Fifty Layers Deep

Five decades, seven turning points, and the threshold I'm standing on now

If you’ve been on this earth long enough you’ve realized that growth doesn’t happen in a straight line. I often say it’s subtle and incremental, yet when you zoom out, it can be quite profound. That’s what I’ve been doing these past few weeks as I’m cruising into the start of my 50th year in a few days.

I’ve read about the spiritual belief that we evolve in some significant way every 7 years. Then last year at the CP Enneagram retreat I learned about shock point moments, and in further reading about those, the “law of seven.” All of this led me to want to see what my life looked like when I map it to every seven years — and wow, I couldn’t believe what I saw.

This is what I’m sharing with you today in honor of my milestone birthday week — five decades re-told through seven turning points of my adult development, and where that leaves me now as I start this next one.

AGE 7 — The core wound

Seven years old. I don't have a memory of it, but my body clearly does. It took until I was forty-nine at a psychological Enneagram retreat for the (repressed) trauma to emerge. What I now know and feel is this is when it all began. The trauma I experienced in my childhood at age seven solidified itself as the core wound that my personality would then be organized around. While I don’t recall the details, I know that by the final day of that retreat I was that terrified and sad little girl. As the guide Urânio invited me to take my shoes off and come onto the Enneagram mat, my hands were trembling so badly I needed the person to my left and to my right to untie my shoelaces. Urânio later told me he'd never forget the humility running through me in that moment — humility, fittingly, is the virtue a Type 2 is working toward.

Over this past year I’ve spent a lot of time connecting to that little girl. Learning to take care of her and my repressed self preservation instinct. It also reminded me how much my childhood dog, Yeller, was the one place I always felt safe, which speaks volumes to the role that Koko has played in my adult life. More on that when we cover my 30s-40s.

AGE 14 — Learning to be wanted

The start of high school. All I can remember is boys, boys, boys. As early as middle school I started day dreaming, while “Crazy for You” by Madonna played, about finding my soulmate. By 14 my best gal Johanna and I were getting into all sorts of trouble from hanging out in Philadelphia with older guys to telling the cute lifeguards on the beach in Ocean City, NJ that we were 16 (instead of 14!). I was boy crazed and I fell in love with the idea of being wanted — clearly the childhood wound had fermented into personality.

Age 21 — Achievement as proof

No better place to be 21 than finishing up your senior year at Penn State University. To top it off we placed second out of 13 schools in the National Student Advertising Competition which got me a paid internship at NYC ad agency and ultimately led to my first salaried job and the start of 14-year career in advertising. This began my relentless drive to climb the metaphorical ladder with the Mad Men of New York to prove my worth and allow each raise and promotion define me.

This era of my life, my early twenties in NYC, also played out a pattern I now can name and understand, thanks to the Enneagram. My type 2, dominant SX instinct had me running around Manhattan trying to seduce every man I found attractive in order to feed my deep longing to be loved, wanted, and ultimately chosen. Yet at that time, I couldn’t figure out why I was never able to attract the devotion I longed for. Now I understand that was my blindspot (and my dominant instinct running around untrained off leash!).

AGE 28 — The crack

Now living in center city Philadelphia to be closer to my family and my little nieces and nephews, many of my friends have started to get engaged. I finally meet my guy. For over a year it was picture perfect; I wholeheartedly believed he was “the one.”

Until the day he told me I was not the one.

This was the first heartache I ever experienced (even worse than losing my childhood dog). I was a mess — I lost 15 lbs, cried all the time, and for the first time started reading books and doing yoga at 6am because that was the only way I could take my mind off of my broken heart.

I look back now and realize this was the first crack to my armor - my protective strategies of achieving and seducing to receive external validation and love. I didn’t need to earn this guy’s love — it was rare and it was true. And when he took it away, it broke me.

AGE 33 — The ultimate shock

While it didn’t fall on a 7-year, age 33 certainly serves as the ultimate shock point moment of my life. On January 8, 2010 my mom was diagnosed with stage 4 colon cancer. On February 13, 2010 she died.

34 days from diagnosis to death.

This loss was like an earthquake that causes aftershock ripples for the hours or days following, only this one lasted for years. Like I lost a limb to my body and it was taking forever to adapt to this new way of living, so I stayed stuck in grief and the patterns it opened up in me.

Just six months prior in June 2009, I went to see my first therapist to share that I wanted to move to California but I was worried about leaving my mom behind — what if something happens to her? In those few therapy sessions it was the first time I considered making my own needs and wants a priority. I was able to overcome (what seemed irrational at the time) that fear and I did indeed move to Santa Monica on September 9, 2009. And the following February my worst nightmare came true.

What I did not know was that my move to CA was the first step in re-building every single aspect of my life without my mom in it, and in doing so, ensuring it was in complete alignment with me. I share about how I did this in this week’s birthday episode [airing Wed July 22nd] on The Work of You Podcast.

AGE 35 — Rebirth

“What would it mean to you to have a dog, Jen?” That was the question that changed everything back in June of 2012.

This one powerful coaching question helped me get past my own mindset blocks of “I can’t afford it,” “I’ll have to move apartments,” “I just launched a new career and I’m living off loans…is the timing right?” In the end I let my heart answer this one. A few weeks after graduating from the Hudson Institute as a certified coach, launching ostrich coaching and consulting, and just shy of turning 36 — I rescued a thin chocolate lab mix named Lewis. When it came time to name him, regardless of him being chocolate brown, I knew the only name that made sense was the initials of the one who first taught me what unconditional love is. My mom, KO. Just last week, July 17th, was his “Gotcha Day” and we celebrated 14 years together.

