“You’ve held a lot of diverse roles and responsibilities. What exactly are you looking for now?” a recent recruiter asked me in regards to my job search.

“Something like a fourth marriage.” I replied.

My snarky response to the recruiter came from a conversation many years ago when I began to learn about relationships, desires, and life.

I was maybe twelve or thirteen. Not yet old enough to have endured heartbreak or even my first kiss. Despite my youth, I had some awareness as to the meaning of marriage. . . or enough to know that people in love get married.

At a friend’s house during a sleep over, I learned that his dad had been married four times. I had never heard of such a thing, My curiosity exceeded my manners and I approached him directly, “Sir, why have you been married four times?”

“Because the first three didn’t take.” He wasn’t offended by the question, in fact he smiled as he spoke.

“Huh, I can see why people marry and why they divorce. But why four times?” I was sure there was more to this.

“No one has ever asked me that, not even my wife. Well, looking back it’s simple.”

“I married my first wife for passion. In those days, we were young and crazy for each other. Sadly, passion is important but alone it can not sustain a relationship nor does it pay the bills.”

“I married my second wife for money. She was smart, disciplined, and ambitious. She brought structure to my life. But we lacked empathy for one another. No deep connection. Before long we devolved to roommates sharing space between work hours.”

“I married my third wife for youth. She had a sense of adventure and spirit. She was popular, fun, and had boundless energy. Every night there was somewhere to be, a party to go to, a gala to attend, people to see. Before long, I couldn’t keep up.” He sighed. A look of resignation crossed his face.

“Now I’m old and tired. I learned that the most important thing in life is how you spend your time.”

“I married my current wife because she’s who I most want to be with.” His smile brightened as his thoughts turned to his lovely bride.

Well, I told the recruiter that I just want to serve in an organization where I’m surrounded by people I respect, can learn from, share knowledge with, but mostly, I want to be with people I enjoy spending time with.

For the past few days, my thoughts keep coming back to my oldest son. From my perspective, I see his current stage in life as one of those moments where his future path is being decided whether he is aware of it or not. Pivotal. He’s sixteen, finding his independence, considerably more mature than just six months ago, however he still has a very long way to go.

I don’t know my role as a father in this situation. Part of me wants to do things for him like I had to years ago when he was younger. Other parts of me want to let go of the wheel and let him find himself and make his own mistakes. I know the answer is somewhere between those two, but I don’t know where. At some point he will be entirely on his own. Me personally, I actively ran towards independence as fast as I could. My reasons were personal, but one big driver was the motivation to explore. I had a bottomless curiosity that seemed to override my desires for comfort and familiar. My son has a touch of this as I see it in him. However we are very different creatures and I think he is much more risk adverse than I ever was.

As a family, my wife has led sessions where he and I sit on the couch and talk colleges. As a second semester junior, this is certainly the time for him to engage in these conversations. While he doesn’t complain nor tune out during these family meetings, he is very much the passenger and not the pilot. I too am very much the passenger and my wife is doing the bulk of the work listing schools, looking up videos with pros/cons, asking him questions about likes/dislikes, etc. She’s frustrated at both of us for our passive participation. In my defense, I’m focused on my son, looking for any sign or signal that he has interest or is curious about something related to college.

Overall this process has not been much fun for any of us. I guess this is a sign of the times. Truly a first world problem. Compared to the other billions of people on this planet, we have all the resources, time, and ability to carefully select and send our son to a program where he can find his tribe and develop into a mature, engaging, and responsible member of our society. On one level any of the fifty schools we considered would work for him. The stress seems to originate from finding the “right” one, yet we don’t have enough information from our son to reasonably assess which schools would be a “better” fit. Part of me feels this marginal exercise is a waste of time and unnecessary stress. Pick 15 schools: five reach schools, five interesting schools, and five backups. Apply to all, await results, then visit the few that you get into. Pick one. Know that there’s no magic recipe and don’t stress over the process.

I don’t know how important college is nor how important it will be in the future for the world my son will live in. In my life, career, and experiences, I know it matters but not necessarily why. I know many successful people who didn’t go to college and many people who failed at life despite amazing college experiences.

Distilling the ideal college experience through my life, I want three things for my son in his college experience:

1) I want him to explore his intellectual and artistic curiosities. College is a well tested environment where you get exposure to new ideas and people without much negative consequences.

2) I want him to develop foundational habits and refined skills that are necessary for a successful professional career. This means being able to write well, speak clearly, and effectively communicate your ideas and thoughts with others. College is where I learned to write and think critically. This has paid massive dividends in my life and set me up for many great professional experiences.

