Or perhaps more accurately, I’ve finally stopped believing I have to choose just one thing.

For most of our lives, we’re asked some version of the same question:

“What do you want to be when you grow up?”

“What do you want to major in? And what are you planning to do with that?”

And eventually, “So, what do you DO?” (As though that defines your existence)

And we’re expected to have a tidy answer.

A noun, preferably.

I’m a hospitality manager.

I’m a director of catering.

I’m a director of sales & marketing.

I’m an executive.

I’m a professional event designer, planner, & coordinator.

I’m a fundraiser.

I’m a coach.

I’m a celebrant.

I’m a wine educator.

Pick ONE.

Except I’ve been all of those things. And at various points in my life, each one has been true.

For a long time, I think I assumed that moving into a new chapter meant leaving the previous one behind. That reinvention required replacing one identity with another.

At 60, I’m beginning to understand something very different.

Maybe we aren’t supposed to discard the previous versions of ourselves. Maybe we’re supposed to bring them with us.

Starting over without throwing anything away

Over the past year, my life has changed in ways I could never have fully anticipated.

A few months before I turned 60, I moved to Europe.

I’ve learned how to do the Schengen Shuffle. (If you don’t know what that is, ask me. I have thoughts.)

I’ve studied wine more seriously than I ever dreamed possible — and discovered that the more I learn, the more there is to learn. It is fascinating and challenging and occasionally humbling, and I am enjoying every minute of it.

I’ve traveled extensively, and along the way, I’ve questioned my previous life choices more than once.

I’ve committed to starting over... this time, with no guilt and no regrets.

And yes, there have been more than a few moments when I’ve wondered:

What the hell am I doing?

But somewhere in the middle of all that uncertainty, something became unexpectedly clear.

The various things I’ve done with my life aren’t nearly as disconnected as they look on paper.

Because the things I love doing most have always been about connection.

Subscribe now

The thread that was there all along

I’ve spent years helping two people understand one another better.

I’ve sat with people whose lives no longer looked anything like the lives they thought they were building and helped them begin to ask, What now?

I’ve created experiences that brought people together around tables, in ballrooms, at conferences, at celebrations and during some of the most important moments of their lives.

And now I can sit across a table with a bottle of wine and become completely absorbed in the story of the people who made it, the place it came from, and what happened in that particular vineyard in that particular year to create what’s in my glass.

On the surface, those things might look completely unrelated.

To me, they aren’t.

They’re all about creating experiences that enrich, fulfill, inspire, connect us and bring more joy into our lives.

And suddenly, the seemingly disconnected chapters I’ve accumulated over six decades don’t feel so strange.

And then there was wine

Wine was different.

I didn’t stumble into it accidentally or wake up one morning surprised to discover that it had somehow become part of my life. I had worked with it as part of my hospitality and event industry jobs — it was seriously some of the most enjoyable work I could remember doing throughout my career. Hosting winemaker dinners with one of my all-time favorite executive chefs. Leading wine tastings at local Virginia wineries.

I loved wine! Wait, that sounds slightly... suspicious… off. I had traveled to countries specifically to tour the wine regions, to add to my collection (well over 300 bottles at one point), to see the vineyards, to talk to the winemakers. I had done all this… for FUN!

Now, I wanted to study it seriously. I wanted to understand it deeply. I wanted to work in it, teach it, travel through it, and build experiences around it.

I wanted wine to become one of the defining things I did for the rest of my life.

For years, coaching had been work I knew I was very good at — and work that mattered deeply to me — making a difference in people’s lives, helping them grow, helping them heal — it meant, and means, the world to me. But with the move to Europe looming, I thought that I would need to rebuild a practice from the ground up, effectively beginning all over again.

Wine felt like a new direction.

And when I moved to Europe, I gave myself permission to pursue it with everything I had.

The more I learned, the more I wanted to know.

There was the wine itself, of course. But then there were the places.

The history.

The geology.

The climate.

The food.

The families who have farmed the same vineyards for generations.

The people trying something completely different from what their parents did.

The traditions preserved because they matter and the traditions being challenged because maybe there’s another way.

I loved all of it.

