The art of making the big decisions well

By Steve Conley, founder of the Academy of Life Planning

Is your planner focusing on getting the small things right while you’re getting the big things wrong?

I ask because I did it myself.

I got on the property ladder early. I saved to pay off my mortgage. I joined good pension schemes and bought the right financial contracts. I knew how to make those decisions. I could compare the options and see whether I was making progress.

At 18, I chose a career in financial services. At 24, I met the woman I would marry. I put work before family. I divorced at 42, married again at 44, left corporate life at 50 to become self-employed and divorced again at 52.

Today I have no financial assets. When I trace how I got here, the decisions that explain it are the ones I made about my work, my relationships and how I spent my time. I could have made every financial decision a little better and still lived much the same life.

That’s what I mean when I say every decision is a life decision. Some choices shape an afternoon. Some shape decades. The size of a decision is measured by what it can change in your life.

How big decisions happen

Leaving corporate life was a decision I could put a date on. Putting work before family was a decision I made over and over. Each late evening may have seemed reasonable on its own. Add enough of them together and you’ve decided how much of yourself your family gets.

Sometimes we decide what matters first, and that gives an everyday choice its weight. If you’ve decided you want to be there when your children come home, an offer to work another afternoon becomes a decision about family life. You might still take the work. You know what you’re choosing and can ask whether you want to make that choice every week.

Indecision has consequences too. Waiting can be a deliberate choice if you know what you’re waiting for and when you’ll decide. Sometimes you keep putting a decision off, or you don’t see a decision to make at all. The working week fills up, another year passes, and an arrangement you fell into becomes harder to change.

Looking back, it helps to ask three different questions. Did I make the decision well with what I could reasonably know at the time? Was it right for the life I wanted and the people affected? How did it turn out? A carefully considered decision can turn out badly. A lucky outcome can follow a careless choice. And a decision can serve a goal you’ve set while asking more of someone else than you were entitled to assume.

The questions I wish someone had asked me at 18

In the GAME Plan, we ask four questions about work.

  1. What are you good at?
  2. What do you love to do?
  3. What does the world need?
  4. What will the world pay you for?

I answered two. I was good at maths, and financial services would pay me for it. I didn’t particularly enjoy maths. After thirty years in the industry, I’d seen ways in which it exploited people. I wish someone had asked whom I wanted my talents to serve, and whether the work would let me serve them.

I couldn’t have known at 18 what I’d come to know after thirty years. I could have spoken to people doing the work and asked what an ordinary Tuesday looked like, what they were rewarded for and what happened when a customer’s interests clashed with the firm’s. I could have explored other ways to use the same talents. I could have asked the four questions again a few years in.

For me, purpose means using your talents in acts of service. A career decision gives that idea practical consequences. Who benefits when you do your job well?

Marriage begins with Goals

Marriage is one of the biggest decisions we make. In the GAME Plan, I’d begin with Goals. Each person gets to answer for themselves first. What do I want my next chapter to look like? What place do I want family, work, friendship and service to have in it? What do I want us to build together?

Then talk about a choice you could actually face. If one of you gets a job offer that means moving, whose work, friendships or caring responsibilities would have to change? If you want children, what do you each imagine an ordinary week looking like? Think about a real disagreement you’ve already had. Could both of you say what mattered and have a part in the decision?

You can learn something about the marriage you’re considering from the way you make those decisions together. Can each of you shape the life you’re agreeing to?

What the usual financial planning conversation assumes

Take a traditional needs analysis. The PRISM framework covers protection, retirement, investments, savings and mortgages. Here’s what you’ve got. Here’s what you need. Here’s the shortfall. Here’s a product to close the gap.

Or take the retirement forecast. Here’s where you’ll end up if your working life carries on as it is. Want a better retirement? Here’s how much more you’ll need to invest.

A forecast can tell you where the status quo might lead. The life decision is whether you want to carry it forward. Once you assume someone will stay in the same job until retirement, putting more money away becomes an obvious way to improve the result. Where a firm earns more as the client invests more, that answer also suits the business model.

You can have a technically excellent debate about active versus passive investing while the decision to stay in a career for another decade never comes up. You can bring an adviser an eighteen-month problem and come away with a thirty-year solution. Before you plug the gap, ask who decided what was missing.

The same framework can reach us through a Google search, a TikTok, a YouTube Short, an Instagram post or an AI chat. You ask a familiar financial question and get a useful financial answer. Then you get on with a life whose biggest assumptions you’ve never had a chance to examine.

I wish that whenever someone typed “How much should I save for retirement?” into AI, it came back with a question.

“Do you want to spend the next twenty years doing the work you do now?”

If the answer is no, ask what you’d like to do with those years. Would you change careers, work fewer hours or spend more time with people who need you now? Once you’ve explored that, the forecast has something worth testing.

How the GAME Plan puts life first

I built the GAME Plan to help people make decisions well, with agency. Goals and Actions come before Means and Execution. We plan the life first, work out what would support it, then put it into practice.

  • Goals. Begin with values and talents. What matters to you? What are you good at? How could you use those talents in service? Look at your wealth across mind, body, heart and spirit. Set your own goals and picture the next chapter on your path of purpose.
  • Actions. Think like a project manager. What needs to happen, in what order, and who needs to be involved? Create options. If you’re considering leaving a career, a trial project or a spell of reduced hours might let you find out what a different working life feels like before you commit.
  • Means. Put the human and financial capital in place to support the life you’ve chosen. That may mean developing a skill, calling on a relationship, arranging practical help or finding the income and time to make the change possible.
  • Execution. Take the next step, see what happens and review what you’ve learnt. As your circumstances change, use that experience to make the next choice.

Agency means creating options, choosing among them and acting on your choice. It includes deciding what to delegate. You can ask someone else to handle an investment decision within limits you set, with a way to review it and take it back. Abdication is letting someone else settle what matters and where you’re going. Sometimes an institution or another person has the power to limit your options. An employer can turn down a request for shorter hours. Seeing who has the power to decide helps you work out where you still have room to act.

Build decision capital before you need it

I use decision capital to mean what you can draw on to make and act on a good decision. It includes knowing what matters to you, experience, trusted people who can challenge you, useful information, and enough time and room to think. You build it every time you test an assumption, learn from a choice or create an option you didn’t have before. A big commitment can also use up some of that room. Ask what it will make easier or harder to choose next.

If you want to start today, pick one live decision that could shape the next chapter of your life. Give it a page.

  1. Name what’s at stake. If this goes badly, what could take years to rebuild? Who else will live with the consequences?
  2. Say what you want the decision to serve. What would a good outcome look like in your daily life?
  3. Create an option. Could you try it on a smaller scale, change the terms or take more time? What would happen if you simply carried on as you are?
  4. Check what has to be true. What assumption, if wrong, would change your choice? Ask someone with no stake in the answer to help you test it.
  5. Choose, act and review. Write down what you’ve decided, why, what you’ll do next and what would make you reconsider. If you choose to wait, set a point to come back to it.

Think back to your last planning conversation, whether it was with an adviser, a search engine or an AI. What was the biggest decision in your life at the time? Did it come up?


What’s the big decision in front of you?

Bring it to a 50-minute Zoom meeting with me. We’ll start with what matters to you, explore the options you could create and work out what you need to know or do next. You make the decision. My job is to help you think it through.

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