3) I want him to find his tribe. We are social creatures and a good life means being surrounded by others we respect, love and appreciate. College should be a time to meet new people who challenge your beliefs but share your values. At it’s best, college is a crucible of talent, ideas, cultures, intelligence, and backgrounds. Few times in one’s life will you be surrounded by new people who are the same age and are open to new connections. Once you leave campus, the world of easy new friends starts to shrink. Looking back, I met hundreds of great people and found that part of the experience as my favorite. In fact, I met the most important, intelligent, and influential person in my life while at college. I can only hope that my son is as fortunate.

Quick setting. . . very warm and wet outside today. It’s a dark, rainy January day with storms looming in the distance. I’m sitting at Quills in Norton Commons awaiting a friend for coffee. I’m ten days into our annual dry Jan and a few observations come to mind: 1) I’m having vivid dreams every night, 2) my mind feels sharper than ever, and 3) my resting heart rate has not returned to my historical baseline, it has held about 5-7 beats higher than normal.

From a health perspective, I have been putting off going to see someone despite having reason to do so and the time to do it. I need a primary care doctor as I haven’t had one in years. My wife keeps nagging reminding me to see a dermatologist as there’s new moles and skin tags popping up everywhere (family condition). I haven’t had blood work in a few years and could benefit from getting an updated panel to see where my numbers are. I also still have fears that my aerobic performance declines in the past few months signal something bigger than just getting older. I struggle to maintain my run pace despite rest and strength training. As mentioned after the Flying Monkey in November, the decline was shocking and kinda scary. Nonetheless, there’s a background voice in my head that keeps saying, “you are fine, eat well, exercise daily, take deep breaths, and all will be OK.” Still, I ignoring my general health won’t make it better.

Professionally I have doubled down on my networking while trying to remain optimistic about the future. As my package from my last role is coming to an end, I have failed to secure a steady job with income. Also, other than canceling Hulu, I haven’t taken any other steps to cut back on our household expenses. Given our monthly burn rate, we will have to tap retirement accounts sooner rather than later if we choose to maintain our current spending. This gives me stress that I know how to address, yet like avoiding setting up a PCP appointment, my head remains buried in the sand.

On a positive note, my efforts to network have yielded some opportunities. I have two job interviews this afternoon and I also have a check in meeting with my consulting project client. With respect to the job hunt, I’m sticking to the mental model of being a 44 year mother trying to get pregnant one last time. The process consumes all of my time and emotions yet I don’t want to discuss it with others until that baby is going off to kindergarten. The mix of pity, unsolicited advice, glad I’m not you, and general sympathy others share in this journey though well intended is not helpful at all. I suppose it’s human nature, but during conversations when others ask about my search and situation, I see past their expressions and read “glad I’m not you” in their eyes. A better man wouldn’t care. . . but I do.

So when in discussion with others as I search for the next . . . thing, I stick to three general topics: 1) family/life updates – always safe and helps keep the bonds alive, 2) updates on former colleagues and other professionals with their careers – this is where opportunity lies and historically how i have stumbled into a job, and 3) what ambitions both professional and personal the other person is working towards. With respect to the the third topic, I learned long ago that it is better to get the other person to tell me their story versus sharing too much of my own. I don’t know if this is the best course of action but inserting a few of my thoughts into the conversation tends to have longer legs and put you in a positive light when the other person mentions you to someone in their universe.(especially someone who might want to meet/hire you). I borrowed this from Dale Carnegie years ago and it has worked for me in the past.

The biggest reason I’m not sleeping well right now is that I’m worrying about my family. Good worry for sure as my wife and sons are dealing with first world problems (grades, independence, social acceptance, professional challenges, etc.) but it is worry nonetheless. Forrest is accelerating into adulthood now that he has a driver’s license and has taken responsibility for both managing his schedule and getting himself to school/swimming. It’s been a hard week for him as he had his first fender bender on Monday while driving to school, Tuesday he overslept for morning practice, and Thursday he got his first parking ticket. This weekend he will learn about auto body shops and the life lesson that sometimes it costs money to get back to zero.

I think a lot about Wyatt at the moment too. He’s going thru middle school which isn’t a picnic for any boy but I recall struggling a lot with that era of life as well. I owe him more 1:1 time, preferably in a travel or exploratory setting. He and I spent a weekend in NYC a few years ago and I use that time/memory a lot to get through my days. I want more of that. Unfortunately, my professional and financial challenges keep me grounded from random getaways to urban adventures with my rapidly growing 13 year old.

I don’t know how I will feel about this period in my life when I look back in the future. Such a weird statement to write but all periods in my life are fair game for reflection. I hope that this moment leads to a better place and that I somehow find the exit to this purgatory stage, yet I also want time to stand still. I know that I will very much miss the days when my boys lived at home, family dinners were routine, and I could still run freely outside without pain. I both want change while keeping somethings constant. Best of times, worst of times.