My How of Happiness by Jacob Sokol



“The heaviness of being successful was replaced by the lightness of being a beginner again, less sure about everything.” – Steve Jobs

Editor’s note: This is a guest post from Jacob Sokol.  It’s the story of how he found his happiness path.

I say path because it’s a journey.  What Jacob figured out is how to drive from his happiness. That doesn’t mean there are no setbacks and things don’t go wrong.  They do.  But driving from happiness mean Jacob sets the stage to spend more of his time doing what he loves, having less regrets, and enjoying the journey along the way.  Happiness is his North Star and guide through life.

I think we can always learn from other people’s lessons and stories.  I’m really enjoy learning how people find their paths of happiness.  I especially enjoyed Jacob’s story and I think you will too.

Without further ado, here’s Jacob …

I had just turned 21 and narrowly escaped college. With my departure came an associate’s degree that landed me a position at a suburban sports bar. Not quite what my Mom had imagined when she hung my diploma on her office wall just weeks earlier.

I partied hard that summer and had some of the best nights of my life, but then, something surprising happened that suddenly change everything… I landed my dream job!

My Dream Job

I was taken under the wing of a wise young CEO for an IT consulting firm, who over the years would evolve into a great friend and invaluable mentor. The consulting company felt just as much like a frat house as a technology firm and was located in the heart of Times Square NYC – WOW! It was the birth of my career and I didn’t even know what a “server” was.

Life was Good

Over the course of that next year, I learned more than I ever could have imagined: mail-servers, domain controllers, BES servers, SQL servers, SharePoint services, virtual machines plus a massive amount of technical jargon. Most of all, I learned how to talk to “adults” – ones who managed 100s of millions of dollars – just as we managed their networks. My growth was explosive and I was happy to put partying in my past for the opportunity to evolve.

As the years rolled forward, I found that the learning curve was catching up to me. What once had the thrill of new and adventurous, had turned into a monotonous and regular routine.

Something was Missing

Sure – it moved me outta’ my Mom’s place and into a pad of my own. And yeah – I enjoyed having a nice car to go along with my motorcycle. That year I became certified in the future of technology, something called VMware. I was 23 years old and making good money. But something was missing ….

No Enthusiasm, Peace of Mind, or Purpose

I was missing an enthusiastic feeling when I woke up in the morning. What didn’t exist was peace of mind when I laid down at night. What was most absent from my life was a purpose for existing. Ouch.

I didn’t know what to do about that. I didn’t know what the next step was. But I knew a change needed to come.

Off to Europe … Alone

I was now 24 years old and had told myself by the time I turned 25, I would go to Europe. So I managed to finagle my way into five weeks off from work (I’m telling you, best boss ever!) What ensued was an exuberant trip that ended up altering the course of my life forever.

There’s one little itsy bitsy minor minute detail worth mentioning: no one I knew was willing to come with me! Although at first disappointing, that crucial component and key detail ended up being the best possible scenario there was. And so, I went alone!!

How My Trip to Europe Changed Me

Could you spend five weeks without anyone that you know? It’s a wild thought and I want you to think about what would happen if you tried. Here’s what happened to me:

  • I found myself. I developed an undeniable sense of who I am. The only person who was making decisions for my life during that time was me. I never realized back home how easily my friends’ and family’s opinions would sway me in a particular direction. Being forced to figure things out on my own helped me find a deeper understanding of who I am.
  • Live to work, over work to live. I learned that not everyone in the world is a workaholic with an anal affinity for spending their life in front of a computer. I bet you didn’t know that but it’s true. In fact, the feeling that I felt in Europe was that most people worked in order to live. Quite the contrary concept since unconsciously in America, most people live to work. Without our jobs, we wouldn’t know what to do with ourselves and our time.
  • I became comfortable talking to everyone. I had to speak to strangers to survive so being shy was not something that would work. I used body language, hand-signals, facial gestures, and most of all, BIG SMILES to communicate with people who didn’t even speak the same language as me.
  • I broke my patterns. I broke my “patterns” and THAT was the game changer. What I realized is that I’m not my thoughts. Our thoughts are actually just habits and patterns and they can be changed! Studies show that 95% of your thoughts today are the same as they were yesterday. Imagine thinking that those thoughts are fundamentally who you are… they’re not!! Research shows it takes 21 days to develop a habit. Without people reaffirming to me who I was (and supposed to be,)  I started to let myself just be me.

After about 3 weeks on the road, I fundamentally felt that I was no longer my mind. With that epiphany came hope that I could change my thoughts, and as I found, I could and I did!

