision? Executive coaching and an advisory retainer are available once we have worked together.
What people take from the work.
How clients describe what changed after a hard decision made well.
“He listens properly, picks up on what is really being said, and helps slow things down enough to think clearly. A lot of the work has been around judgement: where to put my energy, how to approach difficult conversations, how to communicate more clearly, how to stay grounded when there are several competing pressures at the same time. I have become clearer about my priorities, more confident in my decision-making, and better able to step back from day-to-day pressure without losing sight of what needs to be done.”
“Michael was providing me with the tools to understand my situation, a wise sounding board to reflect my own thoughts and appreciate the importance of my own agency. I became captain of my ship, confidence grew with humility and a clarity of what was important to me. I made the career change without anxiety, I navigated a few serious life events during my journey and am now confident in my job.”
“Working with Michael gave me the clarity and confidence I needed to regain control, redesign my life and re-engineer my personal and business outlook for the future. The coaching helped me reassess setbacks, identify opportunities, overcome challenges, and take meaningful action.”
“When I first moved back to New Zealand, I was navigating a major career and life transition, and Michael was an incredibly valuable sounding board. He connected me with a startup opportunity, but more importantly, he provided thoughtful, non-judgmental advice that helped me see things more clearly and approach decisions with more confidence. His ability to listen, ask the right questions, and offer practical perspective made a real difference. I'd highly recommend him to anyone navigating change, leadership decisions, or the startup space.”
“One of the most impactful things Michael worked on with me was understanding my own values and how these fit into my personal and working life. From the business perspective, his input enabled me to be brave enough to employ a secretary and grow my business by 15% in a year. I would recommend Michael to anyone who may be at a crossroad in their career, or embarking on something new and/or outside their comfort zone.”
“Michael helped me navigate several high-pressure, emotionally charged situations with greater perspective and composure. His calm presence, thoughtful questions and ability to listen without judgement proved invaluable. More than anything, he helped me respond thoughtfully rather than simply react. I cannot recommend him highly enough.”
Independently referenced on Founders Signal, where Michael is listed under JTJ Services.
Captaincy
Captaincy is the framework underneath the work. Clients do not come for Captaincy; they come to make an important decision well. What they receive is Captaincy: a practical methodology for thinking clearly and deciding with judgment under uncertainty and pressure. It is the intellectual property behind the advisory, and the subject of the Captaincy book, currently in development.
I have made this kind of decision myself.
I spent more than two decades in senior corporate and operating roles, rising from intern to General Manager in high-risk, high-growth environments. Then I left to build a more independent life across advisory, writing and investing. I know what it is to leave an old operating system behind and build a new one, and to make the high-stakes calls about identity, income, autonomy and family that come with it. My work now helps others make those decisions with more clarity, judgment and care.
Have a decision you are carrying?
Book a free fit call, or start with the free Decision Scorecard. Either way, you will leave clearer than you came.