I began imagining a life built around it: wine education, experiences, retreats, travel. Sharing not simply what was in the glass, but the people, places, history and stories that put it there.

And then something else started happening.

The more I learned about wine, the more I found myself thinking about relationships.

A vineyard can’t simply be planted and forgotten. It has to be tended.

What it needs changes with the season. Sometimes growth needs to be encouraged. Sometimes things need to be cut back. There are periods of abundance and periods of dormancy. Difficult conditions can create extraordinary complexity — but only if what is growing has been cared for well enough to survive them.

And wine itself asks something of us, too.

Time.

Patience.

Attention.

An appreciation for the way something changes as it matures—not expecting it to taste exactly as it did when it was young, but becoming curious about what it is becoming.

I kept thinking: relationships need this, too.

We spend so much time celebrating the beginning of love. The falling. The wedding. The building of a life together.

But relationships mature.

People mature.

The conditions around them change.

We often talk about mature relationships as though their success should be measured by how well they preserve what was there at the beginning.

But perhaps maturity isn’t about preservation.

Children arrive and eventually leave. Careers consume us and then end. Bodies change. Dreams change. We become people neither of us could possibly have been when we first chose one another.

And perhaps the question isn’t How do we get back to what we were?

Perhaps it’s What could we become from here, if we tended to this relationship with the same care?

Perhaps, like wine, some of the beauty is in allowing something to evolve — and learning to appreciate what time, experience, challenge, and care have created together.

That connection between wine and relationships became more than an interesting metaphor for me. It began inspiring something tangible: couples retreats built around both — time away together in beautiful wine regions, using wine, place, shared experiences, and intentional conversation as ways to rediscover one another.

Suddenly, two pieces of my professional life that I had thought belonged in completely different boxes weren’t quite so separate after all.

And yet, at the time, I still thought wine was going to be the thing.

Or, more accurately, one of the things. I never intended to stop being a celebrant. Listening to people’s stories, and then writing a ceremony that honors their love, their life, their everything... Standing with those people at those extraordinary threshold moments in their lives — marriages, commitments, their beginnings and their endings — is something I can’t imagine ever completely giving up. There are some kinds of work that become too much a part of who you are to simply retire from them.

But coaching?

I thought perhaps I was done.

The funny thing was, coaching apparently wasn’t done with me.

Even when I wasn’t actively looking for clients, people kept finding me. Old clients going through new challenges reached out. New clients who were referred by old clients sought me out despite being in a different time zone.

And somewhere along the way, I began to understand that perhaps I’d been asking myself the wrong question.

Maybe wine didn’t have to replace the work I’d done before.

Maybe I didn’t have to choose between the work that had shaped me and the work I was choosing for what came next.

And perhaps the reason all of it could belong in the same life was something I’d understood all along without quite recognizing it:

No matter what I was doing, I was still bringing people together.

Around tables. In conversations. Through shared experiences.

Talking. Tasting. Learning. Laughing. Sharing stories.

Connecting.

Well, shit.

There it was again.

Maybe reinvention isn’t really about becoming someone new

We talk a lot about reinvention, especially as we get older.

Starting over.

The next chapter.

The second act.

But I wonder whether we’ve misunderstood what reinvention can be.

Maybe it isn’t about becoming someone completely new.

Maybe it’s about finally becoming more completely ourselves.

There are things I know at 60 that I couldn’t possibly have known at 30.

Not because I wasn’t smart enough.

Because I hadn’t lived them yet.

I hadn’t loved enough.

Lost enough.

Succeeded enough.

Failed enough.

Changed enough.

Started over enough.

I hadn’t yet accumulated all the pieces.

And perhaps one of the privileges of getting older is realizing that we don’t have to keep putting those pieces into separate boxes.

So what do I do?

These days, answering that question takes me a little longer.

I’m a life and relationship coach.

I’m a retreat leader.

I’m a wine educator.

And increasingly, I don’t feel any need to decide which one is the “real” answer.

Through A Passionate Life, I work with people navigating relationships and the transitions that can completely rearrange the lives we thought we knew — from couples just beginning their lives together to those discovering that after decades together, they need to learn one another again. I work with people rebuilding after relationships end, and with those who simply keep hearing that persistent little voice asking:

Is there more than this?