I had no way of knowing then that my patterns were far from finished wreaking havoc on my life (primarily in the category of the men I was choosing to date) OR that Koko would be the very love that allowed me the safe space to finally heal. To stop chasing the love that I knew and start accepting the love that I need.

AGE 42 — Building the container

I remember learning at the Hoffman Process (among the most profound experiences of my life at age 38) that it can take a massive life event to reveal a pattern you never knew you had. For me that was losing my mom as suddenly and as young as I did. I always knew I wanted to feel wanted; I never knew that same wound could cause me to need to feel needed. This distinction and pattern defined my dating from age 35 to 45. This decade is what’s revealed boy by boy, lesson by lesson, pain and joy in my DATING IN DOG YEARS manuscript.

Though through all the dating upsets and the business highs and lows, I created a steady foundation for myself — with Koko and the house that would become our home. After renting and having to abruptly move out of three different houses in Austin, I finally could afford to buy one at age 42. I remember telling my best friend Sarah — this feels like “the new relationship” I need - something to pour my heart into that will actually invest back into me, unlike the men I had been dating.

What I didn’t know was this would be the home where Koko and I would get through a worldwide pandemic, where he’d beat an aggressive cancer at age 9, where I’d host so many parties (especially the epic Eagles Super Bowl win), where Koko would nearly die from a splenic mass leaking, and where I’d sit next to him to ask if he could be a very brave boy one more time at age 12.5 and push through a massive surgery, and a home that of course my mom would never see, but also my Dad because of a difficult but grounding choice I made.

In this era I learned what I was willing and no longer willing to tolerate, claimed my worth in the process, and discovered what can happen when you lead with a lil’ trust and faith and let go of what no longer serves you.

AGE 49 — The wound returns - full circle

One month before 49 I was at the CP Enneagram psychological retreat when my body started showing me over and over again what I had been through as a child. I returned home a shell of myself and year 49 became the year of trauma therapy, perimenopause, and an emotional rollercoaster of heightened anticipatory grief around losing Koko. I needed his safe, steady, and secure love more than ever.

As they say — you need darkness to see the light. Somehow in all of this darkness that’s exactly what I found. I felt the calling to launch The Work of You - first as a podcast, now as an entire personal growth platform.

I became crystal clear on who I am, what my passions + strengths are, and what I’m here to do. I experienced a Life Activation ceremony in Nov 2025 that affirmed all of this for me (thank you, Andrew). And each month as I worked through the darkness, the clearer everything else became. Right up to my latest decision — to take this beautiful home I've invested in, nurtured, and loved, and list it for sale.

The home with the huge tree outback where younger Koko chased squirrels to his heart’s content, with my beautifully re-done bedroom that became my peaceful retreat from trauma therapy and perimenopause, and the home where I’ve lain in bed trying to wrap my head around a day without Koko. Every memory in this house has Koko in it, and he's nearly 15 now.

I’ve had to face what I know is my truth — I don’t want to be alone in this house once he's gone. Meeting myself in this moment with self-compassion instead of judgement shows me just how far I’ve come.

I sold a condo once in a terrible market (2009) so I’m betting on me again. If timing allows, Koko and I have one more adventure in us and it’s a luxury apartment building here in Austin where he has his own dog park and I have a pool! And even more importantly, a place to build community and be around more people (and dogs!) so I can finally close this chapter of feeling so alone.

49 + 363 days — The countdown

At this wiser age of (almost) 50, I can finally grasp the concept of surrender. It is far from easy for me, but now it’s what keeps me grounded. So I’ve asked the Universe to show me the timing — if the house sells quickly while Koko is still lively and mobile, we are headed to what’s next. If it does not sell, then I’m trusting we are meant to be here a bit longer and I will revisit things in another season. Until then, one thing I can do regardless of where we are living, is to fill all the days I have left with my best friend with lots and lots of joy.

In the meantime, this week I have 20+ people flying to Austin to help me celebrate this big birthday followed by a much needed beach vacation with ten childhood friends. Two weeks of celebrating and I can hardly wait.

Life truly is so fascinating if you pause long enough to pay attention. In these final days of my 40s I can see, and feel, this full circle moment. From age 7 to age 49, the same wound, the same fear, the same desire. Yet I’m aware of it, and I’m in choice.

Things are no longer happening “to me”; things are happening because of me.

AGE 50 — The threshold

Not yet a chapter…the next note in the octave, unplayed. I’m strong, single, with Koko, for now. Anticipating his loss the way I once couldn’t anticipate my mom’s — except this time, awake to it. Not organizing myself around avoiding the pain. Staying present to it as it approaches and prioritizing what I need for me to move through it.

Beyond that, what unfolds in this chapter I genuinely don’t know yet. But what I feel unflappable about is the pain and patterns of the “before 50 Jen” are fading to the background, and the “after 50 Jen” will be basking in the glow of healing, growth, and…humility.

Look out world, I’m here to shine.

The Work of You

What are your seven-year marks?

Not forced to fit a pattern — just notice what lines up. Where have your own cracks, shocks, and rebirths actually occurred? What wound built the architecture you're still living inside — or still growing beyond?

I’m so grateful for the coaches, therapists, retreats, and workshops that have helped me arrive at where I am today. A special shout out to The Hoffman Process, Beatrice Chestnut & Urânio Paes for the CP Enneagram Psychological Retreat, and honest to goodness most of all to the Enneagram as it’s helped me make sense of every single part of what I’ve shared here today. My ultimate “birthday wish” is to help others make sense of themselves, their wounds, patterns, and who they can still become. I hope you’ll learn more about what I’m up to at www.theworkofyou.com/thework