Your Career as a Human Being: Redefining Success in Midlife

There are no coincidences.

You can take that statement however you want. 

For me, I take it to mean that things, people, ideas come into our lives when we are most receptive. When our awareness is heightened, and most attuned to receiving. That’s when we notice. That’s when we connect the dots.

I was on Instagram the other day and landed on a Humans of New York (HONY) reel. I’ve followed the account for years, but hadn’t seen it show up in my feed in ages. Even though I was doing the scroll-y thing where you mindlessly swipe, I was compelled to stop and watch this one in its entirety.

On any other day, this HONY profile might not have landed so powerfully. But I’d recently had a conversation with my mom that was lingering in my subconscious. I’d asked her what she would want her obituary to say.

Now, my mom is, thank goodness, healthy. Writing her obituary is not an imminent task. My question was more a curious and philosophical one. In hindsight, though, it was practical, too. Because, there will come a day when we do need to write it. And as much as the topic is potentially triggering, I’m realizing it’s a privilege to have these conversations at a time when she can make conscious choices about her future.

And, really, it’s a win/win.

My mom gets to maintain control in the afterlife, and my sister and I can rest easy knowing she would have approved of our efforts.

This conversation happened the last time I was up visiting with her.

Like most mornings when I’m there, I’d brought in The Boston Globe from the front steps, and laid it at her place setting for when she came downstairs for breakfast. The first section she usually looks at after brewing her coffee and setting out her pills is the obituaries.

As she was scanning the pages for familiar faces, she noted a few names, and read a couple out loud. 

“What would you want yours to say,” I blurted out, and then immediately apologized. “You don’t have to answer that if you don’t want to,” I backtracked. 

She paused for a second.

“No. That’s ok,” she said. “I’ve thought about it before.”

After a beat, she answered the way most of us probably would. With things that could be verified – schools she went to, careers, titles…and then she fell quiet.

We shared the silence for a few moments.

“I’m not really sure,” she finally said, perhaps contemplating the resume and the life and the space in between.

We left it at that.

The next morning, I was back in my spot at the kitchen table when she came in carrying a handful of photos, papers and letters.      

“I didn’t go to sleep until after 3 a.m.,”  she informed me.

Turns out while looking for some paperwork, she stumbled upon a treasure trove of memories and proceeded to spend the early morning hours reliving them. There were yellowing pictures, old report cards, camp letters from homesick kids, and also a stack of birthday cards from a surprise 60th celebration my dad, sister and I had thrown in her honor.

She pushed a few of the papers and photos my way to check out.

Then she announced “This one,” holding up a greeting card, “This is it.” 

“This is what?” I responded.

“This is my obituary,” she said.

The card she was holding contained a hand-written birthday message from a dear friend.

She read it aloud to me then.

And, wow. Just wow. This friend captured her completely.

There wasn’t one word about the universities she’d attended. No mentions of her career in sales or entrepreneurship.

Instead, she extolled her gift of storytelling; her Borscht Belt-worthy Yiddish accent; her capacity for love and caring for others; her artistry and talent; her impeccable style; and her unmatched reliability in sending out annual birthday and anniversary greetings to family and friends.

She rounded out the list of accolades with my mom’s greatest joy and purpose – her family. 

It was a tribute to a remarkably rich life. 

And this brings me back to the HONY Instagram post, and why it stirred up so many emotions.        

In it, a man is reflecting back on a moment most of us know all too well: getting pulled into the “what could have been” spiral. A friend’s success triggers it, and suddenly he’s replaying an old decision, imagining a different version of his life, a different career, a different outcome.

But then his daughter interrupts the spiral with a single, grounding truth: if he had made that different choice, she wouldn’t exist.

And just like that, his entire lens shifts.

What begins as a story about comparison and regret turns into something much deeper – a reframing of success itself. He realizes that maybe the metric isn’t the career he could have had, but the life he actually built. The people in it. The impact he has. The kind of human he’s choosing to be.

My career as a human being.

The line slayed me.

It also took me right back to those two moments with my mom: the extended silence as she struggled to reconcile proof of an impressive life, and the following morning, with actual receipts in hand of her incredibly successful career as a human being.

We've all heard the sentiment “Nobody on their deathbed ever said, 'I wish I had spent more time at the office.'” And yet, most of us – myself included – still let societal measures of success creep in.

That's why I can't quite shake this notion of my career as a human being.

In my lowest moments, I've struggled to reconcile whether I should look for incremental work while continuing to build my coaching practice. Entrepreneurship is not the easy path, and there are days when a 9-5 job sounds refreshingly straightforward. And then the ego swoops in with its own torture – would that be seen as an admission of failure? Would I lose all credibility?

I coach women through this exact thing. And I am not immune to it myself.

Some days the belief comes easy. Some days I have to rebuild it from scratch. And it's honestly the unexpected text, the client email, the DM from someone experiencing a shift – those are the things that remind me the work matters.

Those are receipts. 

So I’m going to keep looking for them – proof of my own rich life continuing to unfold.

This week, my receipts looked like two of my children asking if I’d be their well being accountability partner, a heart to heart with my other child, a client checking in with an enthusiastic update and a friend sharing how much she needed to hear something I shared on social media.

And yes, my ego would love it if I could also add to that list that my client roster is bursting at the seams (it’s not). But since I’m pretty sure that won’t end up in my obituary some day, I’m choosing to not let it define me now.

So maybe you’ll ask yourself, too: what are your receipts? Not the verifiable ones. The other ones. The ones that really matter at the end of the day.

Proof of your ever-evolving career as a human being.