Within the past few weeks, I had three key moments of self-exploration or self-doubt that made me think about where I have been, where I thought I was heading, where I am now and, finally, where I want to be. As a parent, I want to know how I can convey my expectations and disappointments to my kids so they can understand where they are and where they are going someday. And for them to understand that goals and expectations will change with time and circumstances.

First, I stumbled upon a bunch of college acceptance letters from 23 years ago. I had acceptance letters from Purdue, Villanova, Tennessee, etc.

Second, I had a wonderful visit with a law school friend who has been travelling the world working for international organization(s) empowering women and fighting human trafficking. To say the least, I was envious and fascinated.

Third, I had a job offer two (2) weeks into a new job within my department which had me question what my career path really should be.

I sat and thought about where I’d been. A quick summary of my last 40 years is this:

Survived meningitis as an infant and endured physical effects from hip dysplasia and luxating patella (floating kneecaps) in both knees to be a pretty good high school athlete with opportunities for college scholarships in soccer or tennis. I got accepted into, got my Letter of Nomination from my congressman and passed the physical fitness test for the Air Force Academy in Colorado but decided not to go. I choose tennis as my sport and spent 4 years at a great small DI school majoring in Political Science. I took classes most winter and summer breaks my 3rd and 4th years and graduated with a PoliSci major and 3 minors (Communications, Women’s Studies and American Studies). I spent my Spring semester my junior year at American University in DC interning at a lobbying firm representing federally employed women, took classes in Public Law and wrote a (small) undergrad thesis on ow Reinventing Government (Drucker/Gore) impacted federally employed women. I brought my horrid GPA from my 1st year of college to making the Dean’s List 3 out of my last 4 semesters, even winning the Senior Scholar/Athlete Award before I graduated. I had promise. I wanted grad school or to do something huge. I got a job in corporate telephone system sales. I lasted a few weeks before I quit. I worked at the golf course, I worked as a manager at Bloomingdales’, moved to Hoboken, NJ and took a job near Wall Street selling stock market research products. I was frustrated with all of it. I lost that job, moved home and waited tables while I took my LSATs and applied to law schools.  I got into (and was offered a scholarship) to a Tier II law school and went on my way, moving to south NJ for three (3) years. I was in the student government for 3 years there, even being student bar president for a year, helped run the LGBT student organization, worked in the civil practice clinic and even won an award for NJ practice and procedure. I was offered a clerkship after graduation for a well-known family court judge and decided to move back to the CT/NY area to start my full-time life with my wife. I studied for and passed both the CT and NY bar exams. I had no job prospects and ended up taking a job doing relocation real estate for less than I made as a retail manager prior to law school. I spent 4 years working through smaller firms to get to a larger one that was supposed to be my final career stop. After 5 years, I was burnt out and I knew I never wanted to be a senior partner in a law firm. For the past 6 years, I’ve spent the time being humbled (unemployed for 10 months), worked as in-house counsel for 2+ years and then taking a “step down” in career and salary but a “step up” in work-life balance in higher ed.

So, here I am.  I feel unchallenged. I look at where I am and wonder if I should BE more by now. Maybe I should have accomplished more or be on a higher rung somewhere. I feel like I should have done more with my experiences and been solving bigger issues by now (while also have more $ and a bigger retirement fund).

When I think about mid-life crises, job dissatisfaction or just general frustration of purpose, I wonder how much of it spawns from our expectations. We talk to our kids about having extraordinary lives and possibilities. But what are our expectations of where we should be and what we should accomplish?

Are we shorting ourselves by not shooting for extraordinary?

Or will we just leave the legacy we can leave? We can’t all be Mother Theresa’s and Martin Luther King Jr.’s, can we? We can’t all have a big idea that makes us billionaires or play sports in the pros for millions, can we? Should we be disappointed if we don’t reach the stars?

My answer is that the disappointment is about expectations and priorities.

My life is far from unremarkable. I do know that. It has been quite a ride so far. I have some fantastic stories and have met some remarkable people. I have been truly blessed. I have a great family. I have the love of an amazing wife and I have 2 beautiful healthy little boys who do make me nuts, but I wouldn’t have any of it any other way.

I am not travelling the world saving lives, but I also will not sit in one place and just be bored with something I’m not challenged with. If it’s boring and you can’t change it, you make a change for yourself.

I want my kids to understand that life itself is absolutely extraordinary but don’t settle for something you know in your heart isn’t extraordinary enough for you. Not landing your dream job or making it to the big leagues may be disappointing, but not appreciating where you are and who you are with is far more disappointing and heartbreaking. 

When I first opened the folder with those old college acceptance letters, I thought “damn, look at where I could have gone. Where would I be now if I’d made a different choice?” It didn’t take long for the rest of my heart and brain to come together and say, “well, you wouldn’t be here. You wouldn’t have had these boys, this wife, this life.”

As for me, I will be moving on in my career to something more challenging. I could have stayed put and kept peddling along but I know I want more. The expectations and priorities are in check and I know where I need to go from here. But I have no regrets. Just lessons. Extraordinary lessons.

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