Snapped Back to “Reality”

When I came back to NYC, I knew a change had to come. So, I spent the next six months figuring out how to reduce my reoccurring expenses. These were some things I did:

  • Sold my motorcycle
  • Sold my car
  • Canceled my cable TV
  • Canceled my home phone
  • Stopping buying new clothing
  • Cut back on going out socially
  • Learned (through practice) how to cook
  • Brought my own lunches to work

My family and friends thought that I had lost my mind, and on some level, they were right!!

Opening Up to the Unknown

During this time, two quotes from Steve Job’s Stanford commencement speech kept coming to mind:

  • “You can’t connect the dots looking forward; you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future. You have to trust in something — your gut, destiny, life, karma, whatever. This approach has never let me down, and it has made all the difference in my life.”
  • “I didn’t see it then, but it turned out that getting fired from Apple was the best thing that could have ever happened to me. The heaviness of being successful was replaced by the lightness of being a beginner again, less sure about everything. It freed me to enter one of the most creative periods of my life.”

After 6 months of saving, I left my job. I had no clue how the dots would connect looking forward, but I thought Hawaii would be a good place to find out. An old roommate of mine had moved there and she said I could sleep on her floor for six weeks! So I subleased my apartment, threw up the duces, and said peace out New York.

Asking Quality Questions for a Quality Life

Introspection through Quality Questions leads to a deeper understanding of self, and according to Socrates, that’s what it’s all about! There’s no “knowledge of self” class in college though – this is work that you’ll have to do on your own. As Tony Robbins said, “Quality questions create a quality life. Successful people ask better questions, and as a result, they get better answers.”

During my time in Hawaii, in between surf lessons and camping on the beach, I was introduced to the concept of Quality Questions. I got acquainted with the idea of consciously creating what my ideal life would look like in my mind. Here were some questions that I asked myself:

  • What do I want my life to look like in 50 years?
  • If I had all the time and all the money in the world, what would I do?
  • What makes me most come alive?
  • What one great thing would I dare to dream if I knew I could not fail?
  • Where do these 3 circles meet: my passions, my strengths, and a service that the world is willing to pay for? (also known as the hedgehog concept)
  • How can I get paid to do what I love?
  • Does this path have a heart?

Here’s a heads up if you decide to ask yourself some of these questions: the answers don’t always come right away (although sometimes they do.) Don’t give up! Rather, hold the intention lightly and give the answers space to appear.

If you get funny looks when you ask these questions, a quote from Krishnamurti comes to mind: “It is no measure of health to be well adjusted to a profoundly sick society.”

Being a Non-Conformist

Emerson has a way with words and I like the way he sheds some light on non-conformity:

  • “Society everywhere is in conspiracy against the manhood of every one of its members. Society is a joint-stock company in which the members agree, for the better securing of his bread to each share-holder, to surrender the liberty and culture of the eater. The virtue in most request is conformity.”
  • “And truly it demands something god like in him who has cast off the common motives of humanity, and has ventured to trust himself for a taskmaster. High be his heart, faithful his will, clear his sight, that he may in good earnest be doctrine, society, law, to himself, that a simple purpose may be to him as strong as iron necessity is to others!”
  • “What I must do is all that concerns me, not what the people think. This rule, equally arduous in actual and in intellectual life, may serve for the whole distinction between greatness and meanness. It is the harder because you will always find those who think they know what is your duty better than you know it. It is easy in the world to live after the world’s opinion; it is easy in solitude to live after our own; but the great man is he who, in the midst of the crowd, keeps with perfect sweetness the independence of solitude.”

Live with Virtue

A few things come to mind when I think about the “recipe” for the journey I’m enjoying. Let’s start with some meditation from Marcus Aurelius. Marcus says:

“No man can escape his destiny, the next inquiry being how he may best live the time that he has to live.”

So since death is inevitable, does it matter if you die tomorrow, or die 100 years from now? Marcus says it doesn’t, but what does matter, is how you live while you’re still alive. His strong suggestion is to live with virtue! You know … wisdom, courage, love, justice, spirituality, temperance, etc… I think about that often.

Support Yourself on Purpose

There’s no question that we westerners live in a material world. While living with virtue is essential, there’s no denying that we still need to find a way to pay the bills at the same time.

I’m going to lean on my homeboy Deepak Chopra and bring up his 7th spiritual law of success. Deepak says:

“Everyone has a purpose in life … a unique gift or special talent to give to others. And when we blend this unique talent with service to others, we experience the ecstasy and exultation of our own spirit, which is the ultimate goal of all goals.”

It can sound scary, daunting, and even horrible to have to face figuring out what makes you different from everyone else. So I would suggest starting with figuring out what it is you love – what makes you most excited in life? Once you’ve played with that, start journaling around how you can do it in some type of service to people. With service come value and with value comes money. For me, it’s sharing what I’m learning surrounding how to create and extraordinary life.