Through UNCORKED, I’m building another kind of space for connection — through wine, travel, place, shared tables and meaningful experiences.

There are wine education classes coming.

There are experiences still taking shape.

And I’ll plant one little seed here:

There’s a wine retreat coming next spring in Hungary and Austria. 😉

More on that soon.

A Passionate Life isn’t one thing

Perhaps that’s the realization I’ve been working my way toward all along.

A passionate life doesn’t have to fit neatly into a job title.

It doesn’t have to follow a straight line.

It doesn’t require us to choose one thing we care about and politely abandon everything else.

And starting over doesn’t have to mean declaring everything that came before it a mistake.

I’m not throwing away the decades I spent creating experiences because I’m studying wine.

I’m not abandoning coaching because I’m building retreats.

I’m not leaving the woman I was in America behind because I’m creating a life in Europe.

I’m bringing her with me.

The executive.

The event producer.

The fundraiser.

The coach.

The celebrant.

The educator.

And always the student.

Because obviously, I never want to stop learning and growing and becoming MORE.

I am a woman who has loved deeply, screwed things up, figured some things out, changed her mind, begun again and still wakes up curious about what comes next.

All of her.

Maybe that’s what I’m finally learning about reinvention.

It isn’t always about having the courage to become someone else.

Sometimes it’s about having the courage to stop cutting pieces off ourselves simply because they don’t fit neatly into the answer to:

“So... what do you do?”

Apparently, figuring out what I want to be when I grow up meant giving myself permission to be all of it.

And damn, it took me long enough. ❤️

P.S. Since we’re talking about what I’m doing now: I am currently accepting new virtual coaching clients through A Passionate Life. If something in this piece made you think of yourself — or someone you care about — you can find more about my work at passionatelives.com.

And if the wine retreat was the part that made your ears perk up... stay tuned. 🍷

It took several of you to reach out and ask if everything was ok, because I wasn’t being my usual “engaging” self.

First of all, to those who inquired, thank you.

The short answer is yes, I’m ok – ish...

I knew that I was “head down” in the most intensive and focused studies I’ve ever undertaken. Frankly I flew by the seat of my pants through most of my younger school days. But there was something about the combination of facing an exam that I knew over 50% of those who take it fail, and the realization that I was now SIXTY, and no longer a 20-something who was able to party all night, roll into class in the morning, and sail through whatever I happened to be studying at the time. There was also the fact that I actually CARED about what I was learning. I recognize that I had (have?) placed an inordinate amount of importance on not just passing, but doing so with the highest level of distinction. I was so absorbed (obsessed?) with getting a perfect score, that I let the rest of life fade into the background.

Well... life had other plans.

Maybe I should back up a bit… when I wrote my last post, I was preparing for what felt like one of the biggest academic challenges of my life: the WSET Level 3 Wine certification exam in London. For months, my world revolved around grape varieties, climates, soils, winemaking decisions, and blind tasting practice. To say that I began seeing wine regions in my sleep is NOT an exaggeration.

But as I was galloping at full speed toward the finish line, my stress levels went through the roof, and my diet became predominantly Hackney Gelato ( https://www.instagram.com/hackneygelato/?hl=en – and NO, they didn’t pay me to promote them, though they should as I’m certain that I’ve purchased more than any other single human in a 1 month time span).

Life started waving little red flags.

Literally.

A few weeks before my exam, I took a small tumble and caught myself with my left hand – my writing hand (did I mention that this exam is an old-fashioned PENCIL & PAPER style?) At first, I thought I’d simply strained a wrist. But then both wrists began hurting. The kind of pain that’s easy to dismiss at first because you’re busy and have other, more important things to do.

So I did what many women do.

I ignored it.

Or at least I tried.

Then, one evening, while walking back to the train station after a “BONUS class”, something hard struck my left eye. It was the kind of sharp pain that stops you in your tracks and makes you exclaim out loud, “WTF was that?”

I seriously thought it was just a big bug that flew in my eye… until I got home, looked in the mirror, and discovered that the entire inside portion of my eye had turned a shocking shade of red.

At 10:30 at night.

Alone.

In a foreign city.

Less than two weeks before my exam.

