Asher's Blog

I have long changed the word dream to goals. So, I often say that I don’t have dreams. I have goals, and I’m in charge of getting to them. But for the purpose of this blog post, let’s use the word, “dream”, since everyone has them. Or don’t you? Every person reading this is carrying something, an idea they keep coming back to, a life they imagine when they allow themselves to think beyond the immediate demands of today. A business. A contribution. A version of themselves that feels more fully realised than the current one.

The question I am attempting to write about is not whether you have a dream buy why so many people carry one their entire lives and never actually reach it.

I have spent some time around very successful people, and I have made it a habit of asking them questions. Not just about what they built, but about how they think, what drove them, and what almost stopped them. One of the things I have come to believe deeply is this: the more reasons you have to achieve your dream, the higher the odds that you will. The more rooted your dream is in something real, personal and specific, the harder it becomes to walk away from it when things get difficult.

And things will get difficult. So before you make plans, before you build strategies, before you announce anything to the world, there is a test worth taking. Ten questions worth sitting with honestly. Because the number of genuine yes answers you have will tell you more about your likelihood of reaching your dream than any plan you could put on paper.

Let the test begin. 🙂

1. The Ownership Question: Is this dream actually mine?

This is the first and perhaps the most important question, because a dream you borrowed will not sustain you through the hard seasons. Most people, if they are honest, are chasing someone else’s vision of a good life. Their parents’ expectations. Their peer group’s definition of success. A version of achievement they absorbed from their environment before they were old enough to question it. And for a while, borrowed dreams can feel convincing. They come with external validation, with the approval of people who matter to you. But when the going gets hard, and it always does, a borrowed dream gives you nothing to hold onto.

Think about the difference between a car you own and a car you are renting. When something goes wrong with a rental, you return it. You do not repair it. You do not fight for it. You hand it back and pick up another model. But when something goes wrong with a car you own, something you saved for, worked for, chose specifically, you fix it. You invest in it. You do not abandon it over inconvenience.

Your dream has to be yours in the same way. Not something you are leasing from someone else’s expectations. When it is truly yours, it does not feel like a burden you are carrying. It feels like a direction you are moving in.

2. The Clarity Question: Is my dream clear enough to chase?

Nobody commits deeply to something they cannot see. Vague dreams produce vague effort, and vague effort produces vague results.

Is your dream on paper? Can you describe it in specific terms? Do you know what it looks like when you have achieved it? Can you feel the difference between where you are now and where you are going?

Clarity is not just a planning tool. It is a motivational one. The more vividly you can see your dream, the more real it becomes to your mind, and the more your daily decisions begin to align with it. A dream that lives only as a feeling is fragile. A dream that has been written down, described in detail, given a shape and a timeline, becomes something you can actually move toward.

If you cannot describe your dream clearly to someone else, it is worth spending more time there before you go any further.

3. The Reality Question: Is my dream within my power to achieve?

This is not a question about whether your dream is big enough. It is a question about control.

The more the achievement of your dream depends on things outside your control, the lower your odds of reaching it. The more it depends on decisions, habits and commitments that are within your own hands, the higher your odds become.

This does not mean your dream has to be small. It means you have to be honest about what is yours to do and what is not. You cannot control markets perfectly. You cannot control other people’s decisions. But you can control how hard you work, how much you learn, how consistently you show up, and how you respond when things do not go as planned. A dream that is anchored in those things is a dream you can actually pursue with confidence.

4. The Pressing Question: Does my dream compel me?

Do you need someone else to motivate you to work toward your dream, or does it pull you forward on its own?

There is a version of ambition that requires constant external fuel, encouragement, accountability, pressure from others, and the fear of embarrassment. And while those things are not bad, they are not enough on their own. Because there will be seasons where no one is cheering, where the results are invisible, where the path feels uncertain. In those seasons, the only thing that keeps you moving is an internal compulsion.

