ruby slippers for your journey to oz - grass is greener

I consider myself lucky.
I have a loving family, a good job, and a nice home.

Working in technology we are so fortunate because we get paid very well to solve interesting problems.  For most of us we enjoy a large part of our jobs, we use our minds (no hard physical labor – which after watching my father deal with major back pain and other “aging” industries from years of construction work it makes this a big perk), and we live in an existence where the problems people complain about are things considered “First World Problems.”

first world problems diagram

When you look at all the good things in my life most might ask the question, what more could she want?  Why wouldn’t she be happy with all of her belongings, relationships, career, and success?

I wish I knew the answer to these questions.

I find myself asking questions like: What is it that makes me so driven and tenacious?  And why can’t I be content?

These questions haunt me.  And I know that I am not alone.

It is likely you have come across statistics, studies, or articles like this one, Science of Happiness, talking about how money and success is not the key to happiness.   Yet for me, those are the things I want.  How could I possibly make enough money or have enough success?  How could I ever achieve enough, build enough projects or accomplish enough to be satisfied?

In college I couldn’t decide what to major in.  I tested out of a lot of the initial introductory courses, and despite starting with a lot of credits, I then took 6-7 classes most semesters (a normal load was 4).  I loved learning and I wanted to take advanced chemistry, physics, math, economics – I couldn’t get enough.  And I agonized over the course catalog of all the exciting things you could learn about, and I chose computer science because I loved it most.  However, at the end of the day I still wonder about what else I could have done had I picked a different major; what else I might have become when I grew up.

Because I know all the things I didn’t choose that I could have been successful at, I become aware that there is an opportunity cost with all the choices I did make.  And this realization causes me to wonder about “did I make the right choice?” and would I be more content if this happened instead.

The grass certainly looks greener.

If you are smart, and can do anything that you put your mind to, then are you destined to be unhappy because you will always be aware of what you didn’t do instead?

And does this drive us to keep searching, working and growing to achieve more?

I have tried therapy, counseling, and coaching.  I have read more self help books than I would ever publicly admit.  And despite all of my inner work to understand who I am and define my purpose, I will admit to all of you that I still feel lost.

However, that is the thing about this journey called life, the path isn’t clear.  And in fact, sometimes the path is overgrown and you really don’t know if you are even on a path anymore.  At least Dorothy had the yellow brick road, but what about the rest of us?  How will we find our Oz, and what if we aren’t sure if Oz is even where we want to end up? (And on a side note, if we are headed to Oz why don’t I have any ruby slippers?)

ruby slippers for your journey to oz - grass is greener

Well, I wish I could say I had the answers to these questions, but I don’t.  What I do have though, is some ideas that have helped me find clarity and steer me in a direction where I know I am lucky and am mostly happy.  And even though I don’t know where I am going in the future, I am confident I am headed in the right direction.


Understand yourself.

The first step is to really take the time to understand who you are and what you like and don’t like.  Many people I meet end up in a role because it is what society, or the parents, or their partner dictated to them.  They have chosen their path to please others, even though day in and out, they may dread waking up each morning and justifying why what they do everyday is a good thing.  For some, they have been doing this so long, they don’t even know what they like or want to do anymore.

If this could be you, then start with a list – write down what you like to do, what you don’t like to do, and what you wish you could do.  Since this is just for you, and you never have to show it to anyone else, be honest.  Don’t be afraid to let yourself dream and imagine what could be.

Create a map of what you loved to do as a child, or what you would do if money weren’t a factor.  What is the common theme?  Understanding what you are good at, and what you want to do, is the first to step to getting on a path in that direction.  As long as you feel like you missed your calling, or spend your days doing something you aren’t good at or don’t enjoy, you will feel restless.  For most of us even figuring out what that is can be a struggle.  There are lots of books and articles that can help you find your path, purpose, and mission in life – just take the time to understand yourself and dare to let yourself dream.


Choose to be happy. 

I have this theory that a lot of people in technology are snarky, cynical and pessimistic because deep down they are insecure and unhappy, and it bubbles to the surface because they haven’t taken control of that behavior.  Of course, lots of people are truly happy being that way.

I used to be like that – I was a very unhappy person.  I couldn’t get a guy to go on a date with me. I was overweight and always looked like I just got out of bed.  I don’t think my coworkers liked me very much so I ate lunch alone while I worked in my office.  But most of all I was lonely and felt unaccepted.  Even though I don’t think I could admit it (and may not have even understood) at the time, I was the person who had created that situation for myself.  My insecurity and experience had turned me into a toxic person, I was smart at least, but I didn’t have a lot of other redeeming factors.

I was teased so much in school growing up, that I bristled at the idea people could really like and be friends with me.  I retreated into a world of books and computers.  And because I picked up on things faster, the fact that I was smart was the one thing I lauded over others.  I was the person, who like all the haters online, would have something snarky or negative to say about everything – no matter what it was.  Thankfully I had wake up call and since my early 20s have made efforts to change.

I only tell you all of this because in my circumstances I had chosen to be unhappy.  I would see everything as bad or negative, and as a result missed out on all the beauty, wonder and opportunity in the world.  Of everything I have done in my life, making this change has had the largest impact on my outlook, opportunity, and disposition.  If you are feeling down, know that only you can make yourself feel that way.  And you can choose to be happy.

Learning to see the glass half full was hard for someone who considered their strength solving problems and so looked at everything in life as inherently broken so I could have value in worth from being able to fix it.  However, it can be done.  And if you can learn to see the best in people and situations, and to hear an idea and instead of shooting it down see the potential, then you can learn to change the way you think.  And that is one of the biggest keys to being happy and finding satisfaction in life [1].


Build relationships and learn to have deep meaningful conversations.

We are human and I have yet to meet or encounter someone that doesn’t crave the feeling to be loved and cared for by someone else.  Our personal relationships are said to eclipse the happiness derived from our jobs [2].  Nurturing your relationships and learning how to be a good friend (which was something I had to do, because my lack of trust and insecurity got into the way) are key elements of your happiness and satisfaction in your life.

Since each person is different it is harder to give good advice on this topic – but I will say for me there were a few things that helped a lot.  I spend a lot of time learning to be a good listener (making eye contact, not getting distracted, and being open to alternative views) and asking good questions.  I had to learn to listen to the ideas of others and be supportive of them – to help them overcome obstacles (instead of just pointing them out) and asking good questions to help them along the way.  To do these things well I really had to overcome my inner obstacles around jealousy and insecurity, but it has made a big difference in my life and has really enriched my personal relationships.


As really smart people are we all destined to be restless and unsatisfied?  It is possible.  However, by focusing on happiness and your strengths, it certainly makes it easier to see the brighter side.

I know there are many things people do to help find happiness and satisfaction in their lives, and if you have other ideas or tips definitely leave them in the comments.  I am still on my path and it never hurts to have additional signs to the right place – until next time.

-kate 🙂


[1] The Science of Lasting Happiness

[2] The connection between a good job and happiness is overrated


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