Now, if you’ve never experienced this particular joy, let me assure you that Googling “impact to eyeball,” “bright red cornea” before bed is an excellent way to guarantee absolutely no sleep whatsoever.

Thankfully, an ophthalmologist confirmed the next day that there was NO permanent damage, NO serious concerns, and everything would heal on its own… in about 2 weeks… lovely.

Still.

Between the wrists and the eye, I started feeling like my body was in cahoots with the Universe, and they were both trying to get my attention.

And if I’m honest, I wasn’t listening very well.

I was focused on passing an exam.

Focused on work visas.

Focused on applications for the next level.

Focused on building a future.

Focused on figuring out where I’ll live and what comes next.

Focused on proving to myself that this dream I’ve been chasing is possible.

Somewhere in all of that, I forgot something important.

Even vineyards have dormant seasons.

The vines aren’t producing fruit every day of the year.

They aren’t constantly growing.

They rest.

They recover.

They gather strength for what’s next.

And, more importantly, one rough season doesn’t define a vineyard. It’s defined by the continuous nurturing, growth, and maturation.

For someone who has spent most of her life solving problems, pushing through challenges, and figuring things out, this has been an uncomfortable lesson.

I like forward momentum – preferably at breakneck speeds.

I like detailed plans where every possibility is considered and backups are in place.

I like progress – no, that’s over-simplifying, I like quantifiable success.

What I don’t particularly enjoy is being forced to slow down.

Yet that’s exactly what this season seems determined to teach me.

The irony isn’t lost on me.

I’ve spent years encouraging clients to stop “shoulding” on themselves.

To stop measuring their worth by productivity.

To stop believing they have to earn rest.

Apparently, life decided it was time for me to revisit my own curriculum.

That’s been the hardest part.

Somewhere along the line, passing became tangled up with proving that I belonged here.

Not just in a classroom.

In this life.

I had quietly convinced myself

• that I was only worthy of this path if I could be “the best”…

• that starting over at 60 wasn’t foolish…

• that I hadn’t made a mistake by leaving my old life behind and following a dream that made perfect sense to me and very little sense to some other people...

The truth is, the exam was never just an exam.

It became a referendum on every decision I’d made over the past two years.

That’s a lot of pressure to put on a pencil-and-paper test.

I’m still working on rewriting that inner voice that keeps trying to prove itself to everyone and anyone who will listen. … and, at an even deeper level, still trying to prove my worth to myself.

Maybe this is why it’s called a “practice” and not “the end result” – you need to continually stop yourself from the “shoulding” before it consumes another aspect of your life.

The good news is that I completed the exam.

Now I’m waiting for results – 10 painful, tortuous weeks (expected date is September 8^th for those who are curious.)

I’ve already applied for the next stage of wine education and am now living in that uncomfortable place between effort and outcome.

I’m continuing to build the vision for wine retreats that blend travel, connection, storytelling, and the beautiful lessons hidden inside every bottle.

And yes, I’m still figuring out the ever-changing puzzle of European residency while studying Hungarian, job hunting, and doing the infamous Schengen Shuffle.

But perhaps the biggest lesson of the past six weeks isn’t about wine, visas, or certifications.

It’s this:

Sometimes growth looks like movement.

Sometimes growth looks like sitting still long enough to hear what your life is trying to tell you.

I’m still learning the difference.

And if you’re in a season where your own body, heart, or circumstances are asking you to slow down, maybe this is your reminder that dormancy isn’t failure.

It’s part of the process.

Just ask the vineyard.

Life is too short for bad wine, boring relationships, and believing that one difficult season gets to define the vineyard.

Cheers,

Jamie

Recently, my son’s kitchen in Vienna was alive with that exact kind of magic.

My best friend, Nora, and her wonderful friend Sue (who at 80-plus years young possesses more curiosity and zest for world travel than people half her age) traveled nearly halfway around the world from Seattle to visit us. Welcoming them into his home wasn’t just a casual get-together; it felt like a profound bridging of worlds.

The true joy, though, was sharing this moment with my son, Logan. Watching him step into his role as a host, helping me welcome these deeply meaningful figures from my life into our shared space, was a milestone of its own. Together, we uncorked special bottles from my private collection, pouring a liquid welcome that set the stage for what would become an unforgettable journey upriver.