Passion is often misunderstood. It is not always a feeling of excitement. Sometimes it is simply a stubborn refusal to stop. A quiet insistence that this is the thing I am here to do, regardless of how it feels today. That is the kind of pressing that sustains a dream over the long haul. If you need to be talked into working on your dream regularly, it is worth asking whether it is truly yours or whether the clarity question has not yet been fully answered.

5. The Pathway Question: Do I have a strategy to get there?

A dream without a pathway is just a wish. The gap between where you are and where your dream lives can feel enormous, and sometimes it is. But you do not close that gap in one leap, you close it one step at a time. The question is not whether you can see the entire staircase from where you are standing. The question is whether you know what step one looks like today.

We do not fly to our dreams. We walk to them, one deliberate step at a time. And each step, taken consistently, builds the momentum that eventually makes the distance feel less impossible. The strategy does not need to be perfect. It needs to be present. It needs to give you something concrete to do today that is directionally connected to where you are going.

6. The People Question: Do I have the right team around me?

Show me who is around you and I will show you what you are likely to build.

No significant dream has ever been realised entirely alone. At some point, you need people whose strengths cover your weaknesses, people who believe in the direction even when the progress is slow, people who will tell you the truth when you need to hear it and encourage you when you are running low. If you do not have those people around you, finding them is not a luxury. It is a requirement.

This does not mean you need a large team. Sometimes it is one person. A mentor, a partner, a collaborator who sees what you are trying to build and chooses to stand beside it. But that person, or those people, matter enormously. The right environment accelerates everything. The wrong one quietly drains it.

7. The Cost Question: Am I willing to pay the price?

This is the question I believe stops more people than any other. Because the dream is free but the ride is not.

Every dream worth reaching has a price attached to it. It costs time you could have spent elsewhere. It costs comfort you could have kept. It costs relationships that cannot survive the demands of what you are building. It costs versions of yourself that you have to outgrow. And it costs the willingness to keep paying, day after day, even when you cannot yet see the return.

I believe most people do not reach their potential not because they lack ability or opportunity, but because they are unwilling to pay the price consistently. They want the destination without the journey. But there is no such thing. The price is part of the process, and the process is part of the person you are becoming on the way.

8. The Tenacity Question: Am I still moving closer?

You are not there yet. The question is whether you are closer today than you were yesterday.

Tenacity is not glamorous. It does not make for exciting stories in the moment. It is the quiet decision, made over and over again, to keep going when stopping would be easier. It is getting up after a setback and taking the next step anyway. It is resisting the temptation to measure your progress against someone else’s timeline and staying committed to your own.

Winston Churchill said it in a way that has never lost its power: “Success is not final, failure is not fatal: it is the courage to continue that counts.” That courage is not a feeling. It is a practice. And it is practiced most powerfully in the small moments when no one is watching and stopping would cost you nothing except the dream itself.

9. The Fulfilment Question: Does my dream bring me satisfaction?

Not just achievement. Satisfaction.

There is a kind of success that looks impressive from the outside and feels hollow from the inside. People reach the destination they spent years chasing and discover that it does not feel the way they imagined it would. That is a painful realisation to arrive at after a long journey.

The work toward a genuine dream should carry meaning even before the destination is reached. The process itself should feel worthwhile. There should be moments along the way where you look up and think, even imperfectly and incompletely, this is the right thing for me to be doing with my life. That sense of rightness is not a guarantee of ease. But it is a sign that you are pointed in the right direction.

10. The Significance Question: Does my dream benefit other people?

This is the question that separates a goal from a calling.

A goal is something you achieve for yourself. A dream, at its deepest level, extends beyond you. It touches other people. It solves something. It adds something. It improves lives beyond your own. The wider the reach of your dream, the more meaning it carries, and interestingly, the more sustainable your motivation tends to be.

Ask yourself honestly: what I am building, does it benefit me only, or does it reach further? How many people are better off because of what I am working toward? Because when your dream is connected to something larger than your own comfort or success, you tap into a reservoir of purpose that personal ambition alone cannot provide.

Now Turn the Dream into a Destination

Go back through those ten questions. Count your honest yes answers. The more you have, the stronger your foundation. The fewer you have, the more work there is to do before the strategy matters.