5 months ago, I was stuck.

Stuck with a question I’ve never had to face.


In completely new territory.

And the more I asked myself this question, the more inconclusive I became.

The question was:

“What do you do when you get everything you’ve ever wanted in life?!”

I thought about it for weeks.

Because for the first time ever, I had it all.

My health is great.

I’m living on purpose.

My girlfriend is amazing.

Sensophy is killin’ it.

My skills are improving.

I’m traveling the world for a few months (Japan, Thailand, Bali).

I’ve got a great group of friends and mentors.

Freedom. Contribution. Growth. Authenticity. Connection. Excitement.

It’s all there.


What do you do when you get everything you want in life?!

I didn’t know.

So I started to ask around.

Now there’s not too many people I’ve met who I’ve ever heard ask this question.

But, part of the reason I’ve been able to consciously create my ideal life is because I surround myself with other people who have the courage and tenacity to create theirs as well.

So I asked my homey Andy: “Dude, what do you do when you get everything you want in life?!”

And with no hesitation, he replied…

“That’s just a shitty question.”

Fuck, he was right.

How about a better question…

“What would be the most meaningful thing I could do with my life right now?”

Or the most exciting…

Or the most fulfilling…

I’ll never forgot those “it’s just a shitty question” words.

Because so many of us keep ourselves feeling stuck by asking shitty questions.

We ask: “Who am I to be successful?”

Or: “What will they think of me if I speak my truth and express myself authentically?”

Or: “Why can’t I ever seem to finish what I start?”

All of these are shitty questions that keep us feeling stuck, small, and fearful.

The power of coaching lies in asking good questions.

You can create a new reality with the right type of inquiry.

So remember this:

The quality of your life is directly related to the quality of the questions you ask yourself.

Now my question to you is…

What questions are actually worth asking yourself?!

Drop a comment and let us know your favorite questions and/or the ones that have kept you stuck in the past.


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  • Rodrigo

    “Why can’t I ever seem to finish what I start?” – This one visits me sometimes. Have to change that. Thanks for the message!

    • Jacob Sokol


  • Mauja

    What is the meaning of my life? I have intimations of a higher purpose.

    • Jacob Sokol

      Whatever meaning you give to it. :o)

  • Kim

    How can I be of value in this situation?

    • Jacob Sokol

      Love it.

  • Joanna Fiminska

    What would happen if I could – my all time favourite question:)

    • Jacob Sokol


  • Carie Bean

    Ask and it is given….. You get what you ask for….
    When I’m down and out there is the -why me? But I try to turn that around to what is this here to teach me as quickly as I can.

    I love the question how did I ever get so lucky (blessed_fortunate) to have all that I have. Makes me spin into an appreciation momentum which is always helpful.

    Very thought provoking, Jacob

    Here’s one for you. What would you say is one of the most necessary steps to living your life on purpose? What are some of the questions that helped you find your way to where you are now?

    • Jacob Sokol

      Early on in my Sensophy journey, we used to have a category for blog posts called “Quality Questions.”

      It was those big self-reflective questions which opened the space for me to learn more about myself.

      What would I do if i had all the money/time in the world and couldn’t fail?
      What do I love to do SO much that I’d pay to do it everyday? (Now, how can I get paid to do that?)
      What does success mean to me?

      Etc. Etc. :o)

      • Carie Bean

        Great questions. And I’ve asked myself that. I went to the first live your legend meeting in Orlando after receiving your email about it. That’s what lyl is all about asking yourself those very questions. Love Scott Dinsmore and the work he does to help others find their way into life with meaning. Thank you for reminding me of this Jacob. Because I do know the answer but fear holds me back.

        Yes yes and more yes!!

  • Alyssa

    How do I find authentic and consistent clarity to finally know what I want?

    • Jacob Sokol

      Sweet, Alyssa!

      How about: “What would energize me?”

      • Alyssa

        That works, too!

  • xandy

    “what else?” or “what’s next?”

    • Jacob Sokol

      Sounds like you hold a lot of space! ;)

      • xandy

        i like to think that i make space for what is important.

        beyond that, i love asking this question because it can trigger something forgotten, and it lets the other person know you are actively listening :)

        • Jacob Sokol


  • Stephanie

    Great article. I then tried quickly to think of questions worth asking myself and fear reared it’s ugly head to make me stop. No, fear will not stop me. I will take the time, effort, and face vulnerability to get this done. Now I think I am starting to understand the “on purpose” .
    Holy crap! Lol And thanks.

    • Jacob Sokol

      My pleasure! Let me know what you come up with!

