Defining A Successful Life On Your Own Terms

What would you do if you knew you couldn’t fail? The first time I had this question put to me I was 25, lying face down in my bed, living at my mom’s house and going through a monumental quarter-life crisis. Unemployed and feeling utterly dejected from my job search, and life in general, I was lost. It was a far cry from the successful life I had pictured for myself when I pranced across the stage at graduation a year or so before. However, I believe my meek answer at the time was landscape architecture, if I couldn’t fail, I’d continue trying to land a job as a landscape designer.

So young, so clueless (so hungover)

Six years later and looking back, I can see, I answered that question all wrong. I was thinking too small. I was thinking more about instant gratification, what would solve my problems in the moment: getting a job (per that five year program/degree), getting some money, and getting the f*** out of my mom’s house so I could live it up like I thought every other 20 something was doing! I wasn’t thinking enough about the details of that successful life I thought I had envisioned for myself. But I think about it often now, how I finally think I’m living a successful life, understanding that the key is defining success for yourself.

What Does A Successful Life Look Like To You?

If this feels like one of those loaded and deep questions, that’s because it is. I sincerely believe this question, if answered correctly or incorrectly, is the framework, the rough sketch of what your life will be like. But spoiler alert, no one’s answer is going to be the same as anyone else’s. I’m sure we have all heard some version of “the list”, the one that someone rattles off to you for all the reasons you put one foot in front of the other each day: a high paying job, a big house, a nice family, luxury items, vacations. Sounds impressive! Sounds like something the 25 year old me was all about! Not so much the current me.

It turns out, I eventually landed a job at one of the best firms in Chicago (and arguably, the country). It was a contracted position, but nevertheless, I had my foot in the door and I was elated! At 29, I felt like the pendulum was swinging up and it was finally my turn. I was making enough money to move out of my “charming” old apartment into my downtown apartment (with a balcony!); I could afford to travel (I went to Napa for my 30th) and was even starting to date again.

Turning 30 in Napa with the fam :: we cute!

And secretly, the dread I had for going to work each day was mounting. It wasn’t the people (they were lovely), some days it was the work duties, and some days it was just this overwhelming feeling, that I was just waiting for the day to be over. And then the best thing ever happened to me, I got pulled aside at work one day and told that my position was ending. And just like that, I was free. Not free from this horrible place, it is probably the best office I have ever worked in! I was free from “the list” and unknowingly trying to conform to it. I was unemployed, in a city I loved, and free to do whatever I wanted.

I did the super cliché soul-searching thing for the summer, not the glamorous backpack around the world kind. The file for unemployment, eat way too much takeout, and watch my credit card balance creep up kind. But along with putting myself into debt, I also finally started thinking about what I wanted my life to look like and to be. At 30, I had released myself from the impossible task of living up to some random’s idea of success and started thinking about my own. And what 12 years of flopping and flailing boiled down to was happiness.

I wanted a life of genuine happiness. The kind of happiness where you just naturally have pep in your step, where a bad day is a rarity only meant to remind you of how great all the other days are, and where you can feel the energy of the moment and inspiration all around you. That is what a successful life looks like to me.

I’m sure that sounds kind of hippy-dippy (a guy I once dated called me that, I think as an insult – I loved it) but happiness is my success. It’s my truth, and the guiding factor for how I live my life. From personal experience I can attest it can be really unsettling when your idea of success doesn’t remotely resemble the list, but don’t shy away from that. I think that means you’re on your authentic path – push forward! There will definitely be naysayers, people who don’t understand what you’re doing and think they are entitled to an explanation… they’re not. Don’t listen to them.

And you may not figure out all of your terms for success in one sitting, in one year, in one decade. That’s ok! With age comes confidence, the confidence necessary to make changes once you define your success. I was a server, completely embarrassed about my life for two years (in the midst of my quarter life crisis). And now, I am the proudest server you will ever meet. As it happens, serving makes me happy. Being able to connect with people all around me, and help them enjoy big celebrations, or small nameless nights out, I simply love it. I can assure you letting go of the list will be a game changer.

Me (left) and one of my best friends to date on NYE… we met while serving during my quarter life crisis.

And when you do let go of the list and start embracing your own truth, I think you will be amazed by how the universe responds to your energy. With a clear and focused headspace, it will probably feel like opportunities are just being thrown at you. Say yes to as many of them as possible! Knowing that with your own guiding principals, you don’t need to have it all figured out at once. In a couple of weeks I’ll begin my level one sommelier classes, something that was never even on my 25 year old self’s’ radar. And I have no idea where that will take me, but I know I’m happy. So I’ll ask you this again, what would you do if you knew you couldn’t fail?

Turns out serving isn’t the only thing I love! I love decorating my little apartment too!

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