A Path with a Heart

The next thing I like to keep in mind when figuring out what I want to do is ask: does this path have a heart? You know, is it helping people? Is the world a better place because you’re doing this? You don’t need to solve world hunger but will benefit from you doing this? If you are becoming a better person because of it – the answer’s yes!

I got this concept from Carlos Castaneda. Carlos says:

“Does this path have a heart? If it does, the path is good; if it doesn’t, it is of no use. Both paths lead nowhere; but one has a heart, the other doesn’t. One makes for a joyful journey; as long as you follow it, you are one with it. The other will make you curse your life. One makes you strong; the other weakens you.”

Make an Impact

I was once watching a seminar where a guy named David was speaking. He told a story about meeting Eric Schmidt, the CEO of a small company you may have heard of… GOOGLE!  David had the opportunity to ask him one question and he went this route:

“How is it that Google is able to retain the top talent in the world?”

Were they paying these people more money than other companies were willing to pay them? Nope! Eric’s answer was this: our employees work for IMPACT (and not primarily for money!) This is something I think about all the time – how can I create massive impact (that inspires and empowers people).

The How of Happiness

50% of your happiness is said to be come from your genes.  Where does the other 50% come from?  Here’s the shocker: it’s been scientifically proven the material affluence only makes up for 10% of happiness. That includes how much money you make, your marital status, what kind of car you drive, etc…

Where does the other 40% come from then? Well that’s supposed to be the solution. These are the things you can control on a daily basis, like how you behave, what you think, and the types of goals you set. Positive psychologist Sonja Lyubomirsky wrote an acclaimed book about this called The How of Happiness: A Scientific Approach to Getting the Life You Want that scientifically proves how to be happy.

Here are Sonja’s 12 happiness-generating activities:

  1. Expressing gratitude
  2. Cultivating optimism
  3. Avoiding over-thinking and social comparison
  4. Practicing acts of kindness
  5. Nurturing social relationships
  6. Developing strategies for coping
  7. Learning to forgive
  8. Increasing flow experiences
  9. Savoring life’s joys
  10. Committing to your goals
  11. Practicing religion and spirituality
  12. Taking care of your body

Being Unrealistic

Since the day I decided to sign my resignation papers from the rate race, there’s something else I’ve become super passionate about. Most call it “doing the unrealistic.” Tim Ferriss, author of The 4-Hour Workweek: Escape 9-5, Live Anywhere, and Join the New Rich says this:

“Ninety-nine percent of people in the world are convinced they are incapable of achieving great things, so they aim for mediocre. The level of competition is thus fiercest for “realistic” goals, paradoxically making them the most time-consuming.”

When you dare to dream big, it’s like taking a spiritual syringe and giving yourself a strong shot of enthusiasm laced with adrenaline, right in your forehead! There’s something magical about it. I used this mindset to go to a Jets game with Gary Vaynerchuck and demonstrate to people that following your heart is possible. My current “unrealistic” goal is to inspire eight million people.

Balancing Tomorrow with Today

There’s a paradox of time in my mind and I think about two periods often. The first period is right now. The second is 50 years from right now.

Each day that I wake up, I remind myself that I will soon expire. I don’t know if it will happen today, or tomorrow, or in a week. What I do know is that I have to love what I’m doing every day of my life. There is no other time to live but right now!

Here’s the paradox: there’s a possibility that I’ll live for another 50 years. And with that in mind, I make sure I’m on my way to becoming the man I want to be then. I’ll leave you with a quote from Tal Ben Shahar:

Attaining lasting happiness requires that we enjoy the journey on our way toward a destination we deem valuable. Happiness is not about making it to the peak of the mountain nor is it about climbing aimlessly around the mountain; happiness is the experience of climbing toward the peak.

I hope that this article will help you with your climb – enjoy!

Jacob Sokol is committed to living an extraordinary life. He shares what he’s learning surrounding how to do that at He recently learned what 48 of his favorite peoples’ most unrealistic accomplishments were.


  1. Jacob – that was a wonderfully crafted article, detailing your path to happiness. Thank you for sharing. By the way, thanks for including the words from your homeboy(!): ““Everyone has a purpose in life…” Can’t beat that!

  2. Thanks Jacob, I love that last quote from Tal.

    My question (hopefully a quality one): How do I get wealthy doing what I love? (Currently experimenting with blogging.)

  3. @Matt… Thanx so much dude!! -=)

    @JK… hahaha, glad you dug him. He’s a keeper!