Beyond the ‘Cheap Wine’ Tour

Tuesday morning, Logan, Nora, Sue, and I set out for the Wachau Valley, where the Danube cuts a dramatic path through ancient, terraced stone vineyards.

If you’ve ever booked a standard wine tour, you know how they usually go. A generic guide drives you to a high-volume tasting room, recites a few Wikipedia facts, and points to the gift shop with a pitch of, “This place sells good, cheap wine.” It reduces centuries of agricultural poetry into a transaction.

We wanted something different, and we found it in *Camilo, our guide.

Camilo isn’t just someone who knows where the tasting rooms are; he is a deep student of the vine, currently preparing his final research paper for the rigorous WSET Level 4 Diploma. Spending the day with him was a masterclass in how expertise transforms an experience. His own journey in life through Latin American countries to a host of European nations, ultimately landed him in Austria, and his global perspective shines through his narrative.

Instead of transactions, Camilo gave us the stories.

We started our journey at **Weingut & Heuriger Rehrl-Fischer, nestled in a charming riverside village directly opposite the picturesque town of Dürnstein on the northern bank of the Danube. It lies in the heart of the UNESCO-listed Wachau Valley, and the family has been cultivating wine in Rossatzbach since 1783. Because this side of the river is slightly less commercialized than the northern cruise-ship path, its wine culture feels deeply intimate. These are families that have had each others backs for centuries and they truly understand the meaning of community!

As we looked out over the steep, hand-carved terraces, Camilo didn’t just rattle off a list of grape names; he explained how, unlike the steep, sheer primary rock (gneiss) of the opposite bank, the rolling hills around Rossatzbach are characterized by deep blankets of loess, sand, and Danube gravel. This specific terroir imparts a pronounced, salty minerality and a creamy texture to the Austrian Riesling and Grüner Veltliner, setting them apart from the sharper, rock-driven profiles across the river. He talked about the families who have hand-harvested these vineyards for generations, treating the vines not as commodities, but as living extensions of their own history.

To sit at a table with my son, my lifelong best friend, and an incredible woman navigating her ninth decade of life, all of us listening to a passionate young professional share the soul of a region… it was a reminder of why travel matters. Sue, with her sharp wit and decades of perspective, reminded us all that the capacity to marvel at the world doesn’t expire with age. If anything, it deepens.

The Perfect Kickoff

Looking back, that slightly tipsy day in the Wachau was more than just a beautiful memory; it was the ultimate, poetic kickoff to the intense professional chapter I was about to embark on.

Within days of that trip, I would find myself navigating the beautiful madness of the VieVinum international wine festival at the Hofburg Palace, tasting the pinnacle of Austrian winemaking and connecting with visionary producers. And now, as I write this from London, completely immersed in my own formal advanced wine training, I keep returning to that afternoon on the Danube.

It reminded me of what I want my own path in this industry to look like—whether through my writing, or the wine retreats I am designing. I don’t ever want to tell people where to find “good, cheap wine.” I want to take them by the hand, look out over the landscape, and tell them the story of the people, the soil, and the time it took to create something beautiful.

Because whether you are talking about a bottle of Smaragd Riesling, or a friendship that spans a lifetime, the magic is always in the history.

Life is short… eat the dessert, and drink the wine!

Jamie Dee Schiffer is a relationship coach, author, and wine enthusiast currently navigating a new life in Europe. You can find her at PassionateLives.com.

*You can find Camilo Mejia on Instagram @wine_pilgrim and on LinkedIn at Camilo Mejia. – He is a Wine Merchant, Educator, experienced cook, and natural storyteller on a quest for wines with soul, savouring the tales they tell, and sharing the passion.

**Discover the Rehrl-Fischer Winery and Wine Tavern.

What are the rules anymore? We’ve all seen them change… time and time and time again… how do we even know what we “should” be doing now?

Ahhhhh… there it is… SHOULD… Respectfully, in the words of Bob Newhart during his guest appearance as the psychologist, Dr. Switzer, on MADtv, “STOP IT.”

