One of the first things I ask new clients is what they want their life to look like 5–10 years from now.
Not a rigid plan. Not a perfect timeline. More like a vision.
A sense of where they’re headed.
Most people pause when I ask this. They need a minute. Then they usually offer vague “concepts of a vision.”
Something like:
“I want to feel more successful.”
“I want to be in a relationship.”
“I want more freedom.”
“I want to feel settled.”
None of that is wrong. But it’s incomplete.
That’s where better coaching questions come in.
And I’m not just talking about the obvious ones:
What do you want to be doing in your career?
Where do you want to live?
What kind of relationship do you want?
Those are not bad questions. They matter.
But they mostly describe what your life might look like from the outside.
A real life vision needs to go deeper. It needs to ask about the texture of your life.
What does it feel like to be you, living fully and honestly inside the life you’ve built?
That is where the more useful questions begin.
Here are three questions I often ask clients when they are trying to create a clearer vision for the next chapter of their lives.
1. What kind of problems do I want to have?
Every life has problems.
The goal is not to create a problem-free life. That does not exist.
The goal is to build a life with problems that feel worthy of the life you actually want.
Do you want the problems of being rich?
The problems of raising kids?
The problems of being highly visible?
The problems of being in a committed relationship?
The problems of being your own boss?
The problems of being deeply honest instead of quietly resentful?
Most people fantasize about the reward but ignore the maintenance cost.
They want the relationship, but not the conversations.
They want the business, but not the responsibility.
They want visibility, but not criticism.
They want freedom, but not the discipline required to sustain it.
This question forces you to look at the full picture.
Because your future is not just what you desire.
It is what you are willing to be responsible for.
2. What would make me proud in 10 years, even if it feels boring now?
Your brain is wired to prefer what feels exciting now.
Another party.
Another distraction.
Another emotionally unavailable man.
Another expensive thing you can technically afford but probably should not buy.
Another shiny little dopamine snack dressed up as a life choice.
The annoying truth is that many of the things that create a great life are boring while you are building them.
Consistent workouts.
Saving money instead of spending it.
Going to therapy.
Building a business.
Keeping your commitments.
Having the uncomfortable conversation.
Learning to leave earlier.
Learning to stay when you usually run.
None of this is especially glamorous in the moment.
But in 10 years, these are often the choices you will thank yourself for making.
A lot of people overvalue what feels exciting now and undervalue what will make them proud later.
That is how people end up with lives that look busy but feel strangely empty.
Your future life is built by the boring choices your current self keeps dismissing.
3. What does a Tuesday afternoon look like?
When people imagine their dream life, they usually imagine the highlight reel.
The villa in Tuscany.
The wedding to Prince Charming.
The perfect body.
The standing ovation.
The business success.
The big trip.
The dramatic before-and-after moment.
Fine. Enjoy the fantasy.
But most of life is not a highlight reel.
Most of life is a regular Tuesday.
Coffee. Calendar. Lunch. Messages. Errands. Dinner. Sleep. Repeat.
So the better question is:
What does a beautiful ordinary day look like?
How rushed are you?
How much alone time do you have?
What kind of work are you doing?
Who are you texting?
What responsibilities are on your plate?
What do you do after dinner?
Who do you say goodnight to?
Do you feel held by your life, or are you constantly trying to escape it?
This matters because your dream life is mostly made of normal days.
Design those first.
Seven years ago, I asked myself better questions
In 2019, I was writing in my journal during a lunch break at my 9–5 wealth management job.
Back then, I felt trapped in my job. Imagining a different future gave me room to breathe.
I wrote that I wanted the problems of being a successful life coach.
I wanted the problems of being my own boss.
And I distinctly remember writing:
“I will never wake up to an alarm clock, and I will never ask anyone for permission to take a vacation.”
At the time, learning, coaching, and personal development were not exactly the default hobbies of most 30-something gay men I knew.
But I cared about it anyway.
I followed the thread anyway.
I took it seriously anyway.
Seven years later, I am living that life.
Not perfectly. Not without problems. And definitely not exactly according to plan.
A lot of things went sideways. A lot of things changed. A lot of things took longer than I wanted.
But that is not the point.
The point is that better questions helped me stop fantasizing about a different life and start actually building one.
They helped me move from vague desire into real direction.
And that is exactly the kind of work I do with clients.
Not vague vision boarding.
Not “manifest your dream life” glitter-glue affirmations.
We look at the future you say you want, the patterns blocking it, and the identity you will need to build in order to actually live it.
Because your life is not just something to dream about.
It is something to design, build, and revel in.
1-on-1 Coaching
If you’re ready to stop fantasizing about a different life and start actually building one, let’s talk.
Book a free discovery call to start designing a life that feels clear, intentional, and actually yours.