    @Evan… I love the one man. I also play with “How can i create X amount of value?” and in return obtain a minor percentage of X. Still working along those lines tho! Thanx for the connection -=)

  4. “Each day that I wake up, I remind myself that I will soon expire.” Powerful sentence. I remind myself the same thing – almost every day, and definitely when I become absorbed in unimportant things (power struggles, pettiness etc.)

  5. Jacob – Nice article. Thought provoking. You might also wants to consider reading “Joy: The Happiness That Comes from Within (Insights for a New Way of Living)” From OSHO

  6. @Vered… Powerful mindset and thanx for reflecting it back onto me. -=)

    @Ajay… Thanx!! I’ve heard some great things about Osho – i’ll hold the intention to check him out lightly and i trust that our paths will cross when the time is right. Appreciate the insight!

  7. Jacob,
    Very inspiring! And very awesome what you have done with your life. I especially love how you have created happiness that reaches deep into your soul…lasting and real happiness…

  8. Jacob,
    Well done! I had a similar European experience traveling alone, and you nailed the nuances of the most special aspects of my journey as well. This post is a treasure. How cool would it be for colleges to give credit for Traveling Alone 101- how to tune out the “shoulds”, tune into YOU, and listen to your heart as you ask yourself the BIG questions. You rock!

  9. @Lance… Thanx so much for the kind words. Appreciate you appreciating it and i trust that some of the principles are evident in your days. -=)

    @Electra… What i’m hearing you say is that it’s time we start our own college. Correct?! 😉 Traveling Alone 101, Optimal Living 101, Quality Questions, Following Your Intuition…. Love where your mind and heart are. Virtual Bear Hug Baby!

  10. @Alik… hahaha – most def!! Riding with one hand on and one hand up -=) How about yourself? What’s exciting you these days?

  11. So many folks I know seem to be studying happiness right now and wow I am ready to just go for it and be happy every minute because I am doing what makes me happy.

    Though at 60 I am having a hard time saying do what you love and the money will follow – that has not be true for me – I think I have a “must work 10 little jobs to get what you want” at least that was how it worked when I was just loving parenting and wanted to get scouts, tennis lessons, surgery, tutoring for my daughters. I burned myself out, along the way.

    I just received the gift of a very happy puppy and I seem to be staying the moment more and laughing and enjoying his right here and now life lessons.

    I would still like to get paid for doing the work I love and the tons and tons of volunteer work I have already done. I have not figured out the money part.

    Wonderful post, I am passing it on to my book group and kids
    Thank you – high energy inspiration here.

  12. Hi JD and Jakob .. we all live in the moment of existing, without taking the opportunity that we have to step outside normality and become something else .. just by a little change. Mostly it’s change, not risk until later on .. once the initial excitement has worn off.

    I can totally understand the feeling you had of moving away from family and friends, the norms that were expected of you. I did that when I went to SA .. what I didn’t do was what you went on to do. Now I must actually do it again, but this time pursue on along the path .. I know I can do it.

    I’ve subscribed to Sensophony .. and read through the 48 unrealistic accomplishments .. a really good inspiration.

    Thanks JD .. glad I read this today .. cheers Hilary

  13. Hey there Jacob,
    Love the way you break down all of your story into heart inspiring sections that really capture my desire & give it a loving boost in a most positive direction.
    Reading all of the wonderful things you share with us on a very regular basis finds me smiling & breathing in ‘OPTIMISM’ more & more – day by day. (‘Cultivating optimism’ my choice from your other newsletter recently & on day 10 already – woop woop!)
    So very happy & appreciative that I have found you & so grateful to be able to connect with you. As always my friend All good things to you. x

  14. @Alik… Awesome dude.

    @Patricia… Thanx for the kind words… That puppy even brought a smile to MY face! -=)

    @Hilary… Glad to hear that you enjoyed it and thrilled to connect more on “sensophy”!

    @Lynne… Haha!! Happy to hear you’re diligently at work, rocking out with an optimistic mindset. Greatness.

  15. Jacob — wow, what an inspiring journey. I am delighted when I hear of people looking for more human wholeness in their lives and finding a path with heart.

    Please check out this week’s post “Claiming Your Calling” at It ties nicely into your journey.

    Best wishes.

  16. Hey Jacob,
    It’s always inspiring to read ur words and this one’s no exception.
    All I wanna say is Thank you…
    Thank u for sharing ur incredible experiences and insights ..that give slipping people like me,the much needed nudges to stay on track 🙂

  17. @Susie… Awesome! Thanx so much for the kind words. Gotta’ love the path with the heart<3 -=) Sweet blog!

    @Gunja… Well, you're welcome! -=) And thank you too!

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