*see the link below if you don’t remember, or shockingly, have never actually seen it. ***Warning, it does NOT meet PC standards for modern day, but if you can get beyond that… it’s still funny.

Ok, where was I? Right, Stop “Shoulding” on Yourself! Here are 10 ways to set yourself free from this burden… and don’t kid yourself, that is exactly what it is. So the first step, as with anything, is awareness.

1. Awareness... The BFF Litmus Test ~

Let’s start with a litmus test… the thing you’re saying to yourself, the thing you think you should do, or should have done… would you say that to your best friend? Ok, to ANY friend? Can you even imagine that conversation?

“Jane, I can’t believe you are 60 and you still haven’t ____(FILL IN THE BLANK)____, you really should have done that by now, what’s wrong with you?”

You wouldn’t, would you? I didn’t think so. What’s next? Understanding where this jerky inner voice came from.

2. Deconstruction ~ What is this list? And, more importantly, WHERE did this collective belief even come from? ~

“You should ____ (pick one: be nicer, be more forgiving, be stronger, get over it, move on, not nag, be a better wife, mother, friend, keep a cleaner home, eat better, exercise more, don’t complain… you get the idea, the list is endless)___”

Ok, let’s dig into this... Where did these notions even arise? This list of “Shoulds”... Let’s examine it and see if it resonates or if you wholly reject it… and if you do reject it, then WHYYYY do you keep repeating this self-sabotaging mantra to yourself?

Ready? Hang on, because here’s the ugly truth…

This all started with the Patriarchy… that’s right… MEN! Ok, ok, I’m NOT on a men-hating kick, seriously. What I DO want to shine a light on is the SYSTEM that developed this rigid list, the “tyranny of shoulds” to manage, control, and commodify women’s behavior, bodies, and time. And what’s almost worse, and more than a little sad, is that we likely heard this from our mothers, who heard it from their mothers, who heard it from their husbands at a time when they didn’t have many choices and believed this is what would bring them peace, and security. This wasn’t about love. It was about control.

Ewww, right? Right! So what now? How do I turn this thing off?

3. STOP AND DROP! ~

No, you’re not on fire, not literally anyway… but if you think of this when you hear those words echoing in your head, or heaven forbid, you’ve actually said it out loud to yourself, this is your opportunity to flip your script. Drop that negative, judgmental phrase and flip it into a conscious CHOICE. When your internal monologue kicks in and you say something that sounds innocuous on the surface like, “I should go to the gym” (with the hidden underlying message being that if you don’t, you’re lazy, fat, or worse”), try flipping it into an option, a conscious choice… “I want to go to the gym” or even kinder, “I want to do something to get myself moving because I know I always feel better when I do.” This is about restoring your agency. And if during your gut check, you find that you actually don’t WANT to do the thing that you thought you “should”… STOP, and OWN IT. You don’t need to justify it or explain it to anyone.

Not gonna lie, this next one is harder...

4. Stop “Shoulding” on Your Emotions ~

Emotions are not logical. They are also NOT WRONG... they just… ARE. When we tell ourselves how we “should” feel, we add a layer of shame on top of something that is already hard, or painful. Embrace the practice of radical acceptance.

5. The Power of “NO” Without an Explanation ~

Do you feel compelled to say “yes” to every request? Or, when you literally CAN’T, do you then feel the need to justify it to the Nth degree? You are not doing yourself, nor anyone else, any favors if you commit yourself to anything that you don’t have the capacity for in heart, mind, body, and soul. Practice the art of the “Clean No.” “I can’t” is a complete sentence. Throw in an “I’m sorry” if you genuinely are, skip it if you’re not. (Yes, that’s permission to not feel bad about it.)

6. Embrace the “B-Minus” Effort ~

I am not perfect. You are not perfect. NONE of us are. Embrace that! Revel in it! It means you are HUMAN <3 Just for one day, leave something undone… don’t fold the laundry, leave it on the chair (no, it doesn’t count if you always leave it there.) Pick something that pains you, just a little, because it triggers that internal “should” response. Recognize that the world doesn’t end when you stop trying to be perfect. What does happen, is that your peace of mind can finally begin.

