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5 Questions That Will Change Your Life

A powerful question will stop you in your tracks…Ultimately it will bring you closer to you, where all your best wisdom hangs out.

“The marvelous thing about a good question is that it shapes our identity as much by the asking as it does by the answering.”— David Whyte

Asking powerful questions is how to move deliberately along the winding path toward you. Which is where the real raw deep motivation comes. Not from the outside. But from the inside.

A powerful question will stop you in your tracks. It will make you tilt your head and say, “Well, I never thought about that.” Ultimately it will bring you closer to you, where all your best wisdom hangs out.

Here are five game-changers. You don’t have to prod yourself to write each question down and journal on it for hours. (Though if that’s your go-to starting point…have at it.) These are for contemplation, observation and discovery. The answers you find will sometimes arrive without any words. Just a knowing. For now, just know there is no wrong way to play with these…

1 — What really matters?

It’s a noisy world. Everyone agrees. People feel pounded by messages, marketing and mindless opinions.

But there’s a gift in this noisy world. And that is this: If you aspire to be conscious, powerful and aware, then it is mandatory to go inward and know yourself.

That goes for business owners and job holders alike.

In business, especially, there is such a temptation to “do this quick fix” or “try that marketing hack.” Until soon, you find yourself in a very noisy business grabbing for every bright shiny thing outside of you — and you don’t even know yourself, your business or why you’re doing any of it in the first place.

So start here. Find out what really matters. Not in a binge of list-making and over-thinking. (Though that could work as a springboard). But in a compassionate kind observational way. Spend time pondering this question, watching your actions to see what compels you, observing your smile to see what truly delights you. The answer to this question points the way for so many directions in your work and your world.

2 — What am I avoiding by worrying?

Every time (and I mean EVERY time) I sit down to write an article or an eBook, or my book, or create trainings for my clients, I witness myself go through a ring of fire. That fire is a low-grade “worry.” Worry about the content being good enough. Worry about the people who will surely think it’s lame. Worry about whether or not I should stop what I’m doing to make sure that I remembered to put collard greens on my assistant’s grocery list this morning. You name it, the brain can come up with it.

Of course I discovered that this worry is a way to avoid the deep work of writing or creating ways to teach strategies to my clients.

And yes, I discovered that I was also avoiding the probability of getting some lame comment from someone who’s pissed at me for not playing music anymore and wants to accuse me of selling out.

But when I really dove into this question, I discovered that what I’m really avoiding — what many of us are really avoiding — is intimacy and vulnerability. With myself, with others, with my writing, with the moment.

And so, in order to avoid intimacy, my mind can drum up all kinds of shit to worry about, fiddle with, pretend is important.

The thing you are avoiding is usually less rewarding to your mind than worrying. As my client best-selling author Colleen O’Grady said once… Getting the idea for her book was really great. Sitting down each day to write it? Not so great.

If you chose a Word-of-the-Year or set an intention that has called you to expand, then it’s probably also calling you to execute. As in, “get some stuff done.” As in, “take some steps.” As in, “call someone,” or “go somewhere.” The word, the intention, the idea is so much more exciting than the actual doing.

And so? Our mind tries to distract us with worry, obsession, thoughts that keep us from taking steps. Ask yourself honestly, what you are avoiding by doing this.

3 — Whose business am I in?

Byron Katie says, “When I am mentally in your business, it keeps me from being present in my own.”

We are “mentally in someone’s business” when we think we know what’s best for others, when we spend our time worrying and wondering what someone else is up to, and whether or not they’re going to let us down, piss us off, or keep us up. When we do this, we literally absent our spirit from our own bodies.

Come back to you and ask what’s your business. What’s best for you, what matters for you, and if you are being honest, or feeling needy or out of control. And then you can give yourself the stunning power of all that attention.

Otherwise, your days become a wellspring of anxiety. It will be uncomfortable at first to come back home, back to your center. But slowly, you will find that it’s really the only place where true power and strength resides.

Byron Katie also says, “To think that I know what’s best for anyone else is to be out of my business. Even in the name of love, it is pure arrogance, and the result is tension, anxiety, and fear. Do I know what’s right for me? That is my only business. Let me work with that before I try to solve your problems for you.” (Here’s a really quick video of Byron Katie sharing this idea.)

4 — Where can I spend money to save time (or eliminate stress)?

I start each and every one of our Uplevel client retreats with a hand-selected set of questions designed to move these business owners out of small constricted work-a-day thinking and into a more expansive entrepreneurial approach to their work and their lives.

This one question — “Where can I spend money to save time or eliminate stress?” is the all-time client favorite. I adapted it from one of my coaches, Dan Sullivan, who likes to say, “If you have a problem and you have the money to fix it, then you don’t have a problem.”

As business owners, our unique advantage is that when we are free to create…we make money. We’re the rainmakers. When we have the space to make rain, we make it!

Most of us, however, spend way too much time and struggle on things that don’t allow us this necessary space. We’ve been well-trained by a lifetime of institutional thinking to believe we’re the indentured servants. That we must slog along doing and being things just because we’ve always done and been them.

The answers I’ve gotten to this question have changed everything for me: For instance, I fly out of Charlotte, NC, which is 2 hours from Asheville where I live. I decided to take Uber each time. Yes, it’s pricey. And yes, my drivers think I’m a whack job. But I get a solid 90 minutes of work done in the back, and my mental energy is not spent finding the business valet parking deck, and dealing with tickets and shuttles. It’s a massive ROI for me and eliminates all kinds of extra stress. You may believe that you’re not in a financial state to make such a bold move — but remember to consider that there’s a more powerful way to view your time and money.

5 — The peace I’m seeking…is it true that it’s not already here?

This is what I ask myself before I sit down to meditate each morning. It’s not a question that your mind can find the answer to. (In fact, your mind will most likely want to chime in and let you know that there is no peace anywhere. And then it will list all the reasons why.) This is a question that sets you up to actually experience that — holyshit! — yes, there is a sense of peace that’s already here. Maybe it’s buried under a million thoughts, maybe it’s just a small little glow. But I can sense it and feel it. But I’m not here to give you the answer to this. You get to go find out for yourself. And yes, you may have to play with this one. But that’s the fun of it.

And the real gift of all of these questions is that they get to be fun. Playful. They create curiosity, not duty. I get hundreds of notes from clients thanking me for “changing their lives.” The truth is that they changed their lives. At Uplevel, we teach our clients how to grow and build their business — and one of the ways we do it is by connecting them to who they truly are. And we do that by asking questions.

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People look for retreats for themselves, in the country, by the coast, or in the hills . . . There is nowhere that a person can find a more peaceful and trouble-free retreat than in his own mind. . . . So constantly give yourself this retreat, and renew yourself.

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