  • Amy

    Great article Jacob. What ever you are not giving, could be lacking in any situation, how can I see this differently?, how is this happening for me? are the empowering questions I am asking myself these days. Now the ones that stop me and keep me in the fear/ego cycle are, what would happen if I could? Do I have enough time and money?? Why can’t I just follow through? Why am I taking on too much?

    • Jacob Sokol

      Yeeeeah. Super cool.

  • Kate Boden

    Awesome thought provoking post, thanks for sharing Jacob. I think I’ve been asking myself some shitty questions… Time to re-think/re-feel and create new questions for myself. Seems to me like the ‘how’ and the ‘what’ questions are a good starting place. :-)

    • Jacob Sokol


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  • Jen

    instead of “why is this happening to me?” – I ask, “Why is this happening FOR me?” Flips perspective PDQ

  • Guido

    My answers to the initial question in the blog:
    1) I don’t believe you. I believe your successtory is true. But I also know people don’t linger long on succes stories. Unless you have a deep spiritual life and lots of self control, sooner or later (probably sooner) you are going to ask for more. More freedom, connection,… . Also stuff gets boring after a while. For example, travel is great but living out of a suitcase and constantly changing time zones is not.
    2) Enjoy, this is not going to last. Life is going to throw a spanner in the works, like sick and old parents, a baby at the wrong moment, unforseen expenses… However bad luck has an up side, it lets you know who your real friends are.
    3) This is the time to find the stuff that gives you the same sensation but doesn’t depend on external things. Even things like health, connection, working for a purpose,… depend on external things. This is the moment to investigate religion or philosophy (in the Acient Greek style, not the acedemic style).

  • Guido

    A question that keeps creeping up on me more and more:

    How does what I do make an actual, physical, tangible difference in the world?
    I feel that I have spent too much of my time caring and nurturing paper tigers.

  • Larissa

    I think it’s important to continue to give back… as somebody who works with the “down and outs” I believe we who are able to cognitively and financially get ourselves into a space of happiness, it’s important to continue giving. Which you are. So keep on keeping on :) You give best when you’re happy.

  • This article resonated with me on a very profound basis! No really, I’m not just flattering anyone here…

    There are really tons of “very shitty” questions that we’ve been asking ourselves for so long, I think we can afford to stop that madness.
    We all get one bite of the apple, this is it…

    I must say that one of your sentences (probably it’s your own unique) should be considered as one of the best quotes ever said:

    The quality of your life is directly related to the quality of the questions you ask yourself.

    It indeed is. It’s completely related…

    Thanks a ton for this great article!
    Very Short, but Very Powerful!

  • I’m reading Martin Seligman’s “Learned Optimism” right now and it’s really, really good. It’s not so much about optimism as it is about the psychological facts we have about what it takes to live a good, meaningful life.

    One of the things that he mentions is using your strengths most days to create something that’s meaningful to you. That has been with me ever since and I’m playing around with it. Maybe that book would be for you right now too?

    He also mentions something about the kind of hangover you get when you get to the top of something and feel like you’ve got everything you want, and I believe he says that using your strengths for something bigger than yourself is helpful at that stage too.

    Sending love!

  • I really apteicrape free, succinct, reliable data like this.

  • Dumbass marijuana doesn’t make yu stupid or anything. Neither does heroin, I’m on it right now. It’s just while you’re on it sometimes its harder to do certain things, which is why you don’t do it when you need to do shit. But heroin addiction is a bitch. If you don’t use a needle though theres really not many bad effects next to depressed breathing,overdose and addiction

  • September 26, 2011  11:53 pm by ESPY I’m enjoying the notable new 52’s. I just read Detective Comics and Batman #1 the other day. The art was top notch on Batman. As for Marvel, I am trying to get into X-Men Schism (not feeling it). The new Ultimate Series with throwback bags are pretty good. Looking forward to where Daredevil is going. This week I am looking forward to Geoff Johns writing of Aqua Man.

  • That’s really thinking of the highest order

  • Although I haven’t agreed with some of these guys outlook on the never ending smith saga. I’ve offered to have a beer with some at the tailgate party’s. I can’t take different opinions to serious. I’d be in prison. Lol except one niner…. He is the truest form of a blog low life there is. There is no way on earth I could ever be seen or even sit with a dude like that. Jail I’d be a going. Hospital he’d be a going. Most of the others bay is talking about at least have some class. Hoff by far has the most, even though he is the king of Alexcuses. :-) lil dig Hoff. Lol

  • SueK wrote:“….Wouldn’t it be something if this turned out to be the ‘little thing’ that finally brings the bastid down?”which reminded me of this…okee-dokee, folks… (SueK, this one’s for you!)time for some Friday funnies…let ‘er roll:———————————————————–———————————————————–(beverage warning!)