7. Prioritize “Pleasure” Over “Productivity” ~

Somehow we convinced ourselves that we are only “allowed” to rest after all of the work is done. Here’s the spoiler: it’s NEVER ALL done! There will always be more to do. Stop “shoulding” on your downtime and recognize that you can’t give from an empty well. Self-care is the greatest gift you can give to everyone you actually care about. You have the right to treat your personal joy, and rest, as non-negotiables… they are not the rewards earned after self-sacrificing for everything and everyone else around you.

8. Mind Your Input and Consciously Curate What You Consume ~

No, I’m not talking about food… I’m talking about the messages that are seeping into your head and shaping your reality. If some “Influencer” has you “shoulding” all over yourself because you’re not doing whatever crazy, trendy thing that they claim is going to make you “perfect”… STOP, and hit that UNFOLLOW button! Dump anything that makes you feel guilty and doesn’t align with the reality you are CHOOSING.

9. Burn the “Timeline” Map ~

Society hands women a falsely constructed map of where we “should” be by __(fill in the blank)__ age. It has tried to convince us that we’re failing if we don’t meet this standard. And that? That is utter crap! Whether you’re 60, going through a reinvention phase, and launching a new career, or your relationships are based on choices that make YOU happy… those are YOUR choices and they cannot be measured or judged by anyone else’s standards. Stop “Shoulding” on your stage of life and start living the one you’re actually in. It’s empowering!

10. Reclamation ~

Realize and claim that YOU, and only YOU, are the expert on your lived experience. When you stop comparing yourself to a false notion of perfection, you can reclaim your true self… and that is soooo freeing! Look inside yourself, and feel into what you actually need… what you actually want for yourself. That is how all those “shoulds” ultimately lose their power.

Life is too short to drink bad wine or to spend it “shoulding” all over yourself!

Jamie Dee Schiffer is a relationship coach, author, and wine enthusiast currently navigating a new life in Europe. You can find her at PassionateLives.com.

***Here’s that link to the Bob Newhart skit… you’ve been warned ;) https://youtu.be/EsNgQf-DaGU?si=Lr19QOfEaknbnJ

Why I Traded the Boardroom for a Life of Passion

For well over 30 years (yikes, more like 40), my life was measured in floor plans, BEOs (banquet event orders - the complex 'scripts' that make massive events run like clockwork), and the never-ending, round-the clock whirl of the adrenaline filled world of the hospitality industry.  As an Executive Director of a Tier 1 Convention Center, I was the “go-to” expert who knew how to create “the experience” that drew people in, kept them engaged, and kept them coming back for more.  I hosted presidential debates, world-class trade shows, and educational symposiums for some of the top speakers in the industry.  Every single detail ran across my desk, along with every back-up and crisis intervention plan.  

I became the hired contractor who was brought into private country clubs to create a new identity after the old ones felt stale and uninspired. I took over catering companies, golf clubs, event venues, and turned their flagging revenue into gold mines for their owners.  I taught the staff how to communicate in a way that made every guest feel like they were the most important person to walk through the door, and I taught the Executive Teams how to communicate with the staff in a way that lifted them up and inspired them to grow with the company instead of running away screaming.

I was often asked how I ended up in those roles, and it was honestly as perplexing to me as it was to others when I shared that I actually started on this path when I got bored while pursuing a career in psychology, and ended up volunteering to coordinate every fund-raiser that came across my path.  One thing led to another, and I accepted a role as an event coordinator… and then a manager role… then a director role… and before I knew it, I owned an event firm, and became an ordained minister so that I could marry the couples I was working with, and perform commitment ceremonies long before marriage equality laws were passed. I spent the next few decades of my life creating experiences for others… all the while I still had my own life, with everything but the literal white-picket fence.  

The Moment The Blueprint Shifted ~ 

And then, my marriage collapsed, and everything changed.  After years of couple’s counseling from people who just listened, but didn’t DO anything to help us change, we went our separate ways.  Only I couldn’t shake the feeling that the therapy that I had experienced was really leaving more than a little undone.  We had been heard, but we hadn't been healed, and we certainly hadn't been given the tools to build something new.  I knew there had to be a way to move beyond just 'listening' and into 'doing.'  I knew I could do it better, differently… but the world of personal and couple’s coaching wasn’t a thing at that time.  Slowly, I started to find others like me… trained in the traditional methodologies, but inspired to consciously GUIDE their couples, not just… listen.  Little by little, I spent more and more time, and met more therapists turned coaches who felt the same pull that I did.  I enrolled in coaching classes and played guinea-pig for others to practice on.  It was enlightening and inspiring, and quickly became all-consuming.  That 'undone' feeling became the blueprint for my coaching practice, A Passionate Life.

I joined women’s groups and think tanks, I became an author of inspirational compilation books, and created a new business offering couple’s coaching - all while maintaining a full time position running weddings at local venues and vineyards… because, well, honestly,... the bills needed to be paid, and as a single mom, it was all on me to keep the roof over our heads.  

Don’t get me wrong, life was good… very good… I traveled the world both personally and professionally, and lived in what was really my dream home.  When the pandemic hit, most of my business income collapsed, and the winery where I was working was forced to close to the public.  My son and I shifted, working side by side educating the public about COVID, and I returned to the non-profit sector for security.

The Empty Nest and the Radical Leap ~ 

Then came 2025. My son moved to Austria for a research position in February, and for the first time in 30 years, the house was empty. Just me, two orange kittens, and a sudden, jarring clarity: I was living in a place I never fit in, doing work that was sucking the life out of me, both mentally and physically… and I KNEW that I needed to make a radical change.  I realized that while I had been a master of logistics for others, I was craving a deeper mastery… one of my own life, my own heart… and I knew that I needed to do something that LIT ME UP, or frankly, none of it felt like it was worth doing any more.

I rebranded my couple’s coaching business to Passionate Lives, and I made a plan to escape… not on a vacation to the islands, or some other temporary respite, but to a new life, in a new country!  

I realized that all those skills that I had honed in the boardroom and in the event spaces I lived in for decades - mediation, crisis counseling, and the high-level communication that was required to make it successful, were the very same things that people were starving for in their personal lives.  I witnessed a connection crisis in my colleagues,... so many women who achieved incredible professional success, raised their children and watched them fly the nest, only to look at their personal relationships and see that they had withered on the vine - they were logistically functional at best, but lacked any sense of vibrancy and joy.

Complexity, Layers, and Fine Wine ~ 

I saw the correlation between one of my other great passions in life - wine - and the story of what makes a great wine, were also the same things that make a great relationship (we’ll get more into that as this story progresses, I promise!)

Moving to Europe wasn’t a spur of the moment decision… not really… I’ve spent the better part of my life in love with Europe and the European lifestyle.  I’ve traveled to over 50 countries, and have spent extensive time in many of them… plus, now my son was living there, so WHY NOT?  This wasn’t just a relocation… this is the physical manifestation of my entire philosophy behind my business, A Passionate Life… it’s what I’m claiming.  And no, it’s not easy… not by a long shot.  But, everything has been sold, and what’s not just arrived in a cargo container to my son’s apartment in Vienna, so there’s no going back now!

I am inspired by the idea that we are all collectively evolving, and that there are others, such as myself, who don’t need “safe” advice,... we need our partners, and our circle of friends, to be actively involved in supporting us as we navigate the aging process and the rediscovery of who we are when the old titles are stripped away.

I hope I’ve inspired you to join me on this adventure as I navigate the complexities of gaining my European citizenship, earning my WSET wine certification, and claiming a life where passion isn’t a cliché word that’s thrown around, it’s a daily practice to which I’m wholeheartedly committed.

To those women “of a certain age” who may be wondering if your best years are behind you… I’m here to reaffirm that we are just reaching our peak complexity, and like a fine vintage, we’ve not lost any value, we’ve only added nuanced layers.

I don’t pretend to have the answers… I only have a LOT of questions… some of which may inspire you, some of which may scare the bejeebers out of you, and some of which may have you questioning my sanity!  I am honored to share a piece of this journey with you.  I hope you join me as I talk about wine, travel, resilience, passion, and the art of building a life that you don’t need to escape from.  

Life is too short for bad wine and boring relationships!

Jamie Dee Schiffer is a relationship coach, author, and wine enthusiast currently navigating a new life in Europe. You can find her at PassionateLives.com.